An alternative concept for the molecular nature of the peroxidating ability of anthracycline anti-tumor antibiotics and anthracenodiones.
Quantum chemical calculations of model anthraquinone molecules using the CNDO/2 method have revealed that superoxide anion radical formation following the single electron transfer mediated by anthraquinone anti-tumor antibiotics may occur in aerobic conditions as a result of the direct addition of an electron to the anthraquinone-oxygen low energy charge transfer complex that is formed with singlet oxygen. Cyclovoltammetric measurements have been performed in order to provide experimental evidence supporting the hypothesis. The structural requirements for an anthraquinone molecule not exhibiting peroxidating ability by the above mechanism have been postulated. They include maximum symmetry of electron density distribution (symmetry of the molecule), a decrease of the electron density of the pi electron system and an increase in the rigidity of the molecule.
Tempczyk
A
A
Department of Pharmaceutical Technology and Biochemistry, Technical University of Gdansk, Poland.
Tarasiuk
J
J
Ossowski
T
T
Borowski
E
E
D000880:Anthraquinones / Q000494:pharmacology*; D000903:Antibiotics, Antineoplastic / Q000494:pharmacology*; D016227:Benzoquinones; D009279:Naphthacenes / Q000494:pharmacology; D010545:Peroxides / Q000378:metabolism*; D011809:Quinones
D000880:Anthraquinones; D000903:Antibiotics, Antineoplastic; D016227:Benzoquinones; D009279:Naphthacenes; D010545:Peroxides; D011809:Quinones; C004532:quinone