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Test of chiral recognition in the salmonella typhimurium (TA100) mutagenicity of mucochloric acid‐cysteine adducts
Author(s) -
Lalonde Robert T.,
Xie Shan,
Bu Lin
Publication year - 1993
Publication title -
environmental and molecular mutagenesis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1
H-Index - 87
eISSN - 1098-2280
pISSN - 0893-6692
DOI - 10.1002/em.2850220311
Subject(s) - mutagen , enantiomer , chemistry , genotoxicity , ames test , salmonella , cysteine , stereochemistry , racemic mixture , adduct , dna , antimutagen , stereoisomerism , biochemistry , enzyme , toxicity , organic chemistry , bacteria , biology , genetics , catalysis
A difference in biological response to enantiomers is not an uncommon observation and is, therefore, to be expected in various manifestations of genotoxicity. The bacterial mutagen mucochloric acid (2,3‐dichloro‐5‐hydroxy‐2(5H)‐furanone) has one chiral center, at C‐5, but this mutagen exists in racemic form because of the facile stereoisomerization occurring by the mechanism of ring‐chain tautomerism. Two readily synthesized enantiomeric analogs of mucochloric acid, as well as the racemic form of the two, were prepared from mucochloric acid and (R)‐(+)‐, (S)‐(‐)‐, and (R,S)‐(+/‐)‐cysteine. Using Salmonella typhimurium (TA100), the enantiomeric compounds were assayed together in four dose/response assays along with mucochloric acid, the reference mutagen. In three of the same four assays, the racemic form was also assayed. Neither statistically significant differences in mutagenicity, as determined in slope responses, nor distinctions from the plotted curves were observed among the two enantiomers and their racemic form. Therefore, no enantiospecific interaction between enantiomers and chiral DNA or enzymes involved in repair or replication could be concluded. © 1993 Wiley‐Liss, Inc.