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Journal articles on the topic 'Sulfate groups'

Author: Grafiati
Published: 14 March 2023

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1

Arnoštová, Libuše, Ivan Černý, Vladimír Pouzar, and Pavel Drašar. "Synthesis of 5α-Cholestane Type Glycoside Sulfates." Collection of Czechoslovak Chemical Communications 58, no. 5 (1993): 1180–90. http://dx.doi.org/10.1135/cccc19931180.

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Synthesis of steroid glycoside sulfates sulfated both on the steroid skeleton and in sugar part are presented. Sodium salts of 5α-cholestane-3β,6α-diol 6-β-D-glucoside 3-sulfate V and 3-β-D-glucoside 6-sulfate XI were prepared from 3β-(2-tetrahydropyranyloxy)-5α-cholestan-6α-ol (I) using acetyl and methoxymethyl groups for temporary protection. Sulfation in the sugar part was at first checked in pregnane series and triethylammonium salts of 3β-(β-D-glucopyranosyloxy)pregn-5-en-20-one 6'-sulfate (XXVI) and 4'-sulfate 2',3'-diacetate XXVII were prepared. Application of the method on cholestane derivatives gave triethylammonium salt of 5α-cholestan-3β-yl β-D-glucopyranoside-6-sulfate (XXXI).
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2

Reinehr, Thomas, Alberto Sánchez-Guijo, Nina Lass, and Stefan A. Wudy. "Higher steroid sulfation is linked to successful weight loss in obese children." Endocrine Connections 7, no. 10 (October 2018): 1020–30. http://dx.doi.org/10.1530/ec-18-0233.

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Objective Little information is available on the steroid sulfates profile in obese children. Therefore, we examined whether sulfated steroids are linked with weight status and associated comorbidities in obese children. Methods We analyzed 66 obese children (mean age 10.5 ± 2.5 years, 57.6% female, 53.9% prepubertal, mean BMI 27.0 ± 4.6 kg/m2, 50% with BMI-SDS reduction >0.5, 50% without BMI-SDS reduction) who participated in an outpatient 1-year intervention program based on exercise, behavior and nutrition therapy. We measured intact sulfated steroids (cholesterol sulfate (CS), pregnenolone sulfate (PregS), 17αOH pregnenolone sulfate (17OH-PregS), 16αOH dehydroepiandrosterone sulfate (16OH-DHEAS), DHEAS, androstenediol-3-sulfate, androsterone sulfate and epiandrosterone sulfate) by LC–MS/MS, and insulin resistance index HOMA, lipids, blood pressure at baseline and 1 year later. Results All sulfated steroids except 17OH-PregS, 16OH-DHEAS, androsterone sulfate and epiandrosterone sulfate were higher in boys compared to girls. Concentrations of CS before intervention were higher in children who lost weight. After 1 year of treatment, both groups showed increased levels of DHEAS, 16OH-DHEAS and androstenediol-3-sulfate, but PregS was only increased in children with weight loss. None of the steroid sulfates was significantly related to cardiovascular risk factors or HOMA except 17OH-PregS, which was associated with systolic blood pressure both in cross-sectional (β-coefficient: 0.09 ± 0.07, P = 0.020) and longitudinal analyses (β-coefficient: 0.06 ± 0.04, P = 0.013) in multiple linear regression analyses. Conclusions Since higher steroid sulfation capacity was associated with successful weight intervention in children disruption of sulfation may be associated with difficulties to lose weight. Future studies are necessary to prove this hypothesis.
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3

Hobkirk, R., and Catherine A. Cardy. "The in vitro formation of sulfates and glucuronides of estrogens by adult and fetal ovine tissues." Canadian Journal of Biochemistry and Cell Biology 63, no. 8 (August 1, 1985): 785–91. http://dx.doi.org/10.1139/o85-100.

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Incubation of nanomolar concentrations of [3H]estrone with ovine liver slices from adult and fetal animals demonstrated, in particular, the production of estrogen sulfates together with smaller amounts of glucuronides, even although microsomal estrogen glucuronyltransferase (GT) and sulfatase activities were high, especially in adult tissue. [3H]Estriol was conjugated almost exclusively as sulfate under the same experimental conditions. Slices of maternal and fetal kidney medulla were also strikingly active in promoting estrogen sulfate production as were slices of fetal kidney cortex. Adult kidney cortex conjugated estrogen only in the glucuronide form. These data indicate the possibility that maternal and fetal liver and kidney might contribute to the high circulating level of estrone sulfate in the pregnant sheep. Through the use of [3H]estrone and [3H]estrone sulfate as substrates, it was possible to demonstrate that adult slices of kidney medulla possessed relatively low sulfatase, considerable sulfotransferase (ST), and virtually no GT activity, whereas cortex had high sulfatase, little or no ST, and low, though demonstrable, GT activity. The ST activity of kidney high-speed supernatants was stimulated by the presence of sulfhydryl groups, whereas that in liver was not. Enzymic reduction of estrone and (or) estrone sulfate by liver and kidney slices indicated that, in the former, 17α-reduction prevailed and, in the latter with the exception of the maternal medulla, 17β-reduction was the main pathway, particularly in the fetus.
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4

Drouet, B., S. Matou, P. A. S. Mourão, A. Bros, D. Letourneur, A. M. Fischer, and J. Tapon-Bretaudière. "Modulation of Vascular Human Endothelial and Rat Smooth Muscle Cell Growth by a Fucosylated Chondroitin Sulfate from Echinoderm." Thrombosis and Haemostasis 84, no. 08 (2000): 332–37. http://dx.doi.org/10.1055/s-0037-1614016.

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SummaryFucosylated chondroitin sulfate is a glycosaminoglycan extracted from the sea cucumber Ludwigothurea grisea. This polysaccharide has the same structure as a mammalian chondroitin sulfate but some of the glucuronic acid residues display sulfated fucose branches. Anticoagulant and antithrombotic properties of fucosylated chondroitin sulfate have already been described. In order to further investigate its potential therapeutic use as an antithrombotic agent, we studied its effect on vascular smooth muscle cell (SMC) proliferation and endothelial cell proliferation, migration and Tissue Factor Pathway Inhibitor (TFPI) release. The experiments were performed on SMC from rat thoracic aorta and on human umbilical vein endothelial cell (HUVEC) in culture with or without added fibroblast growth factors (FGF-1 and FGF-2). Our results showed that: (i) fucosylated chondroitin sulfate had a strong inhibitory effect on SMC proliferation (IC50 =10 ± 5 µg/ml) and (ii) no effect on HUVEC proliferation and migration assays, in the absence of exogenous FGF, while heparin had inhibitory effects; (iii) fucosylated chondroitin sulfate (10 µg/ml) enhanced FGF-1 and FGF-2 induced HUVEC proliferation by 45% (145.4 ± 7.2%) and 27% (126.9 ± 4.2%), respectively; (iv) on FGF-induced HUVEC migration, fucosylated chondroitin sulfate (10 µg/ml) had a strong enhancing effect with FGF-1, +122% (222.2 ± 15.8%), three times higher than that of heparin, and a lower enhancing effect with FGF-2, +43% (142.7 ± 4.6%), whereas heparin had no effect; (v) fucosylated chondroitin sulfate stimulated TFPI release, mainly on the free form, +98% (198.2 ± 25.%). In addition, the structural features of the polysaccharide associated with its biological activity were resolved using chemically modified fucosylated chondroitin sulfates. Sulfated fucose branches groups are essential to the potentiating effect of the polysaccharide on HUVEC proliferation and migration. Surprisingly, removal of fucose branches from the fucosylated chondroitin sulfate did not abolish TFPI release. Finally, partial reduction of the glucuronic acid carboxyl groups limited the potentiating effect on HUVEC proliferation and migration but did not affect TFPI release. In conclusion, this fucosylated chondroitin sulfate from invertebrate origin reveals useful properties for an antithrombotic agent: inhibition of SMC proliferation, enhancement of endothelium wound repair and TFPI release. These properties on vascular cells, associated with a low bleeding tendency and an antithrombotic activity, strongly suggest its potential use as a new therapeutic agent in arterial thrombosis and restenosis, with a more favorable effect than heparin.
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5

Fishbain, Susan, Jesse G. Dillon, Heidi L. Gough, and David A. Stahl. "Linkage of High Rates of Sulfate Reduction in Yellowstone Hot Springs to Unique Sequence Types in the Dissimilatory Sulfate Respiration Pathway." Applied and Environmental Microbiology 69, no. 6 (June 2003): 3663–67. http://dx.doi.org/10.1128/aem.69.6.3663-3667.2003.

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ABSTRACT Diversity, habitat range, and activities of sulfate-reducing prokaryotes within hot springs in Yellowstone National Park were characterized using endogenous activity measurements, molecular characterization, and enrichment. Five major phylogenetic groups were identified using PCR amplification of the dissimilatory sulfite reductase genes (dsrAB) from springs demonstrating significant sulfate reduction rates, including a warm, acidic (pH 2.5) stream and several nearly neutral hot springs with temperatures reaching 89�C. Three of these sequence groups were unrelated to named lineages, suggesting that the diversity and habitat range of sulfate-reducing prokaryotes exceeds that now represented in culture.
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6

Kazachenko, Aleksandr S., Natalia Yu Vasilieva, Yaroslava D. Berezhnaya, Olga Yu Fetisova, Valentina S. Borovkova, Yuriy N. Malyar, Irina G. Sudakova, et al. "Sulfation of Birch Wood Microcrystalline Cellulose with Sulfamic Acid Using Ion-Exchange Resins as Catalysts." Polymers 15, no. 5 (February 23, 2023): 1116. http://dx.doi.org/10.3390/polym15051116.

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Cellulose sulfates are important biologically active substances with a wide range of useful properties. The development of new methods for the production of cellulose sulfates is an urgent task. In this work, we investigated ion-exchange resins as catalysts for the sulfation of cellulose with sulfamic acid. It has been shown that water-insoluble sulfated reaction products are formed in high yield in the presence of anion exchangers, while water-soluble products are formed in the presence of cation exchangers. The most effective catalyst is Amberlite IR 120. According to gel permeation chromatography, it was shown that the samples sulfated in the presence of the catalysts KU-2-8, Purolit s390 plus, and AN-31 SO42− underwent the greatest degradation. The molecular weight destribution profiles of these samples are noticeably shifted to the left towards low-molecular-weight compounds with an increase in fractions in the regions Mw ~2.100 g/mol and ~3.500 g/mol, indicating the growth of microcrystalline cellulose depolymerization products. The introduction of a sulfate group into the cellulose molecule is confirmed using FTIR spectroscopy by the appearance of absorption bands at 1245–1252 cm−1 and 800–809 cm−1, which correspond to the vibrations of the sulfate group. According to X-ray diffraction data, amorphization of the crystalline structure of cellulose is observed during sulfation. Thermal analysis has shown that with an increase in the content of sulfate groups in cellulose derivatives, thermal stability decreases.
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7

Kazachenko, Aleksandr Sergeyevich, Vladimir Aleksandrovich Levdansky, Aleksandr Vladimirovich Levdansky, and Boris Nikolayevich Kuznetsov. "MATHEMATICAL OPTIMIZATION OF THE PROCESS OF BIRCH WOOD XYLAN SULFATION BY SULFAMIC ACID IN N, N-DIMETHYLFORMAMIDE MEDIUM." chemistry of plant raw material, no. 2 (June 10, 2021): 87–94. http://dx.doi.org/10.14258/jcprm.2021027558.

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The effect of temperature and duration of sulfation of birch wood xylan by sulfamic acid in N, N-dimethylformamide (DMF) medium in the presence of urea on the yield of sulfated xylan and on the sulphur content was studied. By mathematical optimization, the sulfation conditions have been established allowing to achieve a high yield of the obtained xylan sulfates with a high sulphur content. Under optimal sulfation conditions: temperature 100±3 °C, duration 1.5 hours, the yield of sulfated xylan reaches to 63% mas. and the content of sulfur – 17.6% mas. The presence of sulfate groups in sulfated xylan samples obtained under optimal conditions was confirmed by elemental analysis and FTIR and 13C NMR spectroscopy.
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8

Kazachenko, Aleksandr S., Yuriy N. Malyar, and Anna S. Kazachenko. "Synthesis of Galactomannan Sulfate-Citrate." Materials Science Forum 1049 (January 11, 2022): 218–23. http://dx.doi.org/10.4028/www.scientific.net/msf.1049.218.

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Sulfated derivatives of polysaccharides have anticoagulant, hypolipedimic and other biological activity. In this work, a complex mixed ester of galactomannan, its sulfate-citrate, was obtained for the first time. The introduction of citrate and sulfate groups was proved by FTIR spectroscopy by the appearance of corresponding absorption bands. It was shown by X-ray diffraction that the introduction of the citrate group leads to the amorphization of the galactomannan structure.
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9

Kim, B. Moon, and K. Barry Sharpless. "Cyclic sulfates containing acid-sensitive groups and chemoselective hydrolysis of sulfate esters." Tetrahedron Letters 30, no. 6 (1989): 655–58. http://dx.doi.org/10.1016/s0040-4039(01)80274-4.

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10

Farzan, Michael, Christine E. Schnitzler, Natalya Vasilieva, Doris Leung, Jens Kuhn, Craig Gerard, Norma P. Gerard, and Hyeryun Choe. "Sulfated Tyrosines Contribute to the Formation of the C5a Docking Site of the Human C5a Anaphylatoxin Receptor." Journal of Experimental Medicine 193, no. 9 (May 7, 2001): 1059–66. http://dx.doi.org/10.1084/jem.193.9.1059.

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The complement anaphylatoxin C5a and its seven-transmembrane segment (7TMS) receptor play an important role in host defense and in a number of inflammation-associated pathologies. The NH2-terminal domain of the C5a receptor (C5aR/CD88) contributes substantially to its ability to bind C5a. Here we show that the tyrosines at positions 11 and 14 of the C5aR are posttranslationally modified by the addition of sulfate groups. The sulfate moieties of each of these tyrosines are critical to the ability of the C5aR to bind C5a and to mobilize calcium. A C5aR variant lacking these sulfate moieties efficiently mobilized calcium in response to a small peptide agonist, but not to C5a, consistent with a two-site model of ligand association in which the tyrosine-sulfated region of the C5aR mediates the initial docking interaction. A peptide based on the NH2 terminus of the C5aR and sulfated at these two tyrosines, but not its unsulfated analogue or a doubly sulfated control peptide, partially inhibited C5a association with its receptor. These observations clarify structural and mutagenic studies of the C5a/C5aR association and suggest that related 7TMS receptors are also modified by functionally important sulfate groups on their NH2-terminal tyrosines.
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11

Kowalewski, Björn, Heike Lange, Sabrina Galle, Thomas Dierks, Torben Lübke, and Markus Damme. "Decoding the consecutive lysosomal degradation of 3-O-sulfate containing heparan sulfate by Arylsulfatase G (ARSG)." Biochemical Journal 478, no. 17 (September 7, 2021): 3221–37. http://dx.doi.org/10.1042/bcj20210415.

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The lysosomal degradation of heparan sulfate is mediated by the concerted action of nine different enzymes. Within this degradation pathway, Arylsulfatase G (ARSG) is critical for removing 3-O-sulfate from glucosamine, and mutations in ARSG are causative for Usher syndrome type IV. We developed a specific ARSG enzyme assay using sulfated monosaccharide substrates, which reflect derivatives of its natural substrates. These sulfated compounds were incubated with ARSG, and resulting products were analyzed by reversed-phase HPLC after chemical addition of the fluorescent dyes 2-aminoacridone or 2-aminobenzoic acid, respectively. We applied the assay to further characterize ARSG regarding its hydrolytic specificity against 3-O-sulfated monosaccharides containing additional sulfate-groups and N-acetylation. The application of recombinant ARSG and cells overexpressing ARSG as well as isolated lysosomes from wild-type and Arsg knockout mice validated the utility of our assay. We further exploited the assay to determine the sequential action of the different sulfatases involved in the lysosomal catabolism of 3-O-sulfated glucosamine residues of heparan sulfate. Our results confirm and extend the characterization of the substrate specificity of ARSG and help to determine the sequential order of the lysosomal catabolic breakdown of (3-O-)sulfated heparan sulfate.
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12

Zhao, Tingting, Xiaoguang Lu, Neal M. Davies, Yuewen Gong, Jingzhen Guo, Haojun Zhang, Zhiguo Li, Jing Hong, Guixiang Fu, and Ping Li. "Diabetes Results in Structural Alteration of Chondroitin Sulfate in the Urine." Journal of Pharmacy & Pharmaceutical Sciences 16, no. 3 (July 30, 2013): 486. http://dx.doi.org/10.18433/j3gs3c.

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Purpose. The assessment of the clinical significance of chondroitin sulfate in patients with type 2 diabetes mellitus (T2DM) and diabetic nephropathy (DN) for the detection of the relationship between chondroitin sulfate (CS) structure and disease. Methods. Healthy control (n=15), type 2 diabetic patients with normalbuminuria (n=12), and patients with microalbuminuria (n=13) were enrolled in the study. Total sulfated glycosaminoglycans (GAGs) concentration in the first morning urine was evaluated by 1,9-dimethylmethylene blue method and the composition was determined by agarose gel electrophoresis. Urinary chondroitin sulfate was quantified by a combination of treatment with specific lyase digestions and separation of products by SAX-HPLC. Results: GAGs concentration significantly increased in diabetic patients with microalbuminuria compared to diabetic patients with normalbuminuria. Qualitative analysis of urinary GAGs revealed the presence of chondroitin sulfate, heparan sulfate, and low-sulphated chondroitin sulphate-protein complex (LSC-PG). There was a decrease in CS and an increase in LSC-PG in the urine of patients with diabetes compared to healthy controls. Moreover, in diabetic patients, chondroitin sulfate contains more 6-sulfated disaccharide and less 4-sulfated disaccharide. There was a statistically significant difference in ratio of 6-sulfated disaccharide to 4-sulfated disaccharide among the three groups. Conclusions: GAGs were significantly increased in diabetic patients with microalbuminuria. The levels of urinary GAGs, ratio of LSC-PG/CS, as well as ratio of 6-sulfated to 4-sulfated disaccharides could be useful markers for diagnosis of patients with diabetic nephropathy. This article is open to POST-PUBLICATION REVIEW. Registered readers (see “For Readers”) may comment by clicking on ABSTRACT on the issue’s contents page.
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13

Zhang, Cong, Ding An, Qiong Xiao, Fu-Quan Chen, Yong-Hui Zhang, Hui-Fen Weng, and An-Feng Xiao. "Convenient Agarose Preparation with Hydrogen Peroxide and Desulfation Process Analysis." Marine Drugs 19, no. 6 (May 23, 2021): 297. http://dx.doi.org/10.3390/md19060297.

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Agarose is a natural seaweed polysaccharide and widely used in the medicine, food, and biological fields because of its high gel strength, non-toxicity, and electrical neutrality. The sulfate group is one of the main charged groups that affect the performance of agarose. In the present study, a simple, eco-friendly, and efficient method was explored for agarose preparation. After desulfation with hydrogen peroxide (H2O2), the sulfate content of agar reached 0.21%. Together with gel strength, electroendosmosis, gelling and melting temperature, the indicators of desulfated agar met the standards of commercially available agarose. Notably, the desulfated agar can be used as an agarose gel electrophoresis medium to separate DNA molecules, and the separation effect is as good as that of commercially available agarose. Further, the H2O2 desulfation process was analyzed. The addition of a hydroxyl radical (HO•) scavenger remarkably decreased the H2O2 desulfation rate, indicating that HO• has a certain role in agar desulfation. Sulfate content detection indicated that sulfur was removed from agar molecules in the form of sulfate ions (SO42−) and metal sulfate. The band absence at 850 cm−1 indicated that the sulfate groups at C-4 of D-galactose in sulfated galactan were eliminated.
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14

Levdansky, Alexander V., Natalya Yu Vasilyeva, Yuriy N. Malyar, Alexander A. Kondrasenko, Olga Yu Fetisova, Aleksandr S. Kazachenko, Vladimir A. Levdansky, and Boris N. Kuznetsov. "An Efficient Method of Birch Ethanol Lignin Sulfation with a Sulfaic Acid-Urea Mixture." Molecules 27, no. 19 (September 26, 2022): 6356. http://dx.doi.org/10.3390/molecules27196356.

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For the first time, the process of birch ethanol lignin sulfation with a sulfamic acid-urea mixture in a 1,4-dioxane medium was optimized experimentally and numerically. The high yield of the sulfated ethanol lignin (more than 96%) and containing 7.1 and 7.9 wt % of sulfur was produced at process temperatures of 80 and 90 °C for 3 h. The sample with the highest sulfur content (8.1 wt %) was obtained at a temperature of 100 °C for 2 h. The structure and molecular weight distribution of the sulfated birch ethanol lignin was established by FTIR, 2D 1H and 13C NMR spectroscopy, and gel permeation chromatography. The introduction of sulfate groups into the lignin structure was confirmed by FTIR by the appearance of absorption bands characteristic of the vibrations of sulfate group bonds. According to 2D NMR spectroscopy data, both the alcohol and phenolic hydroxyl groups of the ethanol lignin were subjected to sulfation. The sulfated birch ethanol lignin with a weight average molecular weight of 7.6 kDa and a polydispersity index of 1.81 was obtained under the optimum process conditions. Differences in the structure of the phenylpropane units of birch ethanol lignin (syringyl-type predominates) and abies ethanol lignin (guaiacyl-type predominates) was manifested in the fact that the sulfation of the former proceeds more completely at moderate temperatures than the latter. In contrast to sulfated abies ethanol lignin, the sulfated birch ethanol lignin had a bimodal and wider molecular weight distribution, as well as less thermal stability. The introduction of sulfate groups into ethanol lignin reduced its thermal stability.
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Bar-Ner, M., A. Eldor, L. Wasserman, Y. Matzner, IR Cohen, Z. Fuks, and I. Vlodavsky. "Inhibition of heparanase-mediated degradation of extracellular matrix heparan sulfate by non-anticoagulant heparin species." Blood 70, no. 2 (August 1, 1987): 551–57. http://dx.doi.org/10.1182/blood.v70.2.551.551.

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Abstract Incubation of human platelets, human neutrophils, or highly metastatic mouse lymphoma cells with sulfate-labeled extracellular matrix (ECM) results in heparanase-mediated release of labeled heparan sulfate cleavage fragments (0.5 less than Kav less than 0.85 on Sepharose 6B). This degradation was inhibited by native heparin both when brought about by intact cells or their released heparanase activity. Degradation of heparan sulfate in ECM may facilitate invasion of normal and malignant cells through basement membranes. The present study tested the heparanase inhibitory effect of nonanticoagulant species of heparin that might be of potential use in preventing heparanase mediated extravasation of bloodborne cells. For this purpose, we prepared various species of low-sulfated or low-mol-wt heparins, all of which exhibited less than 7% of the anticoagulant activity of native heparin. N-sulfate groups of heparin are necessary for its heparanase inhibitory activity but can be substituted by an acetyl group provided that the O-sulfate groups are retained. O-sulfate groups could be removed provided that the N positions were resulfated. Total desulfation of heparin abolished its heparanase inhibitory activity. Heparan sulfate was a 25-fold less potent heparanase inhibitor than native heparin. Efficiency of low-mol-wt heparins to inhibit degradation of heparan sulfate in ECM decreased with their main molecular size, and a synthetic pentasaccharide, representing the binding site to antithrombin III, was devoid of inhibitory activity. Similar results were obtained with heparanase activities released from platelets, neutrophils, and lymphoma cells. We propose that heparanase inhibiting nonanticoagulant heparins may interfere with dissemination of bloodborne tumor cells and development of experimental autoimmune diseases.
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Bar-Ner, M., A. Eldor, L. Wasserman, Y. Matzner, IR Cohen, Z. Fuks, and I. Vlodavsky. "Inhibition of heparanase-mediated degradation of extracellular matrix heparan sulfate by non-anticoagulant heparin species." Blood 70, no. 2 (August 1, 1987): 551–57. http://dx.doi.org/10.1182/blood.v70.2.551.bloodjournal702551.

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Incubation of human platelets, human neutrophils, or highly metastatic mouse lymphoma cells with sulfate-labeled extracellular matrix (ECM) results in heparanase-mediated release of labeled heparan sulfate cleavage fragments (0.5 less than Kav less than 0.85 on Sepharose 6B). This degradation was inhibited by native heparin both when brought about by intact cells or their released heparanase activity. Degradation of heparan sulfate in ECM may facilitate invasion of normal and malignant cells through basement membranes. The present study tested the heparanase inhibitory effect of nonanticoagulant species of heparin that might be of potential use in preventing heparanase mediated extravasation of bloodborne cells. For this purpose, we prepared various species of low-sulfated or low-mol-wt heparins, all of which exhibited less than 7% of the anticoagulant activity of native heparin. N-sulfate groups of heparin are necessary for its heparanase inhibitory activity but can be substituted by an acetyl group provided that the O-sulfate groups are retained. O-sulfate groups could be removed provided that the N positions were resulfated. Total desulfation of heparin abolished its heparanase inhibitory activity. Heparan sulfate was a 25-fold less potent heparanase inhibitor than native heparin. Efficiency of low-mol-wt heparins to inhibit degradation of heparan sulfate in ECM decreased with their main molecular size, and a synthetic pentasaccharide, representing the binding site to antithrombin III, was devoid of inhibitory activity. Similar results were obtained with heparanase activities released from platelets, neutrophils, and lymphoma cells. We propose that heparanase inhibiting nonanticoagulant heparins may interfere with dissemination of bloodborne tumor cells and development of experimental autoimmune diseases.
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17

Barron, Denis, and Ragai K. Ibrahim. "Synthesis of Flavonoid Sulfates. III. Synthesis of 3′,4′-ortho Disulfates Using Sulfur Trioxide-trimethylamine Complex, and of 3′-SuIfates Using Aryl Sulfatase." Zeitschrift für Naturforschung C 43, no. 9-10 (October 1, 1988): 631–35. http://dx.doi.org/10.1515/znc-1988-9-1002.

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Abstract A number of flavonoid 3′,4′-disulfates were synthesized from the corresponding 4′-sulfate esters, using sulfur trioxide-trimethylamine complex. Desulfation of the sulfate esters using aryl sulfatase demonstrated that the rate of hydrolysis of the 3′-sulfate group was slower than either the 7- or 4′ groups, thus allowing the specific synthesis of flavonol 3,3′-disulfates. The effects of ortho-disulfation on the 13C NMR spectra of flavonoids, and the regative FAB-MS spectra of diand trisulfated flavonoids are discussed.
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18

Tangelder, GJ, and KE Arfors. "Inhibition of leukocyte rolling in venules by protamine and sulfated polysaccharides." Blood 77, no. 7 (April 1, 1991): 1565–71. http://dx.doi.org/10.1182/blood.v77.7.1565.1565.

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Abstract Intravital video microscopy was used to investigate leukocyte margination in 80 mesenteric venules (19 to 54 microns) of 50 anesthetized rabbits. After intravenous (IV) bolus injection, sulfated polysaccharides reduced in a reversible and dose-dependent way the number of leukocytes rolling slowly along the venular wall. The presence of sulfate groups is essential because other negatively charged or neutral polysaccharides had no effect. It was not caused by an increase in RBC velocity or chelation of divalent cations. Inhibition by sulfated dextrans (n = 7) was independent of molecular weight (mol wt 13,000 to 500,000) but was influenced by the average number of sulfate groups per monosaccharide. With substitution 0.13, the 90%-inhibition dose was 104 mg/kg, with 0.7 it was 56 mg/kg, and between substitution 1 and 2 it ranged from 20 to 23 mg/kg. At 100 mg/kg, plasma concentration was 0.6 to 0.7 mg/mL. Xylan sulfate (mol wt 6,000, substitution 1.8) gave 90% inhibition at 11 mg/kg, and heparin gave 90% inhibition at 97 mg/kg. Duration of inhibition (0.5 to 2 hours) depended on mol wt and appeared to be related to plasma clearance. Because protamine also inhibited rolling (12 mg/kg; less than 10 minutes), we propose that repetitive formation and breakup of ionic bonds between sulfate groups and positively charged amino acids is involved in leukocyte rolling. During inhibition of rolling, systemic lymphocyte/monocyte levels appeared to increase. Granulocyte counts did not change, indicating that rolling is not the main mechanism responsible for the marginal granulocyte pool.
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Tangelder, GJ, and KE Arfors. "Inhibition of leukocyte rolling in venules by protamine and sulfated polysaccharides." Blood 77, no. 7 (April 1, 1991): 1565–71. http://dx.doi.org/10.1182/blood.v77.7.1565.bloodjournal7771565.

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Intravital video microscopy was used to investigate leukocyte margination in 80 mesenteric venules (19 to 54 microns) of 50 anesthetized rabbits. After intravenous (IV) bolus injection, sulfated polysaccharides reduced in a reversible and dose-dependent way the number of leukocytes rolling slowly along the venular wall. The presence of sulfate groups is essential because other negatively charged or neutral polysaccharides had no effect. It was not caused by an increase in RBC velocity or chelation of divalent cations. Inhibition by sulfated dextrans (n = 7) was independent of molecular weight (mol wt 13,000 to 500,000) but was influenced by the average number of sulfate groups per monosaccharide. With substitution 0.13, the 90%-inhibition dose was 104 mg/kg, with 0.7 it was 56 mg/kg, and between substitution 1 and 2 it ranged from 20 to 23 mg/kg. At 100 mg/kg, plasma concentration was 0.6 to 0.7 mg/mL. Xylan sulfate (mol wt 6,000, substitution 1.8) gave 90% inhibition at 11 mg/kg, and heparin gave 90% inhibition at 97 mg/kg. Duration of inhibition (0.5 to 2 hours) depended on mol wt and appeared to be related to plasma clearance. Because protamine also inhibited rolling (12 mg/kg; less than 10 minutes), we propose that repetitive formation and breakup of ionic bonds between sulfate groups and positively charged amino acids is involved in leukocyte rolling. During inhibition of rolling, systemic lymphocyte/monocyte levels appeared to increase. Granulocyte counts did not change, indicating that rolling is not the main mechanism responsible for the marginal granulocyte pool.
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Silchenko, Kalinovsky, Avilov, Kalinin, Andrijaschenko, Dmitrenok, Popov, and Chingizova. "Structures and Bioactivities of Psolusosides B1, B2, J, K, L, M, N, O, P, and Q from the Sea Cucumber Psolus fabricii. The First Finding of Tetrasulfated Marine Low Molecular Weight Metabolites." Marine Drugs 17, no. 11 (November 6, 2019): 631. http://dx.doi.org/10.3390/md17110631.

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Ten new di-, tri- and tetrasulfated triterpene glycosides, psolusosides B1 (1), B2 (2), J (3), K (4), L (5), M (6), N (7), O (8), P (9), and Q (10), were isolated from the sea cucumber Psolus fabricii collected in the Sea of Okhotsk near the Kurile Islands. Structures of these glycosides were established by two-dimensional (2D) NMR spectroscopy and HR-ESI mass-spectrometry. It is particularly interesting that highly polar compounds 9 and 10 contain four sulfate groups in their carbohydrate moieties, including two sulfates in the same terminal glucose residue. Glycoside 2 has an unusual non-holostane aglycone with 18(16)-lactone and a unique 7,8-epoxy fragment. Cytotoxic activities of compounds 1–10 against several mouse cell lines such as Ehrlich ascites carcinoma cells, neuroblastoma Neuro 2A, normal epithelial JB-6 cells, and erythrocytes were quite different depending both on structural peculiarities of these glycosides and the type of cells subjected to their actions. Psolusoside L (5), pentaoside, with three sulfate groups at C-6 of two glucose and one 3-O-methylglucose residue and holostane aglycone, is the most active compound in the series. The presence of a sulfate group at C-2 of the terminal glucose residue attached to C-4 of the first (xylose) residue significantly decreases activities of the corresponding glycosides. Psolusosides of group B (1, 2, and known psolusoside B) are inactive in all tests due to the presence of non-holostane aglycones and tetrasaccharide-branched sugar chains sulfated by C-2 of Glc4.
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Silchenko, Alexandra S., Sergey A. Avilov, Roman S. Popov, Pavel S. Dmitrenok, Ekaterina A. Chingizova, Boris B. Grebnev, Anton B. Rasin, and Vladimir I. Kalinin. "Chilensosides E, F, and G—New Tetrasulfated Triterpene Glycosides from the Sea Cucumber Paracaudina chilensis (Caudinidae, Molpadida): Structures, Activity, and Biogenesis." Marine Drugs 21, no. 2 (February 5, 2023): 114. http://dx.doi.org/10.3390/md21020114.

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Three new tetrasulfated triterpene glycosides, chilensosides E (1), F (2), and G (3), have been isolated from the Far-Eastern sea cucumber Paracaudina chilensis (Caudinidae, Molpadida). The structures were established based on extensive analysis of 1D and 2D NMR spectra and confirmed by HR-ESI-MS data. The compounds differ in their carbohydrate chains, namely in the number of monosaccharide residues (five or six) and in the positions of sulfate groups. Chilensosides E (1) and F (2) are tetrasulfated pentaosides with the position of one of the sulfate groups at C-3 Glc3, and chilensoside G (3) is a tetrasulfated hexaoside. The biogenetic analysis of the glycosides of P. chilensis has revealed that the structures form a network due to the attachment of sulfate groups to almost all possible positions. The upper semi-chain is sulfated earlier in the biosynthetic process than the lower one. Noticeably, the presence of a sulfate group at C-3 Glc3—a terminal monosaccharide residue in the bottom semi-chain of compounds 1 and 2—excludes the possibility of this sugar chain’s further elongation. Presumably, the processes of glycosylation and sulfation are concurrent biosynthetic stages. They can be shifted in time in relation to each other, which is a characteristic feature of the mosaic type of biosynthesis. The hemolytic action of compounds 1–3 against human erythrocytes and cytotoxic activities against five human cancer cell lines were tested. The compounds showed moderate hemolytic activity but were inactive against cancer cells, probably because of their structural peculiarities, such as the combination of positions of four sulfate groups.
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Voronova, M. I., O. V. Surov, and A. G. Zakharov. "Nanocrystalline cellulose with various contents of sulfate groups." Carbohydrate Polymers 98, no. 1 (October 2013): 465–69. http://dx.doi.org/10.1016/j.carbpol.2013.06.004.

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23

Ding, Kan, Staffan Sandgren, Katrin Mani, Mattias Belting, and Lars-Åke Fransson. "Modulations of Glypican-1 Heparan Sulfate Structure by Inhibition of Endogenous Polyamine Synthesis." Journal of Biological Chemistry 276, no. 50 (September 27, 2001): 46779–91. http://dx.doi.org/10.1074/jbc.m105419200.

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Cell surface heparan sulfate proteoglycans facilitate uptake of growth-promoting polyamines (Belting, M., Persson, S., and Fransson, L.-Å. (1999)Biochem. J.338, 317–323; Belting, M., Borsig, L., Fuster, M. M., Brown, J. R., Persson, L., Fransson, L.-Å., and Esko, J. D. (2001)Proc. Natl. Acad. Sci. U. S. A., in press). Here, we have analyzed the effect of polyamine deprivation on the structure and polyamine affinity of the heparan sulfate chains in various glypican-1 glycoforms synthesized by a transformed cell line (ECV 304). Heparan sulfate chains of glypican-1 were either cleaved with heparanase at sites embracing the highly modified regions or with nitrite atN-unsubstituted glucosamine residues. The products were separated and further degraded by heparin lyase to identify sulfated iduronic acid. Polyamine affinity was assessed by chromatography on agarose substituted with the polyamine spermine. In heparan sulfate made by cells with undisturbed endogenous polyamine synthesis, free amino groups were restricted to the unmodified, unsulfated segments, especially near the core protein. Spermine high affinity binding sites were located to the modified and highly sulfated segments that were released by heparanase. In cells with up-regulated polyamine uptake, heparan sulfate contained an increased number of clusteredN-unsubstituted glucosamines and sulfated iduronic acid residues. This resulted in a greater number of NO/nitrite-sensitive cleavage sites near the potential spermine-binding sites. Endogenous degradation by heparanase and NO-derived nitrite in polyamine-deprived cells generated a separate pool of heparan sulfate oligosaccharides with an exceptionally high affinity for spermine. Spermine uptake in polyamine-deprived cells was reduced when NO/nitrite-generated degradation of heparan sulfate was inhibited. The results suggest a functional interplay between glypican recycling, NO/nitrite-generated heparan sulfate degradation, and polyamine uptake.
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Zsiška, Marianne, and Bernd Meyer. "Influence of sulfate and carboxylate groups on the conformation of chondroitin sulfate related disaccharides." Carbohydrate Research 243, no. 2 (May 1993): 225–58. http://dx.doi.org/10.1016/0008-6215(93)87031-m.

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Левданский (Levdanskii), Владимир (Vladimir) Александрович (Aleksandrovich), Александр (Aleksandr) Александрович (Aleksandrovich) Кондрасенко (Kondrasenko), Александр (Aleksandr) Владимирович (Vladimirovich) Левданский (Levdanskii), and Борис (Boris) Николаевич (Nikolaevich) Кузнецов (Kuznetsov). "SYLFATION OF XYLAN WITH SULFAMIC ACID IN N,N-DIMETHYLFORMAMIDE." chemistry of plant raw material, no. 1 (December 6, 2017): 29–36. http://dx.doi.org/10.14258/jcprm.2018012268.

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Sulfation of birch wood xylan by sulfamic acid in N,N-dimethylformamide (DMF) in the presence of urea was studied for the first time. The effect of the duration of sulfation of xylan with a mixture of sulfamic acid–urea in DMF on the yield and substitution degree of xylan sulfates was studied. The sulfur content in the obtained samples was determined using chemical method. It was found, that the degree of substitution in the obtained xylan sulfates was in the range from 1.30 to 1.64 at sulfation for 1–2 hours. The structure of initial and sulfated xylan was investigated with the use of FTIR and 13C NMR spectroscopy methods. The introduction of sulfate groups into the structure of xylan was confirmed by appearance in FTIR spectra new absorption bands characteristic for the stretching vibrations n (C–O–S) at 804 cm-1, symmetric stretching vibrations ns (SO2) at 1009 cm-1, asymmetric stretching vibrations nas (SO2) at 1244 and 1260 cm-1.Studying of 13C NMR spectrum of the obtained xylan sulfates showed that there was partial substitution of hydroxyl groups at С2 and С3 positions of anhydroxylose units of xylan.
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Minh Ly, Bui, Ngo Quoc Buu, Nguyen Duy Nhut, Pham Duc Thinh, and Tran Thi Thanh Van. "STUDIES ON FUCOIDAN AND ITS PRODUCTION FROM VIETNAMESE BROWN SEAWEEDS." ASEAN Journal on Science and Technology for Development 22, no. 4 (November 11, 2017): 371. http://dx.doi.org/10.29037/ajstd.173.

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Sulfated fucans are among the most widely studied of all the sulfated polysaccharides of plant origin that exhibit biological activities in mammalian systems. In this report fucoidans from some Vietnamese Sargassumspecies such as S.polycystum, S.oligocystum, S.mcclurei, S. Swartzii and denticaprum were extracted and fractionated on a DEAE-Sephadex A-25 column. On the basis of chemical and spectral analyses, the fucoidan fractions obtained were found to be the sulfated fucogalactans containing sulfate ester groups and uronic acid, and composed essentially of fucose and galactose, as well as a minor amount of other sugars. The polysaccharide fractions were tested for anticancer activity. The primarily obtained results showed that all fucoidan fractions isolated from S. swartziidemonstrate bioactivity effects against cancer cells, while fraction F5 with a highest sulfate content exhibits the strongest anti-invasion activity. This indicates that sulfate content plays an important role in the anticancer activity of the brown algal fucoidans. A laboratory scale pilot for fuco idan production from Vietnamese brown seaweeds has been set with a capacity of 500 g of crude fucoidan per day.
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Qi, Yihui, Lilong Wang, Ying You, Xiaona Sun, Chengrong Wen, Yinghuan Fu, and Shuang Song. "Preparation of Low-Molecular-Weight Fucoidan with Anticoagulant Activity by Photocatalytic Degradation Method." Foods 11, no. 6 (March 13, 2022): 822. http://dx.doi.org/10.3390/foods11060822.

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It is a challenge to degrade sulfated polysaccharides without stripping sulfate groups. In the present study, a photocatalytic method was applied to degrade fucoidan, a sulfated polysaccharide from brown algae. The degradation with varying addition amounts of H2O2 and TiO2 were monitored by high performance gel permeation chromatography (HPGPC) and thin layer chromatography (TLC), and fucoidan was efficiently degraded with 5% TiO2 and 0.95% H2O2. A comparison of the chemical compositions of 2 products obtained after 0.5 h and 3 h illumination, DF-0.5 (average Mw 90 kDa) and DF-3 (average Mw 3 kDa), respectively, with those of fucoidan indicates the photocatalytic degradation did not strip the sulfate groups, but reduced the galactose/fucose ratio. Moreover, 12 oligosaccharides in DF-3 were identified by HPLC-ESI-MSn and 10 of them were sulfated. In addition, DF-0.5 showed anticoagulant activity as strong as fucoidan while DF-3 could specifically prolong the activated partial thromboplastin time. All samples exerted inhibition effects on the intrinsic pathway FXII in a dose-dependent manner. Thus, photocatalytic degradation demonstrated the potential to prepare sulfated low-molecular-weight fucoidan with anticoagulant activity.
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Holmborn, Katarina, Johan Ledin, Emanuel Smeds, Inger Eriksson, Marion Kusche-Gullberg, and Lena Kjellén. "Heparan Sulfate Synthesized by Mouse Embryonic Stem Cells Deficient in NDST1 and NDST2 Is 6-O-Sulfated but Contains NoN-Sulfate Groups." Journal of Biological Chemistry 279, no. 41 (August 19, 2004): 42355–58. http://dx.doi.org/10.1074/jbc.c400373200.

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Сherednichenko, D. V., P. D. Vorobiev, V. V. Shevchuk, A. D. Vorobiev, T. N. Potkina, and E. V. Layevskaya. "Influence of polymer and inorganic modifiers on the process of phase formation in potassium sulfate saturated solutions." Proceedings of the National Academy of Sciences of Belarus, Chemical Series 59, no. 1 (March 5, 2023): 18–25. http://dx.doi.org/10.29235/1561-8331-2023-59-1-18-25.

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The process of potassium sulfate crystallization from aqueous solutions in the presence of organic modifiers containing phosphonic, phosphate, sulfonic, sulfate and carboxyl functional groups has been studied. It is shown that the introduction of organic substances has an inhibitory effect on the formation of potassium sulfate crystals. Modifiers containing sulfonic, sulfate and phosphonic functional groups have the greatest inhibitory effect. The effectiveness of modifiers containing carboxyl groups is significantly lower. The formation of stable supersaturated solutions of potassium sulfate is achieved by introducing organic modifiers in an amount of 0.25 – 0.50%.
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Burkov, V. I., Yu V. Denisov, and Z. B. Perekalina. "Circular dichroism of uniaxial sulfate crystals in the range of electronic transitions of sulfate groups." Crystallography Reports 47, no. 2 (March 2002): 313–17. http://dx.doi.org/10.1134/1.1466509.

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31

Zhang, Kai, Dieter Peschel, Thomas Klinger, Kathrin Gebauer, Thomas Groth, and Steffen Fischer. "Synthesis of carboxyl cellulose sulfate with various contents of regioselectively introduced sulfate and carboxyl groups." Carbohydrate Polymers 82, no. 1 (August 2010): 92–99. http://dx.doi.org/10.1016/j.carbpol.2010.04.027.

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Stoeckli-Evans, Helen, Olha Sereda, Antonia Neels, Sebastien Oguey, Catherine Ionescu, and Yvan Jacquier. "In situsingle-crystal to single-crystal (SCSC) transformation of the one-dimensional polymercatena-poly[[diaqua(sulfato)copper(II)]-μ2-glycine] into the two-dimensional polymer poly[μ2-glycine-μ4-sulfato-copper(II)]." Acta Crystallographica Section C Structural Chemistry 70, no. 11 (October 15, 2014): 1057–63. http://dx.doi.org/10.1107/s2053229614021123.

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The one-dimensional coordination polymercatena-poly[diaqua(sulfato-κO)copper(II)]-μ2-glycine-κ2O:O′], [Cu(SO4)(C2H5NO2)(H2O)2]n, (I), was synthesized by slow evaporation under vacuum of a saturated aqueous equimolar mixture of copper(II) sulfate and glycine. On heating the same blue crystal of this complex to 435 K in an oven, its aspect changed to a very pale blue and crystal structure analysis indicated that it had transformed into the two-dimensional coordination polymer poly[(μ2-glycine-κ2O:O′)(μ4-sulfato-κ4O:O′:O′′:O′′)copper(II)], [Cu(SO4)(C2H5NO2)]n, (II). In (I), the CuIIcation has a pentacoordinate square-pyramidal coordination environment. It is coordinated by two water molecules and two O atoms of bridging glycine carboxylate groups in the basal plane, and by a sulfate O atom in the apical position. In complex (II), the CuIIcation has an octahedral coordination environment. It is coordinated by four sulfate O atoms, one of which bridges two CuIIcations, and two O atoms of bridging glycine carboxylate groups. In the crystal structure of (I), the one-dimensional polymers, extending along [001], are linkedviaN—H...O, O—H...O and bifurcated N—H...O,O hydrogen bonds, forming a three-dimensional framework. In the crystal structure of (II), the two-dimensional networks are linkedviabifurcated N—H...O,O hydrogen bonds involving the sulfate O atoms, forming a three-dimensional framework. In the crystal structures of both compounds, there are C—H...O hydrogen bonds present, which reinforce the three-dimensional frameworks.
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Kensinger, Richard D., Bradley J. Catalone, Fred C. Krebs, Brian Wigdahl, and Cara-Lynne Schengrund. "Novel Polysulfated Galactose-Derivatized Dendrimers as Binding Antagonists of Human Immunodeficiency Virus Type 1 Infection." Antimicrobial Agents and Chemotherapy 48, no. 5 (May 2004): 1614–23. http://dx.doi.org/10.1128/aac.48.5.1614-1623.2004.

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ABSTRACT Evidence indicates that galactosyl ceramide (GalCer) and its 3′-sulfated derivative, sulfatide (SGalCer), may act as alternate coreceptors for human immunodeficiency virus type 1 (HIV-1) in CD4− cells. Glycosphingolipids (GSLs) may also be necessary for fusion of HIV-1 and host cell membranes. Using an enzyme-linked immunosorbent assay to determine which GSL was the best ligand for both recombinant and virus-associated gp120, we found that SGalCer was the best ligand for each rgp120 and HIV-1 isolate tested. Therefore, novel multivalent glycodendrimers, which mimic the carbohydrate clustering reportedly found in lipid rafts, were synthesized based on the carbohydrate moiety of SGalCer. Here we describe the synthesis of a polysulfated galactose functionalized, fifth generation DAB dendrimer (PS Gal 64mer), containing on average two sulfate groups per galactose residue. Its ability to inhibit HIV-1 infection of cultured indicator cells was compared to that of dextran sulfate (DxS), a known, potent, binding inhibitor of HIV-1. The results indicate that the PS Gal 64mer inhibited infection by the HIV-1 isolates tested as well as DxS.
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Karr, Elizabeth A., W. Matthew Sattley, Melissa R. Rice, Deborah O. Jung, Michael T. Madigan, and Laurie A. Achenbach. "Diversity and Distribution of Sulfate-Reducing Bacteria in Permanently Frozen Lake Fryxell, McMurdo Dry Valleys, Antarctica." Applied and Environmental Microbiology 71, no. 10 (October 2005): 6353–59. http://dx.doi.org/10.1128/aem.71.10.6353-6359.2005.

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ABSTRACT The permanently frozen freshwater Lake Fryxell, located in the Dry Valleys of Antarctica, exhibits an ideal geochemistry for microbial sulfate reduction. To investigate the population of sulfate-reducing bacteria in Lake Fryxell, both 16S rRNA gene and metabolic primer sets targeting the dsrA gene for the dissimilatory sulfite reductase alpha subunit were employed to analyze environmental DNA obtained from the water column and sediments of Lake Fryxell. In addition, enrichment cultures of sulfate-reducing bacteria established at 4°C from Lake Fryxell water were also screened using the dsrA primer set. The sequence information obtained showed that a diverse group of sulfate-reducing prokaryotes of the domain Bacteria inhabit Lake Fryxell. With one exception, the enrichment culture sequences were not represented within the environmental sequences. Sequence data were compared with the geochemical profile of Lake Fryxell to identify possible connections between the diversity of sulfate-reducing bacteria and limnological conditions. Several clone groups were highly localized with respect to lake depth and, therefore, experienced specific physiochemical conditions. However, all sulfate-reducing bacteria inhabiting Lake Fryxell must function under the constantly cold conditions characteristic of this extreme environment.
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Hayes, Anthony J., and James Melrose. "HS, an Ancient Molecular Recognition and Information Storage Glycosaminoglycan, Equips HS-Proteoglycans with Diverse Matrix and Cell-Interactive Properties Operative in Tissue Development and Tissue Function in Health and Disease." International Journal of Molecular Sciences 24, no. 2 (January 6, 2023): 1148. http://dx.doi.org/10.3390/ijms24021148.

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Heparan sulfate is a ubiquitous, variably sulfated interactive glycosaminoglycan that consists of repeating disaccharides of glucuronic acid and glucosamine that are subject to a number of modifications (acetylation, de-acetylation, epimerization, sulfation). Variable heparan sulfate chain lengths and sequences within the heparan sulfate chains provide structural diversity generating interactive oligosaccharide binding motifs with a diverse range of extracellular ligands and cellular receptors providing instructional cues over cellular behaviour and tissue homeostasis through the regulation of essential physiological processes in development, health, and disease. heparan sulfate and heparan sulfate-PGs are integral components of the specialized glycocalyx surrounding cells. Heparan sulfate is the most heterogeneous glycosaminoglycan, in terms of its sequence and biosynthetic modifications making it a difficult molecule to fully characterize, multiple ligands also make an elucidation of heparan sulfate functional properties complicated. Spatio-temporal presentation of heparan sulfate sulfate groups is an important functional determinant in tissue development and in cellular control of wound healing and extracellular remodelling in pathological tissues. The regulatory properties of heparan sulfate are mediated via interactions with chemokines, chemokine receptors, growth factors and morphogens in cell proliferation, differentiation, development, tissue remodelling, wound healing, immune regulation, inflammation, and tumour development. A greater understanding of these HS interactive processes will improve therapeutic procedures and prognoses. Advances in glycosaminoglycan synthesis and sequencing, computational analytical carbohydrate algorithms and advanced software for the evaluation of molecular docking of heparan sulfate with its molecular partners are now available. These advanced analytic techniques and artificial intelligence offer predictive capability in the elucidation of heparan sulfate conformational effects on heparan sulfate-ligand interactions significantly aiding heparan sulfate therapeutics development.
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Hempel, Ute, Carolin Preissler, Sarah Vogel, Stephanie Möller, Vera Hintze, Jana Becher, Matthias Schnabelrauch, Martina Rauner, Lorenz C. Hofbauer, and Peter Dieter. "Artificial Extracellular Matrices with Oversulfated Glycosaminoglycan Derivatives Promote the Differentiation of Osteoblast-Precursor Cells and Premature Osteoblasts." BioMed Research International 2014 (2014): 1–10. http://dx.doi.org/10.1155/2014/938368.

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Sulfated glycosaminoglycans (GAG) are components of the bone marrow stem cell niche and to a minor extent of mature bone tissue with important functions in regulating stem cell lineage commitment and differentiation. We anticipated that artificial extracellular matrices (aECM) composed of collagen I and synthetically oversulfated GAG derivatives affect preferentially the differentiation of osteoblast-precursor cells andearlyosteoblasts. A set of gradually sulfated chondroitin sulfate and hyaluronan derivatives was used for the preparation of aECM. All these matrices were analysed with human bone marrow stromal cells to identify the most potent aECM and to determine the influence of the degree and position of sulfate groups and the kind of disaccharide units on the osteogenic differentiation. Oversulfated GAG derivatives with a sulfate group at the C-6 position of the N-acetylglycosamine revealed the most pronounced proosteogenic effect as determined by tissue nonspecific alkaline phosphatase activity and calcium deposition. A subset of the aECM was further analysed with different primary osteoblasts and cell lines reflecting different maturation stages to test whether the effect of sulfated GAG derivatives depends on the maturation status of the cells. It was shown that the proosteogenic effect of aECM was most prominent inearlyosteoblasts.
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Salek-Ardakani, Shahram, John R. Arrand, David Shaw, and Mike Mackett. "Heparin and heparan sulfate bind interleukin-10 and modulate its activity." Blood 96, no. 5 (September 1, 2000): 1879–88. http://dx.doi.org/10.1182/blood.v96.5.1879.

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Abstract Glycosaminoglycans (GAG) are a group of negatively charged molecules that have been shown to bind and directly regulate the bioactivity of growth factors and cytokines such as basic fibroblast growth factor, transforming growth factor-β, IL-7, and interferon-γ. The ability of GAG to interact with human IL-10 (hIL-10) and the effect of these interactions on its biologic activity were analyzed. It was demonstrated by affinity chromatography that hIL-10 binds strongly to heparin–agarose at physiological pH. Biosensor-based binding kinetic analysis indicated an equilibrium dissociation constant, Kd, of 54 nmol/L for this interaction. Human IL-10 stimulated CD16 and CD64 expression on the monocyte/macrophage population within peripheral blood mononuclear cells, with optimal concentrations between 1 and 10 ng/mL. Soluble heparin, heparan sulfate, chondroitin sulfate, and dermatan sulfate were shown to inhibit the hIL-10–induced expression of CD16 and CD64 in a concentration-dependent manner. Heparin and heparan sulfate were most effective with IC50 values of 100 to 500 μg/mL. Considerably higher concentrations of dermatan sulfate and chondroitin 4-sulfate were required with an IC50 of 2000 to 5000 μg/mL, whereas chondroitin 6-sulfate was essentially inactive. The antagonistic effect of heparin on hIL-10 activity was shown to be dependent on N-sulfation, inasmuch as de-N-sulfated heparin had little or no inhibitory effect on the IL-10– induced expression of CD16, whereas the effect of de-O-sulfated heparin was comparable to that of unmodified heparin. Furthermore, the inhibition of cell-bound proteoglycan sulfation reduced the hIL-10–mediated expression of CD16 molecules on monocytes/macrophages. Taken together, these findings support the hypothesis that soluble and cell-surface GAG and, in particular, their sulfate groups are important in binding and modulation of hIL-10 activity.
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38

Salek-Ardakani, Shahram, John R. Arrand, David Shaw, and Mike Mackett. "Heparin and heparan sulfate bind interleukin-10 and modulate its activity." Blood 96, no. 5 (September 1, 2000): 1879–88. http://dx.doi.org/10.1182/blood.v96.5.1879.h8001879_1879_1888.

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Glycosaminoglycans (GAG) are a group of negatively charged molecules that have been shown to bind and directly regulate the bioactivity of growth factors and cytokines such as basic fibroblast growth factor, transforming growth factor-β, IL-7, and interferon-γ. The ability of GAG to interact with human IL-10 (hIL-10) and the effect of these interactions on its biologic activity were analyzed. It was demonstrated by affinity chromatography that hIL-10 binds strongly to heparin–agarose at physiological pH. Biosensor-based binding kinetic analysis indicated an equilibrium dissociation constant, Kd, of 54 nmol/L for this interaction. Human IL-10 stimulated CD16 and CD64 expression on the monocyte/macrophage population within peripheral blood mononuclear cells, with optimal concentrations between 1 and 10 ng/mL. Soluble heparin, heparan sulfate, chondroitin sulfate, and dermatan sulfate were shown to inhibit the hIL-10–induced expression of CD16 and CD64 in a concentration-dependent manner. Heparin and heparan sulfate were most effective with IC50 values of 100 to 500 μg/mL. Considerably higher concentrations of dermatan sulfate and chondroitin 4-sulfate were required with an IC50 of 2000 to 5000 μg/mL, whereas chondroitin 6-sulfate was essentially inactive. The antagonistic effect of heparin on hIL-10 activity was shown to be dependent on N-sulfation, inasmuch as de-N-sulfated heparin had little or no inhibitory effect on the IL-10– induced expression of CD16, whereas the effect of de-O-sulfated heparin was comparable to that of unmodified heparin. Furthermore, the inhibition of cell-bound proteoglycan sulfation reduced the hIL-10–mediated expression of CD16 molecules on monocytes/macrophages. Taken together, these findings support the hypothesis that soluble and cell-surface GAG and, in particular, their sulfate groups are important in binding and modulation of hIL-10 activity.
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39

Haroun-Bouhedja, Ferial, Mostafa Ellouali, Corinne Sinquin, and Catherine Boisson-Vidal. "Relationship between Sulfate Groups and Biological Activities of Fucans." Thrombosis Research 100, no. 5 (December 2000): 453–59. http://dx.doi.org/10.1016/s0049-3848(00)00338-8.

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40

Thomas, Maud, Gaëlle Chauvelon, Marc Lahaye, and Luc Saulnier. "Location of sulfate groups on sulfoacetate derivatives of cellulose." Carbohydrate Research 338, no. 8 (April 2003): 761–70. http://dx.doi.org/10.1016/s0008-6215(03)00010-7.

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Prieto, Jorge J., Maria E. Rubio, and Jaime A. Merchan. "Localization of anionic sulfate groups in the tectorial membrane." Hearing Research 45, no. 3 (May 1990): 283–93. http://dx.doi.org/10.1016/0378-5955(90)90127-b.

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42

Bychkhov, S. M., and S. A. Kuz'mina. "Functions of the carboxyl and sulfate groups of proteoglycans." Bulletin of Experimental Biology and Medicine 119, no. 4 (April 1995): 344–46. http://dx.doi.org/10.1007/bf02445888.

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43

Fernández-Díaz, Lurdes, Ángeles Fernández-González, and Manuel Prieto. "The role of sulfate groups in controlling CaCO3 polymorphism." Geochimica et Cosmochimica Acta 74, no. 21 (November 2010): 6064–76. http://dx.doi.org/10.1016/j.gca.2010.08.010.

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44

Akahane, Tooru, Sadaaki Takeuchi, and Akira Minakata. "Conductimetric titration of polyelectrolytes having sulfate and carboxyl groups." Polymer Bulletin 24, no. 4 (October 1990): 437–44. http://dx.doi.org/10.1007/bf00294098.

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45

Straßburger, David, Svenja Herziger, Katharina Huth, Moritz Urschbach, Rainer Haag, and Pol Besenius. "Supramolecular polymerization of sulfated dendritic peptide amphiphiles into multivalent L-selectin binders." Beilstein Journal of Organic Chemistry 17 (January 12, 2021): 97–104. http://dx.doi.org/10.3762/bjoc.17.10.

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The synthesis of a sulfate-modified dendritic peptide amphiphile and its self-assembly into one-dimensional rod-like architectures in aqueous medium is reported. The influence of the ionic strength on the supramolecular polymerization was probed via circular dichroism spectroscopy and cryogenic transmission electron microscopy. Physiological salt concentrations efficiently screen the charges of the dendritic building block equipped with eight sulfate groups and trigger the formation of rigid supramolecular polymers. Since multivalent sulfated supramolecular structures mimic naturally occurring L-selectin ligands, the corresponding affinity was evaluated using a competitive SPR binding assay and benchmarked to an ethylene glycol-decorated supramolecular polymer.
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46

Khil'chenko, S. R., T. S. Zaporozhets, T. N. Zvyagintseva, N. M. Shevchenko, and N. N. Besednov. "The Role of Sulfates in Fucoidan Extracted from Fucus evanescens in Proinflammatory Cytokines Production by Human Peripheral Blood Cells in vitro." Antibiotics and Chemotherapy 65, no. 5-6 (August 26, 2020): 3–10. http://dx.doi.org/10.37489/0235-2990-2020-65-5-6-3-10.

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Fucoidans, sulfated polysaccharides extracted from brown algae (Phaeophyceae), have a wide spectrum of bioactivity. Studies of molecular structures of fucoidans and deciphering of molecular elements' impact on their biological activities are at their active stage. The article shows the role of sulfates and acetyl groups in fucoidan isolated from Fucus evanescens in proinflammatory cytokines production by human heparinized unfractionated peripheral blood cells. Material and Methods. The cells were incubated with native fucoidan (N) and its deacetylated (deA), partially desulfated (deS), and both deacetylated and partially desulfated (deAdeS) derivatives (100 μg/mL). Cytokine concentrations were determined in cell supernatants by ELISA in a 'sandwich' modification with commercial kits. Results. Incubation with N fucoidan led to an increase of IL-6, TNF-α, IL-8 levels in supernatants. Partial removal of sulfate groups cancelled or decreased stimulating effect for IL-6, TNF-α, cytokines, but not for IL-8. deAc fucoidan action was comparable with N polysaccharide. Native polysaccharide and its chemically modified derivatives did not change IFN-γ и IL-10 cytokine production. Conclusion. The obtained results suggest that sulfates have a significant role in cytokine-producing properties of fucoidan extracted from brown algae F.evanescens.
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47

Loy, Alexander, Kirsten Küsel, Angelika Lehner, Harold L. Drake, and Michael Wagner. "Microarray and Functional Gene Analyses of Sulfate-Reducing Prokaryotes in Low-Sulfate, Acidic Fens Reveal Cooccurrence of Recognized Genera and Novel Lineages." Applied and Environmental Microbiology 70, no. 12 (December 2004): 6998–7009. http://dx.doi.org/10.1128/aem.70.12.6998-7009.2004.

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ABSTRACT Low-sulfate, acidic (approximately pH 4) fens in the Lehstenbach catchment in the Fichtelgebirge mountains in Germany are unusual habitats for sulfate-reducing prokaryotes (SRPs) that have been postulated to facilitate the retention of sulfur and protons in these ecosystems. Despite the low in situ availability of sulfate (concentration in the soil solution, 20 to 200 μM) and the acidic conditions (soil and soil solution pHs, approximately 4 and 5, respectively), the upper peat layers of the soils from two fens (Schlöppnerbrunnen I and II) of this catchment displayed significant sulfate-reducing capacities. 16S rRNA gene-based oligonucleotide microarray analyses revealed stable diversity patterns for recognized SRPs in the upper 30 cm of both fens. Members of the family “Syntrophobacteraceae” were detected in both fens, while signals specific for the genus Desulfomonile were observed only in soils from Schlöppnerbrunnen I. These results were confirmed and extended by comparative analyses of environmentally retrieved 16S rRNA and dissimilatory (bi)sulfite reductase (dsrAB) gene sequences; dsrAB sequences from Desulfobacca-like SRPs, which were not identified by microarray analysis, were obtained from both fens. Hypotheses concerning the ecophysiological role of these three SRP groups in the fens were formulated based on the known physiological properties of their cultured relatives. In addition to these recognized SRP lineages, six novel dsrAB types that were phylogenetically unrelated to all known SRPs were detected in the fens. These dsrAB sequences had no features indicative of pseudogenes and likely represent novel, deeply branching, sulfate- or sulfite-reducing prokaryotes that are specialized colonists of low-sulfate habitats.
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Kellner Filho, Luis C., Bruno W. Picão, Marcio L. A. Silva, Wilson R. Cunha, Patricia M. Pauletti, Gustavo M. Dias, Brent R. Copp, Camila S. Bertanha, and Ana H. Januario. "Bioactive Aliphatic Sulfates from Marine Invertebrates." Marine Drugs 17, no. 9 (September 9, 2019): 527. http://dx.doi.org/10.3390/md17090527.

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The occurrence of sulfated steroids and phenolics in marine organisms is quite widespread, being typically reported from Echinoderms. In contrast, alkane and alkene aliphatic sulfates are considerably rarer with examples being reported from a diverse array of organisms including echinoderms, sponges and ascidians. While no ecological roles for these metabolites have been proposed, they do exhibit a diverse array of biological activities including thrombin inhibition; the ability to induce metamorphosis in larvae; antiproliferative, antibacterial and antifungal properties; and metalloproteinase inhibition. Of particular interest and an avenue for future development is the finding of antifouling properties with low or nontoxic effects to the environment. This review focuses on alkyl sulfates and related sulfamates, their structures and biological activities. Spectroscopic and spectrometric techniques that can be used to recognize the presence of sulfate groups are also discussed, data for which will enhance the ability of researchers to recognize this class of chemically- and biologically-interesting marine natural products.
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Metzger, Christoph, David Auber, Stephan Dähnhardt-Pfeiffer, and Heiko Briesen. "Agglomeration of cellulose nanocrystals: the effect of secondary sulfates and their use in product separation." Cellulose 27, no. 17 (October 9, 2020): 9839–51. http://dx.doi.org/10.1007/s10570-020-03476-0.

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AbstractThis study was aimed at the development of a better understanding of the agglomeration behavior of sulfated cellulose nanocrystals (CNCs) in the presence of sulfates with monovalent (NH4+, K+, Na+) and divalent (Ca2+) cations, and to demonstrate their potential in simple and efficient product separation. Protonated CNCs were counterion-exchanged and their ionic strength was increased by adding sulfates of the respective cation to trigger agglomeration. The critical concentrations of agglomeration (CAC) and peptization (CPC) were determined. We found that the agglomeration behavior of CNCs could be attributed to matching affinities between the cations and the sulfate half-ester groups on the CNC surfaces. Based on these findings, a facile and efficient downstream process was designed to separate CNCs from neutralized reactant solutions using CAC and CPC. This method provides colloidally stable CNCs at high yield provided by centrifugation. When salt concentrations in the product are maintained below the CAC, as prepared CNCs from neutralized reactant solutions might be used in hydrogels and emulsions.
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Shaon, Md Taohid Wasim, Md Nurul Amin, Sabbir Hossen Sabuz, and Mst Deloara Begum. "Comparative Effects of Copper Sulfate and Zinc Sulfate on Performances of Broiler Chickens." Research in Agriculture Livestock and Fisheries 7, no. 3 (December 31, 2020): 465–74. http://dx.doi.org/10.3329/ralf.v7i3.51366.

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To investigate the effects of copper sulfate (CuSO4.5H2O) and zinc sulfate (ZnSO4) on growth performance, feed intake, feed efficiency and carcass characteristics of commercial broiler an experiment was conducted. Total 80 Cobb-500 of 07 days old chicks were randomly divided into four dietary groups having four replications in each. Four diets were considered: control (T0); CuSO4.5H2O @ 150 mg/kg of commercial diet (T1); ZnSO4 @100 mg/kg on diet (T2); and combination of CuSO4.5H2O + ZnSO4 @ 150 mg/kg + 100 mg/kg of diet (T3), respectively. Initial live weight, live weight gain and feed intake were recorded. Carcass characteristics were observed after slaughtering of birds. The final live weight was significantly (P<0.05) differed among the experimental groups where highest live weight was recorded in T2 (2440 g/bird) group. Broilers in T2 group showed the best feed efficiency (1.67) that varied significantly (P<0.05). Daily live weight gain was differed significantly (P<0.05) among the experimental groups where highest value at 3rd and 4th weeks of experiment was found in birds of T2 group. There were no significant (P>0.05) differences observed among the dietary treatment groups in terms of de-feathering percentages, liver, heart and abdominal fat weight. On the contrary, significant (P<0.05) difference were observed in carcass weight, where highest value was recorded in T3 group. Thigh and breast weight was also differed significantly (P<0.05) in T3 group compared to control and other groups. Use of copper sulfate pentahydrate in diet was economic in terms of cost benefit analysis. Res. Agric., Livest. Fish.7(3): 465-474, December 2020
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