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- Title
Jacobsen Catalyst as a Cytochrome P450 Biomimetic Model for the Metabolism of Monensin A.
- Authors
Rocha, Bruno Alves; De Oliveira, Anderson Rodrigo Moraes; Pazin, Murilo; Dorta, Daniel Junqueira; Nascimento Rodrigues, Andresa Piacezzi; Berretta, Andresa Aparecida; Ferranti Peti, Ana Paula; De Moraes, Luiz Alberto Beraldo; Lopes, Norberto Peporine; Pospíšil, Stanislav; Gates, Paul Jonathan; das Dores Assis, Marilda
- Abstract
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 biomimeticmodel 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 livermitochondria 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 drugmetabolites, providing metabolites for biological tests and other purposes.
- Publication
BioMed Research International, 2014, Vol 2014, p1
- ISSN
2314-6133
- Publication type
Article
- DOI
10.1155/2014/152102