Formation of 1,N-6-etheno-2 '-deoxyadenosine adducts by trans,trans-2,4-decadienal

dc.contributorUniversidade de São Paulo (USP)
dc.contributorUniversidade Estadual Paulista (Unesp)
dc.contributorCEA
dc.creatorCarvalho, V. M.
dc.creatorDi Mascio, P.
dc.creatorCampos, IPD
dc.creatorDouki, T.
dc.creatorCadet, J.
dc.creatorMedeiros, MHG
dc.date2015-03-18T15:54:15Z
dc.date2015-03-18T15:54:15Z
dc.date1998-09-01
dc.date.accessioned2023-09-12T03:00:16Z
dc.date.available2023-09-12T03:00:16Z
dc.identifierhttp://dx.doi.org/10.1021/tx9800710
dc.identifierChemical Research In Toxicology. Washington: Amer Chemical Soc, v. 11, n. 9, p. 1042-1047, 1998.
dc.identifier0893-228X
dc.identifierhttp://hdl.handle.net/11449/116843
dc.identifier10.1021/tx9800710
dc.identifierWOS:000076103000008
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/8766328
dc.descriptiontrans,trans-2,4-Decadienal (DDE) is an important breakdown product of lipid peroxidation. This aldehyde is cytotoxic to mammalian cells and is known to be implicated in DNA damage. Therefore, attempts were made in this work to assess the reactivity of DDE with 2'-deoxyadenosine (dAdo). It was shown that DDE is able to bind to 2'-deoxyadenosine, yielding highly fluorescent products. Besides 1,N-6-etheno-2'-deoxyadenosine (epsilon dAdo), two other related adducts, 1-[3-(2-deoxy-beta-D-erythro-pentofuranosyl)3H-imidazo[2,1-i]purin-7-yl]-1,2,3-octanetriol and 1-[3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3H-imidazo[2,1-i]purin-7-yl]-1,2-heptanediol, were isolated by reverse phase high-performance liquid chromatography and characterized on the basis of their UV, fluorescence, nuclear magnetic resonance, and mass spectrometry features. The reaction mechanism for the formation of the DDE-2'-deoxyadenosine adducts involves 2,4-decadienal epoxidation and subsequent addition to the N-2 amino group of 2'-deoxyadenosine, followed by cyclization at the N-1 site. Adducts differ by the length of carbon side chain and the number of hydroxyl groups. The present data indicate that DDE can be epoxidized by peroxides, and the resulting products are able to form several adducts with 2'-deoxyadenosine and/or DNA. Endogenous DNA adduct formation can contribute to the already reported high cytotoxicity of DDE to mammalian cells.
dc.descriptionUniv Sao Paulo, Inst Quim, Dept Bioquim, BR-05599970 Sao Paulo, Brazil
dc.descriptionUniv Estadual Paulista, Inst ciencias Exatas & Tecnol, BR-06500000 Sao Paulo, Brazil
dc.descriptionCEA, LAN, Dept Rech Fondamentale Mat Condensee, SCIB, F-38054 Grenoble, France
dc.descriptionUniv Estadual Paulista, Inst ciencias Exatas & Tecnol, BR-06500000 Sao Paulo, Brazil
dc.format1042-1047
dc.languageeng
dc.publisherAmer Chemical Soc
dc.relationChemical Research In Toxicology
dc.relation3.432
dc.rightsAcesso restrito
dc.sourceWeb of Science
dc.titleFormation of 1,N-6-etheno-2 '-deoxyadenosine adducts by trans,trans-2,4-decadienal
dc.typeArtigo


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