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PHOTOBIOLOGICAL ACTIVITY IN YEAST OF DERIVATIVES OF PSORALEN SUBSTITUTED AT THE 3,4 AND/OR THE 4',5' REACTION SITE
Author(s) -
Averbeck D.,
Bisagni E.,
Marquet J. P.,
Vigny P.,
Gaboriau F.
Publication year - 1979
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.1751-1097.1979.tb07179.x
Subject(s) - psoralen , chemistry , stereochemistry , functional group , reactivity (psychology) , derivative (finance) , yeast , organic chemistry , dna , biochemistry , medicine , alternative medicine , pathology , financial economics , economics , polymer
Abstract— Derivatives of psoralen substituted at the position 3 and/or 5′ with various substituents (CN, CO‐R or COO‐R) have been newly synthesized. Their photobiological reactivity was determined by measuring the effects on survival and the induction of cytoplasmic ‘petite’ mutations (rho‐) in the haploid yeast Saccharomyces cereuisiae after treatment with 365‐nm irradiation in the presence of the different compounds. The effects were compared to those of known mono‐functional compounds such as angelicin, 3‐carbethoxypsoralen and 5,7‐dimethoxycoumarin and bi‐functional compounds such as psoralen and 8‐methoxypsoralen for which the photoaffinity to DNA is well known. The derivative carrying a CN group in position 3 of the psoralen molecule exhibited effects comparable to those of the bi‐functional agent 8‐methoxypsoralen. Three derivatives substituted at position 3 showed a biological activity comparable to those of the mono‐functional agent 3‐carbethoxypsoralen. Two compounds substituted at position 5′ by COOH or COOCH 3 ‐groups were much less photobiologically active than the corresponding derivatives substituted in position 3. This suggested that the furanic site of the psoralen molecule may be photobiologically more active than the 3,4 site. Four newly synthesized angular derivatives, i.e. furo (2,3 f, g) coumarins, were found to be two to three times less active than angelicin. At the dose rate of 365‐nm irradiation used the measure of survival and rho ‐ induction per viable cell allowed the classification of some of the compounds as mono‐ and some as bi‐functional agents in analogy to known mono‐ and bi‐functional compounds.