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© 1990 Oxford University Press

research-article

Detection of (3'-hydroxy)-3,N4-benzetheno-2'-deoxycytidine-3'-phosphate by 32P-postlabeling of DNA reacted with p-benzoquinone

Krisztina Pongracz, Surinder Kaur 1, Alma L. Burlingame 1 and J. Bodell William 2

Brain Tumor Research Center, Department of Neurological Surgery University of California San Francisco, CA 94143, USA
1Mass Spectrometiy Facility, Department of Pharmaceutical Chemistiy, University of California San Francisco, CA 94143, USA

2To whom correspondence should be addressed at the Radiation Oncology Research Laboratory, MCB-200, University of California San Francisco, CA 94143, USA

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'-deoxycytidlne-3'-phosphate with a hydroquinone-p-benzoquinone mixture. 32P-Postlabeling of calf thymus DNA reacted with p-benzoqulnone 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 multipleDNA adducts. 32P-Postlabeling may allow detection of benzene—DNA adducts in vivo.


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