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-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.
Sinsheimer
J E
JE
College of Pharmacy, University of Michigan, Ann Arbor 48109-1065.
Chakraborty
P K
PK
Messerly
E A
EA
Gaddamidi
V
V
D000477:Alkylating Agents / Q000633:toxicity*; D055598:Chemical Phenomena; D002621:Chemistry; D009152:Mutagenicity Tests; D009153:Mutagens; D012486:Salmonella typhimurium / Q000235:genetics*; D012717:Sesquiterpenes / Q000633:toxicity*; D013141:Spiro Compounds / Q000633:toxicity*; D014255:Trichothecenes / Q000633:toxicity*
D000477:Alkylating Agents; D009153:Mutagens; D012717:Sesquiterpenes; D013141:Spiro Compounds; D014255:Trichothecenes; C001809:diacetoxyscirpenol