Photoproducts of tetracycline and oxytetracycline involving self-sensitized oxidation in aqueous solutions: Effects of Ca 2+ and Mg 2+

Journal of Environmental Sciences

Volumn 23, Issue 10, 2011, Pages 1634-1639

  Chen, Yong ^a   Li, Hua ^a   Wang, Zongping ^a   Tao, Tao ^a   Hu, Chun ^b  

^a HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b RESEARCH CENTER FOR ECO ENVIRONMENTAL SCIENCES   (China)

Author keywords

Complexation; Photoproducts; Self sensitized oxidation; Tetracyclines

Indexed keywords

ADVERSE EFFECT; ENHANCED TC; NATURAL ECOSYSTEM; NATURAL WATER SAMPLES; OXIDATION PROCESS; OXIDATION PRODUCTS; PARENT COMPOUNDS; PH VALUE; PHOTO-TOXICITY; PHOTOPRODUCTS; SELF SENSITIZATION; SELF-SENSITIZED OXIDATION; SIGNIFICANT IMPACTS; SINGLET OXYGEN; TETRACYCLINES;

ANTIBIOTICS; CALCIUM; IONS;

OXIDATION;

ANTIINFECTIVE AGENT; CALCIUM; DIVALENT CATION; MAGNESIUM; TETRACYCLINE DERIVATIVE; WATER;

AQUEOUS SOLUTION; CALCIUM; COMPLEXATION; MAGNESIUM; OXIDATION; OXYTETRACYCLINE; PH; PHOTODEGRADATION;

ARTICLE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; LIQUID CHROMATOGRAPHY; OXIDATION REDUCTION REACTION; PHOTOLYSIS; SOLUTION AND SOLUBILITY; WATER POLLUTANT;

ANTI-BACTERIAL AGENTS; CALCIUM; CATIONS, DIVALENT; CHROMATOGRAPHY, LIQUID; MAGNESIUM; OXIDATION-REDUCTION; PHOTOLYSIS; SOLUTIONS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TETRACYCLINES; WATER; WATER POLLUTANTS, CHEMICAL;

EID: 80054078693     PISSN: 10010742     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1001-0742(10)60625-0     Document Type: Article

References (37)

1. Baciocchi E, Del Giacco T, Lapi A Oxygénation of ben-zyldimethylamine by singlet oxygen: Products and mechanism. Organic Letters 2006, 6(25):4791-4794.
2. Baciocchi E, Del Giacco T, Lapi A Dual pathways for the desilylation of silylamines by singlet oxygen. Organic Letters 2006, 8(9):1783-1786.
3. Batt AL, Aga DS Simultaneous analysis of multiple classes of antibiotics by ion trap LC/MS/MS for assessing surface water and groundwater contamination. Analytical Chemistry 2005, 77(9):2940-2947.
4. Ben WW, Qiang ZM, Adams C, Zhang HQ, Chen LP Simultaneous determination of sulfonamides, tetracyclines and tiamulin in swine wastewater by solid-phase extraction and liquid chromatography-mass spectrometry. Journal of Chromatography A 2008, 1202(2):173-180.
5. Canónica S, Jans U, Stemmler K, Hoigné J Transformation kinetics of phenols in water: photosensitization by dissolved natural organic material and aromatic ketones. Environmental Science and Technology 1995, 29(7):1822-1831.
6. Chen Y, Hu C, Hu XX, Qu JH Indirect photodegradation of amine drugs in aqueous solution under simulated sunlight. Environmental Science and Technology 2009, 43(8):2760-2765.
7. Chen Y, Hu C, Qu JH, Yang M Photodegradation of tetracycline and formation of reactive oxygen species in aqueous tetracycline solution under simulated sunlight irradiation. Journal of Photochemistry and Photobiology A 2008, 197(1):81-87.
8. Daughton CG, Ternes TA Pharmaceuticals and personal care products in the environment: Agents of subtle change?. Environmental Health Perspectives 1999, 107(Suppl. 6):907-938.
9. Davies AK, McKellar JF, Phillips GO, Reid AG Photochemical oxidation of tetracycline in aqueous solution. Journal of the Chemical Society, Perkin Transactions 1979, 2:369-375.
10. Drexel RE, Olack G, Jones C, Chmurny GN, Santini R, Morrison H Lumitetracycline: A novel new tetracycline photoproduct. Journal of Organic Chemistry 1990, 55(8):2471-2478.
11. Dürckheimer W Tetracyclines: Chemistry, biochemistry, and structure-activity relations. Angewandte Chemie International Edition 1975, 14(11):721-734.
12. Eichhorn P, Aga DS Identification of a photooxygenation product of chlortetracycline in hog lagoons using LC/ESI-ion trap-MS and LC/ESI-time-of-flight-MS. Analytical Chemistry 2004, 76(20):6002-6011.
13. Fritz JW, Zuo YG Simultaneous determination of tetracycline, oxytetracycline, and 4-epitetracycline in milk by high-performance liquid chromatography. Food Chemistry 2007, 105(3):1297-1301.
14. g, and vitamin E Solvent and temperature effects. Journal of the American Chemical Society 1984, 106(23):6956-6959.
15. Halling-Sorensen B, Nors Nielsen S, Lanzky PF, Ingerslev F, Holten Lützhoft HC, Jorgensen SE Occurrence, fate and effects of pharmaceutical substances in the environment: A review. Chemo-sphere 1998, 36(2):357-393.
16. Hasan T, Allen M, Cooperman BS Anhydrotetracycline is a major product of tetracycline photolysis. Journal of Organic Chemistry 1985, 50(10):1755-1757.
17. Hirsch R, Ternes T, Haberer K, Kratz KL Occurrence of antibiotics in the aquatic environment. Science of the Total Environment 1999, 225(1-2):109-118.
18. Jacobsen AM, Halling-Sorensen B, Ingerslev F, Hansen SH Simultaneous extraction of tetracycline, macrolide and sulfonamide antibiotics from agricultural soils using pressurised liquid extration, followed by solid-phase extration and liquid chromatography-tandem mass spectrometry. Journal of Chromatography A 2004, 1038(1-2):157-170.
19. Jiao SJ, Zheng SR, Yin DQ, Wang LH, Chen LY Aqueous photolysis of tetracycline and toxicity of photolytic products to luminescent bacteria. Chemosphere 2008, 73(3):377-382.
20. Jiao SJ, Zheng SR, Yin DQ, Wang LH, Chen LY Aqueous oxytetracycline degradation and the toxicity change of degradation compounds in photoirradiation process. Journal of Environmental Sciences 2008, 20(7):806-813.
21. Kolpin DW, Furlong ET, Meyer MT, Thurman EM, Zaugg SD, Barber LB, et al. Pharmaceuticals, hormones, and other organic wastewater contaminants in US streams, 1999-2000: a national reconnaissance. Environmental Science and Technology 2002, 36(6):1202-1211.
22. Lambs L, Decock-Le Reverend B, Kozlowski H, Berthon G Metal ion-tetracycline interactions in biological fluids 9 circular dichroism spectra of calcium and magnesium complexes with tetracycline, oxytetracycline, doxycycline, and chlortetracycline and discussion of their binding modes. Inorganic Chemistry 1988, 27(17):3001-3012.
23. Lindsey ME, Meyer M, Thurman EM Analysis of trace levels of sulfonamide and tetracycline antimicrobials in groundwater and surface water using solid-phase extraction and liquid chromatogra-phy/mass spectrometry. Analytical Chemistry 2001, 73(19):4640-4646.
24. Moore DE, Fallón MP, Burt CD Photo-oxidation of tetracycline - a differential pulse polarographic study. International Journal of Pharmaceutics 1983, 14(2-3):133-142.
25. Morrison H, Olack G, Xiao CH Photochemical and photophysical studies of tetracycline. Journal of the American Chemical Society 1991, 113(21):8110-8118.
26. Oka H, Ikai Y, Kawamura N, Yamada M, Harada K, Ito S, et al. Photodecomposition products of tetracycline in aqueous solution. Journal of Agricultural and Food Chemistry 1989, 37(1):226-231.
27. Oka H, Ito Y, Kagami T, Ikai Y, Harada KI Mass spectrometric analysis of tetracycline antibiotics in foods. Journal of Chromatography A 1998, 812(1-2):309-319.
28. Prüden A, Pei RT, Storteboom H, Carlson KH Antibiotic resistance genes as emerging contaminants: studies in northern Colorado. Environmental Science and Technology 2006, 40(23):7445-7450.
29. Sarmah AJ, Meyer MT, Boxall ABA A global perspective on the use, sales, exposure pathways, occurrence, fate and effects of veterinary antibiotics (VAs) in the environment. Chemosphere 2006, 65(5):725-759.
30. Sanderson H, Ingerslev F, Brain RA, Halling-Sorensen B, Bestari JK, Wilson CJ, et al. Dissipation of oxytetracycline, chlortetracycline, tetracycline and doxycycline using HPLC-UV and LC/MS/MS under aquatic semi-field microcosm conditions. Chemosphere 2005, 60(5):619-629.
31. 2+. PhysChemComm 2000, 3(9):42-55.
32. Schweitzer C, Schmidt R Physical mechanisms of generation and deactivation of singlet oxygen. Chemical Reviews 2003, 103(5):1685-1757.
33. Seto Y, Ochi M, Onoue S, Yamada S High-throughput screening strategy for photogenotoxic potential of pharmaceutical substances using fluorescent intercalating dye. Journal of Pharmaceutical and Biomédical Analysis 2010, 52(5):781-786.
34. Stephens CR, Murai K, Brunings KJ, Woodward RB Acidity constants of the tetracycline antibiotics. Journal of the American Chemical Society 1956, 78(16):4155-4158.
35. Werner JJ, Arnold WA, McNeill K Water hardness as a photochemical parameter: Tetracycline photolysis as a function of calcium concentration, magnesium concentration, and pH. Environmental Science and Technology 2006, 40(23):7236-7241.
36. 2+: a spectroscopic study. Journal of Physical Chemistry B 1998, 102(46):9323-9331.
37. Witte W Medical consequences of antibiotic use in agriculture. Science 1998, 279(5353):996-997.