I read in an article that we have this enzyme called P450 that converts aromatic compounds into water soluble compounds that can be eliminated. This enzyme converts aromatic compounds into arene oxides. For example, benzene can be oxidized into benzene oxide.

In the same article it talked about nucleophilic arene oxides being carcinogenic. The nucleophilic $\ce{NH2}$ group of 2'-deoxyguanosine is known to react with certain arene oxides. Once a molecule of this type becomes covalently bonded to an arene oxide the 2'-deoxyguanosine can no longer fit into the DNA double helix. Since the genetic code can't be transcribed it will lead to mutations that can lead to cancer.

Benzo[a]pyrene is found in cigarette smoke and automobile exhaust. It was the culprit behind the scrotum cancer epidemic among Victorian chimney sweepers in the late 1770s to 1800s. The two most harmful are the 4,5-oxide and 7,8-oxide, but I was wondering do these same oxides react with 2'-deoxyguanosine?


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