Reaction of antibiotic sulfadiazine with manganese dioxide in aqueous phase: Kinetics, pathways and toxicity assessment

References

• Sukul, P.; Lamshöft, M.; Zühlke, S.; Spiteller, M. Photolysis of 14C-sulfadiazine in water and manure. Chemosphere 2008, 71, 717–725.
   PubMed Web of Science ®Google Scholar
• Hardman, J.G.; Limbrid, L.E.; Gilman, A.G.E. Goodman & Gilman's The Pharmacological Basis of Therapeutics; McGraw-Hill: New York, 2001.
   Google Scholar
• Lamshöft, M.; Sukul, P.; Zühlke, S.; Spiteller, M. Metabolism of 14C-sulfadiazine after administration to pigs. Anal. Bioanal. Chem. 2007, 388, 1733–1757.
   PubMed Web of Science ®Google Scholar
• Gao, J.; Pedersen, J.A. Adsorption of sulfonamide antimicrobial agents to clay minerals. Environ. Sci. Technol. 2005, 39, 9509–9516.
   PubMed Web of Science ®Google Scholar
• Zielezny, Y.; Groeneweg, J.; Vereecken, H.; Tappe, W. Impact of sulfadiazine and chlorotetracycline on soil bacterial community structure and respiratory activity. Soil Biol. Biochem. 2006, 38, 2372–2380.
   Web of Science ®Google Scholar
• Hammesfahr, U.; Heuer, H.; Manzke, B.; Smalla, K.; Thiele-Bruhn, S. Impact of the antibiotic sulfadiazine and pig manure on the microbial community structure in agricultural soils. Soil Biol. Biochem. 2008, 40, 1583–1591.
   Web of Science ®Google Scholar
• Heuer, H.; Smalla, K. Manure and sulfadiazine synergistically increased bacterial antibiotic resistance in soil over at least two months. Environ. Microbiol. 2007, 9, 657–666.
   PubMed Web of Science ®Google Scholar
• Heuer, H.; Solehati, Q.; Zimmerling, U.; Kleineidam, K.; Schloter, M.; Müller, T.; Focks, A.; Thiele-Bruhn, S.; Smalla, K. Accumulation of sulfadiazine resistance genes in arable soils due to repeated application of manure containing sulfadiazine. Appl. Environ. Microb. 2011, 77, 2527–2530.
   PubMed Web of Science ®Google Scholar
• Su, H.C.; Ying, G.G.; Tao, R.; Zhang, R.Q.; Zhao, J.L.; Liu, Y.S. Class and integrons, sul resistance genes and antibiotic resistance in Escherichia coli isolated from Dongjiang River, South China. Environ. Pollut. 2012, 169, 42–49.
   PubMed Web of Science ®Google Scholar
• Wenk, J.; Canonica, S. Phenolic antioxidants inhibit the triplet-induced transformation of anilines and sulfonamide antibiotics in aqueous solution. Environ. Sci. Technol. 2012, 46, 5455–5462.
   PubMed Web of Science ®Google Scholar
• Bahnmüller, S.; Gunter, U.; Canonica, S. Sunlight-induced transformation of sulfadiazine and sulfamethoxazole in surface waters and wastewater effluents. Water Res. 2014, 57, 183–192.
   PubMed Web of Science ®Google Scholar
• Yang, J.F.; Ying, G.G.; Yang, L.H.; Zhao, J.L.; Liu, F.; Tao, R.; Yu, Z.Q.; Peng, P. Degradation behavior of sulfadiazine in soils under different conditions. J. Environ. Sci. Health, B 2009, 44, 241–248.
   PubMed Web of Science ®Google Scholar
• Sittig, S.; Kasteel, R.; Groeneweg, J.; Hofmann, D.; Thiele, B.; Köppchen, S.; Vereeecken, H. Dynamics of transformation of the veterinary antibiotic sulfadiazine in two soils. Chemosphere 2014, 95, 470–477.
   PubMed Web of Science ®Google Scholar
• Doretto, K.M.; Rath, S. Sorption of sulfadiazine on Brazilian soils. Chemosphere 2013, 90, 2027–2034.
   PubMed Web of Science ®Google Scholar
• Kreuzig, R.; Höltge, S. Investigates on the fate of sulfadiazine in manured soil: Laboratory experiments and test plot studies. Environ. Toxicol. Chem. 2005, 24, 771–776.
   PubMed Web of Science ®Google Scholar
• Rosendahl, I.; Siemens, J.; Groeneweg, J.; Linzbach, E.; Laabs, V.; Herrmann, C.; Vereecken, H.; Amelung, W. Dissipation and sequestration of the veterinary antibiotic sulfadiazine and its metabolites under field conditions. Environ. Sci. Technol. 2011, 45, 5216–5222.
   PubMed Web of Science ®Google Scholar
• Sukul, P.; Lamshöft, M.; Zühlke, S.; Spiteller, M. Sorption and desorption of sulfadiazine in soil and soil-manure systems. Chemosphere 2008, 73, 1344–1350.
   PubMed Web of Science ®Google Scholar
• Tebo, B.M.; Bargar, J.R.; Clement, B.G.; Dick, G.J.; Murray, K.J.; Parker, D.; Verity, R.; Webb, S.M. Biogenic manganese oxides: Properties and mechanisms of formation. Annu. Rev. Earth. Planet. Sci. 2004, 32, 287–328.
   Web of Science ®Google Scholar
• Tessier, A.; Fortin, D.; Belzile, N.; DeVitre, R.R.; Leppard, G.G. Metal sorption to diagenetic iron and manganese oxyhydroxides and associated organic matter: Narrowing the gap between field and laboratory measurements. Geochim. Cosmochi. Acta 1996, 60, 387–404.
   Web of Science ®Google Scholar
• Ding, J.; Su, M.; Wu, C.; Lin, K. Transformation of triclosan to, 8-dichlorodibenzo-p-dioxin by iron and manganese oxides under near dry conditions. Chemosphere 2015, 133, 41–46.
   PubMed Web of Science ®Google Scholar
• Zhang, H.C.; Huang, C.H. Oxidative transformation of triclosan and chlorophenol by manganese oxides. Environ. Sci. Technol. 2003, 37, 2421–2430.
   PubMed Web of Science ®Google Scholar
• Gao, J.; Hedman, C.; Liu, C.; Pedersen, T.J.A. Transformation of sulfamethazine by manganese oxide in aqueous solution. Environ. Sci. Technol. 2012, 46, 2642–2651.
   PubMed Web of Science ®Google Scholar
• Negra, C.; Ross, D.S.; Lanzirotti, A. Oxidizing behavior of soil manganese: Interactions among abundance, oxidation state, and pH. Soil Sci. Soc. Am. J. 2005, 69, 87–95.
   Web of Science ®Google Scholar
• Lin, K.D.; Liu, W.; Gan, J. Oxidative removal of bisphenol A by manganese dioxide: Efficacy, products, and pathways. Environ. Sci. Technol. 2009, 43, 3860–3864.
   PubMed Web of Science ®Google Scholar
• Lin, K.D.; Yan, C.; Gan, J. Production of hydroxylated polybrominated diphenyl ethers (OH-PBDEs) from bromophenols by manganese dioxide. Environ. Sci. Technol. 2014, 48, 263–271.
   PubMed Web of Science ®Google Scholar
• Clarke, C.E.; Johnson, K.L. Oxidative breakdown of acid orange 7 by a manganese oxide containing mine waste: Insight into sorption, kinetics and reaction dynamics. Appl. Catal., B 2010, 101, 13–20.
   Web of Science ®Google Scholar
• Chen, W.R.; Huang, C.H. Transformation kinetics and pathways of tetracycline antibiotics with manganese oxide. Environ. Pollut. 2011, 15, 1092–1100.
   Web of Science ®Google Scholar
• Chen, W.R.; Ding, Y.J.; Johnston, C.T.; Teppen, B.J.; Boyd, S.A.; Li, H. Reaction of linconsamide antibiotics with manganese oxide in aqueous solution. Environ. Sci. Technol. 2010, 44, 4486–4492.
   PubMed Web of Science ®Google Scholar
• Clarke, C.E.; Kielar, F.; Johnson, K.L. The oxidation of acid azo dye AY 36 by a manganese oxide containing mine waste. J. Hazard. Mater. 2013, 246–247, 310–318.
   PubMed Web of Science ®Google Scholar
• Xiao, X.; Sun, S.P.; McBride, M.B.; Lemley, A.T. Degradation of ciprofloxacin by cryptomelane-type manganese (III/IV) oxides. Environ. Sci. Pollut. Res. 2013, 20, 10–21.
   PubMed Web of Science ®Google Scholar
• Liu, C.; Zhang, L.; Li, F.; Wang, Y.; Gao, Y.; Li, X.; Cao, W.; Feng, C.; Dong, J.; Sun, L. Dependence of sulfadiazine oxidative degradation on physicochemical properties of manganese dioxides. Ind. Eng. Chem. Res. 2009, 48, 10408–10413.
   Web of Science ®Google Scholar
• Dong, J.; Li, Y.; Zhang, L.; Liu, C.; Zhuang, L.; Sun, L.; Zhou, J. The oxidative degradation of sulfadiazine at the interface of α-MnO2 and water. J. Chem. Technol. Biotechnol. 2009, 84, 1848–1853.
   Web of Science ®Google Scholar
• Li, Y.; Wei, X.; Chen, J.; Xie, H.; Zhang, Y. Photodegradation mechanism of sulfonamides with excited triplet state dissolved organic matter: A case of sulfadiazine with 4-carboxybenzophenone as a proxy. J. Hazard. Mater. 2015, 290, 9–15.
   PubMed Web of Science ®Google Scholar
• Murray, J.W. Surface chemistry of hydrous manganese dioxide, J. Colloid Interf. Sci. 1974, 46, 357–371.
   Web of Science ®Google Scholar
• Yang, J.F.; Zhou, S.B.; Xiao, A.G.; Li, W.J.; Ying, G.G. Chemical oxidation of sulfadiazine by the Fenton process: Kinetics, pathways, toxicity evaluation. J. Environ. Sci. Health, B 2014, 49, 909–16.
   Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Zhang, H.C.; Huang, C.H. Reactivity and transformation of antibacterial N-oxides in the presence of manganese oxide. Environ. Sci. Technol. 2005, 39, 593–601.
   PubMed Web of Science ®Google Scholar
• Zhang, H.; Chen, W.R.; Huang, C.H. Kinetic modeling of oxidation of antibacterial agents by manganese oxide. Environ. Sci. Technol. 2008, 42, 5548–5554.
   PubMed Web of Science ®Google Scholar
• Stumm, W.; Morgan, J.J. Aquatic Chemistry, 3rd ed.; Wiley: New York, 1996.
   Google Scholar
• Klausen, J.; Haderlein, S.B.; Schwarzenbach, R.P. Oxidation of substituted anilines by aqueous MnO2: Effect of co-solutes on initial and quasi-steady-state kinetics. Environ. Sci. Technol. 1997, 31, 2642–2649.
   Web of Science ®Google Scholar
• Chen, G.; Zhao, L.; Dong, Y. Oxidative degradation kinetics and products of chlortetracycline by manganese dioxide. J. Hazard. Mater. 2011, 193, 128–138.
   PubMed Web of Science ®Google Scholar
• Li, Y.; Wei, D.; Du, Y. Oxidative transformation of levofloxacin by δ-MnO2: Products, pathways and toxicity assessment. Chemosphere 2015, 119, 282–288.
   PubMed Web of Science ®Google Scholar
• Mijangos, F.; Varona, F.; Villota, N. Changes in solution color during phenol oxidation by Fenton reagent. Environ. Sci. Technol. 2006, 40, 5538–5543.
   PubMed Web of Science ®Google Scholar
• Perez-Moya, M.; Graells, M.; Castells, G.; Amigo, J.; Ortega, E.; Buhigas, G.; Perez, L.M.; Mansilla, H.D. Characterization of the degradation performance of the sulfamethazine antibiotic by photo-Fenton process. Water Res. 2010, 44, 2533–2540.
   PubMed Web of Science ®Google Scholar