Environmental metabolites of fluoroquinolones: Synthesis, fractionation and toxicological assessment of some biologically active metabolites of ciprofloxacin

Environmental Science and Pollution Research

Volumn 19, Issue 7, 2012, Pages 2697-2707

  Lewis, Gareth ^a,b   Juhasz, Albert ^a,b   Smith, Euan ^a,b  

^a UNIVERSITY OF SOUTH AUSTRALIA   (Australia)

^b University of South Australia and CRC for Contamination Assessment and Remediation of the Environment   (Australia)

Author keywords

Biosolid; Ciprofloxacin; Enrofloxacin; Fluoroquinolone; Metabolite; Norfloxacin; PhACs; Pharmaceutically active compounds; Pharmaceuticals and personal care products; PPCPs; Resistance to antibiotics; Risk; Transformation product

Indexed keywords

BACTERIUM; BIOACTIVITY; BIOASSAY; BIOSOLID; DRUG; METABOLITE; SOIL AMENDMENT; TERRESTRIAL ENVIRONMENT; TOXICOLOGY; WASTE DISPOSAL;

ANIMALIA; AZOSPIRILLUM BRASILENSE; BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; MYCOBACTERIUM; MYCOBACTERIUM GILVUM;

EID: 84871718337     PISSN: 09441344     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11356-012-0766-7     Document Type: Article

References (56)

1. Acea MJ, Alexander M (1988) Growth and survival of bacteria introduced into carbon-amended soil. Soil Biol Biochem 20: 703-709.
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. Amoo SO, Ndhlala AR, Finnie JF, van Staden J (2009) Antibacterial, antifungal and anti-inflammatory properties of Burchellia bubalina. South African J Botany 75: 60-63.
5. Anadón A, Martínez-Larrañaga MR, Díaz MJ, Bringas P, Martínez MA, Fernández-Cruz ML, Fernández MC, Fernández R (1995) Pharmacokinetics and residues of enrofloxacin in chickens. Am J Vet Res 56: 501-506.
6. Anadón A, Martínez-Larrañaga MR, Díaz MJ, Fernández-Cruz ML, Martínez MA, Frejo MT, Martínez M, Iturbe J, Tafur M (1999) Pharmacokinetic variables and tissue residues of enrofloxacin and ciprofloxacin in healthy pigs. Am J Vet Res 60: 1377-1382.
7. Anadón A, Martínez-Larrañaga MR, Iturbe J, Martínez MA, Diaz MJ, Frejo MT, Martínez M (2001) Pharmacokinetics and residues of ciprofloxacin and its metabolites in broiler chickens. Res Vet Sci 71: 101-109.
8. Bailey RR (1992) Quinolones in the treatment of uncomplicated urinary tract infections. Int J Antimicrob Agents 2: 19-28.
9. Beausse J (2004) Selected drugs in solid matrices: a review of environmental determination, occurrence and properties of principal substances. TrAC Trends in Analytical Chem 23: 753-761.
10. Bêhal V (2006) Mode of action of microbial bioactive metabolites. Folia Microbiol 51: 359-369.
11. Blau K (1993) Acylation. In: Blau K, Halket JM (eds) Handbook of derivatives for chromatography, 2nd edn. Wiley, Chichester, pp 31-50.
12. Burhenne J, Ludwig M, Nikoloudis P, Spiteller M (1997) Photolytic degradation of fluoroquinolone carboxylic acids in aqueous solution. Part I: primary photoproducts and half-lives. Environ Sci Pollut Res 4: 10-15.
13. Campbell JIA, Jacobsen CS, Sorensen J (1995) Species variation and plasmid incidence among fluorescent Pseudomonas strains isolated from agricultural and industrial soils. FEMS Microbiol Ecol 18: 51-62.
14. Cardoza LA, Knapp CW, Larive CK, Belden JB, Lydy M, Graham DW (2005) Factors affecting the fate of ciprofloxacin in aquatic field systems. Water Air Soil Pollut 161: 383-398.
15. Cester CC, Toutain PL (1997) A comprehensive model for enrofloxacin to ciprofloxacin transformation and disposition in dog. J Pharm Sci 86: 1148-1155.
16. Chien C, Kuo Y, Chen C, Hung C, Yeh C, Yeh W (2008) Microbial diversity of soil bacteria in agricultural field contaminated with heavy metals. J Environ Sci 20: 359-363.
17. Cox CE (1991) Oral temafloxacin compared to norfloxacin for the treatment of complicated urinary tract infections. Am J Med 91: S129-S133.
18. de Mouy D, Fabre R, Cavallo JD (2007) Infections urinaires communautaires de la femme de 15 a 65 ans: sensibilite aux antibiotiques de E. coli en fonction des antecedents: etude AFORCOPI-BIO 2003. Med Mal Infect 37: 594-598.
19. Edlund C, Lindqvist L, Nord CE (1988) Norfloxacin binds to human fecal material. Antimicrob Agents Chemother 32: 1869-1874.
20. Gay JD, DeYoung DR, Roberts GD (1984) In vitro activities of norfloxacin and ciprofloxacin against Mycobacterium tuberculosis, M. avium complex, M. chelonei, M. fortuitum, and M. kansasii. Antimicrob Agents Chemother 26: 94-96.
21. Golet EM, Strehler A, Alder AC, Giger W (2002) Determination of fluoroquinolone antibacterial agents in sewage sludge and sludge-treated soil using accelerated solvent extraction followed by solid-phase extraction. Anal Chem 74: 5455-5462.
22. Golet EM, Xifra I, Siegrist H, Alder AC, Giger W (2003) Environmental exposure assessment of fluoroquinolone antibacterial agents from sewage to soil. Environ Sci Technol 37: 3243-3249.
23. Grobbel M, Lubke-Becker A, Wieler LH, Froyman R, Friederichs S, Filios S (2007) Comparative quantification of the in vitro activity of veterinary fluoroquinolones. Vet Microbiol 124: 73-81.
24. Iravani A (1991) Treatment of uncomplicated urinary tract infections with temafloxacin. Am J Med 91: S124-S128.
25. Isbell RF (1996) The Australian soil classification. CSIRO, Melbourne.
26. Jacobs MR (1991) Evaluation of the bactericidal activity of temafloxacin. Am J Med 91: S31-S34.
27. Jones RN, Hoban DJ (1994) North American (United States and Canada) comparative susceptibility of two fluoroquinolones: ofloxacin and ciprofloxacin: a 53-medical-center sample of spectra of activity. Diagn Microbiol Infect Dis 18: 49-56.
28. Jones RN, Kehrberg EN, Erwin ME, Anderson SC (1994) Prevalence of important pathogens and antimicrobial activity of parenteral drugs at numerous medical centers in the United States I. Study on the threat of emerging resistances: real or perceived? Diagn Microbiol Infect Dis 19: 203-215.
29. Jork H, Funk W, Fischer W, Wimmer H (1990) Thin-layer chromatography: reagents and detection methods, vol 1. Physical and chemical detection methods. VCH Verlagsgesellschaft GmbH, Weinheim.
30. 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.
31. Karl W, Schneider J, Wetzstein H-G (2006) Outlines of an "exploding" network of metabolites generated from the fluoroquinolone enrofloxacin by brown rot fungus Gloeophyllum striatum. Appl Microbiol Biotechnol 71: 101-113.
32. Kim Y-H, Engesser K-H, Cerniglia CE (2003) Two polycyclic aromatic hydrocarbon o-quinone reductases from a pyrene-degrading Mycobacterium. Arch Biochem Biophys 416: 209-217.
33. Kumar K, Gupta SC, Chander Y, Singh AK (2005) Antibiotic use in agriculture and its impact on the terrestrial environment. In: Sparks DL (ed) Advances in agronomy. Academic Press, New York, pp 1-54.
34. Kümmerer K (2003) Pharmaceuticals in the environment: sources, fate, effects and risks, 2nd edn. Springer, Berlin, 55.
35. Lewis G (2011) Thesis: fate and dynamics of fluoroquinolone antibiotics as pharmaceutically active compounds (PhACs) in the soil environment. http://arrow. unisa. edu. au: 8081/1959. 8/119064. Accessed 29th December 2011.
36. Lindberg RH, Björklund K, Rendahl P, Johansson MI, Tysklind M, Andersson BAV (2007) Environmental risk assessment of antibiotics in the Swedish environment with emphasis on sewage treatment plants. Water Res 41: 613-619.
37. Mahamat A, Lavigne J-P, Bouziges N, Daurès J-P, Sotto A (2006) Profils de résistance des souches urinaires de Proteus mirabilis de 1999 à 2005 au CHU de Nîmes. Antimicrobial susceptibility of Proteus mirabilis urinary tract isolates from 1999 to 2005 at Nîmes university hospital. Pathol Biol 54: 456-461.
38. Matthews JNS, Altman DG, Campbell MJ, Royston P (1990) Analysis of serial measurements in medical research. British Medical Journal 300: 230-235.
39. McLafferty W, Turecek F (1993) Interpretation of mass spectra, 4th edn. University Science Books, Mill Valley, pp. 72-76.
40. Mitani K, Kataoka H (2006) Determination of fluoroquinolones in environmental waters by in-tube solid-phase microextraction coupled with liquid chromatography-tandem mass spectrometry. Anal Chim Acta 562: 16-22.
41. Ramirez-Ronda C, Colon M, Saavedra S, Jacobo S, Corrado ML (1987) Treatment of urinary tract infection with norfloxacin: analysis of cost. Am J Med 82: 75-78.
42. Sasabe H, Tsuji A, Sugiyama Y (1998) Carrier-mediated mechanism for the biliary excretion of the quinolone antibiotic grepafloxacin and its glucuronide in rats. J Pharmacol Exp Ther 284: 1033-1039.
43. Smith SR (1996) Agricultural recycling of sewage sludge and the environment. CAB International, Wallingford.
44. Strehler A (2001) Entwicklung einer Extraktionsmethode zur Bestimmung von Fluorochinolones in Klarschlamm. ETH, Zurich.
45. Sunderland J, Tobin CM, Hedges AJ, MacGowan AP, White LO (2001) Antimicrobial activity of fluoroquinolone photodegradation products determined by parallel-line bioassay and high performance liquid chromatography. J Antimicrob Chemother 47: 271-275.
46. Tanaka M, Takahashi K, Saika T, Kobayashi I, Ueno T, Kumazawa J (1998) Development of fluoroquinolone resistance and mutations involving GyrA and ParC proteins among Neisseria gonorrhoeae isolates in Japan. J Urol 159: 2215-2219.
47. US Census Bureau (2009) http://www. census. gov/. Accessed 18 October 2010.
48. USEPA (1999) Biosolids generation, use, and disposal in the United States. US Environmental Protection Agency Municipal and Industrial Solid Waste Division Office of Solid Waste, EPA530-R-99-009.
49. UWI (1993) News: from waste to want-united water biosolids enrich farmlands. United Water Industries. http://www. uwi. com. au/index. php?zoom_query=From+Waste+To+Want-United+Water+Biosolids+Enrich+Farmlands& zoom_per_page=10& zoom_and=0& PID=1& SF=& Go. x=27& Go. y=9. Accessed 26 May 2011.
50. Vieno N, Tuhkanen T, Kronberg L (2007) Elimination of pharmaceuticals in sewage treatment plants in Finland. Water Res 41: 1001-1012.
51. Waites KB, Canupp KC, DeVivo MJ (1991) Efficacy and tolerance of norfloxacinin treatment of complicated urinary tract infection in outpatients with neurogenic bladder secondary to spinal cord injury. Urology 38: 589-596.
52. Walters E, McClellan K, Halden RU (2010) Occurrence and loss over three years of 72 pharmaceuticals and personal care products from biosolids-soil mixtures in outdoor mesocosms. Water Res 44: 6011-6020.
53. Waters B, Davies J (1997) Amino acid variation in the GyrA subunit of bacteria potentially associated with natural resistance to fluoroquinolone antibiotics. Antimicrob Agents Chemother 41: 2766-2769.
54. 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.
55. 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.
56. Wetzstein H-G, Schneider J, Karl W (2009) Comparative biotransformation of fluoroquinolone antibiotics in matrices of agricultural relevance. In: Henderson KL and Coats JR (eds) Veterinary pharmaceuticals in the environment, Chapter 6. American Chemical Society, Washington, pp. 67-91.