دورية أكاديمية
Jacobsen catalyst as a cytochrome P450 biomimetic model for the metabolism of monensin A.
العنوان: | Jacobsen catalyst as a cytochrome P450 biomimetic model for the metabolism of monensin A. |
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المؤلفون: | Rocha BA; Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, 14040-901 Ribeirão Preto, SP, Brazil., de Oliveira AR; Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, 14040-901 Ribeirão Preto, SP, Brazil., Pazin M; Departamento de Análises Clínicas, Toxicológicas e Bromatológicas, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, 14040-903 Ribeirão Preto, SP, Brazil., Dorta DJ; Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, 14040-901 Ribeirão Preto, SP, Brazil., Rodrigues AP; Laboratório de Pesquisa, Desenvolvimento e Inovação, Apis Flora Industrial e Comercial LTDA, 140120-670 Ribeirão Preto, SP, Brazil., Berretta AA; Laboratório de Pesquisa, Desenvolvimento e Inovação, Apis Flora Industrial e Comercial LTDA, 140120-670 Ribeirão Preto, SP, Brazil., Peti AP; Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, 14040-901 Ribeirão Preto, SP, Brazil., de Moraes LA; Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, 14040-901 Ribeirão Preto, SP, Brazil., Lopes NP; Núcleo de Pesquisas em Produtos Naturais e Sintéticos, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, 14040-903 Ribeirão Preto, SP, Brazil., Pospíšil S; Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeňská, CZ-142 20 Prague, Czech Republic., Gates PJ; School of Chemistry, University of Bristol, Bristol BS8 1TS, UK., Assis Md; Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, 14040-901 Ribeirão Preto, SP, Brazil. |
المصدر: | BioMed research international [Biomed Res Int] 2014; Vol. 2014, pp. 152102. Date of Electronic Publication: 2014 May 28. |
نوع المنشور: | Journal Article; Research Support, Non-U.S. Gov't |
اللغة: | English |
بيانات الدورية: | Publisher: Hindawi Pub. Co Country of Publication: United States NLM ID: 101600173 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 2314-6141 (Electronic) NLM ISO Abbreviation: Biomed Res Int Subsets: MEDLINE |
أسماء مطبوعة: | Original Publication: New York, NY : Hindawi Pub. Co. |
مواضيع طبية MeSH: | Antifungal Agents*/pharmacokinetics , Antifungal Agents*/pharmacology , Models, Biological* , Monensin*/pharmacokinetics , Monensin*/pharmacology, Cytochrome P-450 Enzyme System/*metabolism , Mitochondria, Liver/*metabolism, Animals ; Bacteria/growth & development ; Oxidation-Reduction/drug effects ; Rats |
مستخلص: | Monensin A is a commercially important natural product isolated from Streptomyces cinnamonensins that is primarily employed to treat coccidiosis. Monensin A selectively complexes and transports sodium cations across lipid membranes and displays a variety of biological properties. In this study, we evaluated the Jacobsen catalyst as a cytochrome P450 biomimetic model to investigate the oxidation of monensin A. Mass spectrometry analysis of the products from these model systems revealed the formation of two products: 3-O-demethyl monensin A and 12-hydroxy monensin A, which are the same ones found in in vivo models. Monensin A and products obtained in biomimetic model were tested in a mitochondrial toxicity model assessment and an antimicrobial bioassay against Staphylococcus aureus, S. aureus methicillin-resistant, Staphylococcus epidermidis, Pseudomonas aeruginosa, and Escherichia coli. Our results demonstrated the toxicological effects of monensin A in isolated rat liver mitochondria but not its products, showing that the metabolism of monensin A is a detoxification metabolism. In addition, the antimicrobial bioassay showed that monensin A and its products possessed activity against Gram-positive microorganisms but not for Gram-negative microorganisms. The results revealed the potential of application of this biomimetic chemical model in the synthesis of drug metabolites, providing metabolites for biological tests and other purposes. |
References: | Planta Med. 2012 Dec;78(18):1939-41. (PMID: 23150073) J Pharmacol Exp Ther. 2002 Nov;303(2):601-7. (PMID: 12388641) J Anim Sci. 1984 Jun;58(6):1528-39. (PMID: 6378868) Am J Physiol. 1999 Jan;276(1):G1-6. (PMID: 9886971) Life Sci. 1996;59(20):PL309-15. (PMID: 8890952) Environ Toxicol Chem. 2007 Aug;26(8):1614-21. (PMID: 17702333) Toxicon. 2010 Jun 15;55(7):1331-7. (PMID: 20152851) Eur J Med Chem. 2012 Aug;54:804-12. (PMID: 22796040) Anal Bioanal Chem. 2008 May;391(1):79-96. (PMID: 18163163) J Vet Med A Physiol Pathol Clin Med. 2005 Jun;52(5):230-7. (PMID: 15943607) Analyst. 2001 Nov;126(11):1990-5. (PMID: 11763080) Am J Kidney Dis. 2001 Nov;38(5):1108-12. (PMID: 11684567) Basic Clin Pharmacol Toxicol. 2013 Jun;112(6):418-24. (PMID: 23302053) Mol Cancer Ther. 2010 Dec;9(12):3175-85. (PMID: 21159605) Ann Pharm Fr. 2011 Jan;69(1):62-9. (PMID: 21296219) Proc Natl Acad Sci U S A. 2013 May 21;110(21):8638-43. (PMID: 23650379) Anal Biochem. 1983 Oct 1;134(1):111-6. (PMID: 6660480) Pharmacol Rep. 2007 Jul-Aug;59(4):456-61. (PMID: 17901575) Biomed Res Int. 2013;2013:742149. (PMID: 23509771) Arq Neuropsiquiatr. 2001 Sep;59(3-A):596-8. (PMID: 11588643) J Virol. 1982 Sep;43(3):1102-12. (PMID: 6292453) J Chromatogr A. 2012 Aug 31;1253:94-104. (PMID: 22819368) Food Addit Contam. 2006 May;23(5):470-8. (PMID: 16644594) Biochim Biophys Acta. 1990 May 7;1031(2):225-46. (PMID: 2160275) Analyst. 2002 Apr;127(4):503-6. (PMID: 12022649) J Biomed Nanotechnol. 2012 Feb;8(1):172-81. (PMID: 22515105) Bioorg Med Chem Lett. 2012 Dec 1;22(23):7002-10. (PMID: 23063400) Microbiol Res. 2002;157(3):207-11. (PMID: 12398291) Adv Enzymol Relat Subj Biochem. 1956;17:65-134. (PMID: 13313307) J Antimicrob Chemother. 2001 Jul;48 Suppl 1:5-16. (PMID: 11420333) J Cell Biol. 2010 Dec 13;191(6):1141-58. (PMID: 21149567) Mol Microbiol. 2009 Apr;72(2):425-41. (PMID: 19291232) J Antibiot (Tokyo). 2011 Mar;64(3):249-56. (PMID: 21224863) Rapid Commun Mass Spectrom. 2002;16(5):414-20. (PMID: 11857725) Bioorg Med Chem Lett. 2008 Apr 15;18(8):2585-9. (PMID: 18375122) Xenobiotica. 2014 Apr;44(4):326-35. (PMID: 24134149) FEBS Lett. 2001 Apr 20;495(1-2):12-5. (PMID: 11322939) |
المشرفين على المادة: | 0 (Antifungal Agents) 9035-51-2 (Cytochrome P-450 Enzyme System) 906O0YJ6ZP (Monensin) |
تواريخ الأحداث: | Date Created: 20140703 Date Completed: 20150212 Latest Revision: 20211021 |
رمز التحديث: | 20240628 |
مُعرف محوري في PubMed: | PMC4058456 |
DOI: | 10.1155/2014/152102 |
PMID: | 24987668 |
قاعدة البيانات: | MEDLINE |
تدمد: | 2314-6141 |
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DOI: | 10.1155/2014/152102 |