Genotoxicity of quinolones: Substituents contribution and transformation products QSAR evaluation using 2D and 3D models

Chemosphere

Volumn 95, Issue , 2014, Pages 220-226

  Li, Min ^a,b   Wei, Dongbin ^a   Zhao, Huimin ^a   Du, Yuguo ^a,b  

^a RESEARCH CENTER FOR ECO ENVIRONMENTAL SCIENCES   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

CoMFA; Genotoxicity; QSAR; Quinolone

Indexed keywords

ANTIBIOTICS; MOLECULAR GRAPHICS; QUANTUM CHEMISTRY;

COMFA; COMPARATIVE MOLECULAR FIELD ANALYSIS; ELECTROSTATIC PROPERTIES; GENOTOXICITIES; QSAR; QUANTUM CHEMICAL PARAMETERS; QUINOLONES; TRANSFORMATION PRODUCTS;

COMPUTATIONAL CHEMISTRY;

BALOFLOXACIN; CHLORIDE; CINOXACIN; CIPROFLOXACIN; DANOFLOXACIN; DIFLOXACIN; ENOXACIN; ENROFLOXACIN; FLEROXACIN; GATIFLOXACIN; LEVOFLOXACIN; LOMEFLOXACIN; MOXIFLOXACIN; NADIFLOXACIN; NORFLOXACIN; OFLOXACIN; PAZUFLOXACIN; PEFLOXACIN; PIPEMIDIC ACID; QUINOLONE DERIVATIVE; RUFLOXACIN; SPARFLOXACIN; ANTIINFECTIVE AGENT; MUTAGENIC AGENT;

ANTIBIOTICS; ENVIRONMENTAL RISK; GENOTOXICITY; THREE-DIMENSIONAL MODELING; TRANSFORMATION; TWO-DIMENSIONAL MODELING;

ARTICLE; COMPARATIVE MOLECULAR FIELD ANALYSIS; CONTROLLED STUDY; ENVIRONMENTAL IMPACT; GENOTOXICITY; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTUM CHEMISTRY; RISK ASSESSMENT; CHEMICAL STRUCTURE; CHEMISTRY; STATIC ELECTRICITY; TOXICITY;

ANTI-BACTERIAL AGENTS; MODELS, MOLECULAR; MUTAGENS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; QUINOLONES; STATIC ELECTRICITY;

EID: 84887606060     PISSN: 00456535     EISSN: 18791298     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2013.09.002     Document Type: Article

References (40)

1. Andersson M.I., Mac Gowan A.P. Development of the quinolones. J. Antimicrob. Chemother. 2003, 51:1-11.
2. Blum D.J.W., Speece R.E. Determining chemical toxicity to aquatic species. Environ. Sci. Technol. 1990, 24:284-293.
3. Bryan L.E., Bedard J., Wong S., Chamberland S. Quinolone antimicrobial agents: mechanism of action and resistance development. Clin. Invest. Med. 1989, 12(1):14-19.
4. Cramer R.D., Patterson D.E., Bunce J.D. Comparative molecular-field analysis (CoMFA) 1. Effect of shape on binding of steroids to carrier proteins. J. Am. Chem. Soc. 1988, 110:5959-5967.
5. De Witte B., Dewulf J., Demeestere K., De Vyvere V.V., De Wispelaere P., Van Langenhove H. Ozonation of ciprofloxacin in water: HRMS identification of reaction products and pathways. Environ. Sci. Technol. 2008, 42:4889-4895.
6. De Witte B., Van Langenhove H., Hemelsoet K., Demeestere K., De Wispelaere P., Van Speybroeck V., Dewulf J. Levofloxacin ozonation in water: rate determining process parameters and reaction pathway elucidation. Chemosphere 2009, 76:683-689.
7. Dodd M.C., Shah A.D., Von Gunten U., Huang C.H. Interactions of fluoroquinolone antibacterial agents with aqueous chlorine: reaction kinetics, mechanisms, and transformation pathways. Environ. Sci. Technol. 2005, 39:7065-7076.
8. Domagala J.M. Structure-activity and structure-side-effect relationships for the quinolone antibacterials. J. Antimicrob. Chemother. 1994, 33:685-706.
9. Ebert I., Bachmann J., Kuhnen U., Kuster A., Kussatz C., Maletzki D., Schluter C. Toxicity of the fluoroquinolone antibiotics enrofloxacin and ciprofloxacin to photoautotrophic aquatic organisms. Environ. Toxicol. Chem. 2011, 30:2786-2792.
10. Ge L.K., Chen J.W., Wei X.X., Zhang S.Y., Qiao X.L., Cai X.Y., Xie Q. Aquatic photochemistry of fluoroquinolone antibiotics: kinetics, pathways, and multivariate effects of main water constituents. Environ. Sci. Technol. 2010, 44:2400-2405.
11. Golet E.M., Alder A.C., Giger W. Environmental exposure and risk assessment of fluoroquinolone antibacterial agents in wastewater and river water of the Glatt valley watershed, Switzerland. Environ. Sci. Technol. 2002, 36:3645-3651.
12. Hartmann A., Alder A.C., Koller T., Widmer R.M. Identification of fluoroquinolone antibiotics as the main source of umuC genotoxicity in native hospital wastewater. Environ. Toxicol. Chem. 1998, 17:377-382.
13. Hendrickson J.B., Huang P., Toczko A.G. Molecular complexity - a simplified formula adapted to individual atoms. J. Chem. Inf. Comput. Sci. 1987, 27:63-67.
14. Hirsch R., Ternes T., Haberer K., Kratz K.L. Occurrence of antibiotics in the aquatic environment. Sci. Total Environ. 1999, 225:109-118.
15. Hooper D.C. Mechanisms of action of antimicrobials: focus on fluoroquinolones. Clin. Infect. Dis. 2001, 32:S9-S15.
16. Hu J.Y., Wan W.F., Zhu Z., Chang H., Pan F., Lin B. Quantitative structure-activity relationship model for prediction of genotoxic potential for quinolone antibacterials. Environ. Sci. Technol. 2007, 41:4806-4812.
17. ISO, 2000. Water Quality - Determination of the Genotoxicity of Water and Waste Water Using the umu-test, first ed. ISO 13829, Geneva, Switzerland, pp. 1-18.
18. Jia A., Wan Y., Xiao Y., Hu J.Y. Occurrence and fate of quinolone and fluoroquinolone antibiotics in a municipal sewage treatment plant. Water Res. 2012, 46:387-394.
19. Jiao S.J., Zheng S.R., Yin D.Q., Wang L.H., Chen L.Y. Aqueous photolysis of tetracycline and toxicity of photolytic products to luminescent bacteria. Chemsphere 2008, 73:377-382.
20. Lee K.W., Kwon S.Y., Hwang S., Lee J.U., Kim H.J. Quantitative structure-activity relationships (QSAR) study on C-7 substituted quinolone. Bull. Korean Chem. Soc. 1996, 17:147-152.
21. Li Y., Niu J.F., Wang W.L. Photolysis of enrofloxacin in aqueous systems under simulated sunlight irradiation: kinetics, mechanism and toxicity of photolysis products. Chemosphere 2011, 85:892-897.
22. Lindberg R., Jarnheimer P.A., Olsen B., Johansson M., Tysklind M. Determination of antibiotic substances in hospital sewage water using solid phase extraction and liquid chromatography/mass spectrometry and group analogue internal standards. Chemosphere 2004, 57:1479-1488.
23. Llorente B., Leclerc F., Cedergren R. Using SAR and QSAR analysis to model the activity and structure of the quinolone-DNA complex. Bioorg. Med. Chem. 1996, 4:61-71.
24. Mamber S.W., Kolek B., Brookshire K.W., Bonner D.P., Fungtomc J. Activity of quinolones in the Ames Salmonella-TA102 mutagenicity test and other bacterial genotoxicity assays. Antimicro. Agents Chem. 1993, 37:213-217.
25. Martins A.F., Vasconcelos T.G., Henriques D.M., Frank C.D., Konig A., Kummerer K. Concentration of ciprofloxacin in Brazilian hospital effluent and preliminary risk assessment: a case study. Clean - Soil Air Water 2008, 36:264-269.
26. Migliore L., Civitareale C., Brambilla G., DiDelupis G.D. Toxicity of several important agricultural antibiotics to Artemia. Water Res. 1997, 31:1801-1806.
27. Minovski N., Vracko M., Solmajer T. Quantitative structure-activity relationship study of antitubercular fluoroquinolones. Mol. Diversity 2011, 15:417-426.
28. Oda Y., Nakamura S., Oki I., Kato T., Shinagawa H. Evaluation of the new system (umu-test) for the detection of environmental mutagens and carcinogens. Mutat. Res. 1985, 147:219-229.
29. Ohta M., Koga H. 3-dimensional structure-activity-relationships and receptor mapping of N1-substituents of quinolone antibacterials. J. Med. Chem. 1991, 34:131-139.
30. Paul T., Dodd M.C., Strathmann T.J. Photolytic and photocatalytic decomposition of aqueous ciprofloxacin: transformation products and residual antibacterial activity. Water Res. 2010, 44:3121-3132.
31. Robinson A.A., Belden J.B., Lydy M.J. Toxicity of fluoroquinolone antibiotics to aquatic organisms. Environ. Toxicol. Chem. 2005, 24:423-430.
32. Sturini M., Speltini A., Maraschi F., Profumo A., Pretali L., Irastorza E.A., Fasani E., Albini A. Photolytic and photocatalytic degradation of fluoroquinolones in untreated river water under natural sunlight. Appl. Catal. B - Environ. 2012, 119:32-39.
33. Tong C.L., Zhuo X.J., Guo Y. Occurrence and risk assessment of four typical fluoroquinolone antibiotics in raw and treated sewage and in receiving waters in Hangzhou, China. J. Agric. Food Chem. 2011, 59:7303-7309.
34. Wang M.L., Wang K., Yan A.X., Yu C.Y. Classification of HCV NS5B polymerase inhibitors using support vector machine. Int. J. Mol. Sci. 2012, 13:4033-4047.
35. Wei R.C., Ge F., Chen M., Wang R. Occurrence of ciprofloxacin, enrofloxacin, and florfenicol in animal wastewater and water resources. J. Environ. Qual. 2012, 41:1481-1486.
36. 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 fungus Gloeophyllum striatum. Appl. Environ. Microbiol. 1999, 65(4):1556-1563.
37. Xu M., Zhang A.Q., Han S.K., Wang L.S. Studies of 3D-quantitative structure-activity relationships on a set of nitroaromatic compounds: CoMFA, advanced CoMFA and CoMSIA. Chemsphere 2002, 48:707-715.
38. Yang L.H., Ying G.G., Staubner J.L., Adams M.S., Binet M.T. Growth-inhibiting effects of 12 antibacterial agents and their mixtures on the freshwater microalga Pseudokirchneriella subcapitata. Environ. Toxicol. Chem. 2008, 27:1201-1208.
39. Zhang H.C., Huang C.H. Oxidative transformation of fluoroquinolone antibacterial agents and structurally related amines by manganese oxide. Environ. Sci. Technol. 2005, 39:4474-4483.
40. Zhou H., Ouyang Q., Peng M., Li W. Investigation on the reaction of ciprofloxacin and chlorine. J. Sun Yatsen Univ. (Nat. Sci. Ed.) 2011, 50:79-84. (in Chinese).