7-Methyl and 4,7-dimethylallopsoralen: monofunctional photoreagents toward DNA as potential photochemotherapeutic agents in hyperproliferative conditions.
7-Methyl- (1 a) and 4,7-dimethylallopsoralen (1 b), prepared about ten years ago and till now considered non-photosensitizing agents, have been re-investigated for studying their photochemical and photobiological properties. They form a molecular complex with DNA in the ground state, undergoing intercalation between two base pairs of the macromolecule. By successive irradiation with U.V.-A they covalently photobind to DNA inducing only the formation of mono-adducts. They are not able to induce erythema on guinea pig skin, but show evident antiproliferative activity on various biological substrates. Compound (1 b) shows both photochemical and photobiological properties at a degree higher than that of compound (1 a).
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis; D002286:Carcinoma, Ehrlich Tumor / Q000378:metabolism; D003432:Cross-Linking Reagents / Q000138:chemical synthesis*; D004247:DNA / Q000378:metabolism*; D011564:Furocoumarins / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D051379:Mice; D010777:Photochemistry; D010778:Photochemotherapy; D012334:RNA, Neoplasm / Q000096:biosynthesis; D012867:Skin / Q000378:metabolism
D000998:Antiviral Agents; D003432:Cross-Linking Reagents; D011564:Furocoumarins; D012334:RNA, Neoplasm; C040186:7-methylpsoralen; C031825:4,7-dimethylallopsoralen; D004247:DNA