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Cyanoethylation of DNA in Vivo by 3-(Methylnitrosamino)propionitrile, an Areca-derived Carcinogen¹

Naylor Dana Institute for Disease Prevention, American Health Foundation, Valhalla, New York 10595

2-Cyanoethyldiazohydroxide is a likely product of metabolic -hydroxylation of 3-(methylnitrosamino)propionitrile (MNPN). The reaction of 2-(N-carbethoxy-N-nitrosamino)propionitrile, a stable precursor of 2-cyanoethyldiazohydroxide, with deoxyguanosine, catalyzed by porcine liver esterase, was investigated. Two major deoxyguanosine adducts were produced. They were isolated by high-performance liquid chromatography and characterized by their UV spectra, mass spectra, and proton magnetic resonance spectra. On the basis of these spectral data, the structures of the two adducts were assigned as 7-(2-cyanoethyl)guanine and O⁶-(2-cyanoethyl)deoxyguanosine.

The potential of MNPN to cyanoethylate DNA in F344 rats was evaluated by measuring 7-(2-cyanoethyl)guanine and O⁶-(2-cyanoethyl)guanine in the liver, nasal mucosa, and esophagus. The highest levels were detected in the nasal cavity, which is one of the major target organs for the carcinogenic effects of MNPN.

¹ This study was supported by Grant CA-29580 from the National Cancer Institute. This is No. VI in the Series "A Study of Betel Quid Carcinogenesis."

² To whom requests for reprints should be addressed, at the Naylor Dana Institute for Disease Prevention, American Health Foundation, 1 Dana Road, Valhalla, NY 10595.

Received 3/ 7/88. Revised 6/20/88. Revised 8/18/88. Accepted 8/25/88.