Identification of metabolites produced from N-phenylpiperazine by Mycobacterium spp

Journal of Industrial Microbiology and Biotechnology

Volumn 34, Issue 3, 2007, Pages 219-224

  Adjei, M D ^a,b   Deck, J ^a   Heinze, T M ^a   Freeman, J P ^a   Williams, A J ^a   Sutherland, J B ^a  

^a NATIONAL CENTER FOR TOXICOLOGICAL RESEARCH   (United States)

^b Norfolk Department of Public Health   (United States)

Author keywords

Biotransformation; Fluoroquinolones; Mycobacterium; N phenylpiperazine; Piperazine

Indexed keywords

ACETIC ACID ETHYL ESTER; PIPERAZINE; PIPERAZINE DERIVATIVE;

ACETYLATION; ARTICLE; BACTERIAL METABOLISM; BACTERIAL STRAIN; BACTERIUM CULTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITE; MYCOBACTERIUM; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; TEMPERATURE;

MAGNETIC RESONANCE SPECTROSCOPY; MYCOBACTERIUM; PIPERAZINES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

CORYNEBACTERINEAE; MYCOBACTERIUM; MYCOBACTERIUM SP. 7;

EID: 33846866976     PISSN: 13675435     EISSN: 14765535     Source Type: Journal    
DOI: 10.1007/s10295-006-0189-x     Document Type: Article

References (33)

1. Adjei MD, Heinze TM, Deck J, Freeman JP, Williams AJ, Sutherland JB (2006) Transformation of the antibacterial agent norfloxacin by environmental mycobacteria. Appl Environ Microbiol 72:5790-5793
2. Adjei MD, Heinze TM, Deck J, Freeman JP, Williams AJ, Sutherland JB (2007) Acetylation and nitrosation of ciprofloxacin by environmental strains of mycobacteria. Can J Microbiol (in press)
3. Beam HW, Perry JJ (1974) Microbial degradation of cycloparaffinic hydrocarbons via co-metabolism and commensalism. J Gen Microbiol 82:163-169
4. Blevins WT, Perry JJ (1972) Metabolism of propane, n-propylamine, and propionate by hydrocarbon-utilizing bacteria. J Bacteriol 112:513-518
5. Brezna B, Khan AA, Cerniglia CE (2003) Molecular characterization of dioxygenases from polycyclic aromatic hydrocarbon-degrading Mycobacterium spp. FEMS Microbiol Lett 223:177-183
6. Brooke EW, Davies SG, Mulvaney AW, Pompeo F, Sim E, Vickers RJ (2003) An approach to identifying novel substrates of bacterial arylamine N-acetyltransferases. Bioorgan Med Chem 11:1227-1234
7. Bryskier A, Lowther J (2002) Fluoroquinolones and tuberculosis. Expert Opin Invest Drugs 11:233-258
8. Chen Y, Rosazza JPN, Reese CP, Chang H-Y, Nowakowski MA, Kiplinger JP (1997) Microbial models of soil metabolism: biotransformations of danofloxacin. J Ind Microbiol Biotechnol 19:378-384
9. Cohen MR, Hinsch E, Palkoski Z, Vergona R, Urbano S, Sztokalo J (1982) The cardiovascular and autonomic properties of N-phenylpiperazine (NPP) in several animal models. J Pharmacol Exp Ther 223:110-119
10. 1H NMR. Biodegradation 9:433-442
11. Dalhoff A, Bergan T (1998) Pharmacokinetics of fluoroquinolones in experimental animals. In: Kuhlmann J, Dalhoff A, Zeiler H-J (eds) Quinolone antibacterials. Springer-Verlag, Berlin, Germany, pp 179-206
12. 1H NMR study of the biodegradation of xenobiotics: Application to heterocyclic compounds. J Ind Microbiol Biotechnol 26:2-8
13. Dmitrenko GN, Gvozdyak PI, Udod VM (1987) Selection of destructor microorganisms for heterocyclic xenobiotics. Khim Tekhnol Vody (Engl Transl) 9:442-445
14. Domagala JM, Hagen SE (2003) Structure-activity relationships of the quinolone antibacterials in the new millennium: some things change and some do not. In: Hooper DC, Rubinstein E (eds) Quinolone antimicrobial agents, 3rd edn. ASM Press, Washington, DC, USA, pp 3-18
15. Emtiazi G, Knapp JS (1994) The biodegradation of piperazine and structurally-related linear and cyclic amines. Biodegradation 5:83-92
16. Grover JK, Vats V, Uppal G, Yadav S (2001) Anthelmintics: a review. Trop Gastroenterol 22:180-189
17. Kim Y-H, Engesser K-H, Cerniglia CE (2005) Numerical and genetic analysis of polycyclic aromatic hydrocarbon-degrading mycobacteria. Microb Ecol 50:110-119
18. Levy AD, Van de Kar LD (1992) Endocrine and receptor pharmacology of serotonergic anxiolytics, antipsychotics and antidepressants. Life Sci 51:83-94
19. Mjos K (1978) Cyclic amines. In: Grayson M, Eckroth D (eds) Kirk-Othmer Encyclopedia of Chemical Technology, 3rd edn. vol 2. Wiley, New York, NY, USA, pp 295-308
20. Parshikov IA, Freeman JP, Lay JO, Beger RD, Williams AJ, Sutherland JB (2000) Microbiological transformation of enrofloxacin by the fungus Mucor ramannianus. Appl Environ Microbiol 66:2664-2667
21. Parshikov IA, Freeman JP, Lay JO, Moody JD, Williams AJ, Beger RD, Sutherland JB (2001) Metabolism of the veterinary fluoroquinolone sarafloxacin by the fungus Mucor ramannianus. J Ind Microbiol Biotechnol 26:140-144
22. Parshikov IA, Heinze TM, Moody JD, Freeman JP, Williams AJ, Sutherland JB (2001) The fungus Pestalotiopsis guepini as a model for biotransformation of ciprofloxacin and norfloxacin. Appl Microbiol Biotechnol 56:474-477
23. Pauliukonis LT, Musson DG, Bayne WF (1984) Quantitation of norfloxacin, a new antibacterial agent in human plasma and urine by ion-pair reverse-phase chromatography. J Pharm Sci 73:99-102
24. Payton M, Auty R, Delgoda R, Everett M, Sim E (1999) Cloning and characterization of arylamine N-acetyltransferase genes from Mycobacterium smegmatis and Mycobacterium tuberculosis: increased expression results in isoniazid resistance. J Bacteriol 181:1343-1347
25. Payton M, Mushtaq A, Yu T-W, Wu L-J, Sinclair J, Sim E (2001) Eubacterial arylamine N-acetyltransferases-identification and comparison of 18 members of the protein family with conserved active site cysteine, histidine and aspartate residues. Microbiology 147:1137-1147
26. Pietsch J, Hampel S, Schmidt W, Brauch H-J, Worch E (1996) Determination of aliphatic and alicyclic amines in water by gas and liquid chromatography after derivatization by chloroformates. Fresenius J Anal Chem 355:164-173
27. Poupin P, Truffaut N, Combourieu B, Besse P, Sancelme M, Veschambre H, Delort AM (1998) Degradation of morpholine by an environmental Mycobacterium strain involves a cytochrome P-450. Appl Environ Microbiol 64:159-165
28. Schneider J, Grosser R, Jayasimhulu K, Xue W, Warshawsky D (1996) Degradation of pyrene, benz [a]anthracene, and benzo [a]pyrene by Mycobacterium sp. strain RJGII-135, isolated from a former coal gasification site. Appl Environ Microbiol 62:13-19
29. Sheng C-Q, Zhang W-N, Ji H-T, Song Y-L, Yang S, Zhou Y-J, Zhu J, Lü J-G (2003) Synthesis and antifungal activity of 1-(1, 2,4-triazolyl-1H-1-yl)-2- (2,4-difluorophenyl)-3-(4-substituted benzyl-1-piperazinyl)-2-propanols. Acta Pharm Sin 38:665-670 [in Chinese]
30. Tanzi MC, Levi M, Danusso F (1990) Amides from N-phenylpiperazine as low-toxicity activators in radical polymerizations. Polymer 31:1735-1738
31. Wetzstein H-G, Schmeer N, Karl W (1997) Degradation of the fluoroquinolone enrofloxacin by the brown rot fungus Gloeophyllum striatum: identification of metabolites. Appl Environ Microbiol 63:4272-4281
32. Wetzstein H-G, Stadler M, Tichy H-V, Dalhoff A, Karl W (1999) Degradation of ciprofloxacin by basidiomycetes and identification of metabolites generated by the brown rot fungus Gloeophyllum striatum. Appl Environ Microbiol 65:1556-1563
33. Zeiler H-J, Petersen U, Gau W, Ploschke HJ (1987) Antibacterial activity of the metabolites of ciprofloxacin and its significance in the bioassay. Arzneim-Forsch/Drug Res 37:131-134