13312-42-0Relevant articles and documents
Royer et al.
, p. 377,379,380 (1976)
Synthesis of phenol and quinone metabolites of benzo[a]pyrene, a carcinogenic component of tobacco smoke implicated in lung cancer
Xu, Daiwang,Penning, Trevor M.,Blair, Ian A.,Harvey, Ronald G.
body text, p. 597 - 604 (2009/06/20)
Polycyclic aromatic hydrocarbons (PAHs) are widespread environmental pollutants produced in the combustion of organic matter. PAHs are present in automobile exhaust and tobacco smoke, and they have recently been designated as human carcinogens. Current ev
Synthesis and characterization of nucleosides and oligonucleotides with a benzo[a]pyren-6-ylmethyl adduct at adenine N6 or guanine N2
Kim,Cooper,Nechev,Harris,Harris
, p. 1306 - 1314 (2007/10/03)
Benzo[a]pyrene (1) can be converted to reactive electrophilic species by a number of metabolic pathways, of which the route to the mutagenic and carcinogenic diol epoxide(s) is the best studied. An alternative and interesting pathway to a highly genotoxic electrophile is through alkylation at the 6 position to 6-methylbenzo[a]pyrene (2) followed by oxidation of the methyl group to give 6-hydroxymethylbenzo[a]pyrene (3). Esterification of 3, especially to sulfate ester 4, gives compounds which are both mutagenic and carcinogenic. The major DNA adduct identified from exposure of rats and mice to 4 is the guanine N2 adduct [2′-deoxy-N2-(benzo-[a]pyren-6-ylmethyl)guanosine,5] which is also formed via activation of 2 to a radical cation species by horseradish peroxidase/H2O2 or iodine. To study the biological and structural properties of this adduct and the analogous adenine N6 adduct (6), a nonbiomimetic synthesis of the adducted nucleosides 5 and 6 has been developed and has been extended to preparation of oligonucleotides containing 5 or 6 at a single site.
