Please use this identifier to cite or link to this item: https://hdl.handle.net/1959.11/57207
Title: Mutagenicity of N-acyloxy-N-alkoxyamides – QSAR determination of factors controlling activity
Contributor(s): Glover, Stephen A  (author)orcid 
Publication Date: 2023-01-19
Open Access: Yes
DOI: 10.1071/CH22205
Handle Link: https://hdl.handle.net/1959.11/57207
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.

Publication Type: Journal Article
Source of Publication: Australian Journal of Chemistry, 76(1), p. 1-24
Publisher: CSIRO Publishing
Place of Publication: Australia
ISSN: 1445-0038
0004-9425
Fields of Research (FoR) 2020: 340402 Biomolecular modelling and design
340401 Biologically active molecules
340701 Computational chemistry
Socio-Economic Objective (SEO) 2020: 280105 Expanding knowledge in the chemical sciences
280102 Expanding knowledge in the biological sciences
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
Appears in Collections:Journal Article
School of Science and Technology

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