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    Photodegradation of sulfathiazole under simulated sunlight: Kinetics, photo-induced structural rearrangement, and antimicrobial activities of photoproducts

    Access Status
    Fulltext not available
    Authors
    Niu, X.
    Glady-Croué, J.
    Croue, Jean-Philippe
    Date
    2017
    Type
    Journal Article
    
    Metadata
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    Citation
    Niu, X. and Glady-Croué, J. and Croue, J. 2017. Photodegradation of sulfathiazole under simulated sunlight: Kinetics, photo-induced structural rearrangement, and antimicrobial activities of photoproducts. Water Research. 124: pp. 576-583.
    Source Title
    Water Research
    DOI
    10.1016/j.watres.2017.08.019
    ISSN
    0043-1354
    School
    Curtin Water Quality Research Centre
    Funding and Sponsorship
    http://purl.org/au-research/grants/arc/LP130100602
    URI
    http://hdl.handle.net/20.500.11937/57301
    Collection
    • Curtin Research Publications
    Abstract

    © 2017 Elsevier Ltd Photolysis is a core natural process impacting the fate of some sulfonamide antibiotics in sunlit waters. In this study, sunlight-induced phototransformation of sulfathiazole was investigated. A photolytic quantum yield of 0.079 was obtained in buffered water (pH = 8.0). Different natural organic matter isolates inhibited the photolysis of sulfathiazole by light screening effect. A kinetic model was developed to predict the photodegradation rate of sulfathiazole using the light screening correction factor of the water matrix in the wavelength range of 300–350 nm. An isomeric photoproduct of sulfathiazole with a longer retention time was observed on liquid chromatography. Based on its MS/MS spectra and absorption characteristics, the isomer was postulated as 2-imino-3-(p-aminobenzenesulfinyl-oxy)-thiazole. A reaction mechanism for the photo-cleavage and photo-induced structural rearrangement was proposed. The formation mechanism of the isomer was supported by photochemical experiments spiking synthetic 2-aminothiazole; while the formation kinetics were treated with a partly-diffusion-controlled model. The three identified products showed significantly enhanced photo-stability. Antimicrobial assay of irradiated sulfathiazole solutions with Escherichia coli indicated little antimicrobial potency ascribed to photoproducts. This study demonstrates the efficacy of sunlight in rapidly degrading sulfathiazole at a predictable rate, leading to photoproducts of low antimicrobial potency. The mass spectrometry and mechanistic work described here are new insights into the photochemistry of sulfonamides.

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