Oxidative transformation of levofloxacin by δ-MnO2: Products, pathways and toxicity assessment

Chemosphere

Volumn 119, Issue , 2015, Pages 282-288

  Li, Yuan ^a,b   Wei, Dongbin ^a   Du, Yuguo ^a,b  

^a RESEARCH CENTER FOR ECO ENVIRONMENTAL SCIENCES   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Levofloxacin; Manganese oxide; Pathways; Products; Toxicity; Transformation

Indexed keywords

ANTIBIOTICS; ESCHERICHIA COLI; LINEAR TRANSFORMATIONS; NATURAL ATTENUATION; OXIDES; TOXICITY;

ESCHERICHIA COLI GROWTHS; LEVOFLOXACIN; OXIDATIVE TRANSFORMATIONS; PATHWAYS; PRODUCTS; TRANSFORMATION; TRANSFORMATION PATHWAYS; TRANSFORMATION REACTIONS;

MANGANESE OXIDE;

LEVOFLOXACIN; MANGANESE OXIDE; MANGANESE OXIDE DELTA; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT; MANGANESE DERIVATIVE; OXIDE; POLLUTANT;

ANTIBIOTICS; GENOTOXICITY; MANGANESE; MICROBIAL ACTIVITY; OXIDATION; REACTION KINETICS; TOXICITY;

ANTIBACTERIAL ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; DEGRADATION; DEGRADATION KINETICS; DNA DAMAGE; ENVIRONMENTAL IMPACT; ESCHERICHIA COLI; GENOTOXICITY; GENOTOXICITY ASSAY; OXIDATION; REACTION TIME; WASTE WATER; X RAY DIFFRACTION; ZETA POTENTIAL; CHEMISTRY; DRUG EFFECTS; GROWTH, DEVELOPMENT AND AGING; MUTAGEN TESTING; OXIDATION REDUCTION REACTION; POLLUTANT; SALMONELLA ENTERICA SEROVAR TYPHIMURIUM; TOXICITY;

ESCHERICHIA COLI;

ANTI-BACTERIAL AGENTS; ENVIRONMENTAL POLLUTANTS; ESCHERICHIA COLI; LEVOFLOXACIN; MANGANESE COMPOUNDS; MUTAGENICITY TESTS; OXIDATION-REDUCTION; OXIDES; SALMONELLA TYPHIMURIUM;

EID: 84919770026     PISSN: 00456535     EISSN: 18791298     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2014.06.064     Document Type: Article

References (42)

1. Andersson M.I., MacGowan A.P. Development of the quinolones. J. Antimicrob. Chemother. 2003, 51(Suppl. 1):1-11.
2. Alovero F.L., Pan X.-S., Morris J.E., Manzo R.H., Fisher L.M. Engineering the specificity of antibacterial fluoroquinolones: benzenesulfonamide modifications at C-7 of ciprofloxacin change its primary target in Streptococcus pneumoniae from topoisomerase IV to gyrase. Antimicrob. Agents Chemother. 2000, 44:320-325.
3. Carlsson G., Örn S., Larsson D. Effluent from bulk drug production is toxic to aquatic vertebrates. Environ. Toxicol. Chem. 2009, 28:2656-2662.
4. Chen W.-R., Ding Y., Johnston C.T., Teppen B.J., Boyd S.A., Li H. Reaction of lincosamide antibiotics with manganese oxide in aqueous solution. Environ. Sci. Technol. 2010, 44:4486-4492.
5. Chu D., Fernandes P.B. Structure-activity relationships of the fluoroquinolones. Antimicrob. Agents Chemother. 1989, 33:131-135.
6. Dodd M.C. Potential impacts of disinfection processes on elimination and deactivation of antibiotic resistance genes during water and wastewater treatment. J. Environ. Monit. 2012, 14:1754-1771.
7. Ebert I., Bachmann J., Kühnen U., Küster A., Kussatz C., Maletzki D., et al. Toxicity of the fluoroquinolone antibiotics enrofloxacin and ciprofloxacin to photoautotrophic aquatic organisms. Environ. Toxicol. Chem. 2011, 30:2786-2792.
8. Fatta-Kassinos D., Meric S., Nikolaou A. Pharmaceutical residues in environmental waters and wastewater: current state of knowledge and future research. Anal. Bioanal. Chem. 2011, 399:251-275.
9. Feitosa-Felizzola J., Hanna K., Chiron S. Adsorption and transformation of selected human-used macrolide antibacterial agents with iron(III) and manganese(IV) oxides. Environ. Pollut. 2009, 157(4):1317-1322.
10. Gao J., Sheng G.D., Qiu Y.P. Degradation and removal of sulfadiazine from waters by a novel polymer-supported hydrous manganese dioxide (HMO). Chem. J. Chin. Univ. 2012, 33(5):948-953.
11. Gartiser S., Urich E., Alexy R., Kümmerer K. Ultimate biodegradation and elimination of antibiotics in inherent tests. Chemosphere 2007, 67:604-613.
12. Golden D.C., Chen C.C., Dixon J.B. Synthesis of todorokite. Science 1986, 231:717-719.
13. Halling-Sørensen B., Nors Nielsen S., Lanzky P., Ingerslev F., Holten Lützhøft H., Jørgensen S. Occurrence, fate and effects of pharmaceutical substances in the environment - a review. Chemosphere 1998, 36:357-393.
14. Hooper D.C. Mechanisms of action of antimicrobials: focus on fluoroquinolones. Clin. Infect. Dis. 2001, 32:S9-S15.
15. ISO, 2000. Water quality-Determination of the genotoxicity of water and waste water using the umu-test, first ed., ISO 13829, Geneva, Switzerland. 2000, pp. 1-18.
16. Jenne E.A. Controls on Mn Fe Co Ni Cu and Zn concentrations in soils and water-significant role of hydrous Mn and Fe oxides. ACS Adv. Chem. Ser. 1968, 73:337-387.
17. Jiang W.T., Chang P.H., Wang Y.S., Tsai Y.L., Jean J.S., Li Z.H., Krukowski K. Removal of ciprofloxacin from water by birnessite. J. Hazard. Mater. 2013, 250:362-369.
18. Kümmerer K. The presence of pharmaceuticals in the environment due to human use-present knowledge and future challenges. J. Environ. Manage. 2009, 90:2354-2366.
19. Kümmerer K., Al-Ahmad A., Mersch-Sundermann V. Biodegradability of some antibiotics, elimination of the genotoxicity and affection of wastewater bacteria in a simple test. Chemosphere 2000, 40:701-710.
20. 2: effect of co-solutes on initial and quasi-steady-state kinetics. Environ. Sci. Technol. 1997, 31:2642-2649.
21. Laha S., Luthy R.G. Oxidation of aniline and other primary aromatic amines by manganese dioxide. Environ. Sci. Technol. 1990, 24:363-373.
22. Li H., Lee L.S., Schulze D.G., Guest C.A. Role of soil manganese in the oxidation of aromatic amines. Environ. Sci. Technol. 2003, 37:2686-2693.
23. Li M., Wei D., Zhao H., Du Y. Genotoxicity of quinolones: substituents contribution and transformation products QSAR evaluation using 2D and 3D models. Chemosphere 2014, 95:220-226.
24. Lin K., Liu W., Gan J. Oxidative removal of bisphenol A by manganese dioxide: efficacy, products, and pathways. Environ. Sci. Technol. 2009, 43:3860-3864.
25. McArdell C.S., Stone A.T., Tian J. Reaction of EDTA and related aminocarboxylate chelating agents with CoIIIOOH (heterogenite) and MnIIIOOH (manganite). Environ. Sci. Technol. 1998, 32:2923-2930.
26. Murray J.W. The surface chemistry of hydrous manganese dioxide. J. Colloid Interface Sci. 1974, 46:357-371.
27. 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. /Environ. Mutagen. Relat. Subj. 1985, 147:219-229.
28. Picó Y., Andreu V. Fluoroquinolones in soil-risks and challenges. Anal. Bioanal. Chem. 2007, 387:1287-1299.
29. Post J.E. Manganese oxide minerals: crystal structures and economic and environmental significance. Proc. Natl. Acad. Sci. USA 1999, 96:3447-3454.
30. Post J.E., Veblen D.R. Crystal-structure determinations of synthetic sodium, magnesium, and potassium birnessite using TEM and the rietveld method. Am. Mineral. 1990, 75:477-489.
31. Rádl S. Structure-activity relationships in DNA gyrase inhibitors. Pharmacol. Ther. 1990, 48:1-17.
32. Sharma P.C., Jain A., Jain S. Fluoroquinolone antibacterials: a review on chemistry, microbiology and therapeutic prospects. Acta Poloniae Pharm. 2009, 66:587-604.
33. Shindo H., Huang P. The catalytic power of inorganic components in the abiotic synthesis of hydroquinone-derived humic polymers. Appl. Clay Sci. 1985, 1:71-81.
34. Stone A.T. Reductive dissolution of manganese (III/IV) oxides by substituted phenols. Environ. Sci. Technol. 1987, 21:979-988.
35. Sturini M., Speltini A., Maraschi F., Pretali L., Profumo A., Fasani E., Albini A., Migliavacca R., Nucleo E. Photodegradation of fluoroquinolones in surface water and antimicrobial activity of the photoproducts. Water Res. 2012, 46:5575-5582.
36. Ukrainczyk L., McBride M.B. Oxidation and dechlorination of chlorophenols in dilute aqueous suspensions of manganese oxides: Reaction products. Environ. Toxicol. Chem. 1993, 12:2015-2022.
37. Wang D., Shin J.Y., Cheney M.A., Sposito G., Spiro T.G. Manganese dioxide as a catalyst for oxygen-independent atrazine dealkylation. Environ. Sci. Technol. 1999, 33:3160-3165.
38. Witte B.D., Langenhove H.V., Hemelsoet K., Demeestere K., Wispelaere P.D., Van Speybroeck V., et al. Levofloxacin ozonation in water: rate determining process parameters and reaction pathway elucidation. Chemosphere 2009, 76:683-689.
39. Yang L.H., Ying G.G., Su H.C., Stauber 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.
40. Zhang H., Huang C.-H. Oxidative transformation of triclosan and chlorophene by manganese oxides. Environ. Sci. Technol. 2003, 37:2421-2430.
41. Zhang H., Huang C.-H. Oxidative transformation of fluoroquinolone antibacterial agents and structurally related amines by manganese oxide. Environ. Sci. Technol. 2005, 39:4474-4483.
42. Zhang H., Huang C.-H. Reactivity and transformation of antibacterial N-oxides in the presence of manganese oxide. Environ. Sci. Technol. 2005, 39:593-601.