Linked Life Data

11423351

Source:http://linkedlifedata.com/resource/pubmed/id/11423351

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
pubmed:issue
1-2
pubmed:dateCreated
2001-6-25
pubmed:abstractText
N-acyloxy-N-alkoxybenzamides are mutagenic in TA100 without the need for metabolic activation with S9. Electronic effects of substituents on both the benzamide ring in N-acetoxy-N-butoxybenzamides or the benzyloxy ring in N-acetoxy-N-benzyloxybenzamides do not influence mutagenicity levels. For N-benzoyloxy-N-benzyloxybenzamides, mutagenicity levels are inversely related to the electron-withdrawing effect of substituents on the benzoyloxy leaving group. Since reactivities increase with increasing electron-withdrawing effects, mutagenicity correlates with stability rather than reactivity of these mutagens. Hydrophobicity is the dominant factor controlling mutagenicity levels and data for all mutagens correlate with computed logP values with a lower dependence (h=0.22) than that recorded for indirect mutagens (h=1.0), except where a sterically demanding p-tert-butyl substituent or a naphthyl group is present. N-acetoxy-N-butoxynaphthamide exhibits a much higher level of mutagenicity than predicted by its logP value and activity may be ascribed to an intercalative binding process with DNA rather than straightforward hydrophobic binding in the major or minor groove. Since these are direct-acting mutagens, structural factors influence binding and reactivity towards DNA.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Jul
pubmed:issn
0027-5107
pubmed:author
pubmed:issnType
Print
pubmed:day
25
pubmed:volume
494
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
115-34
pubmed:meshHeading
pubmed:year
2001
pubmed:articleTitle
Mutagenicity of electrophilic N-acyloxy-N-alkoxyamides.
pubmed:affiliation
School of Chemistry, University of Sydney, NSW 2006, Sydney, Australia.
pubmed:publicationType
Journal Article