The role of steric effects in the direct mutagenicity of N-acyloxy-N-alkoxyamides

LE Andrews, AM Bonin, LE Fransson…

Index: Andrews, Luke E.; Bonin, Antonio M.; Fransson, Linda E.; Gillson, Ashley-Mae E.; Glover, Stephen A. Mutation Research - Genetic Toxicology and Environmental Mutagenesis, 2006 , vol. 605, # 1-2 p. 51 - 62

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Citation Number: 14

Abstract

Electrophilic N-acyloxy-N-alkoxyamides are mutagenic in Salmonella typhimurium TA100 without the need for S9 metabolic activation and they react with DNA at guanine—N7 at physiological pH. Since these are direct-acting mutagens, structural factors influence binding and reactivity with DNA. Mutagenicity in TA100 can be predicted by a QSAR incorporating hydrophobicity (logP), stability to substitution reactions at nitrogen (pKa of ...