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

The role of steric effects in the direct mutagenicity of N-acyloxy-N-alkoxyamides. Research Abstract Details 

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The role of steric effects in the direct mutagenicity of N-acyloxy-N-alkoxyamides. Abstract Text:

Luke E Andrews,Antonio M Bonin,Linda E Fransson,Ashley-Mae E Gillson,Stephen A Glover,

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 (pK(a) of the leaving acid) and steric effects of para-aryl substituents (E(s)). A number of mutagens exhibit activities that deviate markedly from the predicted values and they fall into two classes: di-tert-butylated N-benzoyloxy-N-benzyloxybenzamides, which - because of their size - are most probably excluded from the major groove or are unable to achieve a transition state for reaction with DNA, and N-benzoyloxy-N-butoxyalkylamides with branching alpha-to the amide carbonyl, which are resistant to S(N)2 reactions at the amide nitrogen.

The role of steric effects in the direct mutagenicity of N-acyloxy-N-alkoxyamides. Publishing Authors By Initials

LE Andrews,AM Bonin,LE Fransson,AM Gillson,SA Glover,

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The role of steric effects in the direct mutagenicity of N-acyloxy-N-alkoxyamides. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Mutation research

VOLUME: 605

Page Numbers: 51-62

Journal Abbreviation: Mutat. Res.

ISSN: 0027-5107

DAY: 15

MONTH: 05

YEAR: 2006

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

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LANGUAGE: eng

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Grant and Affiliation Information for The role of steric effects in the direct mutagenicity of N-acyloxy-N-alkoxyamides.

AFFILIATION: Division of Chemistry, School of Biological, Biomedical and Molecular Sciences, University of New England, Armidale, NSW 2351, Australia.

Country: Netherlands

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MEDLINETA: Mutat Res

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