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Acridine derivatives. VI . Redox chemistry of novel 9‐anilinoacridines with antitumor activities
Author(s) -
Kimura Michio,
Okabayashi Ichizo,
Inoue Hiroaki
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320145
Subject(s) - chemistry , redox , acridine , dna , quinone , intercalation (chemistry) , cleavage (geology) , aniline , cyclic voltammetry , photochemistry , stereochemistry , biochemistry , organic chemistry , electrochemistry , geotechnical engineering , electrode , fracture (geology) , engineering
In order to elucidate the mechanism of deoxyribonucleic acid (DNA) strand breaks caused by 9‐anilino‐acridine DNA intercalators, the antitumor activity of L1210, P388 and the reduction‐oxidation (redox) reaction of 9‐anilinoacridines were studied. The redox reaction induced by two electrons causing structural changes in quinone diimines of 9‐anilinoacridines is believed to be an important factor in DNA strand breaks and was examined by means of temperature‐dependent nuclear magnetic resonance and cyclic voltammetry. The redox reaction of 9‐anilinoacridines is induced by the effect of a low‐energy electron transfer from the acridine to the aniline ring. We propose that the redox reaction plays an important role in the DNA strand cleavage of 9‐anilinoacridine when it is intercalated into double‐strand DNA.