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PHOTOCHEMICAL COUPLING OF BENZO [a]PYEENE WITH 1-METHYLCYTOSINE.POSSIBLE MECHANISM OF THE LINKAGE IN VIVO

Technical Report ·
DOI:https://doi.org/10.2172/928393· OSTI ID:928393

Irradiation of benzo[a]pyrene 1 with 1-methylcytosine hydrochloride 2a (molar ratio 1:10) at 3500 {angstrom} in methanol-acetone produces the 6-(1-methylcytos-5-yl)-benzo[pa]pyrene 3. The structure of the photoproduct shows the hydrocarbon bound through the most active 6-carbon atom to the nucleophilic 5-position of the base. The specific substitution of both moieties combined with other data allows them to understand the carcinogenic activity of the hydrocarbon and thereby to propose a possible mechanism of their linkage in vivo. In this model, the K region does not play a role in triggering the cancer process.

Research Organization:
Ernest Orlando Lawrence Berkeley NationalLaboratory, Berkeley, CA (US)
Sponsoring Organization:
USAEC
DOE Contract Number:
AC02-05CH11231
OSTI ID:
928393
Report Number(s):
UCRL--20061
Country of Publication:
United States
Language:
English