Theoretical design of monofunctional psoralen compounds in photochemotherapy

Ayako Nakata, Takeshi Baba, Hiromi Nakai

    Research output: Contribution to journalArticle

    4 Citations (Scopus)

    Abstract

    The geometries and electronic structures in the lowest triplet (T 1) states of psoralen, 5-methoxypsoralen (5-MOP), 8-methoxypsoralen (8-MOP), and their monoadducts were studied by performing density functional theory (DFT) calculations. It was shown that the pyrone ring of 8-MOP is cleaved in the T1 state and the cleaved pyrone ring loses the ability to bond to the thymine residue. Therefore, 8-MOP in the open-ring structure does not form a diadduct, which is thought to cause side effects. DFT calculations on 20 kinds of substituted psoralens showed that the cleavage of the pyrone ring in the T1 state can be controlled by substituting an electron-donating group, especially one having a strong electron-donating resonance effect, at the 8-position of psoralen.

    Original languageEnglish
    Pages (from-to)1341-1349
    Number of pages9
    JournalBulletin of the Chemical Society of Japan
    Volume80
    Issue number7
    DOIs
    Publication statusPublished - 2007

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    Pyrones
    Methoxsalen
    Ficusin
    Density functional theory
    Electron resonance
    Thymine
    Electronic structure
    Geometry
    Electrons

    ASJC Scopus subject areas

    • Chemistry(all)

    Cite this

    Theoretical design of monofunctional psoralen compounds in photochemotherapy. / Nakata, Ayako; Baba, Takeshi; Nakai, Hiromi.

    In: Bulletin of the Chemical Society of Japan, Vol. 80, No. 7, 2007, p. 1341-1349.

    Research output: Contribution to journalArticle

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