Mutagenicity of N-acyloxy-N-alkoxyamides – QSAR determination of factors controlling activity
Stephen A. Glover
A *
+ Author Affiliations
- Author Affiliations
A Department of Chemistry, School of Physical Sciences, University of New England, NSW 2350, Australia.
Australian Journal of Chemistry 76(1) 1-24 https://doi.org/10.1071/CH22205
Submitted: 23 September 2022 Accepted: 27 October 2022 Published: 19 January 2023
© 2023 The Author(s) (or their employer(s)). Published by CSIRO Publishing. This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC BY-NC-ND)
Abstract
This account describes the origins of our extensive investigations into the mutagenicity of N-acyloxy-N-alkoxyamides. Since their discovery as biologically active anomeric amides that mutate DNA in the Ames reverse mutation assay without the need for metabolic activation, we have used activities in the Ames test to understand the impact of structural variation on cellular access to, binding to and reactivity with DNA. We have developed an understanding of the roles played by hydrophobicity, electrophilic reactivity, steric effects and, importantly, intercalation on mutagenicity levels and therefore interactions with DNA. The evolution and application of meaningful quantitative structure–activity relationships is described, and examples of their utility in explaining molecule–DNA interactions are given. Their ability to explain previous mutagenicity data and, importantly, to predict meaningful mutagenic behaviour is also demonstrated.
Keywords: acyloxy alkoxyamides, ames mutagenicity, anomeric amides, bilinear QSAR, deamination, direct‐acting mutagenicity, DNA binding, groove binding, HERON reactions, intercalation, linear QSAR, mutagenic amides, nitrogen deletion, PAH, pyramidal amides, QSAR, quantitative structure‐activity relationship, skeletal editing, TA98, TA100.
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