Microbial transformations of antimicrobial quinolones and related drugs

Journal of Industrial Microbiology and Biotechnology

Volumn 39, Issue 12, 2012, Pages 1731-1740

  Parshikov, Igor A ^a   Sutherland, John B ^b  

^a I M SECHENOV FIRST MOSCOW STATE MEDICAL UNIVERSITY   (Russian Federation)

^b NATIONAL CENTER FOR TOXICOLOGICAL RESEARCH   (United States)

Author keywords

Biotransformation; Ciprofloxacin; Enrofloxacin; Fluoroquinolones; Pradofloxacin

Indexed keywords

3 HYDROXYDECARBOXYPRADOFLOXACIN; 5,6 DIHYDROXYDEFLUOROPRADOFLOXACIN; 6 HYDROXYDEFLUOROPRADOFLOXACIN; 8 HYDROXYDECYANOPRADOFLOXACIN; ACETIC ACID DERIVATIVE; ALCOHOL; ALIPHATIC COMPOUND; AMINE; AROMATIC COMPOUND; CARBOXYL GROUP; CINOXACIN; CIPROFLOXACIN; CYCLOPENTENONE; DANOFLOXACIN; ENROFLOXACIN; FLUMEQUINE; MARBOFLOXACIN; METHYL [[3 METHYL 2 [[5 METHYL 3 (2 METHYLALLYL) 4 OXO 2 THIAZOLIDINYLIDENE]HYDRAZONO] 4 OXO 5 THIAZOLIDINYL]] PHOSPHATE SODIUM; MOXIFLOXACIN; NALIDIXIC ACID; NORDIFLOXACIN; NORFLOXACIN; PRADOFLOXACIN; QUINOLINE DERIVED ANTIINFECTIVE AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIMICROBIAL ACTIVITY; BACTERIAL INFECTION; BACTERIUM CULTURE; BIOTRANSFORMATION; CONJUNCTIVITIS; DRUG ACETYLATION; DRUG HYDROXYLATION; DRUG TRANSFORMATION; HUMAN; MICROBIAL TRANSFORMATION; NITROSYLATION; NONHUMAN; OXIDATION KINETICS; REVIEW; URINARY TRACT INFECTION;

ANIMALS; ANTI-INFECTIVE AGENTS; BACTERIA; BIOTRANSFORMATION; FLUOROQUINOLONES; HUMANS; HYDROXYLATION; QUINOLONES;

BACTERIA (MICROORGANISMS);

EID: 84872146307     PISSN: 13675435     EISSN: 14765535     Source Type: Journal    
DOI: 10.1007/s10295-012-1194-x     Document Type: Review

References (97)

1. Abd El-Ghany WA, Madian K (2011) Control of experimental colisepticaemia in broiler chickens using sarafloxacin. Life Sci J 8:318-328
2. 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
3. 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 53:144-147
4. Andersson MI, MacGowan AP (2003) Development of the quinolones. J Antimicrob Chemother 51(Suppl S1) :1-11
5. AndrioleVT(2000) The quinolones: prospects. In:AndrioleVT(ed) The quinolones, 3rd edn. Academic Press, San Diego, pp 477-495
6. Appelbaum PC, Hunter PA (2000) The fluoroquinolone antibacterials: past, present and future perspectives. Int J Antimicrob Agents 16:5-15
7. Ball P (2000) Quinolone generations: natural history or natural selection? J Antimicrob Chemother 46(topic T1) :17-24
8. Ball P (2000) The quinolones: history and overview. In: Andriole VT (ed) The quinolones, 3rd edn. Academic Press, San Diego, pp 1-31
9. Basco LK, Mitaku S, Skaltsounis A-L, Ravelomanantsoa N, Tillequin F, Koch M, Le Bras J (1994) In vitro activities of furoquinoline and acridone alkaloids against Plasmodium falciparum. Antimicrob Agents Chemother 38:1169-1171
10. Betts RE, Walters DE, Rosazza JP (1974) Microbial transformations of antitumor compounds. 1. Conversion of acronycine to 9-hydroxyacronycine by Cunninghamella echinulata. J Med Chem 17:599-602
11. Biagini GA, Fisher N, Shone AE et al (2012) Generation of quinolone antimalarials targeting the Plasmodium falciparum mitochondrial respiratory chain for the treatment and prophylaxis of malaria. Proc Nat Acad Sci USA 109:8298-8303
12. Boteva AA, Krasnykh OP (2009) The methods of synthesis, modification, and biological activity of 4-quinolones. Chem Heterocycl Comp 45:757-785
13. Brighty KE, Gootz TD (2000) Chemistry and mechanism of action of the quinolone antibacterials. In: Andriole VT (ed) The quinolones, 3rd edn. Academic Press, San Diego, pp 33-97
14. Burhenne J, Ludwig M, Spiteller M (1997) Photolytic degradation of fluoroquinolone carboxylic acids in aqueous solution. Part II. Isolation and structural elucidation of polar photometabolites. Environ Sci Pollut Res 4:61-67
15. Cattoir V, Nordmann P (2009) Plasmid-mediated quinolone resistance in Gram-negative bacterial species: an update. Curr Med Chem 16:1028-1046
16. 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
17. Chen Y, Zhang H, Luo Y, Song J (2012) Occurrence and dissipation of veterinary antibiotics in two typical swine wastewater treatment systems in east China. Environ Monit Assess 184:2205-2217
18. Dalhoff A, Bergan T (1998) Pharmacokinetics of fluoroquinolones in experimental animals. In: Kuhlmann J, Dalhoff A, Zeiler H-J (eds) Quinolone antibacterials. Springer, Berlin Heidelberg New York, pp 179-206
19. Dalhoff A, Schmitz F-J (2003) In vitro antibacterial activity and pharmacodynamics of new quinolones. Eur J Clin Microbiol Infect Dis 22:203-221
20. Divo AA, Sartorelli AC, Patton CL, Bia FJ (1988) Activity of fluoroquinolone antibiotics against Plasmodium falciparum in vitro. Antimicrob Agents Chemother 32:1182-1186
21. Drlica K, Hiasa H, Kerns R, Malik M, Mustaev A, Zhao X (2009) Quinolones: action and resistance updated. Curr Top Med Chem 9:981-998
22. Drlica K, Malik M (2003) Fluoroquinolones: action and resistance. Curr Top Med Chem 3:249-282
23. Drlica K, Zhao X (1997) DNA gyrase, topoisomerase IV, and the 4-quinolones. Microbiol Mol Biol Rev 61:377-392
24. Emami S, Shafiee A, Foroumadi A (2006) Structural features of new quinolones and relationship to antibacterial activity against Gram-positive bacteria. Mini-Rev Med Chem 6:375-386
25. Engler M, Ru?sing G, So?rgel F, Holzgrabe U (1998) Defluorinated sparfloxacin as a new photoproduct identified by liquid chromatography coupled with UV detection and tandem mass spectrometry. Antimicrob Agents Chemother 42:1151-1159
26. Fujioka H, Nishiyama Y, Furukawa H, Kumada N (1989) In vitro and in vivo activities of atalaphillinine and related acridone alkaloids against rodent malaria. Antimicrob Agents Chemother 33:6-9
27. Giger W, Alder AC, Golet EM, Kohler H-PE, McArdell CS, Molnar E, Siegrist H, Suter MJ-F (2003) Occurrence and fate of antibiotics as trace contaminants in wastewaters, sewage sludges, and surface waters. Chimia 57:485-491
28. Grimaldo ER, Tupasi TE, Rivera AB, Quelapio MID, Cardano RC, Derilo JO, Belen VA (2001) Increased resistance to ciprofloxacin and ofloxacin in multidrug-resistant Mycobacterium tuberculosis isolates from patients seen at a tertiary hospital in the Philippines. Int J Tuberc Lung Dis 5:546-550
29. Hamilton PB, Rosi D, Peruzzotti GP, Nielson ED (1969) Microbiological metabolism of naphthyridines. Appl Microbiol 17:237-241
30. Hammel KE, Green B, Gai WZ (1991) Ring fission of anthracene by a eukaryote. Proc Nat Acad Sci USA 88:10605-10608
31. Jones RN, Erwin ME (1998) In vitro susceptibility testing and quality control parameters for sarafloxacin (A-56620) : a fluoroquinolone used for treatment and control of colibacillosis in poultry. Diagn Microbiol Infect Dis 32:55-64
32. Jung CM, Heinze TM, Strakosha R, Elkins CA, Sutherland JB (2009) Acetylation of fluoroquinolone antimicrobial agents by an Escherichia coli strain isolated from a municipal wastewater treatment plant. J Appl Microbiol 106:564-571
33. Karl W, Schneider J, Wetzstein H-G (2006) Outlines of an ''exploding'' network of metabolites generated from the fluoroquinolone enrofloxacin by the brown rot fungus Gloeophyllum striatum. Appl Microbiol Biotechnol 71:101-113
34. Keating GM, Scott LJ (2004) Moxifloxacin: a review of its use in the management of bacterial infections. Drugs 64:2347-2377
35. Kieslich K, Wieglepp H, Hoyer G-A, Rosenberg D (1973) Mikrobiologische Umwandlungen nichtsteroider Strukturen. V. Mikrobiologische Reaktionen von substituierten 1-A thyl-4- oxo-1,4-dihydrochinolin-3-carbonsauren. Chem Ber 106:2636- 2642
36. Kim D-W, Heinze TM, Kim B-S, Schnackenberg LK, Woodling KA, Sutherland JB (2011) Modification of norfloxacin by a Microbacterium sp. strain isolated from a wastewater treatment plant. Appl Environ Microbiol 77:6100-6108
37. Kim Y-H, Cerniglia CE (2009) An overview of the fate and effects of antimicrobials used in aquaculture. In: Henderson KL, Coats JR (eds) Veterinary pharmaceuticals in the environment (ACS symposium series 1018) . Oxford University Press, New York, pp 105-120
38. Kloskowski T, Gurtowska N, Drewa T (2010) Does ciprofloxacin have an obverse and a reverse? Pulm Pharmacol Ther 23:373-375
39. Koenigs JW (1974) Hydrogen peroxide and iron: a proposed system for decomposition of wood by brown-rot basidiomycetes. Wood Fiber 6:66-80
40. Koga H, Itoh A, Murayama S, Suzue S, Irikura T (1980) Structure- activity relationships of antibacterial 6,7- and 7,8-disubstituted 1-alkyl-1,4-dihydro- 4-oxoquinoline-3-carboxylic acids. J Med Chem 23:1358-1363
41. Ku?mmerer K, Henninger A (2003) Promoting resistance by the emission of antibiotics from hospitals and households into effluent. Clin Microbiol Infect 9:1203-1214
42. Lehman LR, Stewart JD (2001) Filamentous fungi: potentially useful catalysts for the biohydroxylations of non-activated carbon centers. Curr Org Chem 5:439-470
43. Lesher GY, Froelich EJ, Gruett MD, Bailey JH, Brundage RP (1962) 1,8-Naphthyridine derivatives. A new class of chemotherapeutic agents. J Med Chem 5:1063-1065
44. Leung HW, Minh TB, Murphy MB, Lam JCW, So MK, Martin M, Lam PKS, Richardson BJ (2012) Distribution, fate and risk assessment of antibiotics in sewage treatment plants in Hong Kong, south China. Environ Int 42(S1) :1-9
45. Lewis G, Juhasz A, Smith E (2012) Environmental metabolites of fluoroquinolones: synthesis, fractionation and toxicological assessment of some biologically active metabolites of ciprofloxacin. Environ Sci Pollut Res 19:2697-2707
46. Mahmoudi N, Ciceron L, Franetich J-F, Farhati K, Silvie O, Eling W, Sauerwein R, Danis M, Mazier D, Derouin F (2003) In vitro activities of 25 quinolones and fluoroquinolones against liver and blood stage Plasmodium spp. Antimicrob Agents Chemother 47:2636-2639
47. Marengo JR, Kok RA, Burrows LA, Velagaleti RR, Stamm JM (2001) Biodegradation of 14C-sarafloxacin hydrochloride, a fluoroquinolone antimicrobial by Phanerochaete chrysosporium. J Sci Ind Res 60:121-130
48. Marengo JR, Kok RA, O'Brien K, Velagaleti RR, Stamm JM (1997) Aerobic biodegradation of (14C) -sarafloxacin hydrochloride in soil. Environ Toxicol Chem 16:462-471
49. Martens R, Wetzstein HG, Zadrazil F, Capelari M, Hoffmann P, Schmeer N (1996) Degradation of the fluoroquinolone enrofloxacin by wood-rotting fungi. Appl Environ Microbiol 62:4206-4209
50. Martinsen B, Horsberg TE (1995) Comparative single-dose pharmacokinetics of four quinolones, oxolinic acid, flumequine, sarafloxacin, and enrofloxacin, in Atlantic salmon (Salmo salar) held in seawater at 10°C. Antimicrob Agents Chemother 39:1059-1064
51. McClean KL, Hitchman D, Shafran SD (1992) Norfloxacin is inferior to chloroquine for falciparum malaria in northwestern Zambia: a comparative clinical trial. J Infect Dis 165:904-907
52. McGuirk PR, Jefson MR, Mann DD et al (1992) Synthesis and structure-activity relationships of 7-diazabicycloalkylquinolones, including danofloxacin, a new quinolone antibacterial agent for veterinary medicine. J Med Chem 35:611-620
53. Meunier D, Acar J-F, Martel J-L, Kroemer S, Valle M (2004) A seven-year survey of susceptibility to marbofloxacin of pathogenic strains isolated from pets. Int J Antimicrob Agents 24:592-598
54. Miller IM, Wittreich JM, Cook T, Vogel R (1992) The safety and efficacy of topical norfloxacin compared with chloramphenicol for the treatment of external ocular bacterial infections. Eye 6:111-114
55. Mitchell MA (2006) Enrofloxacin. J Exotic Pet Med 15:66-69
56. Mitscher LA, Devasthale P, Zavod R (1993) Structure-activity relationships. In: Hooper DC, Wolfson JS (eds) Quinolone antimicrobial agents, 2nd edn. American Society for Microbiology, Washington, DC, pp 3-51
57. Mugnaini C, Pasquini S, Corelli F (2009) The 4-quinolone-3- carboxylic acid motif as a multivalent scaffold in medicinal chemistry. Curr Med Chem 16:1746-1767
58. Nguyen QC, Nguyen TT, Yougnia R, Gaslonde T, Dufat H, Michel S, Tillequin F (2009) Acronycine derivatives: a promising series of anti-cancer agents. Anti-Cancer Agents Med Chem 9:804-815
59. Oliphant CM, Green GM (2002) Quinolones: a comprehensive review. Am Fam Physician 65:455-464
60. Parshikov IA, Freeman JP, Lay JO, Beger RD, Williams AJ, Sutherland JB (1999) Regioselective transformation of ciprofloxacin to N-acetylciprofloxacin by the fungus Mucor ramannianus. FEMS Microbiol Lett 177:131-135
61. 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
62. 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
63. 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
64. Parshikov IA, Moody JD, Freeman JP, Lay JO, Williams AJ, Heinze TM, Sutherland JB (2002) Formation of conjugates from ciprofloxacin and norfloxacin in cultures of Trichoderma viride. Mycologia 94:1-5
65. Parshikov IA, Moody JD, Heinze TM, Freeman JP, Williams AJ, Sutherland JB (2002) Transformation of cinoxacin by Beauveria bassiana. FEMS Microbiol Lett 214:133-136
66. 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
67. Petersen U (2006) Quinolone antibiotics: the development of moxifloxacin. In: Fischer J, Ganellin CR (eds) Analogue-based drug discovery. Wiley-VCH, Weinheim, pp 315-370
68. Prieto A, Mo?der M, Rodil R, Adrian L, Marco-Urrea E (2011) Degradation of the antibiotics norfloxacin and ciprofloxacin by a white-rot fungus and identification of degradation products. Biores Technol 102:10987-10995
69. Rigos G, Troisi GM (2005) Antibacterial agents in Mediterranean finfish farming: a synopsis of drug pharmacokinetics in important euryhaline fish species and possible environmental implications. Rev Fish Biol Fish 15:53-73
70. Robicsek A, Strahilevitz J, Jacoby GA, Macielag M, Abbanat D, Park CH, Bush K, Hooper DC (2006) Fluoroquinolone-modifying enzyme: a new adaptation of a common aminoglycoside acetyltransferase. Nat Med 12:83-88
71. Sabbour MS, El Bokl MA, Osman LM (1984) Experiences on the efficacy and safety of nalidixic acid, oxolinic acid, cinoxacin and norfloxacin in the treatment of urinary tract infections (UTI) . Infection 12:377-380
72. Sappal R, Chaudhary RK, Sandhu HS, Sidhu PK (2009) Pharmacokinetics, urinary excretion and plasma protein binding of danofloxacin following intravenous administration in buffalo calves (Bubalus bubalis) . Vet Res Commun 33:659-667
73. Sarma PS (1989) Norfloxacin: a new drug in the treatment of falciparum malaria. Ann Intern Med 111:336-337
74. Schlosser D, Fahr K, Karl W, Wetzstein H-G (2000) Hydroxylated metabolites of 2,4-dichlorophenol imply a Fenton-type reaction in Gloeophyllum striatum. Appl Environ Microbiol 66:2479-2483
75. Sellyei B, Varga Z, Szentesi-Samu K, Kaszanyitzky E ́, Magyar T (2009) Antimicrobial susceptibility of Pasteurella multocida isolated from swine and poultry. Acta Vet Hung 57:357-367
76. Sharma PC, Jain A, Jain S, Pahwa R, Yar MS (2010) Ciprofloxacin: review on developments in synthetic, analytical, and medicinal aspects. J Enz Inhib Med Chem 25:577-589
77. Silley P, Bernd S, Greife HA, Pridmore A (2007) Comparative activity of pradofloxacin against anaerobic bacteria isolated from dogs and cats. J Antimicrob Chemother 60:999-1003
78. Sisca TS, Heel RC, Romankiewicz JA (1983) Cinoxacin - a review of its pharmacological properties and therapeutic efficacy in the treatment of urinary tract infections. Drugs 25:544-569
79. Sturini M, Speltini A, Maraschi F, Profumo A, Pretali L, Fasani E, Albini A (2010) Photochemical degradation of marbofloxacin and enrofloxacin in natural waters. Environ Sci Technol 44: 4564-4569
80. Sturini M, Speltini A, Maraschi F, Profumo A, Pretali L, Fasani E, Albini A (2012) Sunlight-induced degradation of soil-adsorbed veterinary antimicrobials marbofloxacin and enrofloxacin. Chemosphere 86:130-137
81. Sugino A, Peebles CL, Kreuzer KN, Cozzarelli NR (1977) Mechanism of action of nalidixic acid: purification of Escherichia coli nalA gene product and its relationship to DNA gyrase and a novel nicking-closing enzyme. Proc Nat Acad Sci USA 74:4767-4771
82. Sukul P, Spiteller M (2007) Fluoroquinolone antibiotics in the environment. Rev Environ Contam Toxicol 191:131-162
83. Tiefenbacher E-M, Haen E, Przybilla B, Kurz H (1994) Photodegradation of some quinolones used as antimicrobial therapeutics. J Pharm Sci 83:463-467
84. Watt G, Shanks GD, Edstein MD, Pavanand K, Webster HK, Wechgritaya S (1991) Ciprofloxacin treatment of drug-resistant falciparum malaria. J Infect Dis 164:602-604
85. Wetzstein H-G (2001) Chinolone in der Umwelt: biologische Abbaubarkeit der Gyrasehemmer. Pharm Unserer Zeit 30:450-457
86. Wetzstein H-G (2005) Comparative mutant prevention concentrations of pradofloxacin and other veterinary fluoroquinolones indicate differing potentials in preventing selection of resistance. Antimicrob Agents Chemother 49:4166-4173
87. Wetzstein H-G, Dalhoff A, Karl W (1997) BAY 12-8039, a new 8-methoxyquinolone, is degraded by the brown rot fungus Gloeophyllum striatum. Abstracts of the 37th Interscience Conference on Antimicrobial Agents and Chemotherapy, Toronto, Canada (p 172, abstract F-157)
88. Wetzstein H-G, Hallenbach W (2011) Tuning of antibacterial activity of a cyclopropyl fluoroquinolone by variation of the substituent at position C-8. J Antimicrob Chemother 66:2801- 2808
89. 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
90. Wetzstein H-G, Schneider J, Karl W (2006) Patterns of metabolites produced from the fluoroquinolone enrofloxacin by basidiomycetes indigenous to agricultural sites. Appl Microbiol Biotechnol 71:90-100
91. Wetzstein H-G, Schneider J, Karl W (2009) Comparative biotransformation of fluoroquinolone antibiotics in matrices of agricultural relevance. In: Henderson KL, Coats JR (eds) Veterinary pharmaceuticals in the environment (ACS Symposium Series 1018) . Oxford University Press, New York, pp 67-91
92. Wetzstein H-G, Schneider J, Karl W (2012) Metabolite proving fungal cleavage of the aromatic core part of a fluoroquinolone antibiotic. AMB Express 2(3) :1-7
93. 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
94. Williams AJ, Deck J, Freeman JP, Chiarelli MP, Adjei MD, Heinze TM, Sutherland JB (2007) Biotransformation of flumequine by the fungus Cunninghamella elegans. Chemosphere 67:240-243
95. Williams AJ, Parshikov IA, Moody JD, Heinze TM, Sutherland JB (2004) Fungal transformation of an antimicrobial fluoroquinolone drug during growth on poultry litter materials. J Appl Poult Res 13:235-240
96. 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 37:131-134
97. Zhang T, Li B (2011) Occurrence, transformation, and fate of antibiotics in municipal wastewater treatment plants. Crit Rev Environ Sci Technol 41:951-998