| Abstract
| - Fifteen anthracene-9,10-dione (“anthraquinone”) derivatives with (ω-aminoalkyl)carboxamidosubstituents at the 1-, 2-, 1,4-, or 2,6-ring positions were tested for bacterial mutagenicity inreverse-mutation assays using Salmonella typhimurium frameshift strains TA1538, TA98, andTA97a, in the presence and absence of a metabolic activation system prepared from the liversof rats treated with Aroclor 1254. Six of the compounds were also tested in S. typhimuriumTA100 and Escherichia coli WP2uvrApKM101 strains, which carry mutations particularlysensitive to reversion by DNA base-pair substitution. Two structurally related compounds,mitoxantrone and bisantrene, were tested in parallel as positive controls. Mitoxantrone wasmutagenic to S.typhimurium TA1538 and TA98, whereas bisantrene was weakly mutagenicto both these strains but strongly mutagenic toward the TA97a variant. By contrast, althoughthey are also DNA-binding intercalators, none of the amide-functionalized anthracene-9,10-diones of the present study showed significant mutagenic activity in any of the bacterial strainsexamined. Further, neither substituent position nor systematic alterations in the nature ofattached side chains appeared to induce mutagenicity with these agents, although other studieshave shown that such structural factors markedly influence their cytotoxic potencies towardmammalian cells in vitro.
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