Structural characterization of an etheno-2 '-deoxyguanosine adduct modified by tetrahydrofuran

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dc.contributor.authorLoureiro, APM
dc.contributor.authorCampos, IPD
dc.contributor.authorGomes, O. F.
dc.contributor.authorPossari, EPM
dc.contributor.authorDi Mascio, P.
dc.contributor.authorMedeiros, MHG
dc.contributor.institutionUniversidade de São Paulo (USP)
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.date.accessioned2015-03-18T15:54:15Z
dc.date.available2015-03-18T15:54:15Z
dc.date.issued2005-02-01
dc.description.abstractThe reaction of 2'-deoxyguanosine with the alpha,beta-unsaturated aldehydes trans-2-octenal, trans-2-nonenal, trans-2-decenal, trans,trans-2,4-nonadienal, and trans,trans-2,4-decadienal in THF gives rise to three novel adducts: 3-(2'-deoxy-beta-D-erythro-pentafuranosyl)-7-[3-hydroxy-1-(3(2'-deoxy-beta-D-erythro-pentafuranosyl)-3,5-dihydro-imidazo[1,2-alpha]purin-9-one-7-yl)-propyl] -3,5-dihydro-imidazo[1,2-alpha]purin-9-one (M) and 3-(2'-deoxy-beta-D-erythro-pentafuranosyl)-7-(tetrahydrofuran-2-yl)-3,5-dihydro-imidazo[1,2-alpha]purin-9-one (A8 and A9), which are not observed in the absence of THF. These adducts were isolated from in vitro reactions by reversed-phase HPLC and fully characterized on the basis of spectroscopic measurements. Adduct A7 consists of two 1,N-2-etheno-2'-deoxyguanosine (1,N-2-epsilondGuo) residues linked to a hydroxy-carbon side chain; adducts A8 and A9 are interconvertible 1,N-2-epsilondGuo derivatives bearing a THF moiety. The proposed reaction mechanism involves the electrophilic attack on 1,N-2-epsilondGuo by the carbonyl of 4-hydroxy-butanal, generated via ring opening of alpha-hydroxy-THF (THF-OH), yielding adducts A8 and A9. A further combination of these adducts with another 1,N-2-epsilondGuo produces the double adduct A7. These findings demonstrate that reactions of unsaturated aldehydes in the presence of THF produce novel condensation 1,N-2-epsilondGuo-THF adducts. Further studies would indicate the relevance of these adducts in THF toxicity.en
dc.description.affiliationUniv Sao Paulo, Inst Quim, Dept Bioquim, BR-05508900 Sao Paulo, Brazil
dc.description.affiliationUniv Estadual Paulista, Inst Ciencias Exatas & Tecnol, Programa Posgrad Engn Prod, BR-04026002 Sao Paulo, Brazil
dc.description.affiliationUniv Sao Paulo, Dept Anal Clin & Toxicol, Fac Ciencias Farmaceut, BR-05508900 Sao Paulo, Brazil
dc.description.affiliationUnespUniv Estadual Paulista, Inst Ciencias Exatas & Tecnol, Programa Posgrad Engn Prod, BR-04026002 Sao Paulo, Brazil
dc.format.extent290-299
dc.identifierhttp://dx.doi.org/10.1021/tx0497494
dc.identifier.citationChemical Research In Toxicology. Washington: Amer Chemical Soc, v. 18, n. 2, p. 290-299, 2005.
dc.identifier.doi10.1021/tx0497494
dc.identifier.issn0893-228X
dc.identifier.urihttp://hdl.handle.net/11449/116841
dc.identifier.wosWOS:000227168000024
dc.language.isoeng
dc.publisherAmer Chemical Soc
dc.relation.ispartofChemical Research In Toxicology
dc.relation.ispartofjcr3.432
dc.rights.accessRightsAcesso restrito
dc.sourceWeb of Science
dc.titleStructural characterization of an etheno-2 '-deoxyguanosine adduct modified by tetrahydrofuranen
dc.typeArtigo
dcterms.rightsHolderAmer Chemical Soc
unesp.author.orcid0000-0002-5438-1174[6]
unesp.author.orcid0000-0003-4125-8350[5]

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