Oxidative degradation kinetics and products of chlortetracycline by manganese dioxide

Journal of Hazardous Materials

Volumn 193, Issue , 2011, Pages 128-138

  Chen, Gao ^a,b   Zhao, Ling ^a   Dong, Yuan hua ^a  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^b MAX PLANCK INSTITUTE FOR MARINE MICROBIOLOGY   (Germany)

Author keywords

MnO 2; Abiotic degradation; Chlortetracycline; Kinetics; Products

Indexed keywords

ABIOTIC DEGRADATION; ABIOTIC TRANSFORMATION; APPARENT ACTIVATION ENERGY; CHLORTETRACYCLINE; CO-SOLUTES; DIMETHYLAMINES; FOURIER; FTIR; HYDROXYL GROUPS; LIQUID CHROMATOGRAPHY-TANDEM MASS SPECTROMETRY; MANGANESE DIOXIDE; OXIDATION PRODUCTS; OXIDATIVE DEGRADATION; PRODUCT IDENTIFICATION; PRODUCTS; SUBSTITUTED PHENOL; TETRACYCLINE ANTIBIOTICS; TRANSFORMATION RATES;

ACTIVATION ENERGY; DEGRADATION; ENZYME KINETICS; FOURIER TRANSFORMS; KINETICS; LIQUID CHROMATOGRAPHY; MANGANESE; MANGANESE OXIDE; MASS SPECTROMETRY; PHENOLS; SURFACE REACTIONS;

TEMPERATURE CONTROL;

4 EPI N DEMETHYLCHLORTETRACYCLINE; 4 EPI N DIDEMETHYLCHLORTETRACYCLINE; 4 EPIANHYDROCHLORTETRACYCLINE; 4 EPICHLORTETRACYCLINE; 4 EPIKETOCHLORTETRACYCLINE; ANHYDROCHLORTETRACYCLINE; CAFFEIC ACID; CHLORTETRACYCLINE; DEMECLOCYCLINE; DIMETHYLAMINE; FERULIC ACID; HYDROXIDE; HYDROXYL GROUP; ISOCHLORTETRACYCLINE; KETOCHLORTETRACYCLINE; MANGANESE; MANGANESE DIOXIDE; N DIDEMETHYLCHLORTETRACYCLINE; PARA COUMARIC ACID; SYRINGOL; UNCLASSIFIED DRUG;

FTIR SPECTROSCOPY; HYDROXYL RADICAL; ION EXCHANGE; MANGANESE OXIDE; OXIDATION; PH; REACTION KINETICS; TRANSFORMATION;

ARTICLE; BIOTRANSFORMATION; CHEMICAL REACTION; CONTROLLED STUDY; INFRARED SPECTROSCOPY; LIQUID CHROMATOGRAPHY; OXIDATION KINETICS; PH; SOLUTE; TANDEM MASS SPECTROMETRY; TEMPERATURE;

CHLORTETRACYCLINE; CHROMATOGRAPHY, LIQUID; KINETICS; MANGANESE COMPOUNDS; OXIDATION-REDUCTION; OXIDES; TANDEM MASS SPECTROMETRY;

EID: 80053247434     PISSN: 03043894     EISSN: 18733336     Source Type: Journal    
DOI: 10.1016/j.jhazmat.2011.07.039     Document Type: Article

References (56)

1. Sarmah A.K., Meyer M.T., Boxall A.B.A. A global perspective on the use, sales, exposure pathways, occurrence, fate and effects of veterinary antibiotics (VAs) in the environment. Chemosphere 2006, 65:725-759.
2. Calisto V., Esteves V.I. Psychiatric pharmaceuticals in the environment. Chemosphere 2009, 77:1257-1274.
3. Yu D.J., Yi X.L., Ma Y.F., Yin B., Zhuo H.L., Li J., Huang Y.F. Effects of administration mode of antibiotics on antibiotic resistance of Enterococcus faecalis in aquatic ecosystems. Chemosphere 2009, 76:915-920.
4. Kim S., Park H.K., Chandran K. Propensity of activated sludge to amplify or attenuate tetracycline resistance genes and tetracycline resistant bacteria: a mathematical modeling approach. Chemosphere 2010, 78:1071-1077.
5. Montforts M.H.M.M., Kalf D.F., van Vlaardingen P.L.A., Linders J.B.H.J. The exposure assessment for veterinary medicinal products. Sci. Total Environ. 1999, 225:119-133.
6. Kolpin D.W., Furlong E.T., Meyer M.T., Thurman E.M., Zaugg S.D., Barber L.B., Buxton H.T. Pharmaceuticals, hormones and other organic wastewater contaminants in US streams 1999-2000: a national reconnaissance. Environ. Sci. Technol. 2002, 36:1202-1211.
7. Boxall A.B.A., Fogg L.A., Blackwell P.A., Kay P., Pemberton E.J., Croxford A. Veterinary medicines in the environment. Rev. Environ. Contam. Toxicol. 2004, 180:1-91.
8. Tylová T., Olšovská J., Novák P., Flieger M. High-throughput analysis of tetracycline antibiotics and their epimers in liquid hog manure using Ultra Performance Liquid Chromatography with UV detection. Chemosphere 2010, 78:353-359.
9. Hamscher G., Sczesny S., Höper H., Nau H. Determination of persistent tetracycline residues in soil fertilized with liquid manure by high-performance liquid chromatography with electrospray ionization tandem mass spectrometry. Anal. Chem. 2002, 74:1509-1518.
10. Hamscher G., Pawelzick H.T., Höper H., Nau H. Different behaviour of tetracyclines and sulfonamides in sandy soils after repeated fertilisation with liquid manure. Environ. Toxicol. Chem. 2005, 24:861-868.
11. Kumar K., Thompson A., Singh A.K., Chander Y., Gupta S.C. Enzyme-linked immunosorbent assay for ultratrace determination of antibiotics in aqueous samples. J. Environ. Qual. 2004, 33:250-256.
12. Kemper N. Veterinary antibiotics in the aquatic and terrestrial environment. Ecol. Indicators 2008, 8:1-13.
13. Katayama A., Bhula R., Burns G.R., Carazo E., Felsot A., Hamilton D., Harris C., Kim Y.H., Kleter G., Koerdel W., Linders J., Peijnenburg J.G.M.W., Sabljic A., Stephenson R.G., Racke D.K., Rubin B., Tanaka K., Unsworth J., Wauchope R.D. Bioavailability of xenobiotics in the soil environment. Rev. Environ. Contam. Toxicol. 2010, 203:1-86.
14. Halling-Sørensen B., Jacobsen A.M., Jensen J., Sengelov G., Vaclavik E., Ingerslev F. Dissipation and effects of chlortetracycline and tylosin in two agricultural soils: a field-scale study in southern Denmark. Environ. Toxicol. Chem. 2005, 24:802-810.
15. Samuelsen O.B., Lunestad B.T., Ervik A., Fjelde S. Stability of antibacterial agents in an artificial marine aquaculture sediment studied under laboratory conditions. Aquaculture 1994, 126:283-290.
16. Alexy R., Kümpel T., Kümmerer K. Assessment of degradation of 18 antibiotics in the closed bottle test. Chemosphere 2004, 57:505-512.
17. Oka H., Ikai Y., Kawamura N., Yamada M., Harada K., Ito S., Suzuki M. Photodecomposition products of tetracycline in aqueous solution. J. Agric. Food Chem. 1989, 37:226-231.
18. 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.
19. Rubert K.F., Pedersen J.A. Kinetics of oxytetracycline reaction with a hydrous manganese oxide. Environ. Sci. Technol. 2006, 40:7216-7221.
20. Chen W.R., Huang C.H. Adsorption and transformation of tetracycline antibiotics with aluminum oxide. Chemosphere 2010, 79:779-785.
21. Jeong J.S., Song W.H., Cooper W.J., Jung J.Y., Greaves J. Degradation of tetracycline antibiotics: mechanisms and kinetic studies for advanced oxidation/reduction processes. Chemosphere 2010, 78:533-540.
22. Park J.W., Dec J., Kim J.E., Bollag J.M. Effect of humic constituents on the transformation of chlorinated phenols and anilines in the presence of oxidoreductive enzymes or birnessite. Environ. Sci. Technol. 1999, 33:2028-2034.
23. Shin J.Y., Cheney M.A. Abiotic transformation of atrazine in aqueous suspension of four synthetic manganese oxides. Colloids Surf. A 2004, 242:85-92.
24. Zhang H.C., Chen W.R., Huang C.H. Kinetic modeling of oxidation of antibacterial agents by manganese oxide. Environ. Sci. Technol. 2008, 42:5548-5554.
25. Søeborg T., Ingerslev F., Halling-Sørensen B. Chemical stability of chlortetracycline and chlortetracycline degradation products and epimers in soil interstitial water. Chemosphere 2004, 57:1515-1524.
26. 2 and Mn (II) species in aqueous solutions. Geochim. Cosmochim. Acta 2004, 69:35-48.
27. Chen W.R., Huang C.H. Transformation of tetracyclines mediated by Mn (II) and Cu (II) ions in the presence of oxygen. Environ. Sci. Technol. 2009, 43:401-407.
28. Stone A.T. Reductive dissolution of manganese (III/IV) oxides by substituted phenols. Environ. Sci. Technol. 1987, 21:979-988.
29. Laha S., Luthy R.G. Oxidation of aniline and other primary aromatic amines by manganese dioxide. Environ. Sci. Technol. 1990, 24:363-373.
30. 2: effect of co-solutes on initial and quasi-steady-state kinetics. Environ. Sci. Technol. 1997, 31:2642-2649.
31. Zhang H.C., Huang C.H. Oxidative transformation of triclosan and chlorophene by manganese oxides. Environ. Sci. Technol. 2003, 37:2421-2430.
32. h and pH environments. Environ. Sci. Technol. 2002, 36:3744-3748.
33. Gao J., Pedersen J.A. Adsorption of sulfonamide antimicrobial agents to clay minerals. Environ. Sci. Technol. 2005, 39:9509-9516.
34. Parolo M.E., Savini M.C., Vallés J.M., Baschini M.T., Avena M.J. Tetracycline adsorption on montmorillonite: pH and ionic strength effects. Appl. Clay Sci. 2008, 40:179-186.
35. Stephens C.R., Murai K., Brunings K.J., Woodward R.B. Acidity constants of the tetracycline antibiotics. J. Am. Chem. Soc. 1956, 78:4155-4158.
36. Tonkin J.W., Balistrieri L.S., Murray J.W. Modeling sorption of divalent metal cations on hydrous manganese oxide using the diffuse double layer model. Appl. Geochem. 2004, 19:29-53.
37. Toner B., Manceau A., Webb S.M., Sposito G. Zinc sorption to biogenic hexagonal-birnessite particles within a hydrated bacterial biofilm. Geochim. Cosmochim. Acta 2006, 70:27-43.
38. Manceau A., Lanson B., Drits V.A. Structure of heavy metal sorbed birnessite. Part III: Results from powder and polarized extended X-ray absorption fine structure spectroscopy. Geochim. Cosmochim. Acta 2002, 66:2639-2663.
39. Junta J.L., Hochella M.F. Manganese (II) oxidation at mineral surfaces: a microscopic and spectroscopic study. Geochim. Cosmochim. Acta 1994, 58:4985-4999.
40. Bialk H.M., Simpson A.J., Pedersen J.A. Cross-coupling of sulfonamide antimicrobial agents with model humic constituents. Environ. Sci. Technol. 2005, 39:4463-4473.
41. Halling-Sørensen B., Sengeløv G., Tjørnelund J. Toxicity of tetracyclines and tetracycline degradation products to environmentally relevant bacterial, including selected tetracycline-resistant bacterial. Arch. Environ. Contam. Toxicol. 2002, 42:263-271.
42. Halling-Sørensen B., Lykkeberg A., Ingerslev F., Blackwell P., Tjørnelund J. Characterisation of the abiotic degradation pathways of oxytetracyclines in soil interstitial water using LC-MS-MS. Chemosphere 2003, 50:1331-1342.
43. Diana J., Vandenbosch L., De Spiegeleer B., Hoogmartens J., Adams E. Evaluation of the stability of chlortetracycline in granular premixes by monitoring its conversion into degradation products. J. Pharm. Biomed. Anal. 2005, 39:523-530.
44. Mitscher L.A. The Chemistry of the Tetracycline Antibiotics. Medicinal Research Series 1978, vol. 9. Marcel Dekker, New York.
45. Hussar D.A., Niebergall P.J., Sugita E.T., Doluisio J.T. Aspects of the epimerization of certain tetracycline derivatives. J. Pharm. Pharmacol. 1968, 20:539-546.
46. Bryan P.D., Hawkins K.R., Stewart J.T., Capomacchia A.C. Analysis of chlortetracycline by high performance liquid chromatography with postcolumn alkaline-induced fluorescence detection. Biomed. Chromatogr. 1992, 6:305-310.
47. Naidong W., Roets R., Busson R., Hoogmartens J. Separation of keto-enol tautomers of chlortetracycline and 4-epichlortetracycline by liquid chromatography on poly(styrene-divinylbenzene) copolymer. J. Pharm. Biomed. Anal. 1990, 8:881-889.
48. Blanchflower W.J., McCracken R.J., Haggan A.S., Kennedy D.G. Confirmatory assay for the determination of tetracycline, oxytetracycline, chlortetracycline and its isomers in muscle and kidney using liquid chromatography-mass spectrometry. J. Chromatogr. B: Biomed. Sci. Appl. 1997, 692:351-360.
49. McCormick J.R.D., Sjolander N.O., Hirsch U., Jensen E.R., Doerschuk A.P. A new family of antibiotics: the demethyl-tetracyclines. J. Am. Chem. Soc. 1957, 79:4561-4563.
50. Nakamoto K. Infrared and Raman Spectra of Inorganic and Coordination Compound 1978, John Wiley, New York. third ed.
51. Gu C., Karthikeyan K.G. Interaction of tetracycline with aluminum and iron hydrous oxides. Environ. Sci. Technol. 2005, 39:2660-2667.
52. Wan Y., Bao Y.Y., Zhou Q.X. Simultaneous adsorption and desorption of cadmium and tetracycline on cinnamon soil. Chemosphere 2010, 80:807-812.
53. Kulshrestha P., Giese R.F.J.R., Aga D.S. Investigating the molecular interactions of oxytetracycline in clay and organic matter: insights on factors affecting its mobility in soil. Environ. Sci. Technol. 2004, 38:4097-4105.
54. Dolliver H., Gupta S., Noll S. Antibiotic degradation during manure composting. J. Environ. Qual. 2008, 37:1245-1253.
55. Arikan O.A., Mulbry W., Rice C. Management of antibiotic residues from agricultural sources: use of composting to reduce chlortetracycline residues in beef manure from treated animals. J. Hazard. Mater. 2009, 164:483-489.
56. Chopra I. Tetracycline analogs whose primary target is not the bacterial ribosome. Antimicrob. Agents Chemother. 1994, 38:637-640.