Mutagenicity of aclacinomycin A and daunomycin derivatives.
An antitumor antibiotic aclacinomycin A, was nonmutagenic in a Salmonella test, but its derivative, N-demethylaclacinomycin A, was mutagenic. Similarly, 1-deoxypyrromycin, a hydrolysis product of aclacinomycin A, was nonmutagenic, but N-demethyl-1-deoxypyrromycin was mutagenic. Daunomycin was highly mutagenic, but N-methyldaunomycin showed only weak mutagenicity, and N-dimethyldaunomycin was nonmutagenic. The aglycones of aclacinomycin A and daunomycin were not mutagenic. Thus, the amino moiety of anthracycline glycosides is concluded to be essential for mutagenesis.
D015250:Aclarubicin / Q000031:analogs & derivatives; D000903:Antibiotics, Antineoplastic / Q000494:pharmacology*; D003630:Daunorubicin / Q000031:analogs & derivatives* / Q000494:pharmacology; D006027:Glycosides / Q000494:pharmacology; D009153:Mutagens; D009154:Mutation / Q000187:drug effects; D009279:Naphthacenes / Q000494:pharmacology*; D012486:Salmonella typhimurium / Q000187:drug effects*; D013329:Structure-Activity Relationship
D000903:Antibiotics, Antineoplastic; D006027:Glycosides; D009153:Mutagens; D009279:Naphthacenes; C011157:aclacinomycins; D015250:Aclarubicin; D003630:Daunorubicin