| dbo:abstract |
(+)-Benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide is an organic compound with molecular formula C20H14O3. It is a metabolite and derivative of benzo[a]pyrene (found in tobacco smoke) as a result of oxidation to include hydroxyl and epoxide functionalities. (+)-Benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide binds to the N2 atom of a guanine nucleobase in DNA, distorting the double helix structure by intercalation of the pyrene moiety between base pairs through π-stacking. The carcinogenic properties of tobacco smoking are attributed in part to this compound binding and inactivating the tumor suppression ability of certain genes, leading to genetic mutations and potentially to cancer. (en) |
| dbo:alternativeName |
(+)-Benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide (en) (7R,8S,8aR,9aS)-7,8,8a,9a-Tetrahydrobenzo[1,12]tetrapheno[10,11-b]oxirene-7,8-diol (en) (+)-7,8,9,10-Tetrahydrobenzo[a]pyrene-7,8-diol-9,10-epoxide (en) 7,8,8a,9a-Tetrahydro-(7R,8S,8aR,9aS)-benzo[10,11]chryseno[3,4-b]oxirene-7,8-diol (en) |
| dbo:iupacName |
(7R,8S,8aS,9aR)-7,8,8a,9a-Tetrahydrobenzo[1,12]tetrapheno[10,11-b]oxirene-7,8-diol (en) |
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(+)-Benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide is an organic compound with molecular formula C20H14O3. It is a metabolite and derivative of benzo[a]pyrene (found in tobacco smoke) as a result of oxidation to include hydroxyl and epoxide functionalities. (+)-Benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide binds to the N2 atom of a guanine nucleobase in DNA, distorting the double helix structure by intercalation of the pyrene moiety between base pairs through π-stacking. The carcinogenic properties of tobacco smoking are attributed in part to this compound binding and inactivating the tumor suppression ability of certain genes, leading to genetic mutations and potentially to cancer. (en) |
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(+)-Benzo(a)pyrene-7,8-dihydrodiol-9,10-epoxide (en) |
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