Metabolite proving fungal cleavage of the aromatic core part of a fluoroquinolone antibiotic

AMB Express

Volumn 2, Issue 1, 2012, Pages 1-7

  Wetzstein, Heinz Georg ^a   Schneider, Josef ^b   Karl, Wolfgang ^c  

^a BAYER AG   (Germany)

^b BAYER CROPSCIENCE AG   (Germany)

^c B   (Germany)

Author keywords

aromatic ring cleavage; fluoroquinolone; fungal degradation; Gloeophyllum striatum; metabolites; pradofloxacin

Indexed keywords

AMINE; CARBOXYL GROUP; CATECHOL; DRUG METABOLITE; FLUORINE; HYDROXYL GROUP; PRADOFLOXACIN;

ARTICLE; ATOM; BIODEGRADATION; DEGRADATION; DRUG STRUCTURE; FUNGUS; GLOEOPHYLLUM STRIATUM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INCUBATION TIME; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE;

FUNGI; GLOEOPHYLLUM STRIATUM;

EID: 84859489450     PISSN: None     EISSN: 21910855     Source Type: Journal    
DOI: 10.1186/2191-0855-2-3     Document Type: Article

References (26)

1. Adjei MD, Heinze TM, Deck J, Freeman JP, Williams AJ, Sutherland JB: Transformation of the antibacterial agent norfloxacin by environmental mycobacteria. Appl Environ Microbiol 2006, 72: 5790-5793.
2. Adjei MD, Heinze TM, Deck J, Freeman JP, Williams AJ, Sutherland JB: Acetylation and nitrosation of ciprofloxacin by environmental strains of mycobacteria. Can J Microbiol 2006, 53: 144-147.
3. Baquero F, Coque TM, de la Cruz F: Ecology and evolution as targets: the need for novel eco-evo drugs and strategies to fight antibiotic resistance. Antimicrob Agents Chemother 2011, 55: 3649-3660.
4. Dalhoff A, Bergan T: Pharmacokinetics of fluoroquinolones in experimental animals. In Quinolone antibacterials. Edited by: Kuhlmann J, Dahlhoff A, Zeiler HJ. Springer, Berlin, Germany; 1998: 179-206.
5. Dewitte B, Dewulf J, Demeestere K, van de Vyvere V, de Wispelaere P, van Langenhove H: Ozonization of ciprofloxacin in water: HRMS identification of reaction products and pathways. Environ Sci Technol 2008, 42: 4889-4895.
6. Domagala JM, Hagen SE: Structure-activity relationships of the quinolone antibacterials in the new millennium: some things change and some do not. In Quinolone antimicrobial agents. 3rd edition. Edited by: Hooper DC, Rubinstein E. American Society for Microbiology, Washington, DC; 2003: 3-18.
7. Goldfine H: Lipids of prokaryotes - structure and distribution. Curr Top Membr Transp 1982, 17: 2-44.
8. Jensen KA Jr, Houtman CJ, Ryan ZC, Hammel KE: Pathways for extracellular Fenton chemistry in the brown rot basidiomyceteGloeophyllum trabeum. Appl Environ Microbiol 2001, 67: 2705-2711.
9. Jung CM, Heinze TM, Strakosha R, Elkins CA, Sutherland JB: Acetylation of fluoroquinolone antimicrobial agents by anEscherichia colistrain isolated from a municipal wastewater treatment plant. J Appl Microbiol 2009, 106: 564-571.
10. Karl W, Schneider J, Wetzstein H-G: Outlines of an "exploding" network of metabolites generated from the fluoroquinolone enrofloxacin by the brown rot fungusGloeophyllum striatum. Appl Microbiol Biotechnol 2006, 71: 101-113.
11. Kim D-W, Heinze TM, Kim B-S, Schnackenberg LK, Woodling KA, Sutherland JB: Modification of norfloxacin by aMicrobacteriumsp. strain isolated from a wastewater treatment plant. Appl Environ Microbiol 2011, 77: 6100-6108.
12. Litster A, Moss S, Honnery M, Rees B, Edingloh M, Trott D: Clinical efficacy and palatability of pradofloxacin 2. 5% oral suspension for the treatment of bacterial lower urinary tract infections in cats. J Vet Intern Med 2007, 21: 990-995.
13. Mueller RS, Stephan B: Pradofloxacin in the treatment of canine deep pyoderma - a multicentered, blinded, randomized parallel trial. Vet Dermatol 2007, 18: 144-151.
14. Parshikov IA, Freeman JP, Lay JO Jr, Beger RD, Williams AJ, Sutherland JB: Microbiological transformation of enrofloxacin by the fungusMucor ramannianus. Appl Environ Microbiol 2000, 66: 2664-2667.
15. 2photocatalysis of fluoroquinolone antibacterial agents. Environ Sci Technol 2007, 41: 4720-4727.
16. Petersen U: In Quinolone antibiotics: the development of moxifloxacin. Edited by: Fischer J, Ganellin CR. 2006.
17. Fischer J, Ganellin CR (Eds): Analogue-based drug discovery. Wiley-VCH, Weinheim, Germany; 315-370.
18. Qi W, Jellison J: Characterization of a transplasma membrane redox system of the brown rot fungusGloeophyllum trabeum. Int Biodeterior Biodegrad 2004, 53: 37-42.
19. Robicsek A, Strahilevitz J, Jacoby GA, Macielag M, Abbanat D, Park CH, Bush K, Hooper DC: Fluoroquinolone-modifiying enzyme: a new adaptation of a common aminoglycoside acetyltransferase. Nat Med 2006, 12: 83-88.
20. Wetzstein H-G, Schmeer N, Karl W: Degradation of the fluoroquinolone enrofloxacin by the brown rot fungusGloeophyllum striatum: identification of metabolites. Appl Environ Microbiol 1997, 63: 4272-4281.
21. Wetzstein H-G, Stadler M, Tichy H-V, Dalhoff A, Karl W: Degradation of ciprofloxacin by basidiomycetes and identification of metabolites generated by the brown rot fungusGloeophyllum striatum. Appl Environ Microbiol 1999, 65: 1556-1563.
22. Wetzstein H-G: Comparative mutant prevention concentrations of pradofloxacin and other veterinary fluoroquinolones indicate differing potentials in preventing selection of resistance. Antimicrob Agents Chemother 2005, 49: 4166-4173.
23. Wetzstein H-G, Schneider J, Karl W: Patterns of metabolites produced from the fluoroquinolone enrofloxacin by basidiomycetes indigenous to agricultural sites. Appl Microbiol Biotechnol 2006, 71: 90-100.
24. Wetzstein H-G, Schneider J, Karl W: Comparative biotransformation of fluoroquinolone antibiotics in matrices of agricultural relevance. In Veterinary pharmaceuticals in the environment. ACS Symposium Series. Volume 1018. Edited by: Henderson KL, Coats JR. American Chemical Society, Washington, DC; 2009: 67-91.
25. Wetzstein H-G, Hallenbach W: Tuning of antibacterial activity of a cyclopropyl fluoroquinolone by variation of the substituent at position C-8. J Antimicrob Chemother 2011, 66: 2801-2808.
26. Xiao X, Zeng X, Lemley AT: Species-dependent degradation of ciprofloxacin in a membrane anodic Fenton system. J Agric Food Chem 2010, 58: 10169-10175.