Mutagenicity of oxaspiro compounds with Salmonella

The spiro attachment of an epoxide group to a tetrahydropyran ring in the trichothecene mycotoxins has prompted this study of the mutagenicity and alkylation rates of the trichothecene, anguidine, and 5 related model oxaspiro compounds. While the model compounds were weak alkylating agents of 4-(4-n...

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Published inMutation Research/Genetic Toxicology Vol. 224; no. 2; pp. 171 - 175
Main Authors Sinsheimer, J.E., Chakraborty, P.K., Messerly, E.A., Gaddamidi, V.
Format Journal Article
LanguageEnglish
Published Netherlands Elsevier B.V 01.10.1989
Subjects
Alkylating Agents - toxicity
Ames test
Chemical Phenomena
Chemistry
Epoxides (spiro)
Mutagenicity Tests
Mutagens
Oxaspiro compounds
S. typhimurium
Salmonella typhimurium - genetics
Sesquiterpenes - toxicity
Spiro Compounds - toxicity
Trichothecenes
Trichothecenes - toxicity
S. typhimurium
Epoxides (spiro)
Trichothecenes
Ames test
Oxaspiro compounds
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Summary:The spiro attachment of an epoxide group to a tetrahydropyran ring in the trichothecene mycotoxins has prompted this study of the mutagenicity and alkylation rates of the trichothecene, anguidine, and 5 related model oxaspiro compounds. While the model compounds were weak alkylating agents of 4-(4-nitrobenzyl)pyridine as a test nucleophile, anguidine lacks such activity. Also, while mutagenicity was not established for anguidine in Salmonella TA100, 3 of the oxaspiro compounds were weakly mutagenic and 2 compounds were toxic to the bacteria. The toxicity and mutagenicity of the model compounds are more related to their polarity than to their alkylation rates.
ISSN:0165-1218
0027-5107
DOI:10.1016/0165-1218(89)90153-5