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Relevant bibliographies by topics / Macrocyclic lactones

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Academic literature on the topic 'Macrocyclic lactones'

Author: Grafiati

Published: 4 June 2021

Last updated: 5 February 2022

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Journal articles on the topic "Macrocyclic lactones"

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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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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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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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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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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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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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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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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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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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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Dissertations / Theses on the topic "Macrocyclic lactones"

1

Reather, James Andrew. "Late steps in the biosynthesis of macrocyclic lactones." Thesis, University of Cambridge, 2000. https://www.repository.cam.ac.uk/handle/1810/251730.

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Savill, Karen. "Investigations of 1,2,4-trioxanes as precursors of macrocyclic lactones." Thesis, Heriot-Watt University, 1993. http://hdl.handle.net/10399/1392.

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Munt, Simon Peter. "Radical cyclizations : an approach to the bryostatins." Thesis, University of Oxford, 1990. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.258009.

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Mowbray, Charles Eric. "Arcimycins : selective degradation and semi-synthesis." Thesis, University of Exeter, 1989. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.235913.

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Yilmaz, Esra [Verfasser]. "Metabolism of macrocyclic lactones and benzimidazoles in parasitic nematodes / Esra Yilmaz." Berlin : Freie Universität Berlin, 2019. http://d-nb.info/1201346665/34.

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Galazzo, Daniel. "A comparison of laboratory and field resistance to macrocyclic lactones in Haemonchus contortus /." Thesis, McGill University, 2004. http://digitool.Library.McGill.CA:80/R/?func=dbin-jump-full&object_id=82236.

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Sustainable parasite control in livestock depends on anthelmintic drugs. The nematode Haemonchus contortus, the most important intestinal parasite of sheep and goats has developed resistance to all classes of anthelmintics including moxidectin, the most potent of the macrocyclic lactones. Pyrosequencing was used to screen H. contortus laboratory and field strains for single nucleotide polymorphisms (SNPs) associated with resistance in three genes, and determine their involvement in field resistance to macrocyclic lactones. Specific SNPs increased in frequency in ivermectin/moxidectin laboratory selected strains for all three genes. These did not protect a resistant field strain from a field dose of ivermectin and were not the major mechanism of resistance in the field strain. A gamma-aminobutyric acid chloride receptor SNP may be a potential marker for moxidectin resistance in the field. This study indicates results obtained from laboratory strains selected with sub-therapeutic doses of drug may not reflect the situation in the field.

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Godoy, Rosas Pablo. "Functional analysis of «Haemonchus contortus» P-glycoprotein-A and interaction with macrocyclic lactones." Thesis, McGill University, 2011. http://digitool.Library.McGill.CA:80/R/?func=dbin-jump-full&object_id=97122.

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Macrocyclic lactone (ML) resistance has been described in the parasitic nematode, Haemonchus contortus. One of the mechanisms involved could be the over expression of P-glycoproteins (Pgps) which are ABC transporters. These proteins may influence the concentration of MLs that reach their target. In H. contortus one ABC transporter that is overexpressed in ML resistant parasites is Pgp-A (HcPgp-A). The goal of this project was the expression of HcPgp-A, in transfected LLC-PK1 cells, and to see the effect of ivermectin and moxidectin on inhibition of rhodamine 123 transport by the transfected cells. Rhodamine123 was actively transported by HcPgp-A. Ivermectin was four fold more potent at inhibiting rhodamine 123 transport by HcPgp-A than was moxidectin. The work provides the first information showing that MLs can inhibit the transport of Pgp substrates by a parasitic nematode ABC transporter and may indicate an active role for H. contortus Ppgs in ML resistance.
La résistance aux lactones macrocycliques (LM) est bien connue chez le parasite nématode Haemonchus contortus. La surexpression de P-glycoprotéines (Pgp), qui sont des ABC transporteurs, pourrait être impliquée dans un des mécanismes de la résistance aux LM. Ces protéines peuvent influencer la concentration de LM qui atteint leur cible. Pgp-A (HcPgp-A) est un ABC transporteur d' H. contortus qui est surexprimé chez les parasites résistants aux LM. Le but de cette étude était d'exprimer la P-glycoprotéine-A d'H. contortus dans des cellules transfectées LLC-PK1 afin d'évaluer les effets de l'ivermectine et de la moxidectine sur l'inhibition du transport de la rhodamine 123. La rhodamine 123 s'est avérée être transportée activement par HcPgp-A. Les effets de l'ivermectine sur l'inhibition du transport de la rhodamine 123 par HcPgp-A étaient quatre fois plus importants que ceux de la moxidectine. L'étude a montré pour la première fois que les LM pouvaient inhiber le transport des substrats de la P-glycoprotéine grâce à un ABC transporteur d'un nématode parasite. Cette information pourrait indiquer un rôle actif des Pgps d'H. contortus dans la résistance aux LM.

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Ramcharitar, Steve Harrinarine. "The synthesis of macrocyclic ketones and lactones : approaches to naturally occurring macrolyde antibiotics." Thesis, University of Oxford, 1991. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.302875.

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Maiti, Tushar B. (Tushar Baran). "An Approach Towards the Total Synthesis of Clonostachydiol." Thesis, University of North Texas, 1995. https://digital.library.unt.edu/ark:/67531/metadc278800/.

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The syntheses of the unsymmetrical 14-membered bismacrolides have been reviewed. A total synthesis of clonostachydiol, the latest to join this family, has been attempted using trimethylsilyl acetylene as the builiding block and palladium catalyzed reactions for the formation of key bonds. The alkyne groups were introduced by Stille coupling of trimethylstannylethynyltrimethylsilane with an acid chloride for one fragment and by addition of lithiotrimethylsilyl acetylene to an aldehyde for the other. Lactic acid derivatives were chosen as starting materials for both fragments, thus introducing two of the chiral centers. The remaining stereocenters were introduced using stereoselective reductions of ketones.

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10

Firas, Bassissi Mohamad. "Le rôle des lipides et des lipoprotéines plasmatiques dans le transport et la pharmacocinétique des lactones macrocycliques (aspects pharmacologiques et toxicologiques)." Toulouse 3, 2006. http://www.theses.fr/2006TOU30025.

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Les Lactones Macrocycliques (LMs) sont des antiparasitaires largement utilisé en médecine vétérinaire contre les endo et les ectoparasites. Nos travaux révèlent pour la première fois l'implication des lipoprotéines dans le transport plasmatique des 5 différentes lactones (Ivermectine, Doramectine, Moxidectine, Abamectine, prinomectine) chez les différentes espèces animales cibles y compris l'homme. De plus nous avons pu mettre en évidence l'impact des perturbations du profil plasmatique en lipides et lipoprotéines sur la pharmacocinétique et la distribution plasmatique des LMs. Au même titre nous avons démontré le rôle crucial de la circulation lymphatique dans l'absorption intestinale de la moxidectine ce que nous a permis d'optimiser leur biodisponibilité suite à une coadministration des lipides par voie orale. De même la mise en oeuvre d'une formulation liposomale de l'ivermectine a produit une biodisponibilité convenable toutefois une évaluation de la distribution tissulaire et de l'efficacité de ces formulations prometteuses s'avérera nécessaire. En conclusion nos travaux suggèrent que les lipides et les lipoprotéines plasmatiques jouent un rôle prépondérant dans le transport et le devenir des LMs dans l'organisme hôte
Macrocyclic Lactones (MLs) are potent anthelmintic drugs widely used for control of both internal and external parasites in domestic animals and livestock. In a first step our work shows that the five MLs tested (Ivermectin, Doramectin, Moxidectin, Abamectin, Eprinomectin) were extensively distributed into plasma lipoproteins with a preferential association to HDL in both animal species including humans. In the second step we have reported the effect of dyslipidemias on the plasma distribution and pharmacokinetic of moxidectin in human and rabbit model. On the other hand our investigation clearly indicated the major contribution of lymphatic circulation in the process of intestinal absorption of moxidectin and subsequently to its systemic bioavailability. Our findings could allow the enhancement of oral MLs bioavailability by using lipid-based ormulation. Finally our data demonstrated that the use of liposomal formulation represents promising tool by improving the bioavailability and the efficacy of ivermectin and related drugs. Furthermore, in vivo and in vitro investigations are needed to demonstrate the ability of liposome to improve the ivermectin efficacy. In conclusion our works suggest that the lipids and lipoproteins play a primordial role in the transport and disposition of MLs in the host's organism

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Books on the topic "Macrocyclic lactones"

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Vercruysse, J., and R. S. Rew, eds. Macrocyclic lactones in antiparasitic therapy. Wallingford: CABI, 2002. http://dx.doi.org/10.1079/9780851996172.0000.

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J, Vercruysse, and Rew Robert S, eds. Macrocyclic lactones in antiparasitic therapy. Oxon, UK: CABI Pub., 2002.

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Vercruysse, J. Macrocyclic Lactones in Antiparasitic Therapy. CABI, 2003.

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Book chapters on the topic "Macrocyclic lactones"

1

Boeckman, R. K., and S. W. Goldstein. "The Total Synthesis of Macrocyclic Lactones." In Total Synthesis of Natural Products, 1–139. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2007. http://dx.doi.org/10.1002/9780470129708.ch1.

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Hong, Johnny C., and Barry D. Kahan. "The potential role of immunosuppressive macrocyclic lactones." In Modern Immunosuppressives, 43–75. Basel: Birkhäuser Basel, 2001. http://dx.doi.org/10.1007/978-3-0348-8352-8_4.

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Kricheldorf, Hans R., Soo-Ran Lee, Sven Eggerstedt, Dennis Langanke, and Karsten Hauser. "Macrocyclic Polymerizations of Lactones: A New Approach to Molecular Engineering." In ACS Symposium Series, 135–45. Washington, DC: American Chemical Society, 2001. http://dx.doi.org/10.1021/bk-2000-0764.ch011.

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"Macrocyclic Lactones." In Encyclopedia of Parasitology, 1509. Berlin, Heidelberg: Springer Berlin Heidelberg, 2016. http://dx.doi.org/10.1007/978-3-662-43978-4_1812.

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Rugg, D., S. D. Buckingham, D. B. Sattelle, and R. K. Jansson. "The Insecticidal Macrocyclic Lactones." In Comprehensive Molecular Insect Science, 25–52. Elsevier, 2005. http://dx.doi.org/10.1016/b0-44-451924-6/00065-x.

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Gwaltney-Brant, Sharon M., Camille DeClementi, and Ramesh C. Gupta. "Macrocyclic Lactone Endectocides." In Veterinary Toxicology, 539–50. Elsevier, 2018. http://dx.doi.org/10.1016/b978-0-12-811410-0.00043-x.

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Gwaltney-Brant, Sharon M., Camille DeClementi, and Ramesh C. Gupta. "Macrocyclic lactone endectocides." In Veterinary Toxicology, 609–19. Elsevier, 2012. http://dx.doi.org/10.1016/b978-0-12-385926-6.00051-x.

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Dueñas-González, Alfonso, and Mandy Juárez-Rodríguez. "Ivermectin: Potential Repurposing of a Versatile Antiparasitic as a Novel Anticancer." In Repurposed Drugs for Cancer [Working Title]. IntechOpen, 2021. http://dx.doi.org/10.5772/intechopen.99813.

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Drug repositioning is a alternative strategy to discover and develop anticancer drugs based on identification of new mechanisms of actions and indications for existing compounds. Ivermectin belongs to the avermectin group of compounds, a series of 16-membered macrocyclic lactone moieties discovered in 1967 and FDA-approved for human use since 1987. Ivermectin has since been used by millions of people worldwide, and have demonstrated a wide margin of clinical safety. Here we summarize the in vitro and in vivo evidence demonstrating ivermectin\'s potential as a multitargeting anticancer drug that exerts antitumor effects against different tumor types. Notably, the in vitro and in vivo antitumor activities of ivermectin are achieved at concentrations that can be clinically achieved based on human pharmacokinetic studies done in the clinical studies. Moreover, repurposed ivermectin safety has been well established recently in clinical studies against COVID-19. Consequently, we believe that ivermectin is an excellent potential candidate drug that can be repurposed for cancer and deserves rigorous evaluation against a variety of cancers in well-designed clinical trials.

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Tidwell, T. T. "A Macrocyclic Lactone by the Ketene-Claisen Reaction of Dichloroketene with a Vinyltetrahydropyran." In Three Carbon-Heteroatom Bonds: Thio-, Seleno-, and Tellurocarboxylic Acids and Derivatives; Imidic Acids and Derivatives; Ortho Acid Derivatives, 1. Georg Thieme Verlag KG, 2006. http://dx.doi.org/10.1055/sos-sd-023-00116.

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Taber, Douglass. "The Ley Synthesis of Rapamycin." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0090.

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Rapamycin 3 is used clinically as an immunosuppressive agent. The synthesis of 3 ( Angew. Chem. Int. Ed. 2007, 46, 591) by Steven V. Ley of the University of Cambridge was based on the assembly and subsequent coupling of the iododiene 1 and the stannyl alkene 2. The lactone of 1 was prepared by Fe-mediated cyclocarbonylation of the alkenyl epoxide 5, following the protocol developed in the Ley group. The cyclohexane of 2 was constructed by SnCl4 -mediated cyclization of the allyl stannane 9, again employing a procedure developed in the Ley group. Hydroboration delivered the aldehyde 11, which was crotylated with 12, following the H. C. Brown method. The alcohol so produced (not illustrated) was used to direct the diastereoselectivity of epoxidation, then removed, to give 13. Coupling with 14 then led to 2. Combination of 1 with 2 led to 15, which was condensed with catechol to give the macrocycle 16. Exposure of 16 to base effected Dieckmann cyclization, to deliver the ringcontracted macrolactone 17, which was carried on to (-)-rapamycin 3.

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