Cross-coupling of sulfonamide antimicrobial agents with model humic constituents

Environmental Science and Technology

Volumn 39, Issue 12, 2005, Pages 4463-4473

  Bialk, Heidi M ^a   Simpson, Andre J ^b   Pedersen, Joel A ^a,c  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b UNIVERSITY OF TORONTO   (Canada)

^c University of Wisconsin Madison   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PHENOLS;

CROSS-COUPLING; HUMIC SUBSTANCES; NATURAL ORGANIC MATTER; SULFONAMIDE ANTIMICROBIAL AGENTS;

SULFUR;

ANTIINFECTIVE AGENT; BENZALDEHYDE DERIVATIVE; BIRNESSITE; COUMARIC ACID; HYDROXYBENZALDEHYDE; HYDROXYBENZOIC ACID; LACCASE; MONOPHENOL MONOOXYGENASE; O DIPHENOL; ORGANIC MATTER; PEROXIDASE; PHENOL; PHENOL DERIVATIVE; PROTOCATECHUIC ACID; SULFADIMIDINE; SULFAMETHOXAZOLE; SULFAPYRIDINE; SULFONAMIDE; SYRINGIC ACID; SYRINGOL; UNCLASSIFIED DRUG;

GEOMICROBIOLOGY;

ARTICLE; BIOLOGICAL ACTIVITY; CHEMICAL STRUCTURE; COVALENT BOND; CROSS COUPLING REACTION; DRUG BIOAVAILABILITY; DRUG DETOXIFICATION; DRUG DISTRIBUTION; DRUG STRUCTURE; DRUG TRANSFORMATION; HUMIC SUBSTANCE; MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ANTI-INFECTIVE AGENTS; HUMIC SUBSTANCES; MAGNETIC RESONANCE SPECTROSCOPY; MONOPHENOL MONOOXYGENASE; OXIDES; PHENOLS; SULFONAMIDES;

EID: 20744445509     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es0500916     Document Type: Article

References (57)

1. RxList: The internet drug index. http://www.rxlist.com/ top200.htm (accessed August 2003).
2. National Research Council. The Use of Drugs in Food Animals: Benefits and Risks; National Academy Press: Washington, DC, 1999.
3. Petri, W. A., Jr. Antimicrobial Agents: Sulfonamides, Trimethoprim-Sulfamethoxazole, Quinolones, and Agents for Urinary Tract Infections. In Goodman & Gilman's The Pharmacological Basis of Therapeutics, 10th ed.; Hardman, J. G., Limbird, L. E., Gilman, A. G., Eds.; McGraw-Hill: New York, 2001; pp 1171-1179.
4. Berger, K. V.; Petersen, B.; Bunning-Pfaue, H. Persistenz von Gülle-Arzneistoffe in der Nahrungskette. Arch. Lebensmittelhyg. 1986, 37, 85-108.
5. Kümmerer, K. Significance of antibiotics in the environment. J. Antimicrob. Chemother. 2003, 52, 5-7.
6. Miao, X.; Bishay, F.; Chen, M.; Metcalfe, C. D. Occurrence of antimicrobials in the final effluents of wastewater treatment plants in Canada. Environ. Sci. Technol. 2004, 38, 3533-3541.
7. Kinney, C.; Furlong, E.; Cahill, J.; Werner, S. Occurrence and behavior of wastewater derived pharmaceuticals in soils irrigated with reclaimed water. Abstracts of Papers, Part 1, 227th National Meeting of the American Chemical Society, March 28 to April 1, 2004; American Chemical Society: Washington, DC, 2004; 112-ENVR.
8. 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 U.S. streams, 1999-2000: A national reconnaissance. Environ. Sci. Technol. 2002, 36, 1202-1211.
9. Ingerslev, F.; Halling-Sørenson, B. Biodegradability properties of sulfonamides in activated sludge. Environ. Toxicol. Chem. 2000, 19, 2467-2473.
10. Christian, T.; Schneider, R. J.; Farber, H. A.; Skutlarek, D.; Meyer, M. T.; Goldbach, H. E. Determination of antibiotic residues in manure, soil, and surface waters. Acta Hydrochim. Hydrobiol. 2003, 31, 36-44,
11. Gao, J.; Bialk, H. M.; Pedersen, J. A. Sorption of sulfonamide antimicrobials to soil constituents. Abstracts of Papers, Part 2, 226th National Meeting of the American Chemical Society, Sept 7-11, 2003; American Chemical Society: Washington, DC, 2003; 159-ENVR.
12. Boxall, A. B. A.; Kolpin, D. W.; Halling-Sørensen, B.; Tolls, J. Are Veterinary medicines causing environmental risks? Environ. Sci. Technol. 2003, 37, 286A-291A.
13. Langhammer, J.-P.; Führ, F.; Bünning-Pfaue, H. Verbleib von Sulfonamid-Rückständen aus der Gülle im Boden und Nutzpflanzen. Lebensmittelchemie 1990, 44, 93.
14. 15N NMR. In Humic and Fulvic Acids: Isolation, Structure and Environmental Role; Gaffney, J. S., Marley, N. A., Clark, S. B., Eds.; ACS Symposium Series 651; American Chemical Society: Washington, DC, 1996; pp 299-326.
15. Li, H.; Lee, L. S.; Jafvert, C. T.; Graveel, J. G. Effect of substitution on irreversible binding and transformation of aromatic amines with soils in aqueous systems. Environ. Sci. Technol. 2000, 34, 3674-3680.
16. Weber, E. J:, Colon, D.; Baughman, G. L. Sediment-associated reactions of aromatic amines. I. Elucidation of sorption mechanisms. Environ. Sci. Technol. 2001, 35, 2470-2475.
17. Post, J. E. Manganese oxide minerals: Crystal structures and economic and environmental significance. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 3447-3454.
18. Gramss, G., Voigt, K.-D., Kirsche, B. Oxidoreductase enzymes liberated by plant roots and their effects on soil humic material. Chemosphere 1999, 35, 1481-1494.
19. Bollag, J.-M. Decontaminating soil with enzymes: An in situ method using phenolic and anilinic compounds. Environ. Sci. Technol. 1992, 26, 1876-1881.
20. 15N NMR investigation of the covalent binding of reduced TNT amines to soil humic acid, model compounds, and lignocellulose. Environ. Sci. Technol. 2002, 36, 3787-3796.
21. Stevenson, F. J. Humus Chemistry: Genesis, Composition, Reaction; John Wiley & Sons: New York, 1994.
22. Dec, J.; Haider, K.; Bollag, J.-M. Decarboxylation and demethoxylation of naturally occurring phenols during coupling reactions and polymerization. Soil Sci. 2001, 166, 660-671.
23. Advanced Chemistry Development (ACD) Software Solaris V4.67; ACD/Labs: Toronto, Canada, 1994-2004.
24. Shah, N. H.; Lazarus, J. H.; Sheth, P. R.; Jarowski, C. I. Carboxymethylcellulose-effect of degree of polymerization and substitution on tablet disintegration and dissolution. J. Pharm. Sci. 1981, 70, 611-613.
25. Lin, C. E.; Chang, C. C.; Lin, W. C. Migration behavior and separation of sulfonamides in capillary zone electrophoresis III. Citrate buffer as a background electrolyte. J. Chromatogr., A 1997, 768, 105-112.
26. Nasipuri, R. N.; Khalil, S. A. H. Adsorption-dissolution relationship in sulfamethazine benzoic acid system. J. Pharm. Sci. 1973, 62, 473-475.
27. Clark, W. G.; Strakosch, E. A.; Levitan, N. I. Solubility and pH data of the commonly used sulfonamides. J. Lab. Clin. Med. 1942, 28, 188-189.
28. Lin, C. E.; Chang, C. C.; Lin, W. C. Migration behavior and separation of sulfonamides in capillary zone electrophoresis. 2. Positively charged species at low pH. J. Chromatogr., A 1997, 759, 203-209.
29. Thiele-Bruhn, S.; Seibicke, T.; Schulten, H.-R.; Leinweber, P. Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions. J. Environ. Qual. 2004, 33, 1331-1342.
30. Kan, C. A.; Petz, M. Residues of veterinary drugs in eggs and their distribution between yolk and white. J. Agric. Food Chem. 2000, 48, 6397-6403.
31. McKenzie, R. M. The synthesis of birnessite, cryptomelane, and some other oxides and hydroxides of manganese. Mineral. Mag. 1971, 38, 493-502.
32. Villalobos, M.; Toner, B.; Bargar, J.; Sposito, G. Characterization of the manganese oxide produced by Pseudomonas putida strain MnB1. Geochim. Cosmochim. Acta 2003, 67, 2649-2662.
33. Kortum, G., Vogel, W.; Andrussow, K. Dissociation Constants of Organic Acids in Aqueous Solution; Butterworth: London, 1961.
34. Bykova L. N., Petrov S. I.; Blagodatskava Z. G. Relative acidity of phenol and its derivatives in a medium of nonaqueous solvents. Zh. Obshch. Khim. 1970, 40, 2295-3000.
35. a Prediction for Organic Acids and Bases; Chapman and Hall: New York, 1981.
36. 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.
37. 14C-labelled catechol. Soil Sci. Am. J. 2000, 64, 157-163.
38. 2: Effect of co-solutes on initial and quasi-steady-state kinetics. Environ. Sci. Technol. 1997, 31, 2642-2649.
39. Bollag, J.-M.; Strynar, M.-Y. A.; Dec, J. Characterization of enzymatic or abiotic immobilization of xenobiotics in soil. In Developments of Soil Science, Vol. 28B; Violante, A., Huang, P. M., Bollag, J.-M., Gianfreda, L., Eds.; Elsevier Science: Amsterdam, 2002; pp 289-299.
40. Wang, C.-J.; Thiele, S.; Bollag, J.-M. Interaction of 2,4,6-trinitrotoluene (TNT) and 4-amino-2,6-dinitrotoluene with humic monomers in the presence of oxidative enzymes. Arch. Environ. Contam. Toxicol. 2002, 42, 1-8.
41. Berry, D. F.; Boyd, S. A. Reaction rates of phenolic humus constituents and anilines during cross-coupling. Soil Biol. Biochem. 1985, 17, 631-636.
42. Figueroa-Espinoza, M. C.; Rouau, X. Effect of cysteinyl caffeic acid, caffeic acid, and L-Dopa on the oxidative cross-linking of feruloylated arabinoxylans by a fungal laccase. J. Agric. Food Chem. 1999, 47, 497-503.
43. Parris, G. E. Covalent binding of aromatic amines to humates. 1. Reactions with carbonyls and quinones. Environ. Sci. Technol. 1980, 14, 1099-1106.
44. Hsu, T.-S.; Bartha, R. Interaction of pesticide-derived chloroaniline residues with soil organic matter. Soil Sci. 1974, 116, 444-452.
45. Weber, E. J.; Spidle, D. L.; Thorn, K. A. Covalent binding of aniline to humic substances. 1. Kinetic studies. Environ. Sci. Technol. 1996, 30, 2755-2763.
46. Colon, D.; Weber, E. J.; Baughman, G. L. Sediment-associated reactions of aromatic amines. 2. QSAR development. Environ. Sci. Technol. 2002, 36, 2443-2450.
47. Bollag, J.-M.; Dec, J. Phenoloxidase-mediated interactions of phenols and anilines with humic materials. J. Environ. Qual. 2000, 29, 665-676.
48. Kobayashi, A.; Koguchi, Y.; Kanzaki, H.; Kajiyama, S.; Kawazu, K. A new type of antimicrobial phenolics produced by plant peroxidases and its possible role in the chemical defense systems against plant pathogens. Z. Naturforsch. 1994, 7-8, 411-414.
49. Rescigno, A.; Sollai, F.; Pisu, B.; Rinaldi, A.; Sanjust, E. Tyrosinase inhibition: General and applied aspects. J. Enzyme Inhib. Med. Chem. 2002, 17, 207-218.
50. Tatsumi, K. A.; Freyer, R. D. Minard.; Bollag, J.-M. Enzyme-mediated coupling of 3,4-dichlooraniline and ferulic acid: A model for pollutant binding to humic materials. Environ. Sci. Technol. 1994, 28, 210-215.
51. Bollag, J.-M.; Liu, S.-Y.; Minard, R. D. Cross-coupling of phenolic humus constituents and 2,4-dichlorophenol. Soil Sci. Soc. Am. J. 1980, 44, 52-56.
52. Prota, G. Melanins and Melanogenesis; Academic Press: New York, 1992.
53. Laha, S.; Luthy, R. Oxidation of aniline and other primary aromatic amines by manganese oxide. Environ. Sci. Technol. 1990, 24, 363-373.
54. McBride, M. B. Adsorption and oxidation of phenolic compounds by iron and manganese oxides. Soil Sci. Soc. Am. J. 1987, 51, 1466-1472.
55. Stone, A. T.; Morgan, J. J. Reduction and dissolution of manganese (III) and manganese (IV) oxides by organics: 2. Survey of the reactivity of organics. Environ. Sci. Technol. 1984, 18, 617-624.
56. Kang, Ki-H.; Dec, J.; Park, H.; Bollag, J.-M. Effect of phenolic mediators and humic acid on cyprodinil transformation in presence of birnessite. Water Res. 2004, 38, 2738-2745.
57. Durán, N.; Esposito, E. Potential applications of oxidative enzymes and phenoloxidase-like compounds in wastewater and soil treatment: a review. Appl. Catal., B 2000, 28, 83-99.