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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||Handle Link:||https://hdl.handle.net/1959.11/69||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||Statistics to Oct 2018:||Visitors: 176
|Appears in Collections:||Journal Article|
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