The association between mutagenicity and adduct formation of 1,2,7,8-diepoxyoctane and 1,2,5,6-diepoxycyclooctane.
The mutagenicity of 1,2,5,6-diepoxycyclooctane (DECO) and 1,2,7,8-diepoxyoctane (DEO) was investigated using diploid Chinese hamster lung cells. 6-thioguanine (6-TG) resistance was used as the marker for mutagenicity testing: DEO was found to be genetically active; DECO, on the contrary, totally inactive. DEO readily formed adducts with radiolabeled nucleotides, while DECO failed to do so, as demonstrated through thin-layer chromatography (TLC) and the shift of the ultraviolet absorption maximum in DEO/nucleotide mixtures. The difference between the two compounds in chemical and genetic activities was attributed to their molecular conformations and the resulting differential flexibilities and adduct-forming abilities. Association between mutagenicity and adduct formation was conclusive.
D000249:Adenosine Monophosphate / Q000378:metabolism; D002478:Cells, Cultured; D003568:Cytidine Monophosphate / Q000378:metabolism; D004852:Epoxy Compounds / Q000378:metabolism / Q000494:pharmacology*; D004988:Ethers, Cyclic / Q000494:pharmacology*; D006157:Guanosine Monophosphate / Q000378:metabolism; D009153:Mutagens; D009711:Nucleotides / Q000378:metabolism*; D009795:Octanes / Q000378:metabolism / Q000494:pharmacology; D013938:Thymidine Monophosphate / Q000378:metabolism
D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D009153:Mutagens; D009711:Nucleotides; D009795:Octanes; D013938:Thymidine Monophosphate; D000249:Adenosine Monophosphate; D006157:Guanosine Monophosphate; D003568:Cytidine Monophosphate