Reaction of Glyoxal with 2'-Deoxyguanosine, 2'-Deoxyadenosine, 2'-Deoxycytidine, Cytidine, Thymidine, and Calf Thymus DNA: Identification of DNA Adducts
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- 作者：Raymond Olsen ; Paal Molander ; Steinar Ø ; vreb
//pubs.acs.org/images/gifchars/oslash.gif" border="0"> ; Dag G. Ellingsen ; Syvert Thorud ; Yngvar Thomassen ; Elsa Lundanes ; Tyge Greibrok
- 刊名：Chemical Research in Toxicology
- 出版年：2005
- 出版时间：April 2005
- 年：2005
- 卷：18
- 期：4
- 页码：730 - 739
- 全文大小：248K
- 年卷期：v.18,no.4(April 2005)
- ISSN：1520-5010
文摘
Glyoxal (ethanedial) is an increasingly used industrial chemical that has been found to bemutagenic in bacteria and mammalian cells. In this study, the reactions of glyoxal with 2'-deoxyguanosine, 2'-deoxyadenosine, 2'-deoxycytidine, cytidine, thymidine, and calf thymus DNAhave been studied in aqueous buffered solutions. The nucleoside adducts were isolated byreversed-phase liquid chromatography and characterized by their UV absorbance and 1H and13C NMR spectroscopic and mass spectrometric features. The reaction with 2'-deoxyguanosinegave one adduct, the previously known 3-(2'-deoxy-
beta2.gif" BORDER=0 ALIGN="middle">-D-erythro-pentofuranosyl)-5,6,7-trihydro-6,7-dihydroxyimidazo[1,2-a]purine-9-one adduct. The reaction of 2'-deoxyadenosine with glyoxalresulted in the formation of a previously not reported N6-(hydroxyacetyl)-2'-deoxyadenosineadduct. In the reaction of glyoxal with 2'-deoxycytidine and cytidine at neutral conditions and37 
C, 5-hydroxyacetyl pyrimidine derivatives were obtained. When the cytidine reaction wasperformed at pH 4.5 and 50 C, the 5-hydroxyacetyl derivative of uridine was formed throughdeamination of cytidine-glyoxal. Adducts in the thymidine reaction could not be detected. Inthe reaction of glyoxal with calf thymus DNA, the 2'-deoxyguanosine-glyoxal and 2'-deoxyadenosine-glyoxal adducts were obtained, the former being the major adduct.
beta2.gif" BORDER=0 ALIGN="middle">-D-erythro-pentofuranosyl)-5,6,7-trihydro-6,7-dihydroxyimidazo[1,2-a]purine-9-one adduct. The reaction of 2'-deoxyadenosine with glyoxalresulted in the formation of a previously not reported N6-(hydroxyacetyl)-2'-deoxyadenosineadduct. In the reaction of glyoxal with 2'-deoxycytidine and cytidine at neutral conditions and37 C, 5-hydroxyacetyl pyrimidine derivatives were obtained. When the cytidine reaction wasperformed at pH 4.5 and 50 C, the 5-hydroxyacetyl derivative of uridine was formed throughdeamination of cytidine-glyoxal. Adducts in the thymidine reaction could not be detected. Inthe reaction of glyoxal with calf thymus DNA, the 2'-deoxyguanosine-glyoxal and 2'-deoxyadenosine-glyoxal adducts were obtained, the former being the major adduct.