Preparation and evaluation of 2-substituted anthraquinones based on the anthracyclines.
Anthraquinones substituted at the 2 position with a basic side chain were prepared, and their binding to DNA was evaluated. All compounds showed an intercalative mode of binding to DNA; 1,4-dihydroxy derivatives bound more strongly than 1-hydroxy or nonhydroxylated compounds. Greatest DNA-binding activity was found where there were five atoms between the anthraquinone ring and the basic nitrogen.
D000818:Animals; D000880:Anthraquinones / Q000032:analysis / Q000138:chemical synthesis* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D004247:DNA / Q000378:metabolism; D006863:Hydrogen-Ion Concentration; D007941:Leukemia P388 / Q000188:drug therapy; D051379:Mice; D009691:Nucleic Acid Denaturation
D000880:Anthraquinones; D000970:Antineoplastic Agents; D004247:DNA