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Correlations between electrochemical behaviors and DNA photooxidative properties of non-steroïdal anti-inflammatory drugs and their photoproducts.

Abstract

Alkali-labile lesion to DNA photosensitized, via an electron transfer mechanism, by three non-steroidal anti-inflammatory drugs (NSAIDs), ketoprofen, tiaprofenic acid and naproxen and their photoproducts during drug photolysis, was investigated using (32)P-end labelled synthetic oligonucleotide. These photooxidative damages were correlated with the photophysical and electrochemical properties of drugs, appearing as the photosensitizer PS. Photophysical studies provided the excited state energies of the photosensitizer while their redox potentials and the relative stabilities of the PS(-) radical-anions were determined by cyclic voltammetry. On the basis of these data, we have calculated the Gibbs energy of photoinduced electron-transfer and evaluated the exergonicity of the oxidative photodamage. Moreover, kinetic control may be invoked according to the stabilities of PS(-). Applied to this NSAIDs family, the photoxidative damages through electron transfer mechanism were analyzed and a good correlation with photoredox and photobiological properties was established.

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  • Publisher Full Text
  • Authors

    Michaud S, Hajj V, Latapie L, Noirot A, Sartor V, Fabre PL, Chouini-Lalanne N

    Source

    Journal of photochemistry and photobiology. B, Biology 110: 2012 May 2 pg 34-42

    MeSH

    Anti-Inflammatory Agents, Non-Steroidal
    DNA
    Ketoprofen
    Naproxen
    Photolysis
    Photosensitizing Agents
    Propionates

    Pub Type(s)

    Journal Article

    Language

    eng

    PubMed ID

    22436506