Acetylation and nitrosation of ciprofloxacin by environmental strains of mycobacteria

被引:22
作者
Adjei, Michael D. [1 ]
Heinze, Thomas M. [1 ]
Deck, Joanna [1 ]
Freeman, James P. [1 ]
Williams, Anna J. [1 ]
Sutherland, John B. [1 ]
机构
[1] US FDA, Natl Ctr Toxicol Res, Jefferson, AR 72079 USA
关键词
acetylation; ciprofloxacin; fluoroquinolones; Mycobacterium; nitrosation;
D O I
10.1139/W06-101
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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/electro spray 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 BB 1, Mycobacterium smegmatis me 2 155, Mycobacterium sp. 7E1B1W, and Mycobacterium sp. RJGII-135. The results suggest that biotransformation may serve as a ciprofloxacin resistance mechanism for these bacteria.
引用
收藏
页码:144 / 147
页数:4
相关论文
共 32 条
[1]   Transformation of the antibacterial agent norfloxacin by environmental mycobacteria [J].
Adjei, Michael D. ;
Heinze, Thomas M. ;
Deck, Joanna ;
Freeman, James P. ;
Williams, Anna J. ;
Sutherland, John B. .
APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 2006, 72 (09) :5790-5793
[2]   The clinical use of fluoroquinolones for the treatment of mycobacterial diseases [J].
Alangaden, GJ ;
Lerner, SA .
CLINICAL INFECTIOUS DISEASES, 1997, 25 (05) :1213-1221
[3]   BIODEGRADATION AND BIOTRANSFORMATION OF GROUNDWATER POLLUTANT MIXTURES BY MYCOBACTERIUM-VACCAE [J].
BURBACK, BL ;
PERRY, JJ .
APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 1993, 59 (04) :1025-1029
[4]   Characterization of bacterial cytochrome cd(1)-nitrite reductase as one enzyme responsible for catalysis of nitrosation of secondary amines [J].
Calmels, S ;
Ohshima, H ;
Henry, Y ;
Bartsch, H .
CARCINOGENESIS, 1996, 17 (03) :533-536
[5]   SCREENING OF MICROORGANISMS FOR NITROSATION CATALYSIS AT PH-7 AND KINETIC-STUDIES ON NITROSAMINE FORMATION FROM SECONDARY-AMINES BY ESCHERICHIA-COLI STRAINS [J].
CALMELS, S ;
OHSHIMA, H ;
VINCENT, P ;
GOUNOT, AM ;
BARTSCH, H .
CARCINOGENESIS, 1985, 6 (06) :911-915
[6]  
CALMELS S, 1988, J GEN MICROBIOL, V134, P221
[7]   Thiomorpholine and morpholine oxidation by a cytochrome P450 in Mycobacterium aurum MO1.: Evidence of the intermediates by in situ 1H NMR [J].
Combourieu, B ;
Poupin, P ;
Besse, P ;
Sancelme, M ;
Veschambre, H ;
Truffaut, N ;
Delort, AM .
BIODEGRADATION, 1998, 9 (06) :433-442
[8]   Occurrence of antibiotic resistance in Escherichia coli from surface waters and fecal pollution sources near Hamilton, Ontario [J].
Edge, TA ;
Hill, S .
CANADIAN JOURNAL OF MICROBIOLOGY, 2005, 51 (06) :501-505
[9]  
Hearn Michael J, 2003, Drug Des Discov, V18, P103, DOI 10.1080/10559610390450705
[10]   METABOLIC-ACTIVATION AND DEACTIVATION OF ARYLAMINE CARCINOGENS BY RECOMBINANT HUMAN NAT1 AND POLYMORPHIC NAT2 ACETYLTRANSFERASES [J].
HEIN, DW ;
DOLL, MA ;
RUSTAN, TD ;
GRAY, K ;
FENG, Y ;
FERGUSON, RJ ;
GRANT, DM .
CARCINOGENESIS, 1993, 14 (08) :1633-1638