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Redox Report
Communications in Free Radical Research
Volume 20, 2015 - Issue 1
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Research Articles

Photodegradation of antibiotic 5-sulfaminouracil in the presence of vitamin B2: A kinetic study

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References

  • Portalone G, Bencivenni L, Colapietro M, Pieretti A, Ramondo F. The effect of hydrogen bonding on the structures of uracil and some methyl derivatives studied by experiment and theory. Acta Chem Scand 1999;53:57–68.
  • Gupta N, Price PM, Aboagye EO. PET for in vivo pharmacokinetic and pharmacodynamic measurements. Eur J Cancer 2002;38:2094–107.
  • Chomicz L, Zdrowowicz M, Kasprzykowski F, Rak J, Buonaugurio A, Wang Y, et al. How to find out whether a 5-substituted uracil could be a potential DNA radiosensitizer. J Phys Chem Lett 2013;4:2853–7.
  • Alcolea Palafox M, Tardajosa G, Guerrero-Martíneza A, Vatsb JK, Hubert J, Rastogib VK. Relationships observed in the structure and spectra of uracil and its 5- substituted derivatives. Spectrochim Acta A 2010;75:1261–9.
  • Shao B, Dong D, Wu Y, Hu J, Meng J, Tu W, et al. Simultaneous determination of 17-sulfonamide residues in porcine meat, kidney and liver by solid-phase extraction and liquid chromatography-tandem mass spectrometry. Anal Chim Acta 2005;546:174–81.
  • Garcia-Galan MJ, Diaz-Cruz MS, Barcelo D. Determination of 19 sulfonamides in environmental water samples by automated on-line solid-phase extraction-liquid chromatography-tandem mass spectrometry. Talanta 2010;81:355–66.
  • Diaz-Cruz MS, Garcia-Galan MJ, Barcelo D. Highly sensitive simultaneous determination of sulfonamide antibiotics and one metabolite in environmental waters by liquid chromatography-quadrupole linear ion trap-mass spectrometry. J Chromatogr A 2008;1193:50–9.
  • Gobel A, McArdell CS, Suter MJF, Giger W. Trace determination of macrolide and sulfonamide antimicrobials, a human sulfonamide metabolite, and trimethoprim in wastewater using liquid chromatography coupled to electrospray tandem mass spectrometry. Anal Chem 2004;76:4756–64.
  • Castiglione S, Bagnati R, Calamari D, Fanelli R, Zuccato E. A multiresidue analytical method using solid-phase extraction and high-pressure liquid chromatography tandem mass spectrometry to measure pharmaceuticals of different therapeutic classes in urban wastewaters. J Chromatogr A 2005;1092:206–15.
  • Batt AL, Snow DD, Aga DS. Occurrence of sulfonamide antimicrobials in private water wells in Washington County, Idaho, USA. Chemosphere 2006;64:1963–71.
  • Sacher F, Lange FT, Brauch HJ, Blankenhorn I. Pharmaceuticals in groundwaters: analytical methods and results of a monitoring program in Baden-Wurttemberg, Germany. J Chomatogr A 2001;938:199–210.
  • Tamtam F, Mercier F, Le Bot B, Eurin J, Tuc Dinh Q, Clement M, et al. Occurrence and fate of antibiotics in the Seine River in various hydrological conditions. Sci Total Environ 2008;393:84–95.
  • Kummerer K. Antibiotics in the aquatic environment. Chemosphere 2009;75:417–34.
  • Chacon JN, McLearie J, Sinchair RS. Singlet oxygen yields and radical contribution in the dye-sensitized photooxidation in methanol of esters of polyunsaturated fatty acids (oleic, linoleic, linolenic and arachidonic). Photochem Photobiol 1988;47:647–56.
  • Trovo AG, Nogueira RFP, Aguera A, Sirtori C, Fernandez-Alba AR. Photodegradation of sulfamethoxazole in various aqueous media: persistence, toxicity and photoproducts assessment. Chemosphere 2009;77:1292–8.
  • Lester Y, Avisar D, Mamane H. Photodegradation of the antibiotic sulphamethoxazole in water with UV/H2O2 advanced oxidation process. Environ Technol 2010;31:175–83.
  • Guerard JJ, Chin YP, Mash H, Hadad CM. Photochemical fate of sulfadimethoxine in aquaculture waters. Environ Sci Technol 2009;43:8587–92.
  • Calisto V, Domingues MRM, Esteves VI. Photodegradation of psychiatric pharmaceuticals in aquatic environments-kinetics and photodegradation products. Water Res 2011;45:6097–106.
  • Homem V, Santos L. Degradation and removal methods of antibiotics from aqueous matrices – a review. J Environ Manage 2011;92:2304–47.
  • Haggi E, Blasich N, Díaz J, Diaz M, Massad WA, Amat-Guerri F, et al. Kinetics and mechanism of the sensitized photodegradation of uracil-modeling the fate of related herbicides in aqueous environments. Photochem Photobiol 2007;85:520–5.
  • Díaz M, Luiz M, Bertolotti S, Miskoski S, García NA. Scavenging of photogenerated singlet molecular oxygen and superoxide radical anion by sulpha drugs. Kinetics and mechanism. Can J Chem 2004;82:1752–9.
  • Wilkinson F, Helman WP, Ross AB. Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation. J Phys Chem Ref Data 1995;24:663–1921.
  • Weast RC, Astle HJ editors. Handbook of chemistry and physics. 62nd ed. Boca Raton, FL: CRC Press; 1981.
  • Criado S, Pajares A, Gianotti J, Stettler G, Escalada JP, Bertolotti S, et al. Kinetic study of the riboflavin-sensitised photooxygenation of two hydroxyquinolines of biological interest. J Photochem Photobiol B 2003;71:19–25.
  • Tratnyek PG, Hoigné J. Oxidation of substituted phenols in the environment: a QSAR analysis of rate constants for reaction with singlet oxygen. Environ Sci Technol 1991;25:1596–604.
  • Baxer RM, Carey JH. Evidence for photochemical generation of superoxide ion in humic waters. Nature 1983;306:575–6.
  • Zang LY, Misra HP. Superoxide radical production during the autoxidation of 1-methyl-4-phenyl-2,3-dihydroxypyridinium perchlorate. J Biol Chem 1992;267:17547–52
  • Lu CY, Lin WZ, Wang WF, Han ZH, Yao SD, Lin NY. Riboflavin (VB2) photosensitized oxidation of 2′-deoxyguanosine-5′-monophosphate (dGMP) in aqueous solution. A transient intermediates study. Phys Chem Chem Phys 2000;2:329–34.
  • Lu C, Bucher G, Sander W. Photoinduced interactions between oxidized and reduced lipoic acid and riboflavin (vitamin B2). Chem Phys Chem 2004;5:47–56.
  • Lu CY, Lin WZ, Wang WF, Han ZH, Lin Z, Han H, et al. Generation and photosensitization properties of the oxidized radicals of riboflavin: a laser flash photolysis study. J Photochem Photobiol B 1999;52:111–6.
  • Massad WA, Bertolotti S, Garcia NA. Kinetics and mechanism of the vitamin B2-sensitized photooxidation of isoproterenol. Photochem Photobiol 2004;79:428–33.
  • Haggi E, Bertolotti S, García NA. Modeling the environmental degradation of water contaminants. Kinetics and mechanism of the riboflavin-sensitised-photooxidation of phenolic compounds. Chemosphere 2004;55:1501–7.
  • Heelis PF. The photophysical and photochemical properties of flavins (isoalloxazines). Chem Soc Rev 1982;11:15–39.
  • Bertolotti SG, Previtali CM, Rufs AM, Encinas MV. Riboflavin triethanolamine as photoinitiator system of vinyl polymerization. A mechanistic study by laser flash photolysis. Macromolecules 1999;32:2920–4.
  • Msagati TAM, Nindi MM. Multiresidue determination of sulfonamides in a variety of biological matrices by supported liquid membrane with high pressure liquid chromatography-electrospray mass spectrometry detection. Talanta 2004;64:87–100.
  • Brown DJ. Pyrimidines and their benzo derivatives. In: Katritzky AR, Rees CW, Boulton AJ, McKillop A, (eds.) Comprehensive heterocyclic chemistry. Oxford: Pergamon Press; 1984. vol. 3, p. 57–155.
  • Lide DR editor. Handbook of chemistry and physics. 87th ed. Boca Raton, FL: CRC Press; 2006. p. 75.
  • Amat-Gerri F, López-González MMC, Matínez-Urtilla R, Sastre R. Singlet oxygen photogeneration by ionized and un-ionized derivatives of Rose Bengal and Eosin Y in diluted solutions. J Photochem Photobiol A Chem 1990;53:199–210.
  • Nonell S, Gonzalez M, Trull FR. 1H-phenalen-1-one-2-sulfonic acid: an extremely efficient singlet molecular oxygen sensitizer for aqueous media. Afinidad 1993;448:445–50.
  • Scully FE, Hoigné J. Rate constants for reactions of singlet oxygen with phenols and other compound in water. Chemosphere 1987;16:681–94.
  • Criado S, Bertolotti S, García NA. Kinetic aspects of the rose bengal-sensitized photo-oxygenation of tryptophan alkyl esters. Ground state and photopromoted dye-tryptophan derivative interactions. J Photochem Photobiol B 1996;34:79–86.
  • García NA. Singlet molecular oxygen-mediated photodegradation of aquatic phenolic pollutants. A kinetic and mechanistic overview. J Photochem Photobiol B 1994;22:185–96.
  • Rodgers MAJ, Snowden PT. Lifetime of O2(1Δg) in liquid water as determined by time-resolved infrared luminescence measurements. J Am Chem Soc 1982;104:5541–3.
  • Heelis PF. The photochemistry of flavins. In: Muller F, (ed.) Chemistry and biochemistry of flavoenzymes. Boca Raton: CRC Press; 1991. vol. 1, p. 171–93.
  • Kanofsky JR. Singlet oxygen production from the reactions of superoxide ion in aprotic solvents: implications for hydrophobic biochemistry. Free Radic Res Commun 1991;12–13(Pt 1):87–92.
  • Rehm D, Weller A. Kinetics of fluorescent quenching by electron transfer and H-atom transfer. Isr J Chem 1970;8:259–71
  • Msagati TAM, Ngila JC. Voltammetric detection of sulfonamides at a poly(3-methylthiophene) electrode. Talanta 2002;58:605–10.
  • Porcal G, Bertolotti SG, Previtali CM, Encinas MV. Electron transfer quenching of singlet and triplet excited states of flavins and lumichrome by aromatic and aliphatic electron donors. Phys Chem Phys 2003;5:4123–8.
  • Murov SL. Handbook of photochemistry. New York: M. Dekker; 1973.

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