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Article: Direct Time-Resolved Spectroscopic Observation of Arylnitrenium Ion Reactions with Guanine-Containing DNA Oligomers

TitleDirect Time-Resolved Spectroscopic Observation of Arylnitrenium Ion Reactions with Guanine-Containing DNA Oligomers
Authors
Issue Date2014
Citation
The Journal of Organic Chemistry, 2014, v. 79, p. 3610-3614 How to Cite?
AbstractThe metabolic activation of a number of aromatic amine compounds to arylnitrenium ions that can react with DNA to form covalent adducts has been linked to carcinogenesis. Guanine in DNA has been shown to be the main target of N-containing carcinogens, and many monomeric guanine derivatives have been utilized as models for product analysis and spectroscopic investigations to attempt to better understand the reaction mechanisms of DNA with arylnitrenium ions. However, there are still important unresolved issues regarding how arylnitrenium ions attack guanine residues in DNA oligomers. In this article, we employed ns-TA and ns-TR3 spectroscopies to directly observe the reaction of the 2-fluorenylnitrenium ion with selected DNA oligomers, and we detected an intermediate possessing a similar C8 structure as the intermediates produced from the reaction of monomeric guanosine derivatives with arylnitrenium ions. Our results suggest that the oligomeric structure can lead to a faster reaction rate of arylnitrenium ions with guanine residues in DNA oligomers and the reaction of arylnitrenium ions take place in a manner similar to reactions with monomeric guanosine derivatives.
Persistent Identifierhttp://hdl.handle.net/10722/202573
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorXue, Jen_US
dc.contributor.authorDu, Len_US
dc.contributor.authorZhu, Ren_US
dc.contributor.authorHuang, Jen_US
dc.contributor.authorPhillips, DLen_US
dc.date.accessioned2014-09-19T08:41:24Z-
dc.date.available2014-09-19T08:41:24Z-
dc.date.issued2014en_US
dc.identifier.citationThe Journal of Organic Chemistry, 2014, v. 79, p. 3610-3614en_US
dc.identifier.urihttp://hdl.handle.net/10722/202573-
dc.description.abstractThe metabolic activation of a number of aromatic amine compounds to arylnitrenium ions that can react with DNA to form covalent adducts has been linked to carcinogenesis. Guanine in DNA has been shown to be the main target of N-containing carcinogens, and many monomeric guanine derivatives have been utilized as models for product analysis and spectroscopic investigations to attempt to better understand the reaction mechanisms of DNA with arylnitrenium ions. However, there are still important unresolved issues regarding how arylnitrenium ions attack guanine residues in DNA oligomers. In this article, we employed ns-TA and ns-TR3 spectroscopies to directly observe the reaction of the 2-fluorenylnitrenium ion with selected DNA oligomers, and we detected an intermediate possessing a similar C8 structure as the intermediates produced from the reaction of monomeric guanosine derivatives with arylnitrenium ions. Our results suggest that the oligomeric structure can lead to a faster reaction rate of arylnitrenium ions with guanine residues in DNA oligomers and the reaction of arylnitrenium ions take place in a manner similar to reactions with monomeric guanosine derivatives.en_US
dc.languageengen_US
dc.relation.ispartofThe Journal of Organic Chemistryen_US
dc.titleDirect Time-Resolved Spectroscopic Observation of Arylnitrenium Ion Reactions with Guanine-Containing DNA Oligomersen_US
dc.typeArticleen_US
dc.identifier.emailXue, J: jennyxue@hku.hken_US
dc.identifier.emailPhillips, DL: phillips@hku.hken_US
dc.identifier.authorityPhillips, DL=rp00770en_US
dc.identifier.doi10.1021/jo500484sen_US
dc.identifier.pmid24665944-
dc.identifier.hkuros237038en_US
dc.identifier.volume79en_US
dc.identifier.spage3610en_US
dc.identifier.epage3614en_US
dc.identifier.isiWOS:000334823800030-

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