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Acetylation and nitrosation of ciprofloxacin by environmental strains of mycobacteria

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To determine the ability of environmental bacteria to metabolize the frequently prescribed fluoroquinolone drug ciprofloxacin, eight Mycobacterium spp. cultures were grown for 4 days in a medium containing sorbitol and yeast extract with 100 mg·L–1 ciprofloxacin. After the cultures had been centrifuged and the supernatants extracted with ethyl acetate, two metabolites were purified by using high-performance liquid chromatography. They were identified with liquid chromatography/electrospray ionization mass spectrometry and proton nuclear magnetic resonance spectroscopy. Ciprofloxacin was transformed to both N-acetylciprofloxacin (2.5%–5.5% of the total peak area at 280 nm) and N-nitrosociprofloxacin (6.0%–8.0% of the peak area) by Mycobacterium gilvum PYR-GCK and Mycobacterium sp. PYR100 but it was transformed only to N-acetylciprofloxacin by Mycobacterium frederiksbergense FAn9, M. gilvum ATCC 43909, M. gilvum BB1, Mycobacterium smegmatis mc2155, Mycobacterium sp. 7E1B1W, and Mycobacterium sp. RJGII-135. The results suggest that biotransformation may serve as a ciprofloxacin resistance mechanism for these bacteria.Key words: acetylation, ciprofloxacin, fluoroquinolones, Mycobacterium, nitrosation.

Afin d'évaluer la capacité qu'ont les bactéries de l'environnement de métaboliser le ciprofloxacin, une fluoroquinolone fréquemment prescrite, huit cultures de Mycobacterium spp. ont été incubées pendant 4 jours dans du milieu contenant du sorbitol, de l'extrait de levure et 100 mg·L–1 de ciprofloxacin. Après avoir centrifugé les cultures et extrait les surnageants avec de l'acétate d'éthyle, deux métabolites ont été purifiés par chromatographie liquide à haute performance. Ils ont été identifiés par chromatographie liquide couplée à la spectrométrie de masse par ionisation en mode électrospray et par spectroscopie par résonnance magnétique nucléaire à protons. Le ciprofloxacin était transformé en N-acétylciprofloxacin (2,5 % à 5,5 % du pic total à 280 nm) et en N-nitrosociprofloxacin (6,0 % à 8,0 % du pic) par Mycobacterium gilvum PYR-GCK et Mycobacterium sp. PYR100, mais était transformé seulement en N-acétylciprofloxacin par Mycobacterium frederiksbergense FAn9, M. gilvum ATCC 43909, M. gilvum BB1, Mycobacterium smegmatis mc2155, Mycobacterium sp. 7E1B1W et Mycobacterium sp. RJGII-135. Ces résultats suggèrent que la biotransformation pourrait servir de mécanisme de résistance au ciprofloxacin chez ces bactéries.Mots clés : acétylation, ciprofloxacin, fluoroquinolones, Mycobacterium, nitrosation.[Traduit par la Rédaction]

Document Type: Research Article

Publication date: January 1, 2007

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  • Published since 1954, this monthly journal contains new research in the field of microbiology including applied microbiology and biotechnology; microbial structure and function; fungi and other eucaryotic protists; infection and immunity; microbial ecology; physiology, metabolism and enzymology; and virology, genetics, and molecular biology. It also publishes review articles and notes on an occasional basis, contributed by recognized scientists worldwide.
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