Research
Interest:
Study on photochemical behavior of biologically active
organic molecules, furocoumarins (psoralens), and PQQ analog.
A: Furocoumarin (Psoralen)
Photochemical reactivity of furocoumarin (psoralen) (see 1 below) toward the thymine residue in DNA has been successfully used for thousands of years in the treatment of skin disorders such as psoriasis (1). Recently, the furocoumarin's photochemical reactivity has been increasingly studied due to its potential application for site-specific modification of DNA.
Our current focus in this project is:
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Study on the mechanistic details involved in the furocoumarins' photochemotherapy. We study the nature of the intercalation that would alter the reactivity of furocoumarin. We synthesize furocoumarin dervatives as a model to DNA-intercalating molecules (see 2 below) and analyze their photochemical reactivity (2).
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Study on a furocoumarin-oligonucleotide conjugate. In order to develop a more effective treatment, we try to introduce, to a furocoumarin, a moiety that would recognize a specific sequence of DNA. Toward this goal, we synthsize a furocoumarin-oligonucleotide conjugate (see 3 below), where an oligonucleotide moiety is expected to recognize a specific sequence of DNA via a triple helix formation, and then we investigate its photochemical reactivity toward DNA.
B: PQQ (Pyrroloquinonline quinone)
Since its discovery
in 1979, PQQ (see 4 below), a redox coenzyme of one-carbon organic molecules,
has attracted considerable attention (3). Although light was not considered
a crucial component for its enzymatic activity, it was recently noticed that
the enzymatic activity of PQQ was found to be enhanced upon illumination with
light. Due to its o-quinonoid structure, it would not be unreasonable to expect
PQQ to be involved in some photochemical processes with various classes of
organic compounds. Nevertheless, the photochemical behavior of PQQ and its
derivatives has never been reported. In order to explore the photochemical
behavior of PQQ, we synthesize PQQ starting with 2-methoxy-4-nitroaniline
(4) and study its photochemical reactivity.
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