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Title: Mutagenicity and DNA damage studies of N-acyloxy-N-alkoxyamides: the role of electrophilic nitrogen
Contributor(s): Banks, T (author); Bonin, A (author); Glover, S (author); Prakash, A (author)
Publication Date: 2003
DOI: 10.1039/b301618h
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Abstract: N-Acyloxy-N-alkoxyamides are anomeric amides that are direct-acting mutagens. They have been shown to damage DNA in the major and the minor grooves in a pH and sequence-selective manner. In acidic media, they damage adenines at N3 in the minor groove but above neutral pH, only guanine is damaged at N7 in the major groove. Both the acyloxy leaving group and the alkoxy group at the amide nitrogen are responsible for their electrophilicity and Salmonella mutagenicities in TA100 and DNA damage data confirm that the mutagens react with DNA in an intact form, rather than by solvolysis to electrophilic nitrenium ions in the cytosol, or in vitro, prior to reacting with DNA. Hydrophobicity plays a role in both mutagenicity and DNA damage.
Publication Type: Journal Article
Source of Publication: Organic & Biomolecular Chemistry, 1(13), p. 2238-2246
Publisher: Royal Society of Chemistry
Place of Publication: Cambridge, England
ISSN: 1477-0520
Field of Research (FOR): 030499 Medicinal and Biomolecular Chemistry not elsewhere classified
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
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