Open AccessPHOTOCHEMICAL COUPLING OF BENZO [a]PYRENE WITH 1-METHYL-CYTOSINE;PHOTO-ENHANCEMENT OF CARCINOGENICITY
Author(s) -
E Cavalieri,
Melvin Calvin
Publication year - 1971
Language(s) - English
Resource type - Reports
DOI - 10.2172/928500
Subject(s) - pyrene , carcinogen , chemistry , benzo(a)pyrene , photochemistry , methanol , acetone , cytosine , organic chemistry , dna , biochemistry
Irradiation of the carcinogenic benzo[a]pyrene (I) with 1-methylcytosine hydrochloride IIa (molar ratio 1:10) at 3500 {angstrom} in methanol-acetone produces the 6-(1-methylcytos-5-yl)-benzo[a]pyrene (III). The structure of the product shows the hydrocarbon bound through the most active 6-carbon atom to the nucleophilic 5-position of the base. In the second part, the possibility of observing carcinogenic effects on the mouse skin from non-carcinogenic hydrocarbons under the action of UV light is investigated. Both experiments provide evidence that the 4,5-double bond (K region) of I presumably does not play a role in triggering the cancer process