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EFFECT OF MOLECULAR STRUCTURE ON THE PHOTOPHYSICAL PROPERTIES, THE PHOTOREACTIVITY WITH DNA AND THE PHOTOBIOLOGICAL ACTIVITY OF MONOFUNCTIONAL PYRIDOPSORALENS
Author(s) -
Blaisi J.,
Averbeck D.,
Moron J.,
Bisagni E.,
Vignv P.
Publication year - 1987
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1987.tb05404.x
Subject(s) - psoralen , chemistry , saccharomyces cerevisiae , furocoumarin , dna , pyridine , nitrogen atom , stereochemistry , yeast , dna damage , photochemistry , medicinal chemistry , ring (chemistry) , biochemistry , organic chemistry
— 7‐Methyl‐pyrido[4,3‐c]psoralen (2N‐MePyPs) has been synthesized in order to investigate the possible effect of the position of the pyridine‐nitrogen atom on the photoreactivity towards DNA and the photobiological activity of pyridopsoralens, a new family of psoralen derivatives. In comparison to its isomer, 7‐methyl‐pyrido[3,4‐c]psoralen (MePyPs), 2N‐MePyPs shows a 2.5 times lower DNA photobinding capacity. Photobiological experiments with diploid yeast ( Saccharomyces cerevisiae ) reveal that this compound differs strikingly from its isomer MePyPs. It has only a weak antiproliferative potential and, per unit dose, a lower capacity than MePyPs for the induction of nuclear genotoxic effects. With respect to these latter features, 2N‐MePyPs resembles the monofunctional furocoumarin 3‐CPs.