US EPA

625392 

Journal Article 

Mutagenesis by 9,10-anthraquinone derivatives and related compounds in Salmonella typhimurium 

Brown, JP; Brown, RJ 

1976 

1 

Mutation Research
ISSN: 0027-5107
EISSN: 1873-135X 

EMICBACK/22864 

40 

3 

203-224 

Ninety 9,10-anthraquinone (AQ) derivatives and related anthracene derivatives were screened for mutagenicity with five Salmonella typhimurium tester strains with and without mammalian microsomal activation. About 35% of the compounds tested are considered to be mutagenic. Three patterns of mutagenesis were apparent.

1. (1)|Direct frameshift mutagenesis by certain AQ compounds bearing free hydroxyl groups. The most potent were anthragallol (1,2,3-trihydroxy-AQ), purpurin (1,2,4-trihydroxy-AQ) and anthrarufin (1,5-dihydroxy-AQ). Some hydroxy-AQ compounds exhibited activation by mammalian microsomal preparations, particularly at lower concentrations, and the majority of mutagenic hydroxy-AQs appeared to revert strain TA1537 (his 3076) specifically.

2. (2)|Frameshift mutagenesis by certain AQ compounds with primary amino and, in a few cases, with secondary amino groups. Mammalian microsomes invariably potentiated frameshift mutagenesis, and activity with strain TA100 (sensitive to base pair substitution) is seen in a few cases, e.g. 1,2-diamino-AQ.

3. (3)|AQ compounds with one or more nitro groups. These derivatives exhibit the least specificity with regard to tester strain reverted and to microsomal activation. All seven nitro-AQ's tested were mutagenic.

In those compounds with mixed “mutagenic” functional groups, the type of mutagenesis observed is usually NO2 > OH > NH2. AQs bearing halogens, sulfonate or alkyl groups were non-mutagenic, as were AQs substituted solely with secondary amines.