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2752648 
Journal Article 
Formation of 1,N6-etheno-2'-deoxyadenosine adducts by trans,trans-2,4-decadienal 
Carvalho, VM; Di Mascio, P; De Arruda CAMPOS, IP; Douki, T; Cadet, J; Medeiros M, HG 
1998 
Yes 
Chemical Research in Toxicology
ISSN: 0893-228X
EISSN: 1520-5010 
BIOSIS/98/34351 
11 
9 
1042-1047 
English 
BIOSIS COPYRIGHT: BIOL ABS. trans,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,N6-etheno-2'-deoxyadenosine (epsilondAdo), 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 th