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.