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Journal articles on the topic 'Macrocyclic lactones'

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1

Lermer, Leonard, Edward G. Neeland, James P. Ounsworth, Russell J. Sims, Samuel A. Tischler, and Larry Weiler. "The synthesis of β-keto lactones via cyclization of β-keto ester dianions or the cyclization of Meldrum's acid derivatives." Canadian Journal of Chemistry 70, no. 5 (May 1, 1992): 1427–45. http://dx.doi.org/10.1139/v92-180.

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Two new methods to synthesize macrocyclic β-keto lactones have been developed. The first involves the synthesis of ω-halo-β-keto esters and an intramolecular alkylation of the dianions to these compounds. The reaction is complicated by elimination in the small and medium ring systems and by difficulties in purifying the final products. However, it is possible to obtain modest yields of the desired β-keto lactones. This procedure was used to synthesize the 25- and 27-membered ring β-hydroxy lactones that are the constituents of termite defense compounds. The second method involves the thermolysis of acylated Meldrum's acid derivatives, which leads directly to β-keto lactones. This process gives modest yields of macrocyclic systems and good yield of the unsubstituted 3-oxopentan-5-olide (25). The 14-mem-[Formula: see text]bered macrocyclic β-keto lactone 9j has a complex 1H NMR spectrum, which has been interpreted in terms of multiple conformations. The temperature dependence of the NMR spectrum of 9j is consistent with entropic, rather than enthalpic, control of the equilibrium. Quasiharmonic entropy calculations are consistent with this model.
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2

J. Wolstenholme, Adrian, and Ray M. Kaplan. "Resistance to Macrocyclic Lactones." Current Pharmaceutical Biotechnology 13, no. 6 (April 1, 2012): 873–87. http://dx.doi.org/10.2174/138920112800399239.

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3

Faizullina, Lily Kh, Yulia A. Khalilova, Artur R. Tagirov, Yulia S. Galimova, Farid A. Valeev, Alyona S. Ryabova, and Naila F. Galimzyanova. "Evaluation of fungicidal, bactericidal and anti-tumor activities of lactones of medium and large sizes of cycles obtained from levoglucosenone." Butlerov Communications 59, no. 9 (September 30, 2019): 100–105. http://dx.doi.org/10.37952/roi-jbc-01/19-59-9-100.

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Medium and large lactones attract the attention of chemists by the uniqueness of their structure, versatile biological activity and limited availability. Among the secondary metabolites of this group, β-lactones are more common, then γ- and δ-lactones, classical and non-classical macrolides, polyene antibiotics, spiro-macrolides and macrolactones. On the basis of many lactones, important preparations of the most diverse pharmacological action have been obtained. Earlier, we proposed a 3-stage scheme for the synthesis of chiral lactones of medium and large size based on levoglucosenone. The lactones obtained according to this scheme contain the carbohydrate residue annelated at the ,γ -positions relative to the hydroxy group. To study the structure-activity relationship, it is necessary to establish the biological role of this carbohydrate residue in reference lactones. For this purpose, a number of lactones were obtained on the basis of levoglucosenone and their in vitro bioscreening of antifungal, antimicrobial, and antitumor activity was performed. It was found that the methyl substituent in the ω-position in the lactone and the benzene ring annulated with the lactone cycle exhibit a slight fungistatic activity towards the fungi: Bipolaris sorokiniana, Fusarium oxysporum, Rhizoctonia solani. Macrocyclic lactone and lactone annelated benzene ring showed weak cytotoxic properties against cells of LOX IMVI (melanoma) and A498, UO-31 (kidney cancer).
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4

Guo, Zhi Wei, and Charles J. Sih. "Enzymic synthesis of macrocyclic lactones." Journal of the American Chemical Society 110, no. 6 (March 1988): 1999–2001. http://dx.doi.org/10.1021/ja00214a073.

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5

Barrow, Colin J. "New Macrocyclic Lactones from aPenicilliumSpecies." Journal of Natural Products 60, no. 10 (October 1997): 1023–25. http://dx.doi.org/10.1021/np970200x.

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6

Burger, B. V., W. M. Mackenroth, Denice Smith, H. S. C. Spies, and P. R. Atkinson. "Chemical Composition of the Wing Gland and Abdominal Hair Pencil Secretions of the Male African Sugarcane Borer, Eldana saccharina (Lepidoptera: Pyralidae)." Zeitschrift für Naturforschung C 40, no. 11-12 (October 1, 1985): 847–50. http://dx.doi.org/10.1515/znc-1985-11-1216.

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Abstract In addition to the previously identified wing gland lactone, eldanolide, and the tail brush components, vanillin and p-hydroxybenzaldehyde, several further terpenoid compounds, saturated and unsaturated alcohols and acids, a thioalcohol, as well as two saturated macrocyclic lactones, were identified in the wing gland and tail brush secretions of the male African sugarcane borer Eldana saccharina (Walker).
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7

Steitz, Iris, Katharina Brandt, Felix Biefel, Ädem Minat, and Manfred Ayasse. "Queen Recognition Signals in Two Primitively Eusocial Halictid Bees: Evolutionary Conservation and Caste-Specific Perception." Insects 10, no. 12 (November 21, 2019): 416. http://dx.doi.org/10.3390/insects10120416.

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Queen signals are known to regulate reproductive harmony within eusocial colonies by influencing worker behavior and ovarian physiology. However, decades of research have resulted in the identification of just a few queen signals, and studies of their mode of action are rare. Our aim was to identify queen recognition signals in the halictid bee Lasioglossum pauxillum and to analyze caste differences in the olfactory perception of queen signals in L. pauxillum and the closely related species L. malachurum. We performed chemical analyses and bioassays to test for caste differences in chemical profiles and worker behavior influenced by queen-specific compounds in L. pauxillum. Our results indicated that caste differences in the chemical profiles were mainly attributable to higher amounts of macrocyclic lactones in queens. Bioassays demonstrated a higher frequency of subordinate behavior in workers elicited by queen-specific amounts of macrocyclic lactones. Thus, macrocyclic lactones function as queen recognition signals in L. pauxillum, as in L. malachurum. Using electrophysiological analyses, we have demonstrated that queens of both tested species lack antennal reactions to certain macrocyclic lactones. Therefore, we assume that this is a mechanism to prevent reproductive self-inhibition in queens. Our results should stimulate debate on the conservation and mode of action of queen signals.
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8

Yang, Chen-Chang. "Acute Human Toxicity of Macrocyclic Lactones." Current Pharmaceutical Biotechnology 13, no. 6 (April 1, 2012): 999–1003. http://dx.doi.org/10.2174/138920112800399059.

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9

Bowman, Dwight D., and Claire Mannella. "Macrocyclic Lactones and Dirofilaria immitis Microfilariae." Topics in Companion Animal Medicine 26, no. 4 (November 2011): 160–72. http://dx.doi.org/10.1053/j.tcam.2011.07.001.

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10

Picinin, L. C. A., I. M. Toaldo, R. B. Hoff, F. N. Souza, M. O. Leite, L. M. Fonseca, S. A. Diniz, et al. "Climate conditions associated with the occurrence of antimicrobial and macrocyclic lactone residues in bulk tank milk." Arquivo Brasileiro de Medicina Veterinária e Zootecnia 69, no. 2 (April 2017): 474–82. http://dx.doi.org/10.1590/1678-4162-8854.

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ABSTRACT The present study aimed to identify the climate condition parameters that are associated with the occurrence of antimicrobial and macrocyclic lactone residues in bulk tank milk using a multivariate principal components analysis (PCA). A total of 132 raw milk samples were collected at dairy farms in Minas Gerais State in Brazil and analyzed for 35 analytes, comprising macrocyclic lactones and antibacterials, using liquid chromatography coupled with mass spectrometry in tandem mode spectrometry. Of the 132 samples, 34 (25.76%) bulk tank milk samples were positive for at least one analyte. PCA showed that antimicrobial residues in bulk tank milk occurred less frequently on days with a higher average temperature, maximum temperature and temperature-humidity index. In contrast, relative humidity was inversely associated with antimicrobial residues in raw milk. The PCA showed that daily milk production was also related to macrocyclic lactone residues, while rainfall showed an inverse association. Thus, some climate conditions, such as average temperature, maximum temperature and temperature-humidity index, can predict the moments with lower risk of occurrence of antimicrobial residues in bulk tank milk, in contrast to relative humidity. Furthermore, the risk of macrocyclic lactone residues in bulk tank milk was higher in months with less rainfall.
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11

Scháňková, Š., M. Maršálek, P. Wagnerová, D. Lukešová, L. Starostová, I. Jankovská, Z. Čadková, et al. "Treatment failure of ivermectin for Oxyuris equi in naturally infected ponies in Czech Republic." Helminthologia 50, no. 3 (September 1, 2013): 232–34. http://dx.doi.org/10.2478/s11687-013-0134-2.

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Abstract Nine ponies (20 months of age) with naturally acquired cyathostome and pinworm infections were treated orally with ivermectin at a dosage of 400 μg /kg. Ivermectin was highly effective on the cyathostome infection. However, adult Oxyuris equi were present in six horses. In recent years, anthelmintic treatment with macrocyclic lactones have not appeared to deliver the expected efficacy against equine pinworms (Oxyuris equi) in the USA. This is the first European study to demonstrate anthelmintic resistance in Oxyuris equi to macrocyclic lactones in naturally infected ponies (Czech Republic).
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12

Hayashikoshi, Takaoki, Motoji Abe, and Takeo Kurata. "A New Synthetic Method of Macrocyclic Ketones and Unsaturated Macrocyclic Lactones." Journal of The Japan Petroleum Institute 39, no. 1 (1996): 74–77. http://dx.doi.org/10.1627/jpi1958.39.74.

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13

A. McKellar, Quintin, and Cengiz Gokbulut. "Pharmacokinetic Features of the Antiparasitic Macrocyclic Lactones." Current Pharmaceutical Biotechnology 13, no. 6 (April 1, 2012): 888–911. http://dx.doi.org/10.2174/138920112800399194.

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14

T. Lyons, E., and S. C. Tolliver. "Macrocyclic Lactones for Parasite Control in Equids." Current Pharmaceutical Biotechnology 13, no. 6 (April 1, 2012): 1070–77. http://dx.doi.org/10.2174/138920112800399310.

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15

Dale, Johannes, Jan-Erik Schwartz, Ji-Yu Chu, Li-An Lu, Pui-Fun Louisa Tang, and Anders Ljungqvist. "Macrocyclic Oligolactones by Oligomerization of Simple Lactones." Acta Chemica Scandinavica 40b (1986): 559–67. http://dx.doi.org/10.3891/acta.chem.scand.40b-0559.

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16

Frank, Judit, Gyula Dékány, and István Pelczer. "Primycin II. New macrocyclic lactones via translactonization." Tetrahedron Letters 33, no. 48 (November 1992): 7393–96. http://dx.doi.org/10.1016/s0040-4039(00)60197-1.

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17

Maguire, Nuala M., Mary F. Mahon, Kieran C. Molloy, Gordon Read, Stanley M. Roberts, and Vladimir Sik. "Chemoenzymatic synthesis of some macrocyclic C13-lactones." Journal of the Chemical Society, Perkin Transactions 1, no. 8 (1991): 2054. http://dx.doi.org/10.1039/p19910002054.

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18

Kubota, Ryou, Shohei Tashiro, and Mitsuhiko Shionoya. "Chiral metal–macrocycle frameworks: supramolecular chirality induction and helicity inversion of the helical macrocyclic structures." Chemical Science 7, no. 3 (2016): 2217–21. http://dx.doi.org/10.1039/c5sc04570c.

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19

Majumdar, Swapan, Jewel Hossain, Ramalingam Natarajan, Ashish K. Banerjee, and Dilip K. Maiti. "Phthalate tethered strategy: carbohydrate nitrile oxide cycloaddition to 12–15 member chiral macrocycles with alkenyl chain length controlled orientation of bridged isoxazolines." RSC Advances 5, no. 129 (2015): 106289–93. http://dx.doi.org/10.1039/c5ra22436e.

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20

Hodge, Philip, and Abdel B. Chakiri. "The use of polymer-supported Candida antarctica lipase B to achieve the entropically-driven ring-opening polymerization of macrocyclic bile acid derivatives via transesterification: selectivity of the reactions and the structures of the polymers produced." RSC Advances 5, no. 113 (2015): 93057–66. http://dx.doi.org/10.1039/c5ra17954h.

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21

Muñoz-Muñoz, Lara, Carolyn Shoen, Gaye Sweet, Asunción Vitoria, Tim J. Bull, Michael Cynamon, Charles J. Thompson, and Santiago Ramón-García. "Repurposing Avermectins and Milbemycins against Mycobacteroides abscessus and Other Nontuberculous Mycobacteria." Antibiotics 10, no. 4 (April 3, 2021): 381. http://dx.doi.org/10.3390/antibiotics10040381.

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Infections caused by nontuberculous mycobacteria (NTM) are increasing worldwide, resulting in a new global health concern. NTM treatment is complex and requires combinations of several drugs for lengthy periods. In spite of this, NTM disease is often associated with poor treatment outcomes. The anti-parasitic family of macrocyclic lactones (ML) (divided in two subfamilies: avermectins and milbemycins) was previously described as having activity against mycobacteria, including Mycobacterium tuberculosis, Mycobacterium ulcerans, and Mycobacterium marinum, among others. Here, we aimed to characterize the in vitro anti-mycobacterial activity of ML against a wide range of NTM species, including Mycobacteroides abscessus. For this, Minimum Inhibitory Concentration (MIC) values of eight ML were determined against 80 strains belonging to nine different NTM species. Macrocyclic lactones showed variable ranges of anti-mycobacterial activity that were compound and species-dependent. Milbemycin oxime was the most active compound, displaying broad-spectrum activity with MIC lower than 8 mg/L. Time kill assays confirmed MIC data and showed bactericidal and sterilizing activity of some compounds. Macrocyclic lactones are available in many formulations and have been extensively used in veterinary and human medicine with suitable pharmacokinetics and safety properties. This information could be exploited to explore repurposing of anti-helminthics for NTM therapy.
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22

Geyer, Joachim, and Christina Janko. "Treatment of MDR1 Mutant Dogs with Macrocyclic Lactones." Current Pharmaceutical Biotechnology 13, no. 6 (April 1, 2012): 969–86. http://dx.doi.org/10.2174/138920112800399301.

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23

KURATA, Takeo, and Ken-ichi NARITA. "Synthesis of Macrocyclic Lactones by Intramolecular Radical Cyclization." Journal of Japan Oil Chemists' Society 40, no. 1 (1991): 39–45. http://dx.doi.org/10.5650/jos1956.40.39.

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24

Zhi-wei, Guo, T. K. Ngooi, A. Scilimati, Gerd Fülling, and Charles J. Sih. "Macrocyclic lactones via biocatalysis in non-aqueous media." Tetrahedron Letters 29, no. 44 (January 1988): 5583–86. http://dx.doi.org/10.1016/s0040-4039(00)80817-5.

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25

Funk, Raymond L., Matthew M. Abelman, and John D. Munger. "Claisen-rearrangement-mediated ring contraction of macrocyclic lactones." Tetrahedron 42, no. 11 (January 1986): 2831–46. http://dx.doi.org/10.1016/s0040-4020(01)90572-1.

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26

Griesbeck, Axel G., Frank Nerowski, and Johann Lex. "Decarboxylative Photocyclization: Synthesis of Benzopyrrolizidines and Macrocyclic Lactones." Journal of Organic Chemistry 64, no. 14 (July 1999): 5213–17. http://dx.doi.org/10.1021/jo990390b.

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27

Galarini, Roberta, Giorgio Saluti, Simone Moretti, Danilo Giusepponi, and Guglielmo Dusi. "Determination of macrocyclic lactones in food and feed." Food Additives & Contaminants: Part A 30, no. 6 (June 2013): 1068–79. http://dx.doi.org/10.1080/19440049.2013.781275.

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28

VEALE, PI. "Resistance to macrocyclic lactones in nematodes of goats." Australian Veterinary Journal 80, no. 5 (May 2002): 303–4. http://dx.doi.org/10.1111/j.1751-0813.2002.tb10852.x.

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29

Yavolovskii, A. A., �. I. Ivanov, and Yu �. Ivanov. "Synthesis of new macrocyclic lactams, lactones, and thiolactones." Chemistry of Heterocyclic Compounds 32, no. 8 (August 1996): 975–78. http://dx.doi.org/10.1007/bf01176976.

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30

Liu, Changhui, Jennifer K. Schilling, Rudravajhala Ravindra, Susan Bane, and David G. I. Kingston. "Syntheses and bioactivities of macrocyclic paclitaxel bis-lactones." Bioorganic & Medicinal Chemistry 12, no. 23 (December 2004): 6147–61. http://dx.doi.org/10.1016/j.bmc.2004.09.002.

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31

Franich, Robert A. "Macrocyclic lactones in radiata pine forest floor litter." Phytochemistry 31, no. 7 (July 1992): 2532–33. http://dx.doi.org/10.1016/0031-9422(92)83318-s.

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32

Hou, Chuan Jin, Xiao Mei Liang, Jing Ping Wu, and Dao Quan Wang. "Synthesis of macrocyclic lactones with methoxysulfonyl side chain." Chinese Chemical Letters 19, no. 4 (April 2008): 403–5. http://dx.doi.org/10.1016/j.cclet.2008.01.039.

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33

Kricheldorf, Hans R., Soo-Ran Lee, and Nicole Schittenhelm. "Macrocycles, 1. Macrocyclic polymerizations of (thio)lactones - stepwise ring expansion and ring contraction." Macromolecular Chemistry and Physics 199, no. 2 (February 1, 1998): 273–82. http://dx.doi.org/10.1002/(sici)1521-3935(19980201)199:2<273::aid-macp273>3.0.co;2-d.

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34

Kricheldorf, Hans R., Soo-Ran Lee, and Nicole Schittenhelm. "Macrocycles, 1. Macrocyclic polymerizations of (thio)lactones – stepwise ring expansion and ring contraction." Macromolecular Chemistry and Physics 199, no. 2 (February 1998): 273–82. http://dx.doi.org/10.1002/macp.1998.021990215.

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35

Pungente, Michael D., Larry Weiler, and Hermann J. Ziltener. "Antibody-catalyzed formation of a 14-membered ring lactone." Canadian Journal of Chemistry 80, no. 12 (December 1, 2002): 1643–45. http://dx.doi.org/10.1139/v02-185.

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Monoclonal antibody (MAb) F123, raised against a macrocyclic phosphonate transition-state analogue, catalyzed an intramolecular transesterification of the corresponding hydroxy ester to give a 14-membered ring lactone. The MAb reaction displayed enzyme-like Michaelis–Menten kinetics with a Km of 255 µM and a kcat of 0.01 min–1 based on p-nitrophenol release and calculated on an active-site basis. Substrate specificity and competitive inhibition by a transition state analogue (Ki = 3 µM) demonstrated that the catalytic activity was associated with binding in the antibody-combining site. The lactone product was isolated from a large-scale catalytic experiment through ether extraction and identified by gas chromatography – mass spectroscopy.Key words: macrocyclization, lactones, catalytic antibodies.
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36

BILMEN, Jonathan G., Laura L. WOOTTON, and Francesco MICHELANGELI. "The inhibition of the sarcoplasmic/endoplasmic reticulum Ca2+-ATPase by macrocyclic lactones and cyclosporin A." Biochemical Journal 366, no. 1 (August 15, 2002): 255–63. http://dx.doi.org/10.1042/bj20020431.

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The pharmacology of macrocyclic lactones is varied, with many beneficial effects in treating disease processes. FK-506, rapamycin and ascomycin have been utilized as immunosuppressant agents. Ivermectin is typically used to treat parasitic worm infections in mammals. Another immunosuppressant, cyclosporin A, is a cyclic oligotide that has similar immunosuppressant properties to those exerted by macrocyclic lactones. Here we report on the inhibition by these compounds of sarcoplasmic/endoplasmic-reticulum Ca2+-ATPase (SERCA) Ca2+ pumps. Ivermectin, cyclosporin A and rapamycin all inhibited the skeletal muscle sarcoplasmic reticulum Ca2+-ATPase (SERCA1). In addition, although ivermectin inhibited brain microsomal endoplasmic reticulum (type 2b) Ca2+-ATPase, cyclosporin A and rapamycin did not. As cyclosporin A also did not inhibit cardiac Ca2+-ATPase activity, this would suggest that it could be an isoform-specific inhibitor. Ivermectin was shown to be the most potent Ca2+-ATPase inhibitor of the macrocyclic lactones (IC50 = 7μM). It appears to show a ‘competitive’ inhibition with respect to high concentrations of ATP by increasing the regulatory binding site Km but without affecting the catalytic site Km. In addition, ivermectin stabilizes the ATPase in an E1 conformational state, and inhibits Ca2+ release from the enzyme during turnover. This would suggest that ivermectin inhibits Ca2+ release from the luminal binding sites of the phosphoenzyme intermediate, a step that is known to be accelerated by high [ATP].
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37

R. Ballweber, Lora, and Laurie A. Baeten. "Use of Macrocyclic Lactones in Cattle in the USA." Current Pharmaceutical Biotechnology 13, no. 6 (April 1, 2012): 1061–69. http://dx.doi.org/10.2174/138920112800399149.

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38

Mealey, Katrina L. "Canine ABCB1 and macrocyclic lactones: Heartworm prevention and pharmacogenetics." Veterinary Parasitology 158, no. 3 (December 2008): 215–22. http://dx.doi.org/10.1016/j.vetpar.2008.09.009.

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39

Noda, Yoshihiro, and Hitoshi Kashin. "Synthesis of Both Enantiomers of Four Different Macrocyclic Lactones." HETEROCYCLES 48, no. 1 (1998): 5. http://dx.doi.org/10.3987/com-97-7991.

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40

Makita, Atushi, Takuya Nihira, and Yasuhiro Yamada. "Lipase catalyzed synthesis of macrocyclic lactones in organic solvents." Tetrahedron Letters 28, no. 7 (January 1987): 805–8. http://dx.doi.org/10.1016/s0040-4039(01)80995-3.

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41

Bayrakcı, M., and Ş. Ertul. "Synthesis of new macrocyclic lactones and their extraction study." Russian Journal of Organic Chemistry 44, no. 9 (September 2008): 1384–88. http://dx.doi.org/10.1134/s1070428008090236.

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42

Neves, José Henrique das, Nadino Carvalho, and Alessandro F. T. Amarante. "Dermatobia hominis : Potencial risk of resistance to macrocyclic lactones." Veterinary Parasitology 212, no. 3-4 (September 2015): 483–86. http://dx.doi.org/10.1016/j.vetpar.2015.06.029.

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43

Smith, Keith, Ian K. Morris, Philip G. Owen, and Robert J. Bass. "Synthesis of novel macrocyclic lactones with potential pharmacological activity." Journal of the Chemical Society, Perkin Transactions 1, no. 1 (1988): 77. http://dx.doi.org/10.1039/p19880000077.

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44

Karim, Mohammad R., and Paul Sampson. "A new and efficient approach to macrocyclic keto lactones." Journal of Organic Chemistry 55, no. 2 (January 1990): 598–605. http://dx.doi.org/10.1021/jo00289a040.

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45

Podda, Gianni, Luciana Corda, Carlo Anchisi, Beatrice Pelli, and Pietro Traldi. "Electron impact mass spectrometry of some macrocyclic polyether lactones." Organic Mass Spectrometry 22, no. 3 (March 1987): 162–68. http://dx.doi.org/10.1002/oms.1210220309.

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46

MAGUIRE, N. M., M. F. MAHON, K. C. MOLLOY, G. READ, S. M. ROBERTS, and V. SIK. "ChemInform Abstract: Chemoenzymatic Synthesis of Some Macrocyclic C13-Lactones." ChemInform 22, no. 46 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199146241.

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47

Matsuyama, Haruo, Takako Nakamura, Akinori Takatsuka, Michio Kobayashi, and Nobumasa Kamigata. "Novel Synthesis of Macrocyclic Lactones from ω-Carboxyalkylsulfonium Salts." Chemistry Letters 17, no. 11 (November 5, 1988): 1931–32. http://dx.doi.org/10.1246/cl.1988.1931.

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48

KAGEYAMA, YUKARI, TAKUYA NIHIRA, and YASUHIRO YAMADA. "Lipase-catalyzed Synthesis of Macrocyclic Lactones in Organic Solvents." Annals of the New York Academy of Sciences 613, no. 1 Enzyme Engine (December 1990): 681–85. http://dx.doi.org/10.1111/j.1749-6632.1990.tb18245.x.

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49

Tomiyama, Kenichi, Kazutoshi Sakurai, Yoshihiro Yaguchi, Yukihiro Kawakami, and Yoshinori Asakawa. "Characteristic Volatile Components of Trifoliate Orange Peel (Poncirus trifoliata)." Natural Product Communications 11, no. 8 (August 2016): 1934578X1601100. http://dx.doi.org/10.1177/1934578x1601100833.

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The volatile components of the peel of trifoliate orange { Poncirus trifoliata (L.) Raf.}, family Rutaceae, were investigated using SAFE technique after solvent extraction. Limonene was the most abundant component in the peel aroma extract, followed by myrcene, trans-β-ocimene, indole, β-caryophyllene, (3 E,6 E)-α-farnesene, germacrene D, and β-phellandrene. In this study, the single sulfur- and nitrogen-containing compound, 4-methyl-5-vinylthiazole, and two macrocyclic lactones, cyclododecanolide and (7 Z,10 Z,13 Z)-hexadecatrien-16-olide, were identified as citrus aroma components for the first time. As a result of AEDA for the polar fraction of the aroma extract, indole, ethyl octanoate and those macrocyclic lactones with musky notes were found to be responsible for the characteristic aroma profile of the peel of trifoliate orange. The enantiomeric distributions of the four odor-active components, linalool, β-citronellol, ethyl 2-methylbutanoate, and 2-methylbutanoic acid, were also determined by means of multidimensional chiral GC/MS.
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Arimura, Junya, Tsutomu Mizuta, Yoshikazu Hiraga, and Manabu Abe. "Formation of macrocyclic lactones in the Paternò–Büchi dimerization reaction." Beilstein Journal of Organic Chemistry 7 (February 28, 2011): 265–69. http://dx.doi.org/10.3762/bjoc.7.35.

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Abstract:
Furan-2-ylmethyl 2-oxoacetates 1a,b, in which the furan ring and the carbonyl moiety were embedded intramolecularly, were synthesized from commercially available furan-2-ylmethanol and their photochemical reaction (hν > 290 nm) was investigated. Twelve-membered macrocyclic lactones 2a,b with C i symmetry including two oxetane-rings, which are the Paternò–Büchi dimerization products, were isolated in ca. 20% yield. The intramolecular cyclization products, such as 3-alkoxyoxetane and 2,7-dioxabicyclo[2.2.1]hept-5-ene derivatives, were not detected in the photolysate.
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