Biomaterial Database

Adducts between the carcinogen 2-acetamidophenanthrene and adenine and guanine of DNA. 1975

J D Scribner, and N K Naimy

The sulfate and acetate esters of the carcinogen N-hydroxy-2-acetamidophenanthrene attack calf thymus DNA in vitro to yield adducts of 2-acetamidophenanthrene with guanine and adenine in the DNA. These adducts were found to be 8-(N-2-phenanthrylacetamido)deoxyguanosine and N6-1-(2-acetamidophenanthryl)deoxyadenosine, respectively. These reactions, and the already known reactions of esters of N-hydroxy-2-acetamidofluorene, together with Hückel molecular orbital calculations, suggest that the relative tendencies of a series of N-aryl-N-acetylnitrenium ions to react with adenine and guanine may be predicted.

UI	MeSH Term	Description	Entries
D010616	Phenanthrenes	POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.
D002273	Carcinogens	Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.	Carcinogen,Oncogen,Oncogens,Tumor Initiator,Tumor Initiators,Tumor Promoter,Tumor Promoters,Initiator, Tumor,Initiators, Tumor,Promoter, Tumor,Promoters, Tumor
D002621	Chemistry	A basic science concerned with the composition, structure, and properties of matter; and the reactions that occur between substances and the associated energy exchange.
D002850	Chromatography, Gel	Chromatography on non-ionic gels without regard to the mechanism of solute discrimination.	Chromatography, Exclusion,Chromatography, Gel Permeation,Chromatography, Molecular Sieve,Gel Filtration,Gel Filtration Chromatography,Chromatography, Size Exclusion,Exclusion Chromatography,Gel Chromatography,Gel Permeation Chromatography,Molecular Sieve Chromatography,Chromatography, Gel Filtration,Exclusion Chromatography, Size,Filtration Chromatography, Gel,Filtration, Gel,Sieve Chromatography, Molecular,Size Exclusion Chromatography
D003839	Deoxyadenosines	Adenosine molecules which can be substituted in any position, but are lacking one hydroxyl group in the ribose part of the molecule.	Adenine Deoxyribonucleosides,Adenylyldeoxyribonucleosides,Deoxyadenosine Derivatives,Deoxyribonucleosides, Adenine,Derivatives, Deoxyadenosine
D003853	Deoxyribonucleosides	A purine or pyrimidine base bonded to DEOXYRIBOSE.
D004247	DNA	A deoxyribonucleotide polymer that is the primary genetic material of all cells. Eukaryotic and prokaryotic organisms normally contain DNA in a double-stranded state, yet several important biological processes transiently involve single-stranded regions. DNA, which consists of a polysugar-phosphate backbone possessing projections of purines (adenine and guanine) and pyrimidines (thymine and cytosine), forms a double helix that is held together by hydrogen bonds between these purines and pyrimidines (adenine to thymine and guanine to cytosine).	DNA, Double-Stranded,Deoxyribonucleic Acid,ds-DNA,DNA, Double Stranded,Double-Stranded DNA,ds DNA
D004952	Esters	Compounds derived from organic or inorganic acids in which at least one hydroxyl group is replaced by an –O-alkyl or another organic group. They can be represented by the structure formula RCOOR’ and are usually formed by the reaction between an acid and an alcohol with elimination of water.	Ester
D006147	Guanine
D006151	Guanosine	A purine nucleoside that has guanine linked by its N9 nitrogen to the C1 carbon of ribose. It is a component of ribonucleic acid and its nucleotides play important roles in metabolism. (From Dorland, 28th ed)