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Journal articles on the topic 'Lipophilic Groups'

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Author: Grafiati

Published: 4 June 2021

Last updated: 20 February 2023

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1

Gaddale Devanna, Kishore K., Justyna M. Gawel, Tracy A. Prime, Filip Cvetko, Cristiane Benincá, Stuart T. Caldwell, Alexander Negoda, et al. "Tetra-arylborate lipophilic anions as targeting groups." Chemical Communications 57, no. 25 (2021): 3147–50. http://dx.doi.org/10.1039/d0cc07924c.

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2

Madak, Joseph, and Nouri Neamati. "Membrane Permeable Lipophilic Cations as Mitochondrial Directing Groups." Current Topics in Medicinal Chemistry 15, no. 8 (March 13, 2015): 745–66. http://dx.doi.org/10.2174/1568026615666150302105622.

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3

Koval'ov, N., I. Kuznetsova, E. Burakova, V. Sil'nikov, M. Zenkova, and V. Vlassov. "Ribonuclease Activity of Cationic Structures Conjugated to Lipophilic Groups." Nucleosides, Nucleotides and Nucleic Acids 23, no. 6-7 (December 31, 2004): 977–81. http://dx.doi.org/10.1081/ncn-200026050.

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4

Villanueva, María Emilia, Ana Salinas, Joaquín Antonio González, Sergio Teves, and Guillermo Javier Copello. "Dual antibacterial effect of immobilized quaternary ammonium and aliphatic groups on PVC." New Journal of Chemistry 39, no. 12 (2015): 9200–9206. http://dx.doi.org/10.1039/c5nj01766a.

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5

Gasiorowski, J., N. Pootrakulchote, C. Reanprayoon, K. Jaisabuy, P. Vanalabhpatana, N. S. Sariciftci, and P. Thamyongkit. "Porphyrin containing lipophilic amide groups as a photosensitizer for dye-sensitized solar cells." RSC Advances 5, no. 89 (2015): 72900–72906. http://dx.doi.org/10.1039/c5ra10538b.

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6

Zhao, Changming, Yulian Jiang, Mengwei Li, Tiexin Cheng, Wensheng Yang, and Guangdong Zhou. "The effect of NaOH on lowering interfacial tension of oil/alkylbenzene sulfonates solution." RSC Advances 8, no. 11 (2018): 6169–77. http://dx.doi.org/10.1039/c7ra11287d.

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The increase of NaOH concentration resulted in the compression of the electrical double layer. The distribution of PDABS in the oil phase improved the mutual attraction of lipophilic chains and the close-packed lipophilic groups at the interface.

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7

Czech, Bronislaw P., Anna Czech, Byungki Son, Han Koo Lee, and Richard A. Bartsch. "Synthesis of lipophilic crown ethers with pendant carboxylic acid groups." Journal of Heterocyclic Chemistry 23, no. 2 (March 1986): 465–71. http://dx.doi.org/10.1002/jhet.5570230231.

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8

Kong, Xiangjun, Junhe Zhao, Lijun Zhang, Zupei Liang, and Jinlan Wang. "Design, synthesis and characterization of bitumen emulsifiers based on molecular simulation." Kemija u industriji 68, no. 1-2 (2019): 1–6. http://dx.doi.org/10.15255/kui.2018.013.

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Under the guidance of molecular simulation technology, the Monte Carlo molecular mechanics simulation was used to calculate the compatibility of different lipophilic groups with each component of bitumen, and the compatibility of different hydrophilic groups with water. Based on the calculated results of interaction parameters Chi and mixture energy Emix, the preferred structures of lipophilic and hydrophilic groups of bitumen emulsifier were determined. The target bitumen emulsifier was then synthesized by the reaction of organic acid and polyamine. The molecular simulation results showed that the compatibility of lipophilic group T11 with the bitumen was the best, and the mixing ability of the hydrophilic group H5 with water was excellent. The experimental results show that the preferred structures T11H5 had a good emulsifying performance to prepare emulsified bitumen with good storage stability, consistent with the results of the molecular simulation.

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9

Degtyareva, Ekaterina Aleksandrovna, Liliya Ivanovna Vyshnevska, Svetlana Vasil'yevna Garnaya, and Ekaterina Aleksandrovna Kalko. "THE STUDY OF PHYSICO-TECHNOLOGICAL FACTORS’ INFLUENCE ON THE OUTPUT OF LIPOPHILIC SUB-STANCES FROM MEDICINAL PLANT MATERIALS." chemistry of plant raw material, no. 3 (April 7, 2019): 299–305. http://dx.doi.org/10.14258/jcprm.2019035098.

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Currently, the lipophilic fractions of well-known medicinal plants are still understudied despite of contains of unique groups of BAS (chlorophylls, carotenoids, tocopherols, sterols, unsaturated fatty acids, phospholipids, etc.), what is the actual task of modern pharmaceutical science. The aim of our work was to perform experimental studies for the choice of optimal conditions of the extraction of lipophilic compounds from the meal of pumpkin pulp. Extraction of lipophilic substances from the meal of pumpkin pulp was carried out in laboratory conditions in the Soxhlet apparatus by the method of circulation extraction. The weight loss on drying, the content of extractive lipophilic substances and the amount of carotenoids (in terms of β-carotene) were determined by compendial procedures. According to the results of the experimental work, the optimum humidity (not more than 7%) and drying temperature (+ 60 °C) of pumpkin pulp meal containing carotenoids were established. The obtained data are necessary for the development of technology of lipophilic pumpkin extract.

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10

Reichardt, Christian, Stefan Löbbecke, Abdol Mohammed Mehranpour, and Gerhard Schäfer. "Pyridinium N-phenoxide betaines and their application to the determination of solvent polarities, XXIV. Syntheses and UV-vis spectroscopic properties of new lipophilic tert-butyl- and 1-adamantyl substituted, negatively solvatochromic pyridinium N-phenolate betaine dyes." Canadian Journal of Chemistry 76, no. 6 (June 1, 1998): 686–94. http://dx.doi.org/10.1139/v98-019.

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Syntheses and negative solvatochromism of two new lipophilic pentaphenyl pyridinium N-phenolate betaine dyes, substituted with seven tert-butyl groups (9) or with three tert-butyl and two 1-adamantyl groups (13) in the peripheral phenyl rings, are described in order to get zwitterionic dyes that are more soluble in nonpolar solvents such as the standard betaine dye, 1, which has been used for the construction of an empirical scale of solvent polarity, called the ET(30) scale.Key words: betaine dyes, ET(30) values, lipophilic dyes, pyridinium N-phenolate betaine dyes, solvatochromism, solvent polarity.

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11

Hu, Hui, and Richard A. Bartsch. "Synthesis of lipophilic lariat ethers with pendantN-(X)sulfonyl carboxamide groups." Journal of Heterocyclic Chemistry 41, no. 4 (July 2004): 557–62. http://dx.doi.org/10.1002/jhet.5570410412.

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12

Özdemir, Mücahit, Begümhan Karapınar, Bahattin Yalçın, Ümit Salan, Mahmut Durmuş, and Mustafa Bulut. "Synthesis and characterization of novel 7-oxy-3-ethyl-6-hexyl-4-methylcoumarin substituted metallo phthalocyanines and investigation of their photophysical and photochemical properties." Dalton Transactions 48, no. 34 (2019): 13046–56. http://dx.doi.org/10.1039/c9dt02687h.

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13

Silverio, Flaviano O., Luiz C. A. Barbosa, Celia R. A. Maltha, Armando J. D. Silvestre, Dorila Pilo-Veloso, and Jose L. Gomide. "Characterization of lipophilic wood extractives from clones of Eucalyptus urograndis cultivate in Brazil." BioResources 2, no. 2 (February 27, 2007): 157–68. http://dx.doi.org/10.15376/biores.2.2.157-168.

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The chemical compositions of the lipophilic extractives from four clones of Eucalyptus urograndis cultivated in Brazil were studied by gas chromatography-mass spectrometry (GC-MS) before and after alkaline hydrolysis. The four E. urograndis clones showed similar amounts of dichloromethane soluble (lipophilic) extractives (0.38-0.55% w/w). The major groups of compounds identified in the lipophilic fraction of extractives consisted mainly of fatty acids (mainly palmitic linoleic and oleic acids and small amounts of a- and w-hydroxyacids), steroids (mainly b-sitosterol, b-sitostanol), followed by minor amounts long chain aliphatic alcohols, hydrocarbons and aromatic compounds. The relative abundances of these groups were similar for three of the clones with exception of the clone Ugc, which was shown to have much higher amounts of fatty acids and sterols. The high amounts of extractives found in these clones, and particularly of Ugc, when compared with other Eucalyptus species, suggests an increased risk of pitch formation during bleached pulp production.

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14

España Orozco, Sebastian, Philipp Zeitlinger, Karin Fackler, Robert H. Bischof, and Antje Potthast. "A solid-phase extraction method that eliminates matrix effects of complex pulp mill effluents for the analysis of lipophilic wood extractives." Nordic Pulp & Paper Research Journal 35, no. 4 (November 18, 2020): 577–88. http://dx.doi.org/10.1515/npprj-2020-0039.

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AbstractThe extraction of lipophilic wood extractives from pulp and paper process waters proves to be a challenging task, due to harsh and alternating process and sample conditions. This study has determined the potential use of polymeric sorbents for solid-phase extraction (SPE) and compared to classical silica-based reversed-phase packed columns, with polymeric hydrophilic-lipophilic balanced (HLB) cartridges being the sorbent with the most potential. Recovery functions were obtained with an internal standard mixture representative for the main lipophilic wood extractive groups, which are fatty acids and alcohols, sterols, sterol esters and triglycerides. The impact of pH, sample volume and sample matrix, expressed as TOC and cations, on the retention behavior of lipophilic extractives during SPE of industrial samples were determined with polymeric HLB sorbent. High variations in the composition of pulp mill matrices led to different optimal extraction conditions. Thus, a new SPE protocol was developed, which bypasses matrix interferences and omits the loss of analytes due to sample preparation. The method is applicable to different pulp mill effluents with large discrepancies in pH and sample matrices, resulting in recoveries >90 % with RSD <5 % for all lipophilic wood extractives.

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15

MacKellar, Calum, Duncan Graham, David W. Will, Stephen Burgess, and Tom Brown. "Synthesis and physical properties ofanti-HIV antisense oligonucleotides bearing terminal lipophilic groups." Nucleic Acids Research 20, no. 13 (1992): 3411–17. http://dx.doi.org/10.1093/nar/20.13.3411.

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16

Kim, Jong Seung, Jin Hyun Pang, Il Hwan Suh, Dae Whang Kim, and Dong Won Kim. "Novel Calix[4]arene Dibenzocrown Ethers Bearing Lipophilic Alkyl Groups Symmetrically Branched." Synthetic Communications 28, no. 4 (February 1998): 677–85. http://dx.doi.org/10.1080/00397919808005940.

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17

Melnyk, Inna, Nadiya Kovalska, Uliana Karpiuk, and Nadiya Skripchenko. "The study of biological active compounds of lipophilic fraction of Schisandra chinensis (Turcz.) Baill seeds." Ukrainian Scientific Medical Youth Journal 131, no. 2 (June 23, 2022): 78–84. http://dx.doi.org/10.32345/usmyj.2(131).2022.78-84.

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Schisandra chinensis (Turcz.) Baill - Chinese magnolia - a well-known fruit plant in traditional Chinese and Korean medicine. The fruits and seeds of S. chinensis are rich in biologically active substances. According to the literature (Irfan M. etc, 2020; Liu G-Z. etc, 2020; Sun W. etc, 2021; Zhao T. etc., 2021; Bodrevich B.B. etc, 2017) the following therapeutic effects of S. chinensis fruits and seeds can be called: immunomodulatory, tonic, adaptogenic, anti-inflammatory, hepatoprotective, nephroprotective, tonic. The study of the S. chinensis raw materials continues in the future, to reveal a wider range of therapeutic actions. The study of S. chinensis seeds is quite relevant to expand the range of standardized medicinal raw materials, which is not included in the monographs of the State Pharmacopoeia of Ukraine. The main purpose of this study is to obtain the lipophilic fraction of S. chinensis seeds and to study the composition of different groups of lipophilic substances in the resulting fraction. The main method of obtaining the lipophilic fraction of S. chinensis seeds is a comprehensive extraction in the Soxhlet apparatus. The chemical reaction was used to determine the presence of tocopherols. The presence of the main groups of biologically active substances in the lipophilic fraction of S. chinensis seeds was established by the method of two-dimensional thin-layer chromatography. The study of fatty acid composition was performed by gas chromatography/mass spectrometry (Su L. etc, 2020). The yield of lipophilic fraction of S. chinensis seeds was 35.79±0.7%. The obtained lipophilic fraction of S. chinensis seeds is an oily liquid of deep yellow color with a characteristic specific odor. The presence of tocopherols was established. Thin layer chromatography in the solvent system: I direction - hexane-acetone (8: 2), II direction - hexane-acetone (8: 4), development reagent - Stahl reagent, identified at least 14 compounds of terpene nature. As a result of studies of fatty acids by gas chromatography/mass spectrometry, the quantitative content of 6 fatty acids was identified and established: palmitic, linoleic, oleic, stearic, gondoic and nonadecanoic. The quantitative content of unsaturated fatty acids significantly exceeded the quantitative content of saturated fatty acids. The results of the study give grounds to draw the following conclusions: the studies confirm the rich composition of the lipophilic fraction of S. chinensis seeds: tocopherols, 14 terpenes, 6 fatty acids, of which saturated fatty acids (palmitic, stearic, nonadecanoic) and unsaturated fatty acids , oleic and gondoin); The results of the study suggest the anti-inflammatory, antioxidant, regenerating effect of the lipophilic fraction of S. chinensis seeds.

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18

Brown, Charles R., David Culley, Meredith Bonierbale, and Walter Amorós. "Anthocyanin, Carotenoid Content, and Antioxidant Values in Native South American Potato Cultivars." HortScience 42, no. 7 (December 2007): 1733–36. http://dx.doi.org/10.21273/hortsci.42.7.1733.

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Tubers of 38 native potato cultivars of different taxonomic groups from South America were analyzed to determine the total anthocyanins, total carotenoids, and antioxidant values. Total anthocyanin ranged from zero to 23 mg cyanidin equivalents/100 g fresh weight (FW). Total carotenoid ranged from 38 to 2020 μg zeaxanthin equivalents/100 g FW. Oxygen radical absorbance capacity (ORAC) was measured for the anthocyanin (hydrophilic) and carotenoid (lipophilic) extracts. The hydrophilic ORAC ranged from 333 to 1408 μm Trolox equivalents/100 g FW. The lipophilic ORAC ranged from 4.7 to 30 nM α-tocopherol equivalents/100 g FW. The cultivars consisted of 23 diploids, seven triploids, and eight tetraploids. Total carotenoids was negatively correlated with total anthocyanins. Total anthocyanins was correlated with hydrophilic ORAC. Among clones with less than 2 mg cyanidin equivalents/100 g FW, total carotenoid and lipophilic ORAC were correlated, but this was not true for analysis of all 38 clones. Although total anthocyanins or hydrophilic ORAC values reported here were not outside of the ranges found in North American and other breeding materials, total carotenoids and lipophilic ORACs are higher than previously reported, suggesting that native cultivars of South America with high levels of total carotenoids and high lipophilic ORAC are a unique germplasm source for introgression of these traits into specific potato cultivars outside the center of origin.

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19

Reguera, Beatriz, and Juan Blanco. "Dinophysis Toxins: Distribution, Fate in Shellfish and Impacts." Toxins 11, no. 7 (July 16, 2019): 413. http://dx.doi.org/10.3390/toxins11070413.

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Several planktonic dinoflagellate species of the genus Dinophysis produce one or two groups of lipophilic toxins: (i) okadaic acid (OA) and its derivatives, the dinophysistoxins (DTXs), and (ii) pectenotoxins (PTXs) [...]

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20

Ueno, Yoshihito, Koshi Kawada, Tomoharu Naito, Aya Shibata, Kayo Yoshikawa, Hye-Sook Kim, Yusuke Wataya, and Yukio Kitade. "Synthesis and silencing properties of siRNAs possessing lipophilic groups at their 3′-termini." Bioorganic & Medicinal Chemistry 16, no. 16 (August 2008): 7698–704. http://dx.doi.org/10.1016/j.bmc.2008.07.010.

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21

Ueno, Y., K. Kawada, A. Shibata, K. Yoshikawa, Y. Wataya, and Y. Kitade. "Synthesis and silencing properties of siRNAs possessing lipophilic groups at their 3'-termini." Nucleic Acids Symposium Series 52, no. 1 (September 1, 2008): 503–4. http://dx.doi.org/10.1093/nass/nrn255.

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22

Berlepsch, H. v., B. N. S. Thota, M. Wyszogrodzka, S. de Carlo, R. Haag, and C. Böttcher. "Controlled self-assembly of stomatosomes by use of single-component fluorinated dendritic amphiphiles." Soft Matter 14, no. 25 (2018): 5256–69. http://dx.doi.org/10.1039/c8sm00243f.

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A series of novel non-ionic amphiphiles with dendritic oligoglycerol head groups and lipophilic/fluorophilic tail segments, comprising single or double tail alkyl chains, C₈F₁₇-perfluoro rod segments as well as flexible spacer groups were designed and their supramolecular behavior characterised by cryo-transmission electron microscopy and tomography.

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23

Kobylańska, A., E. Pluskota, M. Swiatkowska, M. Wójcik, A. Cierniewska-Cieślak, A. Krakowiak, M. Boczkowska, et al. "Inhibition of plasminogen activator inhibitor release in endothelial cell cultures by antisense oligodeoxyribonucleotides with a 5'-end lipophilic modification." Acta Biochimica Polonica 46, no. 3 (September 30, 1999): 679–91. http://dx.doi.org/10.18388/abp.1999_4140.

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A series of conjugates containing residues of lipophilic alcohols covalently bound to 5' end of oligodeoxyribonucleotides targeted against human plasminogen activator inhibitor (PAI-1) mRNA was synthesized via the oxathiaphospholane approach. The highest anti-PAI-1 activity in EA.hy 926 endothelial cell cultures was found for conjugates containing menthyl or heptadecanyl groups linked with an oligonucleotide complementary to a segment of human PAI-1 mRNA. The phosphodiester antisense oligonucleotides, which otherwise exhibit only limited anti-PAI-1 activity, were found to be more active than phosphorothioate oligonucleotides when conjugated to lipophilic alcohol residues. For menthyl conjugates an evidence of antisense mechanism of inhibition was found.

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24

Caldwell, Stuart T., Donald B. McPhail, Garry G. Duthie, and Richard C. Hartley. "Synthesis of polyhydroxylated flavonoids bearing a lipophilic decyl tail as potential therapeutic antioxidants." Canadian Journal of Chemistry 90, no. 1 (January 2012): 23–33. http://dx.doi.org/10.1139/v11-087.

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Antioxidants have potential for the treatment of stroke and neurodegeneration, and chimeric compounds that combine a flavon-3-ol head group related to myricetin and a lipophilic decyl tail are known to protect membranes from oxidative damage at least as well as vitamin E. New flavon-3-ols that are highly hydroxylated in the B ring in ways not found in natural flavon-3-ols and bearing a lipophilic decyl tail have been prepared from trimethoxy- and tetramethoxybenzoic acids accessed by lithiation–carboxylation reactions. Direct enolate acylation was preferred over Baker–Venkataraman rearrangement when there were methoxy groups at both the 2- and the 6-position of the benzoic acid derivatives.

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25

Słota, Rudolf, Gabriela Dyrda, Maria Hofer, Giuseppe Mele, Ermelinda Bloise, and Roberta del Sole. "Novel Lipophilic Lanthanide Bis-Phthalocyanines Functionalized by Pentadecylphenoxy Groups: Synthesis, Characterization and UV-Photostability." Molecules 17, no. 9 (September 7, 2012): 10738–53. http://dx.doi.org/10.3390/molecules170910738.

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26

Seung Kim, J. "Metal ion complexation by acyclic polyethers with lipophilic amide, thioamide, and amine end groups." Talanta 51, no. 1 (January 24, 2000): 99–105. http://dx.doi.org/10.1016/s0039-9140(99)00253-2.

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27

Pozsgay, Vince. "A new strategy in oligosaccharide synthesis using lipophilic protecting groups: synthesis of a tetracosasaccharide." Tetrahedron: Asymmetry 11, no. 1 (January 2000): 151–72. http://dx.doi.org/10.1016/s0957-4166(99)00553-4.

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28

He, Ning, Kevin S. Warner, Doungdaw Chantasart, Dalia S. Shaker, William I. Higuchi, and S. Kevin Li. "Mechanistic study of chemical skin permeation enhancers with different polar and lipophilic functional groups." Journal of Pharmaceutical Sciences 93, no. 6 (June 2004): 1415–30. http://dx.doi.org/10.1002/jps.20030.

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29

Smirnova, Alla L., Serguey S. Levitchev, Valentina L. Khitrova, Aleksandr L. Grekovich, Yurii G. Vlasov, Andree Schwake, and Karl Cammann. "Effect of Simultaneous Existence of Two Ion-Exchangers with Opposite Charges of Lipophilic Groups." Electroanalysis 11, no. 10-11 (July 1999): 763–69. http://dx.doi.org/10.1002/(sici)1521-4109(199907)11:10/11<763::aid-elan763>3.0.co;2-w.

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30

KIM, J. S., J. H. PANG, I. H. SUH, D. W. KIM, and D. W. KIM. "ChemInform Abstract: Novel Calix[4]arene Dibenzocrown Ethers Bearing Lipophilic Alkyl Groups Symmetrically Branched." ChemInform 29, no. 26 (June 21, 2010): no. http://dx.doi.org/10.1002/chin.199826203.

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31

Wu, Ming Hua, Jian Peng Dong, Dong Ming Qi, Chong Qian, and Xin Jiang. "Influence of the Hydrophile-Lipophile Property of Cross-Linker on the Properties of Acrylate Latex and its Film." Advanced Materials Research 441 (January 2012): 466–72. http://dx.doi.org/10.4028/www.scientific.net/amr.441.466.

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A series of acrylate latexes for pigment printing binder were prepared by semi-continuous pre-emulsifying emulsion polymerization, using lipophilic glycidyl meth-acrylate (GMA), ethylene glycol dimethyl acrylate (EGDMA) and hydrophilic HA (containing hydroxyl, acylamino), N-methylol acrylamide (NMA) as cross-linking monomer. The influences of cross-linker type on the particle size, viscosity and film-forming rate of latex, cross-linking degree and tensile properties of latex film were studied. It was found that the latex particle size, viscosity and film-forming rate were closely related with the hydrophile-lipophile property of cross linkers. The acrylate latex synthesized with hydrophilic cross-linkers always exhibits the characteristics of larger particle size, lower film-forming rate, higher viscosity and pseudoplastic fluid. The cross-linking degree and tensile properties of latex film generally depend on the crosslinking groups of cross-linkers and their reactivity.

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32

Leyva-Valencia, Ignacio, Jesús Hernández-Castro, Christine Band-Schmidt, Andrew Turner, Alison O’Neill, Erick Núñez-Vázquez, David López-Cortés, José Bustillos-Guzmán, and Francisco Hernández-Sandoval. "Lipophilic Toxins in Wild Bivalves from the Southern Gulf of California, Mexico." Marine Drugs 19, no. 2 (February 9, 2021): 99. http://dx.doi.org/10.3390/md19020099.

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Most of the shellfish fisheries of Mexico occur in the Gulf of California. In this region, known for its high primary productivity, blooms of diatoms and dinoflagellates are common, occurring mainly during upwelling events. Dinoflagellates that produce lipophilic toxins are present, where some outbreaks related to okadaic acid and dinophisystoxins have been recorded. From January 2015 to November 2017 samples of three species of wild bivalve mollusks were collected monthly in five sites in the southern region of Bahía de La Paz. Pooled tissue extracts were analyzed using LC-MS/MS to detect lipophilic toxins. Eighteen analogs of seven toxin groups, including cyclic imines were identified, fortunately individual toxins did not exceed regulatory levels and also the total toxin concentration for each bivalve species was lower than the maximum permitted level for human consumption. Interspecific differences in toxin number and concentration were observed in three species of bivalves even when the samples were collected at the same site. Okadaic acid was detected in low concentrations, while yessotoxins and gymnodimines had the highest concentrations in bivalve tissues. Although in low quantities, the presence of cyclic imines and other lipophilic toxins in bivalves from the southern Gulf of California was constant.

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33

Marchesi, Elena, Rita Cortesi, Lorenzo Preti, Paola Rimessi, Maddalena Sguizzato, Matteo Bovolenta, and Daniela Perrone. "Antisense Oligonucleotides Conjugated with Lipophilic Compounds: Synthesis and In Vitro Evaluation of Exon Skipping in Duchenne Muscular Dystrophy." International Journal of Molecular Sciences 23, no. 8 (April 12, 2022): 4270. http://dx.doi.org/10.3390/ijms23084270.

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Our groups previously reported that conjugation at 3′-end with ursodeoxycholic acid (UDCA) significantly enhanced in vitro exon skipping properties of ASO 51 oligonucleotide targeting the human DMD exon 51. In this study, we designed a series of lipophilic conjugates of ASO 51, to explore the influence of the lipophilic moiety on exon skipping efficiency. To this end, three bile acids and two fatty acids have been derivatized and/or modified and conjugated to ASO 51 by automatized solid phase synthesis. We measured the melting temperature (Tm) of lipophilic conjugates to evaluate their ability to form a stable duplex with the target RNA. The exon skipping efficiency has been evaluated in myogenic cell lines first in presence of a transfection agent, then in gymnotic conditions on a selection of conjugated ASO 51. In the case of 5′-UDC-ASO 51, we also evaluated the influence of PS content on exon skipping efficiency; we found that it performed better exon skipping with full PS linkages. The more efficient compounds in terms of exon skipping were found to be 5′-UDC- and 5′,3′-bis-UDC-ASO 51.

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34

Gagnon, M. Karen J., Timothy R. St. Germain, Christopher M. Vogels, Robert A. McNamara, Nicholas J. Taylor, and Stephen A. Westcott. "Synthesis and hydroboration of lipophilic hydroxy-pyridinones and their complexes with molybdenum(VI)." Australian Journal of Chemistry 53, no. 8 (2000): 693. http://dx.doi.org/10.1071/ch00094.

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We have prepared four potentially lipophilic N-substituted hydroxypyridinones containing unsaturated hydrocarbon groups. The propyl vinyl ether derivative (3) has been characterized by an X-ray diffraction study. Complexes of the type cis-MoO2L2, where L represents the hydroxypyridinonato ligands, have also been prepared. The pyridinone ligands are bound to molybdenum in a cis bidentate fashion via the deprotonated hydroxy groups and the ketone moieties. Initial investigations into the hydroboration of the alkene groups in the pyridinone ligands and corresponding metal complexes is presented. Crystals of (3) are monoclinic, with a 10.466(1), b 13.388(1), c 15.386(2) Å, β 102.343(8)˚, Z 8, space group P21/n.

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35

Spohr, Ulrike, Naohiko Morishima, Ole Hindsgaul, and Raymond U. Lemieux. "Molecular recognition. IV. The binding of the Lewis b human blood group determinant by a hybridoma monoclonal antibody." Canadian Journal of Chemistry 63, no. 10 (October 1, 1985): 2659–63. http://dx.doi.org/10.1139/v85-441.

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A commercial hybridoma monoclonal anti-Lewis b antibody appears to accept the Lewis b human blood group determinant (αLFuc(1→2)βDGal(1 → 3)[αLFuc(1 → 4)]βDGlcNAc--) by involving OH-3 of the βDGal unit and OH-2 of the αLFuc(1 → 2) unit in a key polar interaction at the periphery of a large wedge-shaped lipophilic surface that extends about the tetrasaccharide and essentially leaves 5 of the 8 other hydroxyl groups in contact with the aqueous phase. It is proposed that the three remaining hydroxyl groups, namely, OH-4of the βDGal unit, OH-3 of the αLFuc(1 → 4) unit, and OH-4 of the αLFuc(1 → 2) unit, become intramolecularly hydrogen bonded for acceptance into a hydrophobic environment. The results are taken as further circumstantial evidence that the stability of the complex is mainly related to the establishment of dispersion forces of attraction between complementary lipophilic surfaces provided by the oligosaccharide and the protein. These forces are expected to be stronger than those prior to binding between the amphiphilic surfaces that are involved and water.

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Grijalvo, Santiago, Montserrat Terrazas, Anna Aviñó, and Ramón Eritja. "Stepwise synthesis of oligonucleotide–peptide conjugates containing guanidinium and lipophilic groups in their 3′-termini." Bioorganic & Medicinal Chemistry Letters 20, no. 7 (April 2010): 2144–47. http://dx.doi.org/10.1016/j.bmcl.2010.02.049.

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37

SVINARCHUK, F., D. KONEVETZ, O. PLIASUNOVA, A. POKROVSKY, and V. VLASSOV. "Inhibition of HIV proliferation in MT-4 cells by antisense oligonucleotide conjugated to lipophilic groups." Biochimie 75, no. 1-2 (1993): 49–54. http://dx.doi.org/10.1016/0300-9084(93)90024-m.

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38

Bratton, Larry D., Hwang Huh, and Richard A. Bartsch. "New lipophilic crown ethers with intraannular carboxylic acid groups: Synthesis and alkali metal cation extraction." Journal of Heterocyclic Chemistry 37, no. 4 (July 2000): 815–19. http://dx.doi.org/10.1002/jhet.5570370424.

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39

Servinis, Linden, Kathleen M. Beggs, Christina Scheffler, Enrico Wölfel, James D. Randall, Thomas R. Gengenbach, Baris Demir, et al. "Electrochemical surface modification of carbon fibres by grafting of amine, carboxylic and lipophilic amide groups." Carbon 118 (July 2017): 393–403. http://dx.doi.org/10.1016/j.carbon.2017.03.064.

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Czech, Bronislaw P., Dhimant H. Desai, Jacek Koszuk, Anna Czech, David A. Babb, Thomas W. Robison, and Richard A. Bartsch. "Synthesis of lipophilic crown ethers with pendant phosphonic acid or phosphonic acid monoethyl ester groups." Journal of Heterocyclic Chemistry 29, no. 4 (July 1992): 867–75. http://dx.doi.org/10.1002/jhet.5570290433.

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41

Xu, Bao Cai, Gui Ju Zhang, Yun Xia Li, and Lu Cui. "Preparation and Properties of Amide Surfactants." Advanced Materials Research 550-553 (July 2012): 99–102. http://dx.doi.org/10.4028/www.scientific.net/amr.550-553.99.

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Amide surfactants have modified structures with lipophilic groups connecting hydrophilic groups through amido bond. The preparation of three families of amide surfactants including long chain N-acyl sarcosinates, amidopropyl dimethyl hydroxypropyl sulfobetaines and lauryl amidopropyl trimethyl ammoniums were discussed. The study of the surface activity of these compounds by measuring the equilibrium surface tensions of their dilute aqueous solutions were described. The minimum surface tension and the critical micelle concentration values of these compounds are given.

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Puchkov, Pavel A., and Michael A. Maslov. "Lipophilic Polyamines as Promising Components of Liposomal Gene Delivery Systems." Pharmaceutics 13, no. 6 (June 21, 2021): 920. http://dx.doi.org/10.3390/pharmaceutics13060920.

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Gene therapy requires an effective and safe delivery vehicle for nucleic acids. In the case of non-viral vehicles, including cationic liposomes, the structure of compounds composing them determines the efficiency a lot. Currently, cationic amphiphiles are the most frequently used compounds in liposomal formulations. In their structure, which is a combination of hydrophobic and cationic domains and includes spacer groups, each component contributes to the resulting delivery efficiency. This review focuses on polycationic and disulfide amphiphiles as prospective cationic amphiphiles for gene therapy and includes a discussion of the mutual influence of structural components.

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Eblinger, Frank, and Hans-Jörg Schneider. "A Stereoselective Peptide-Based Artificial Receptor for Sugar Derivatives." Collection of Czechoslovak Chemical Communications 65, no. 5 (2000): 667–72. http://dx.doi.org/10.1135/cccc20000667.

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A lipophilic sugar receptor containing two phenylalanine moieties shows in chloroform complexation free energies of ∆G = 13 kJ/mol for an alkyl glucoside, discriminating the corresponding galactoside by at least 8 kJ/mol. The observed 1H NMR signal shifts at OH groups suggest the hydrogen bonds as the major driving force, in line with preliminary molecular mechanics simulations.

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Gao, Li Ming, Ramón Hernández, Jaime Matta, and Enrique Meléndez. "Synthesis, Structure, Electrochemistry, and Cytotoxic Properties of Ferrocenyl Ester Derivatives." Metal-Based Drugs 2009 (March 24, 2009): 1–8. http://dx.doi.org/10.1155/2009/420784.

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A series of ferrocenyl ester complexes, varying the lipophilic character of the pendant groups, was prepared and characterized by spectroscopic and analytical methods. The syntheses of Fe(C5H4CO2CH3)2, Fe(CpCOOCH3) (CpCOO CH2CH3), and Fe(CpCOOCH2CH3)2 are reported. The solid-state structure of Fe(C5H4CO2CH3)2 has been determined by X-ray crystallography. Fe(C5H4CO2CH3)2 has the cyclopentadienyl rings virtually in an eclipsed conformation with the pendant groups not completely opposite to each other. Cyclic voltammetry characterization showed that the functionalized ferrocenes oxidize at potentials, Epa, higher than ferrocene as a result of the electro withdrawing effect of the pendant groups on the cyclopentadienyl ligand. The cytotoxicities of Fe(C5H4CO2CH2CH2OH)2, Fe(C5H4CO2CH2CH=CH2)2, Fe(C5H4CO2CH3)2, Fe(CpCOOCH3)(CpCOOCH2CH3), and Fe(CpCOOCH2CH3)2 in colon cancer HT-29 and breast cancer MCF-7 cell lines were measured by the MTT biological viability assay and compared to ferrocene and ferrocenium. Fe(C5H4CO2CH2CH=CH2)2 showed the best IC50 values, 180(10) μM for HT-29 and 190(30) μM for MCF-7 cell lines, with cytotoxicities similar to ferrocenium. The cytotoxic data suggest that as we increase the lipophilic character of the functionalized ferrocene, the cytotoxicity improves approaching to the cytotoxic activity of ferrocenium.

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Burilov, Vladimir, Egor Makarov, Diana Mironova, Elza Sultanova, Islamiya Bilyukova, Kevser Akyol, Vladimir Evtugyn, et al. "Calix[4]arene Polyamine Triazoles: Synthesis, Aggregation and DNA Binding." International Journal of Molecular Sciences 23, no. 23 (November 28, 2022): 14889. http://dx.doi.org/10.3390/ijms232314889.

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Artificial gene delivery systems are in great demand from both scientific and practical biomedical points of view. In this paper, we present the synthesis of a new click chemistry calix[4]arene precursor with free lower rim and new water-soluble calixarene triazoles with 12 amino-groups on the upper rim (one with free phenol hydroxyl groups and two another containing four butyl or tetradecyl fragments). Aggregation in the series of amino-triazole calixarenes of different lipophilicity (calixarene with free phenol hydroxyl groups or butyl and tetradecyl fragments on the lower rim) was studied using dynamic light scattering and fluorescent pyrene probe. It was found that calix[4]arene with a free lower rim, like alkyl-substituted butyl calix[4]arene, forms stable submicron aggregates 150–200 nm in size, while the more lipophilic tetradecyl –substituted calix[4]arene forms micellar aggregates19 nm in size. Using UV-Vis spectroscopy, fluorimetry and CD, it was shown that amino-triazole calix[4]arenes bind to calf thymus DNA by classical intercalation. According to DLS and TEM data, all studied macrocycles cause significant DNA compaction, forming stable nanoparticles 50–20 nm in size. Among all studied calix[4]arenes the most lipophilic tetradecyl one proved to be the best for both binding and compaction of DNA.

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Green, Jerry M., and Theresa Hale. "Increasing and Decreasing pH to Enhance the Biological Activity of Nicosulfuron." Weed Technology 19, no. 2 (June 2005): 468–75. http://dx.doi.org/10.1614/wt-04-001r5.

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Increasing the pH of the spray water to solubilize the weak acid herbicide nicosulfuron and then decreasing pH below its pKaso that it converts into a neutral form enhances biological activity under some conditions. The water-dispersible granule formulation of nicosulfuron starts as dispersed particles. Adding 1% wt/wt K3PO4solubilizes nicosulfuron and increases its activity compared to its dispersion without base. The type of buffer and the surfactant HLB or hydrophilic lipophilic balance, a measure of the molecular balance of the hydrophilic and lipophilic groups, altered the activity of nicosulfuron. Adding 1% wt/wt K3PO4increases the pH, and the optimum HLB ranged from 13 to 17 on large crabgrass. Adding 1% wt/wt H3PO4reduces the pH and lowers the optimum HLB range from 10 to 14 on large crabgrass. Adding the acidic buffer converts the solubilized nicosulfuron into its neutral form and increases activity under some surfactant conditions. Thus, neutral nicosulfuron is more active with lipophilic surfactants, while ionic nicosulfuron is more active with hydrophilic surfactants. When tested on other species, low HLB surfactants are the most active at low pH. These results support the concept that the physicochemical properties of the herbicide, adjuvants, and weed species should be matched for optimum activity.

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Neis, Christian, Günter J. Merten, and Kaspar Hegetschweiler. "Tris(cis-2-hydroxycyclohexane-1,3,5-triaminium) hydrogen sulfate octachloride dihydrate." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (May 26, 2012): o1899—o1900. http://dx.doi.org/10.1107/s1600536812022374.

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The 2-hydroxycyclohexane-1,3,5-triaminium (= H3 L 3+) cation of the title compound, 3C6H18N3O3+·8Cl−·HSO4 −·2H2O, exhibits a cyclohexane chair with three equatorial ammonium groups and one axial hydroxy group in an all-cis configuration. The hydrogen sulfate anion and two water molecules lie on or in proximity to a threefold axis and are disordered. The crystal structure features N—H...Cl and O—H...Cl hydrogen bonds. Three C 3-symmetric motifs can be identified in the structure: (i) Two chloride ions (on the C 3-axis) together with three H3 L 3+ cations constitute an [(H3 L)3Cl2]7+ cage. (ii) The lipophilic C6H6-sides of three H3 L 3+ cations, which are oriented directly towards the C 3-axis, generate a lipophilic void. The void is filled with the disordered water molecules and with the disordered part of the hydrogen sulfate ion. The hydrogen atoms of these disordered moieties were not located. (iii) Three H3 L 3+ cations together with one HSO4 − and three Cl− counter-ions form an [(HSO4)(H3 L)3Cl3]5+ cage. Looking along the C 3-axis, these three motifs are arranged in the order (cage 1)...(lipophilic void)...(cage 2). The crystal studied was found to be a racemic twin.

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48

Lavoie, Jean-Michel, and Tatjana Stevanovic. "Yield and composition of lipophylic extracts of yellow birch (Betula alleghaniensis Britton) as a function of wood age and aging under industrial conditions." Holzforschung 60, no. 2 (March 1, 2006): 184–89. http://dx.doi.org/10.1515/hf.2006.030.

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Abstract The lipophylic extracts of yellow birch (Betula alleghaniensis) have been investigated to detect the effect of tree age and wood storage time on extract composition. A total of 17 wood disks were cut from trees belonging to different age groups at 1 m above ground and the wood was milled as usual for extraction (laboratory samples). In addition, 49 sawdust samples were collected in a lumber mill to study the effect of industrial processing on the extractives (industrial samples). All laboratory and industrial samples were extracted with dichloromethane under sonication. The chemical composition of the lipophilic extracts obtained was analyzed by GC-MS. A systematic (quasi-linear) relationship was found between the lipophilic extract yield and specimen age. A total of 30 constituents from yellow birch extracts have been identified, 26 of which have never been previously reported for B. alleghaniensis wood.

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Steiner, Andreas J., Arnold E. Stütz, Chris A. Tarling, Stephen G. Withers, and Tanja M. Wrodnigg. "Synthesis and Biological Evaluation of 1,5-Dideoxy-1,5-iminoxylitol–Amino Acid Hybrids as Xylosidase Inhibitors." Australian Journal of Chemistry 62, no. 6 (2009): 553. http://dx.doi.org/10.1071/ch09040.

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1,5-Dideoxy-1,5-iminoxylitol–amino acid hybrids have been synthesized by cyclisation via a double reductive amination of xylo-pentodialdose and the respective amino groups of lysine as well as serine components. Further modification with aromatic substituents gave access to lipophilic derivatives. Kinetic studies revealed that all compounds exhibited better inhibitory properties against β-xylosidase from Thermoanaerobacterium sacharolyticum than the parent iminosugar.

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Haverkate, Natalie A., Euphemia Leung, Lisa I. Pilkington, and David Barker. "Tethered Aryl Groups Increase the Activity of Anti-Proliferative Thieno[2,3-b]Pyridines by Targeting a Lipophilic Region in the Active Site of PI-PLC." Pharmaceutics 13, no. 12 (November 26, 2021): 2020. http://dx.doi.org/10.3390/pharmaceutics13122020.

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The compounds 2-amino-3-carboxamido-thieno[2,3-b]pyridines have demonstrated excellent anti-proliferative activity against human cancer cell lines, including the triple-negative breast cancer cell line MDA-MB-231. In this study, 81 novel thieno[2,3-b]pyridines were synthesised in four series to further improve their anti-proliferative activity, in particular by targeting an adjacent lipophilic pocket in the putative target enzyme phosphoinositide phospholipase C (PI-PLC). Overall, it was found that appending a propyl-aryl group at C-5 on 2-amino-3-carboxamido-thieno[2,3-b]pyridine resulted in compounds with potent biological activity, exhibiting IC50 values in the nanomolar range. The propyl linker could be an α,β-unsaturated ketone or a saturated propyl ketone, but the highest activity was obtained when allylic alcohols were the tether between thieno[2,3-b]pyridine and the appended aryl group, with compound 21r having IC50 values lower than 50 nM. Compounds with one extra carbon in the tether (i.e., a four-atom chain) were found to be considerably less active. Molecular modelling revealed this propyl tether places the newly introduced aryl ring in an untargeted lipophilic pocket within the active site of the phosphoinositide phospholipase C (PI-PLC) enzyme.

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