Detection of (3'-hydroxy)-3,N4-benzetheno-2'-deoxycytidine-3'-phosphate by 32P-postlabeling of DNA reacted with p-benzoquinone.
Cytidine-3'-phosphate was reacted with p-benzoquinone under neutral aqueous conditions, and the fluorescent product formed was isolated and characterized. The structure of the covalent adduct was identified as (3'-hydroxy)-3,N4-benzetheno-cytidine-3'-phosphate by high-resolution MS and 1H NMR spectroscopy. A similar product was isolated from the reaction of 2'-deoxycytidine-3'-phosphate with a hydroquinone-p-benzoquinone mixture. 32P-Postlabeling of calf thymus DNA reacted with p-benzoquinone detected several adducts, the principal adduct being (3'-hydroxy)-3,N4-benzetheno-2'-deoxycytidine-3'-phosphate. Our studies demonstrate that the reaction of DNA with p-benzoquinone in vitro leads to multiple DNA adducts. 32P-Postlabeling may allow detection of benzene-DNA adducts in vivo.
Department of Neurological Surgery, University of California, San Francisco 94143.
K
K
Pongracz
S
S
Kaur
A L
AL
Burlingame
W J
WJ
Bodell
D016227:Benzoquinones; D002273:Carcinogens; D003568:Cytidine Monophosphate; D003597:Cytosine Nucleotides; D004247:DNA; D003843:Deoxycytidine Monophosphate / Q000031:analogs & derivatives* / Q000032:analysis; D003845:Deoxycytosine Nucleotides; D010761:Phosphorus Radioisotopes; D011809:Quinones; D011865:Radioisotope Dilution Technique; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet
D016227:Benzoquinones; D002273:Carcinogens; D003597:Cytosine Nucleotides; D003845:Deoxycytosine Nucleotides; D010761:Phosphorus Radioisotopes; D011809:Quinones; D003843:Deoxycytidine Monophosphate; C065824:(3'-hydroxy)-3,N(4)-benzetheno-1'-deoxycytidine 3'-phosphate; C004532:quinone; D004247:DNA; D003568:Cytidine Monophosphate