title: [Mechanism of the interaction of the anticancer antibiotic adriamycin (doxorubicin) with the anion radical O2].
abstract: Interaction of the O2. anion radical with adriamycin in water-acetonitrile mixtures was studied by UV-spectroscopy. It was shown that with changing of the water content in the reaction mixture from 0 to 90 per cent O2. practically irreversibly reacted with adriamycin to form the same product. The spectrum of the reaction product was shifted to the long-wave region as compared to that of adriamycin and depended on the solvent composition. In the presence of the proton donors the "regeneration" of the absorption spectrum of the starting antibiotic was observed. To investigate the mechanism of the reaction product formation, electrochemical reduction of adriamycin and its reaction with benzosemiquinone and alkali were studied. Formation of the same compound under the different conditions showed that the primary step of O2. interaction with adriamycin was one electron reduction of the antibiotic. The study suggested the reaction mechanism involving formation of adriamycin semiquinone as a result of the electron transfer from the O2. molecule, splitting out of the sugar moiety and reduction of deoxyaglycone semiquinone into anion of deoxyaglycone tautomer. The possible role of the oxygen anion radical in the mechanism of activation of adriamycin and other anthracycline antibiotics is discussed.
mesh_terms: D000097:Acetonitriles / Q000494:pharmacology; D000838:Anions / Q000032:analysis / Q000494:pharmacology; D016227:Benzoquinones; D004317:Doxorubicin / Q000032:analysis / Q000494:pharmacology*; D004347:Drug Interactions; D004563:Electrochemistry; D011809:Quinones / Q000494:pharmacology; D012996:Solutions; D013056:Spectrophotometry, Ultraviolet; D013481:Superoxides / Q000032:analysis / Q000494:pharmacology*
chemical_list: D000097:Acetonitriles; D000838:Anions; D016227:Benzoquinones; D011809:Quinones; D012996:Solutions; D013481:Superoxides; C004532:quinone; D004317:Doxorubicin
vernacular_title: Issledovanie mekhanizma vzaimodeĭstviia protivorakovogo antibiotika adriamitsina (doksorubitsina) s anion-radikalom O2..