Enzymatic transformation and bonding of sulfonamide antibiotics to model humic substances

Journal of Chemistry

Volumn 2015, Issue , 2015, Pages

  Schwarz, J ^a,b   Knicker, H ^c   Schaumann, G E ^b   Thiele Bruhn, S ^a  

^a UNIVERSITY OF TRIER   (Germany)

^b Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

^c INSTITUTO DE RECURSOS NATURALES Y AGROBIOLOGÍA DE SEVILLA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84924128488     PISSN: 20909063     EISSN: 20909071     Source Type: Journal    
DOI: 10.1155/2015/829708     Document Type: Article

References (55)

1. A. B. Boxall, L. A. Fogg, P. A. Blackwell, P. Kay, E. J. Pemberton, and A. Croxford, "Veterinary medicines in the environment," Reviews of environmental contamination and toxicology, vol. 180, pp. 1-91, 2004.
2. K.-R. Kim, G. Owens, S.-I. Kwon, K.-H. So, D.-B. Lee, and Y. S. Ok, "Occurrence and environmental fate of veterinary antibiotics in the terrestrial environment," Water, Air, and Soil Pollution, vol. 214, no. 1-4, pp. 163-174, 2011.
3. G. Hamscher, H. T. Pawelzick, H. Höper, and H. Nau, "Different behavior of tetracyclines and sulfonamides in sandy soils after repeated fertilization with liquid manure," Environmental Toxicology and Chemistry, vol. 24, no. 4, pp. 861-868, 2005.
4. H. Schmitt, H. Haapakangas, and P. Van Beelen, "Effects of antibiotics on soil microorganisms: time and nutrients influence pollution-induced community tolerance," Soil Biology and Biochemistry, vol. 37, no. 10, pp. 1882-1892, 2005.
5. P. Sukul and M. Spiteller, "Sulfonamides in the environment as veterinary drugs," Reviews of Environmental Contamination and Toxicology, vol. 187, pp. 67-101, 2006.
6. T. Müller, I. Rosendahl, A. Focks, J. Siemens, J. Klasmeier, and M. Matthies, "Short-term extractability of sulfadiazine after application to soils," Environmental Pollution, vol. 172, pp. 180-185, 2013.
7. Q. Wang, M. Guo, and S. R. Yates, "Degradation kinetics of manure-derived sulfadimethoxine in amended soil," Journal of Agricultural and Food Chemistry, vol. 54, no. 1, pp. 157-163, 2006.
8. S. Thiele-Bruhn and D. Peters, "Photodegradation of pharmaceutical antibiotics on slurry and soil surfaces," Landbauforschung Völkenrode, vol. 57, no. 1, pp. 13-23, 2007.
9. 13 Csulfadiazine residues in soil including simultaneous amendment of pig manure," Journal of Environmental Science and Health. Part. B, Pesticides, Food Contaminants, and Agricultural Wastes, vol. 46, no. 2, pp. 137-149, 2011.
10. 14Csulfadiazine residues contained in the manure of young pigs treated with a veterinary antibiotic," Journal of Environmental Science and Health Part B: Pesticides, Food Contaminants, and Agricultural Wastes, vol. 43, no. 1, pp. 8-20, 2008.
11. R. Kreuzig and S. Höltge, "Investigations on the fate of sulfadiazine in manured soil: laboratory experiments and Test Plot Studies," Environmental Toxicology and Chemistry, vol. 24, no. 4, pp. 771-776, 2005.
12. K. Stoob, H.P. Singer, S. Stettler, N. Hartmann, S.R. Müller, and C. H. Stamm, "Exhaustive extraction of sulfonamide antibiotics fromaged agricultural soils using pressurized liquid extraction," Journal of Chromatography A, vol. 1128, no. 1-2, pp. 1-9, 2006.
13. M. Förster, V. Laabs, M. Lamshöft, T. Pütz, and W. Amelung, "Analysis of aged sulfadiazine residues in soils using microwave extraction and liquid chromatography tandem mass spectrometry," Analytical and Bioanalytical Chemistry, vol. 391, no. 3, pp. 1029-1038, 2008.
14. H.-R. Schulten and M. Schnitzer, "Thechemistry of soil organic nitrogen:a review," Biology and Fertility of Soils, vol. 26, no. 1, pp. 1-15, 1998.
15. N. Senesi, B. Xing, and P. M. Huang, Biophysico-Chemical Processes Involving Natural Nonliving Organic Matter in Environmental Systems, John Wiley & Sons, Hoboken, NJ, USA, 2009.
16. J. M. Bracewell, K. Haider, S. R. Larter, and H. R. Schulten, "Thermal degradation relevant to structural studies of humic substances," in Humic Substances II: In Search of Structure, M. H. B. Hayes, P. MacCarthy, R. L. Malcolm, and R. S. Swift, Eds., pp. 181-222, John Wiley & Sons, New York, NY, USA, 1989.
17. J. M. Suflita and J.-M. Bollag, "Polymerization of phenoliccompounds by a soil-enzyme complex," Soil Science Society of America Journal, vol. 45, pp. 297-302, 1981.
18. S. B. Haderlein and R. P. Schwarzenbach, "Environmental processes influencing the rate of abiotic reduction of nitroaromatic compounds in the subsurface," in Biodegradation of Nitroaromatic Compounds, J. C. Spain, Ed., pp. 199-225, Plenum Press, New York, NY, USA, 1995.
19. J. M. Bollag, "Decontaminating soil with enzymes: an in situ method using phenolic and anilinic compounds," Environmental Science and Technology, vol. 26, no. 10, pp. 1876-1881, 1992.
20. J. Schwarz, M.-O. Aust, and S. Thiele-Bruhn, "Metabolites from fungal laccase-catalysed transformation of sulfonamides," Chemosphere, vol. 81, no. 11, pp. 1469-1476, 2010.
21. H. M. Bialk, A. J. Simpson, and J. A. Pedersen, "Cross-coupling of sulfonamide antimicrobial agents with model humic constituents," Environmental Science and Technology, vol. 39, no. 12, pp. 4463-4473, 2005.
22. H. M. Bialk, C. Hedman, A. Castillo, and J. A. Pedersen, "Laccase-mediated Michael addition of 15N-sulfapyridine to a model humic constituent," Environmental Science and Technology, vol. 41, no. 10, pp. 3593-3600, 2007.
23. H. M. Bialk and J. A. Pedersen, "NMR investigation of enzymatic coupling of sulfonamide antimicrobials with humic substances," Environmental Science and Technology, vol. 42, no. 1, pp. 106-112, 2008.
24. A. Gulkowska, B. Thalmann, J. Hollender, and M. Krauss, "Nonextractable residue formation of sulfonamide antimicrobials: new insights from soil incubation experiments," Chemosphere, vol. 107, pp. 366-372, 2014.
25. A. Gulkowska, M. Krauss, D. Rentsch, and J. Hollender, "Reactions of a sulfonamide antimicrobial with model humic constituents: assessing pathways and stability of covalent bonding," Environmental Science and Technology, vol. 46, no. 4, pp. 2102-2111, 2012.
26. A. Gulkowska, M. Sander, J. Hollender, and M. Krauss, "Covalent binding of sulfamethazine to natural and synthetic humic acids: assessing laccase catalysis and covalent bond stability," Environmental Science and Technology, vol. 47, no. 13, pp. 6916-6924, 2013.
27. A. Gulkowska, J. Hollender, and M. Krauss, "Covalent bonding of sulfonamide antimicrobials with organic matter: dominance of nucleophilic addition over radical coupling," in Proceedings of the SETAC Europe 20th Annual Meeting, Sevilla, Spain, May 2010.
28. F. J. González-Vila, F. Martin, C. Sáiz-Jiménez, and H. H. Nimz, "Thermofractography of humic substances," Journal of Thermal Analysis, vol. 15, no. 2, pp. 279-284, 1979.
29. P. Baldrian, "Fungal laccases-occurrence and properties," FEMS Microbiology Reviews, vol. 30, no. 2, pp. 215-242, 2006.
30. C.-J. Wang, S. Thiele, and J.-M. Bollag, "Interaction of 2,4,6-trinitrotoluene (TNT) and 4-amino-2,6-dinitrotoluene with humic monomers in the presence of oxidative enzymes," Archives of Environmental Contamination and Toxicology, vol. 42, no. 1, pp. 1-8, 2002.
31. J.-E. Kim, E. Fernandes, and J.-M. Bollag, "Enzymatic coupling of the herbicide bentazon with humus monomers and characterization of reaction products," Environmental Science and Technology, vol. 31, no. 8, pp. 2392-2398, 1997.
32. S. Thiele, E. Fernandes, and J. M. Bollag, "Enzymatic transformation and binding of labeled 2,4,6-trinitrotoluene to humic substances during an anaerobic/aerobic incubation," Journal of Environmental Quality, vol. 31, no. 2, pp. 437-444, 2002.
33. S. Thiele-Bruhn and M.-O. Aust, "Effects of pig slurry on the sorption of sulfonamide antibiotics in soil," Archives of Environmental Contamination and Toxicology, vol. 47, no. 1, pp. 31-39, 2004.
34. 15N NMR spectroscopy. 1. Determination and optimization of relevant NMR spectroscopic parameters," Environmental Science and Technology, vol. 33, no. 2, pp. 343-349, 1999.
35. G. E. Schaumann and E. J. LeBoeuf, "Glass transitions in peat: their relevance and the impact of water," Environmental Science and Technology, vol. 39, no. 3, pp. 800-806, 2005.
36. J. Hurrass and G. E. Schaumann, "Is glassiness a common characteristic of soil organic matter?" Environmental Science and Technology, vol. 39, no. 24, pp. 9534-9540, 2005.
37. H. R. Christen, Grundlagen der Organischen Chemie, Salle & Sauerländer, Frankfurt, Germany, 6th edition, 1985.
38. 2 extrusion photoproduct," Environmental Science and Technology, vol. 39, no. 10, pp. 3630-3638, 2005.
39. A. L. Boreen, W. A. Arnold, and K. McNeill, "Photodegradation of pharmaceuticals in the aquatic environment: a review," Aquatic Sciences, vol. 65, no. 4, pp. 320-341, 2003.
40. A. L. Boreen, W. A. Arnold, and K. McNeill, "Photochemical fate of sulfa drugs in then aquatic environment: sulfa drugs containing five-membered heterocyclic groups," Environmental Science and Technology, vol. 38, no. 14, pp. 3933-3940, 2004.
41. P. Sukul, M. Lamshöft, S. Zühlke, and M. Spiteller, "Photolysis of 14C-sulfadiazine in water and manure," Chemosphere, vol. 71, no. 4, pp. 717-725, 2008.
42. W. Tappe, M. Herbst, D. Hofmann et al., "Degradation of sulfadiazine by Microbacterium lacus strain SDZm4, isolated from lysimeters previously manured with slurry from sulfadiazine medicated pigs," Applied and Environmental Microbiology, vol. 79, no. 8, pp. 2572-2577, 2013.
43. M. J. García-Galán, M. Silvia Díaz-Cruz, and D. Barceló, "Identification and determination of metabolites and degradation products of sulfonamide antibiotics," TrAC-Trends in Analytical Chemistry, vol. 27, no. 11, pp. 1008-1022, 2008.
44. S. Camarero, D. Ibarra, M. J. Martínez, and Á. T. Martínez, "Lignin-derived compounds as efficient laccase mediators for decolorization of different types of recalcitrant dyes," Applied and Environmental Microbiology, vol. 71, no. 4, pp. 1775-1784, 2005.
45. J. Schwarz, S. Thiele-Bruhn, K.-U. Eckhardt, and H.-R. Schulten, "Sorption of sulfonamide antibiotics to soil organic sorbents: batch experiments with model compounds and computational chemistry," ISRN Soil Science, vol. 2012, Article ID 159189, 10 pages, 2012.
46. P. S. Guin, S. Das, and P. C. Mandal, "Electrochemical reduction of quinones in different media: a review," International Journal of Electrochemistry, vol. 2011, Article ID 816202, 22 pages, 2011.
47. S.-F. Yang, C.-F. Lin, A. Yu-Chen Lin, and P.-K. Andy Hong, "Sorption and biodegradation of sulfonamide antibiotics by activated sludge: experimental assessment using batch data obtained under aerobic conditions," Water Research, vol. 45, no. 11, pp. 3389-3397, 2011.
48. M. Förster, V. Laabs, M. Lamshöft et al., "Sequestration of manure-applied sulfadiazine residues in soils," Environmental Science and Technology, vol. 43, no. 6, pp. 1824-1830, 2009.
49. S. Thiele-Bruhn, T. Seibicke, H. R. Schulten, and P. Leinweber, "Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions," Journal of Environmental Quality, vol. 33, no. 4, pp. 1331-1342, 2004.
50. G. Fåhraeus and B. Reinhammar, "Large scale production and purification of laccase from cultures of the fungus Polyporus versicolor and some properties of laccase A," Acta Chemica Scandinavica, vol. 21, no. 9, pp. 2367-2378, 1967.
51. 15 N-NMR spectroscopic examination of the transformation of organic nitrogen in plant biomass during thermal treatment," Soil Biology and Biochemistry, vol. 28, no. 8, pp. 1053-1060, 1996.
52. 15N-CPMASNMR spectroscopy," in Proceedings of the EUROSOIL: Soil-Society-Environment Conference, p. 9, European Geosciences Union, Vienna, Austria, 2008.
53. E. J. LeBoeuf and L. Zhang, "Thermal analysis for advanced characterization of natural nonliving organic materials," Biophysico-Chemical Processes Involving Natural Nonliving Organic Matter in Environmental Systems, pp. 783-836, 2009.
54. G. E. Schaumann, E. J. LeBoeuf, R. Delapp, and J. Hurraß, "Thermomechanical analysis of air-dried whole soil samples," Thermochimica Acta, vol. 436, no. 1-2, pp. 83-89, 2005.
55. E. Fukuoka, M. Makita, and S. Yamamura, "Glassy state of pharmaceuticals. III. Thermal properties and stability of glassy pharmaceuticals and their binary glass systems," Chemical and Pharmaceutical Bulletin, vol. 37, no. 4, pp. 1047-1050, 1989.