A Plausible Mechanism for the Mutagenic Activity (Salmonella typhimurium TA100) of MX Compounds: A Formation of CG-CG⁺-CG Radical Cation by One-electron Reduction

Abstract

Combining our previous QSAR work with recent high-level quantum mechanical calculations, a plausible mechanism for the mutagenic activity of halogenated furanones (so called MX compounds) in Salmonella typhimurium TA100 tester strain is proposed. The mechanism involves one-electron reduction as a key step and it seems reasonable to suggest that the mutagenicity of these direct-acting compounds may be a purely thermodynamic phenomenon, rather than the result of site-specific binding or adduct formation. Overall, the proposed model is consistent with the most experimental findings.

Key Words:

• Mutagenicity
• MX compounds
• mechanism
• one-electron reduction
• LUMO