Reactions of a sulfonamide antimicrobial with model humic constituents: Assessing pathways and stability of covalent bonding

Environmental Science and Technology

Volumn 46, Issue 4, 2012, Pages 2102-2111

  Gulkowska, Anna ^a,b   Krauss, Martin ^a,c   Rentsch, Daniel ^d   Hollender, Juliane ^a,b  

^a SWISS FEDERAL INSTITUTE OF AQUATIC SCIENCE AND TECHNOLOGY   (Switzerland)

^b ETH ZURICH   (Switzerland)

^c HELMHOLTZ CENTRE FOR ENVIRONMENTAL RESEARCH UFZ   (Germany)

^d SWISS FEDERAL LABORATORIES FOR MATERIALS SCIENCE AND TECHNOLOGY   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,4-ADDITION; AMINO GROUP; COVALENT BOND FORMATION; COVALENT BONDING; COVALENTLY BOUND; EXTRACTABILITY; FORMATION RATES; HIGH RESOLUTION MASS SPECTROMETRY; INCUBATION TIME; LACCASES; MODEL HUMIC ACIDS; NON-EXTRACTABLE RESIDUES; PRESSURIZED LIQUID EXTRACTION; RADICAL COUPLING REACTIONS; RADICAL SCAVENGERS; RECOVERY RATE; SULFATHIAZOLE; TWO-PRODUCT;

CARBONYL COMPOUNDS; COVALENT BONDS; DESORPTION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC ACIDS;

SULFUR COMPOUNDS;

ANILINE; AROMATIC AMINE; CARBONYL DERIVATIVE; HETEROCYCLIC COMPOUND; HUMIC ACID; LACCASE; PARA PHENETIDINE; POLYMER; QUINONE DERIVATIVE; SULFATHIAZOLE; TERT BUTYL ALCOHOL;

ANTIMICROBIAL ACTIVITY; ASSESSMENT METHOD; CARBONYL COMPOUND; HUMIC SUBSTANCE; NUCLEAR MAGNETIC RESONANCE; NUMERICAL MODEL; POLYMER; SPECTROMETRY;

ARTICLE; COVALENT BOND; DESORPTION; EXTRACTION; HETERONUCLEAR MULTIPLE BOND CORRELATION; MASS SPECTROMETRY; MOLECULAR STABILITY; NITROGEN NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SOIL;

ANILINE COMPOUNDS; ANTI-INFECTIVE AGENTS; HUMIC SUBSTANCES; KINETICS; LACCASE; OXIDATION-REDUCTION; PHENETIDINE; PHENOLS; QUINONES; SULFATHIAZOLES;

EID: 84857770261     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es202272w     Document Type: Article

References (42)

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 (5), 725-759. (Pubitemid 44292205)
2. Kay, P.; Blackwell, P. A.; Boxall, A. B. A. Fate of veterinary antibiotics in a macroporous tile drained clay soil. Environ. Toxicol. Chem. 2004, 23 (5), 1136-1144. (Pubitemid 38621018)
3. Kreuzig, R.; Höltge, S. Investigations on the fate of sulfadiazine in manured soil: Laboratory experiments and test plot studies. Environ. Toxicol. Chem. 2005, 24 (4), 771-776. (Pubitemid 40404543)
4. Burkhardt, M.; Stamm, C.; Waul, C.; Singer, H.; Müller, S. Surface runoff and transport of sulfonamide antibiotics and tracers on manured grassland. J. Environ. Qual. 2005, 34 (4), 1363-1371. (Pubitemid 41045404)
5. Schmidt, B.; Ebert, J.; Lamshöft, M.; Thiede, B.; Schumacher-Buffel, R.; Ji, R.; Corvini, P. F. X.; Schäffer, A. Fate in soil of 14Csulfadiazine residues contained in the manure of young pigs treated with a veterinary antibiotic. J. Environ. Sci. Health, Part B 2008, 43 (1), 8-20.
6. Förster, M.; Laabs, V.; Lamshöft, M.; Groeneweg, J.; Zühlke, S.; Spiteller, M.; Krauss, M.; Kaupenjohann, M.; Amelung, W. Sequestration of manure-Applied sulfadiazine residues in soils. Environ. Sci. Technol. 2009, 43 (6), 1824-1830.
7. Gevao, B.; Semple, K. T.; Jones, K. C. Bound pesticide residues in soils: A review. Environ. Pollut. 2000, 108 (1), 3-14. (Pubitemid 30089396)
8. Stoob, K.; Singer, H. P.; Stettler, S.; Hartmann, N.; Müller, S. R.; Stamm, C. H. Exhaustive extraction of sulfonamide antibiotics from aged agricultural soils using pressurized liquid extraction. J. Chromatogr., A 2006, 1128 (1-2), 1-9. (Pubitemid 44292740)
9. Weber, E. J.; Spidle, D. L.; Thorn, K. A. Covalent binding of aniline to humic substances. 1. Kinetic studies. Environ. Sci. Technol. 1996, 30 (9), 2755-2763.
10. Thorn, K. A.; Kennedy, K. R. 15N NMR Investigation of the covalent binding of reduced TNT amines to soil humic acid, model compounds, and lignocellulose. Environ. Sci. Technol. 2002, 36 (17), 3787-3796. (Pubitemid 35006333)
11. Dec, J.; Bollag, J. M. Phenoloxidase-mediated interactions of phenols and anilines with humic materials. J. Environ. Qual. 2000, 29 (3), 665-676. (Pubitemid 30329201)
12. Parris, G. E. Covalent binding of aromatic amines to humates.1. Reactions with carbonyls and quinones. Environ. Sci. Technol. 1980, 14 (9), 1099-1106. (Pubitemid 10002751)
13. Bialk, H. M.; Simpson, A. J.; Pedersen, J. A. Cross-coupling of sulfonamide antimicrobial agents with model humic constituents. Environ. Sci. Technol. 2005, 39 (12), 4463-4473. (Pubitemid 40853130)
14. Bialk, H. M.; Hedman, C.; Castillo, A.; Pedersen, J. A. Laccasemediated michael addition of 15N-sulfapyridine to a model humic constituent. Environ. Sci. Technol. 2007, 41 (10), 3593-3600. (Pubitemid 350067205)
15. Bialk, H. M.; Pedersen, J. A. NMR investigation of enzymatic coupling of sulfonamide antimicrobials with humic substances. Environ. Sci. Technol. 2008, 42 (1), 106-112.
16. Thorn, K. A.; Goldenberg, W. S.; Younger, S. J.; Weber, E. J. Covalent binding of aniline to humic substances -Comparison of nucleophilic addition, enzyme-, and metal-catalyzed reactions by 15N NMR. Humic Fulvic Acids 1996, 651, 299-326. (Pubitemid 126427777)
17. Laha, S.; Luthy, R. G. Oxidation of aniline and other primary aromatic amines by manganese dioxide. Environ. Sci. Technol. 1990, 24 (3), 363-373. (Pubitemid 20187558)
18. 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 (17), 3674-3680.
19. Knicker, H.; Müller, P. Transport and immobilization of 2,4,6-15N-Trinitrotoluene in soil microcosms subjected to long term incubation under aerobic conditions. Water, Air, Soil Pollut.: Focus 2006, 6 (3), 235-260. (Pubitemid 44313405)
20. Uchimiya, M.; Stone, A. T. Reversible redox chemistry of quinones: Impact on biogeochemical cycles. Chemosphere 2009, 77 (4), 451-458.
21. Ononye, A. I.; Graveel, J. G. Modeling the reactions of 1-naphthylamine and 4-methylaniline with humic acids: Spectroscopic investigations of the covalent linkages. Environ. Toxicol. Chem. 1994, 13 (4), 537-41. (Pubitemid 24116209)
22. Simmons, K. E.; Minard, R. D.; Bollag, J. M. Oxidative cooligomerization of guaiacol and 4-chloroaniline. Environ. Sci. Technol. 1989, 23 (1), 115-121.
23. Tatsumi, K.; Freyer, A.; Minard, R. D.; Bollag, J. M. Enzymatic coupling of chloroanilines with syringic acid, vanillic acid and protocatechuic acid. Soil Biol. Biochem. 1994, 26 (6), 735-742. (Pubitemid 2087398)
24. Thorn, K. A.; Pettigrew, P. J.; Goldenberg, W. S. Covalent binding of aniline to humic substances.2. 15N NMR studies of nucleophilic addition reactions. Environ. Sci. Technol. 1996, 30 (9), 2764-2775.
25. Uchimiya, M.; Stone, A. T. Aqueous oxidation of substituted dihydroxybenzenes by substituted benzoquinones. Environ. Sci. Technol. 2006, 40 (11), 3515-3521. (Pubitemid 43830959)
26. Laskowski, D. E. Influence of structural features on formation of solid charge-Transfer complexes of quinones with carcinogenic and related noncarcinogenic electron donors. Cancer Res. 1967, 27, 903-911.
27. Camarero, S.; Ibarra, D.; Martinez, M. J.; Martinez, A. T. Ligninderived compounds as efficient laccase mediators for decolorization of different types of recalcitrant dyes. Appl. Environ. Microbiol. 2005, 71 (4), 1775-1784. (Pubitemid 40546092)
28. Camarero, S.; Canas, A. I.; Nousiainen, P.; Record, E.; Lomascolo, A.; Martinez, M. J.; Martinez, A. T. p-Hydroxycinnamic acids as natural mediators for laccase oxidation of recalcitrant compounds. Environ. Sci. Technol. 2008, 42 (17), 6703-6709.
29. Carunchio, F.; Crescenzi, C.; Girelli, A. M.; Messina, A.; Tarola, A. M. Oxidation of ferulic acid by laccase:identification of the products and inhibitory effects of some dipeptides. Talanta 2001, 55, 189-200. (Pubitemid 32734699)
30. 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 (12), 2028-2034. (Pubitemid 29288966)
31. 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), 1-8. (Pubitemid 34260147)
32. Colon, D.; Weber, E. J.; Baughman, G. L. Sediment-Associated reactions of aromatic amines. 2. QSAR development. Environ. Sci. Technol. 2002, 36 (11), 2443-2450. (Pubitemid 34595183)
33. Hsu, T.-S.; Bartha, R. Hydrolyzable and nonhydrolyzable 3,4-dichloroaniline-humus complexes and their respective rates of biodegradation. J. Agric. Food Chem. 1976, 24 (1), 118-22.
34. Piechowski, M. V.; Thelen, M.-A.; Hoigné, J.; Bühler, R. E. tert-Butanol as an OH-scavenger in the pulse radiolysis of oxygenated aqueous systems. Berichte der Bunsengesellschaft für physikalische Chemie 1992, 96 (10), 1448-1454.
35. Aybastier, Ö.; Demir, C. Optimization of immobilization conditions of thermomyces lanuginosus lipase on styrene-divinylbenzene copolymer using response surface methodology. J. Mol. Catal. B: Enzym. 2010, 63 (3-4), 170-178.
36. Bell, G.; Janssen, A. E. M.; Halling, P. J. Water activity fails to predict critical hydration level for enzyme activity in polar organic solvents: Interconversion of water concentrations and activities. Enzyme Microb. Technol. 1997, 20 (6), 471-477. (Pubitemid 27204408)
37. Ianni, J. C. KINTECUS, version 3.962; 2010 www.kintecus.com accessed January 5, 2012).
38. Schwarz, J.; Aust, M.-O.; Thiele-Bruhn, S. Metabolites from fungal laccase-catalysed transformation of sulfonamides. Chemosphere 2010, 81 (11), 1469-1476.
39. Arrieta-Baez, D.; Stark, R. E. Modeling suberization with peroxidase-catalyzed polymerization of hydroxycinnamic acids: Crosscoupling and dimerization reactions. Phytochemistry 2006, 67 (7), 743-753.
40. Kutyrev, A. A. Nucleophilic reactions of quinones. Tetrahedron 1991, 47 (38), 8043-8065.
41. Finley, K. T. The Chemistry of the Quinonoid Compounds; Wiley: New York, 1988.
42. Berger, S.; Braun, S.; Kalinowski, H.-O. NMR Spectroscopy of the Non-Metallic Elements; Wiley: New York, 1997.