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REVIEW OF THE SALMONELLA TYPHIMURIUM MUTAGENICITY OF BENZIDINE, BENZIDINE ANALOGUES, AND BENZIDINE-BASED DYES
Citation:
CHUNG, K., S. CHEN, AND L. D. CLAXTON. REVIEW OF THE SALMONELLA TYPHIMURIUM MUTAGENICITY OF BENZIDINE, BENZIDINE ANALOGUES, AND BENZIDINE-BASED DYES. MUTATION RESEARCH - REVIEWS. Elsevier Science Ltd, New York, NY, 612(1):58-76, (2006).
Impact/Purpose:
To review the mutagenicity of benzidine analogues (including benzidine-based dyes) with a primary emphasis on evaluating results of the Salmonella/microsome mutagenicity assay
Description:
The mutagenicity of benzidine analogues (including benzidine-based dyes) was reviewed with a primary emphasis on evaluating results of the Salmonella/microsome mutagenicity assay. Many of these amines are mutagenic in tester strains TA98 and TA100 but require exogenous mammalian activation (S9) for activity. A few amines with halogen or nitro-groups in the structure are directly-acting mutagens. The addition of a sulfonic acid moiety to the molecule of benzidine reduces the mutagenicity of benzidine; whereas, methoxy, chloro, or methyl group additions do not. Complexation with a metal ion also decreases the mutagenicity. A substitution of an alkyl group on the ortho position next to an amine group also influences the mutagenicity. Some parameters such as lowest unoccupied molecular orbital energy (ELUMO), highest occupied molecular orbital energy (EHOMO), and hydrophobicity are related with the mutagenic potentials. Most carcinogenic benzidine analogues are mutagenic, but some are not mutagenic. It was hypothesized that the metabolism of these compounds in vivo generates ultimate active electrophiles that interact with DNA, cause mutations, and eventually lead to the initiation of carcinogenesis.