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Volumn 47, Issue 13, 2013, Pages 6916-6924

Covalent binding of sulfamethazine to natural and synthetic humic acids: Assessing laccase catalysis and covalent bond stability

Author keywords

[No Author keywords available]

Indexed keywords

COVALENT BINDING; COVALENT BOND FORMATION; LOW MOLECULAR WEIGHT; NUCLEOPHILIC ADDITIONS; OXIDOREDUCTASES; RELATIVE CONCENTRATION; SOIL ORGANIC MATTERS; SULFONAMIDE ANTIBIOTICS;

EID: 84880110164     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es3044592     Document Type: Article
Times cited : (64)

References (39)
  • 1
    • 33747876745 scopus 로고    scopus 로고
    • A global perspective on the use, sales, exposure pathways, occurrence, fate and effects of veterinary antibiotics (VAs) in the environment
    • 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
    • (2006) Chemosphere , vol.65 , Issue.5 , pp. 725-759
    • Sarmah, A.K.1    Meyer, M.T.2    Boxall, A.B.A.3
  • 3
    • 35949001198 scopus 로고    scopus 로고
    • Dissipation and transport of veterinary sulfonamide antibiotics after manure application to grassland in a small catchment
    • Stoob, K.; Singer, H. P.; Mueller, S. R.; Schwarzenbach, R. P.; Stamm, C. H. Dissipation and transport of veterinary sulfonamide antibiotics after manure application to grassland in a small catchment Environ. Sci. Technol. 2007, 41 (21) 7349-7355
    • (2007) Environ. Sci. Technol. , vol.41 , Issue.21 , pp. 7349-7355
    • Stoob, K.1    Singer, H.P.2    Mueller, S.R.3    Schwarzenbach, R.P.4    Stamm, C.H.5
  • 4
    • 15544372857 scopus 로고    scopus 로고
    • Test-plot studies on runoff of sulfonamides from manured soils after sprinkler irrigation
    • Kreuzig, R.; Höltge, S.; Brunotte, J.; Berenzen, N.; Wogram, J.; Schulz, R. Test-plot studies on runoff of sulfonamides from manured soils after sprinkler irrigation Environ. Toxicol. Chem. 2005, 24 (4) 777-781
    • (2005) Environ. Toxicol. Chem. , vol.24 , Issue.4 , pp. 777-781
    • Kreuzig, R.1    Höltge, S.2    Brunotte, J.3    Berenzen, N.4    Wogram, J.5    Schulz, R.6
  • 6
    • 15544381211 scopus 로고    scopus 로고
    • Investigations on the fate of sulfadiazine in manured soil: Laboratory experiments and test plot studies
    • 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
    • (2005) Environ. Toxicol. Chem. , vol.24 , Issue.4 , pp. 771-776
    • Kreuzig, R.1    Höltge, S.2
  • 9
    • 33747889499 scopus 로고    scopus 로고
    • Exhaustive extraction of sulfonamide antibiotics from aged agricultural soils using pressurized liquid extraction
    • 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
    • (2006) J. Chromatogr., A , vol.1128 , Issue.12 , pp. 1-9
    • Stoob, K.1    Singer, H.P.2    Stettler, S.3    Hartmann, N.4    Müller, S.R.5    Stamm, C.H.6
  • 10
    • 0034798343 scopus 로고    scopus 로고
    • Veterinary use and antibiotic resistance
    • Teuber, M. Veterinary use and antibiotic resistance Curr. Opin. Microbiol. 2001, 4 (5) 493-499
    • (2001) Curr. Opin. Microbiol. , vol.4 , Issue.5 , pp. 493-499
    • Teuber, M.1
  • 11
    • 20744445509 scopus 로고    scopus 로고
    • Cross-coupling of sulfonamide antimicrobial agents with model humic constituents
    • 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
    • (2005) Environ. Sci. Technol. , vol.39 , Issue.12 , pp. 4463-4473
    • Bialk, H.M.1    Simpson, A.J.2    Pedersen, J.A.3
  • 12
    • 34250856387 scopus 로고    scopus 로고
    • Laccase-mediated Michael addition of N -15-sulfapyridine to a model humic constituent
    • Bialk, H. M.; Hedman, C.; Castillo, A.; Pedersen, J. A. Laccase-mediated Michael addition of N -15-sulfapyridine to a model humic constituent Environ. Sci. Technol. 2007, 41 (10) 3593-3600
    • (2007) Environ. Sci. Technol. , vol.41 , Issue.10 , pp. 3593-3600
    • Bialk, H.M.1    Hedman, C.2    Castillo, A.3    Pedersen, J.A.4
  • 13
    • 37549016408 scopus 로고    scopus 로고
    • NMR investigation of enzymatic coupling of sulfonamide antimicrobials with humic substances
    • 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
    • (2008) Environ. Sci. Technol. , vol.42 , Issue.1 , pp. 106-112
    • Bialk, H.M.1    Pedersen, J.A.2
  • 14
    • 84857770261 scopus 로고    scopus 로고
    • Reactions of a sulfonamide antimicrobial with model humic constituents: Assessing pathways and stability of covalent bonding
    • Gulkowska, A.; Krauss, M.; Rentsch, D.; Hollender, J. Reactions of a sulfonamide antimicrobial with model humic constituents: Assessing pathways and stability of covalent bonding Environ. Sci. Technol. 2012, 46 (4) 2102-2111
    • (2012) Environ. Sci. Technol. , vol.46 , Issue.4 , pp. 2102-2111
    • Gulkowska, A.1    Krauss, M.2    Rentsch, D.3    Hollender, J.4
  • 15
    • 0029659995 scopus 로고    scopus 로고
    • Covalent binding of aniline to humic substances. 1. Kinetic studies
    • 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
    • (1996) Environ. Sci. Technol. , vol.30 , Issue.9 , pp. 2755-2763
    • Weber, E.J.1    Spidle, D.L.2    Thorn, K.A.3
  • 16
    • 0036707420 scopus 로고    scopus 로고
    • 15N NMR Investigation of the covalent binding of reduced TNT amines to soil humic acid, model compounds, and lignocellulose
    • 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
    • (2002) Environ. Sci. Technol. , vol.36 , Issue.17 , pp. 3787-3796
    • Thorn, K.A.1    Kennedy, K.R.2
  • 17
    • 0034115547 scopus 로고    scopus 로고
    • Phenoloxidase-mediated interactions of phenols and anilines with humic materials
    • Dec, J.; Bollag, J.-M. Phenoloxidase-mediated interactions of phenols and anilines with humic materials J. Environ. Qual. 2000, 29 (3) 665-676
    • (2000) J. Environ. Qual. , vol.29 , Issue.3 , pp. 665-676
    • Dec, J.1    Bollag, J.-M.2
  • 18
    • 0019304566 scopus 로고
    • Covalent binding of aromatic-amines to humates. 1. Reactions with carbonyls and quinones
    • Parris, G. E. Covalent binding of aromatic-amines to humates. 1. Reactions with carbonyls and quinones Environ. Sci. Technol. 1980, 14 (9) 1099-1106
    • (1980) Environ. Sci. Technol. , vol.14 , Issue.9 , pp. 1099-1106
    • Parris, G.E.1
  • 19
    • 0033564646 scopus 로고    scopus 로고
    • Effect of humic constituents on the transformation of chlorinated phenols and anilines in the presence of oxidoreductive enzymes or birnessite
    • 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
    • (1999) Environ. Sci. Technol. , vol.33 , Issue.12 , pp. 2028-2034
    • Park, J.W.1    Dec, J.2    Kim, J.E.3    Bollag, J.M.4
  • 20
    • 0036203234 scopus 로고    scopus 로고
    • Interaction of 2,4,6-trinitrotoluene (TNT) and 4-amino-2,6-dinitrotoluene with humic monomers in the presence of oxidative enzymes
    • 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
    • (2002) Arch. Environ. Contam. Toxicol. , vol.42 , Issue.1 , pp. 1-8
    • Wang, C.J.1    Thiele, S.2    Bollag, J.M.3
  • 21
    • 78249246363 scopus 로고    scopus 로고
    • Metabolites from fungal laccase-catalysed transformation of sulfonamides
    • Schwarz, J.; Aust, M.-O.; Thiele-Bruhn, S. Metabolites from fungal laccase-catalysed transformation of sulfonamides Chemosphere 2010, 81 (11) 1469-1476
    • (2010) Chemosphere , vol.81 , Issue.11 , pp. 1469-1476
    • Schwarz, J.1    Aust, M.-O.2    Thiele-Bruhn, S.3
  • 23
    • 0025948552 scopus 로고
    • Nucleophilic reactions of quinones
    • Kutyrev, A. A. Nucleophilic reactions of quinones Tetrahedron 1991, 47 (38) 8043-8065
    • (1991) Tetrahedron , vol.47 , Issue.38 , pp. 8043-8065
    • Kutyrev, A.A.1
  • 25
    • 75349098782 scopus 로고    scopus 로고
    • Novel electrochemical approach to assess the redox properties of humic substances
    • Aeschbacher, M.; Sander, M.; Schwarzenbach, R. P. Novel electrochemical approach to assess the redox properties of humic substances Environ. Sci. Technol. 2010, 44 (1) 87-93
    • (2010) Environ. Sci. Technol. , vol.44 , Issue.1 , pp. 87-93
    • Aeschbacher, M.1    Sander, M.2    Schwarzenbach, R.P.3
  • 26
    • 0033669996 scopus 로고    scopus 로고
    • Chemical heterogeneity of humic substances: Characterization of size fractions obtained by hollow-fibre ultrafiltration
    • Christl, I.; Knicker, H.; Kögel-Knabner, I.; Kretzschmar, R. Chemical heterogeneity of humic substances: Characterization of size fractions obtained by hollow-fibre ultrafiltration Eur. J. Soil Sci. 2000, 51 (4) 617-625
    • (2000) Eur. J. Soil Sci. , vol.51 , Issue.4 , pp. 617-625
    • Christl, I.1    Knicker, H.2    Kögel-Knabner, I.3    Kretzschmar, R.4
  • 27
    • 3242778540 scopus 로고    scopus 로고
    • Sorption of apolar aromatic compounds to soil humic acid particles affected by aluminum(III) ion cross-linking
    • Lu, Y.; Pignatello, J. J. Sorption of apolar aromatic compounds to soil humic acid particles affected by aluminum(III) ion cross-linking J. Environ. Qual. 2004, 33 (4) 1314-1321
    • (2004) J. Environ. Qual. , vol.33 , Issue.4 , pp. 1314-1321
    • Lu, Y.1    Pignatello, J.J.2
  • 29
    • 84880126906 scopus 로고    scopus 로고
    • (accessed 10/10/)
    • http://www.humicsubstances.org/elements.html (accessed 10/10/ 2012).
    • (2012)
  • 30
    • 0026614956 scopus 로고
    • Ammonia fixation by humic substances: A nitrogen-15 and carbon-13 NMR study
    • Thorn, K. A.; Mikita, M. A. Ammonia fixation by humic substances: A nitrogen-15 and carbon-13 NMR study Sci. Total Environ. 1992, 113 (1-2) 67-87
    • (1992) Sci. Total Environ. , vol.113 , Issue.12 , pp. 67-87
    • Thorn, K.A.1    Mikita, M.A.2
  • 31
    • 0022865452 scopus 로고
    • 13C nuclear magnetic resonance spectroscopy of soil humic fractions
    • 13C nuclear magnetic resonance spectroscopy of soil humic fractions Org. Geochem. 1986, 9 (6) 277-284
    • (1986) Org. Geochem. , vol.9 , Issue.6 , pp. 277-284
    • Saiz-Jimenez, C.1    Hawkins, B.L.2    Maciel, G.E.3
  • 33
    • 33645011294 scopus 로고    scopus 로고
    • O-Alkylation of a lignite humic acid by phase-transfer catalysis
    • Piccolo, A.; Conte, P.; Patti, A. O-Alkylation of a lignite humic acid by phase-transfer catalysis Anal. Bioanal. Chem. 2006, 384 (4) 994-1001
    • (2006) Anal. Bioanal. Chem. , vol.384 , Issue.4 , pp. 994-1001
    • Piccolo, A.1    Conte, P.2    Patti, A.3
  • 34
  • 36
    • 0142104156 scopus 로고    scopus 로고
    • Graphical method for analysis of ultrahigh-resolution broadband mass spectra of natural organic matter, the van Krevelen diagram
    • Kim, S.; Kramer, R. W.; Hatcher, P. G. Graphical method for analysis of ultrahigh-resolution broadband mass spectra of natural organic matter, the van Krevelen diagram Anal. Chem. 2003, 75 (20) 5336-5344
    • (2003) Anal. Chem. , vol.75 , Issue.20 , pp. 5336-5344
    • Kim, S.1    Kramer, R.W.2    Hatcher, P.G.3
  • 37
    • 80053427763 scopus 로고    scopus 로고
    • Electrochemical analysis of proton and electron transfer equilibria of the reducible moieties in humic acids
    • Aeschbacher, M.; Vergari, D.; Schwarzenbach, R. P.; Sander, M. Electrochemical analysis of proton and electron transfer equilibria of the reducible moieties in humic acids Environ. Sci. Technol. 2011, 45 (19) 8385-8394
    • (2011) Environ. Sci. Technol. , vol.45 , Issue.19 , pp. 8385-8394
    • Aeschbacher, M.1    Vergari, D.2    Schwarzenbach, R.P.3    Sander, M.4
  • 38
    • 0036006203 scopus 로고    scopus 로고
    • Determination of selected sulfonamide antibiotics and trimethoprim in manure by electrospray and atmospheric pressure chemical ionization tandem mass spectrometry
    • Pfeifer, T.; Tuerk, J.; Bester, K.; Spiteller, M. Determination of selected sulfonamide antibiotics and trimethoprim in manure by electrospray and atmospheric pressure chemical ionization tandem mass spectrometry Rapid Commun. Mass Spectrom. 2002, 16 (7) 663-669
    • (2002) Rapid Commun. Mass Spectrom. , vol.16 , Issue.7 , pp. 663-669
    • Pfeifer, T.1    Tuerk, J.2    Bester, K.3    Spiteller, M.4


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