123994-75-2Relevant articles and documents
Synthesis of N2-(4-hydroxyphenyl)-2'-deoxyguanosine 3'-phosphate: Comparison by 32P-postlabeling with the DNA adduct formed in HL-60 cells treated with hydroquinone
Pongracz,Bodell
, p. 593 - 598 (1996)
A new adduct has been isolated from the reaction of guanosine 3'- phosphate and p-benzoquinone. The structure of this adduct has been determined as N2-(4-hydroxyphenyl)guanosine 3'-phosphate. 32P- Postlabeling showed that this adduct is similar to the DNA adduct formed in HL-60 cells treated with hydroquinone. For comparison with the corresponding deoxyribonucleotide, a synthetic procedure was developed for the preparation of N2-substituted derivatives of 2'-deoxyguanosine 3'-phosphate. 2-Bromo- 2'-deoxyinosine 3'-phosphate was synthesized with a combination of synthetic and enzymatic methods. Reaction of 2-bromo-2'-deoxyinosine 3'-phosphate with 4-hydroxyaniline gave N2-(4-hydroxyphenyl)-2'-deoxyguanosine 3'-phosphate. Using 32P-postlabeling, we compared this product with the DNA adduct produced in HL-60 cells treated with hydroquinone. The results of these studies suggest that the DNA adduct formed in HL-60 cells treated with hydroquinone corresponds to N2-(4-hydroxyphenyl)2'-deoxyguanosine 3'- phosphate.
