Catechol is present in large (milligram) amounts in tobacco cigarettes. Previous work demonstrated that oxidized solutions of catechol mimic the DNA binding and nicking activity of mainstream cigarette smoke extracts. An aqueous solution of catechol was allowed to stand for three weeks in order to compare the resulting polymer of catechol to second and third hand cigarette tar extracts. The aqueous solutions of catechol were purified by Sephadex G-25 chromatography to remove non-polymerized catechol; 48 fractions were collected. The fractions were analyzed by UV spectroscopy and fractions with spectra similar to the cigarette tar fractions were assayed for DNA nicking activity. Gel electrophoresis was used to analyze the nicking of plasmid (pUC18) DNA. The DNA samples that were incubated with buffer (no tar) exhibited 0-3% nicking. The catechol polymer when incubated with the DNA nicked 5-9%. An oxygraph was used to analyze the production of hydrogen peroxide by the aged catechol. The rate of oxygen disappearance is similar to the rate obtained when second hand smoke extracts were analyzed. A paper based Methylene blue assay was used to detect hydroxyl radicals in the catechol and cigarette tar fractions. NMR spectra of fresh and aged catechol solutions were obtained, these spectra show that there is a significant structural change as the catechol ages. The work demonstrates that we are able to use aged catechol solutions to allow us to determine the chemical properties of the cigarette tar radical with only one chemical species in the polymeric mixture.

Aged catechol solutions model the chemical and biochemical properties of the aqueous cigarette tar radical

255th National Meeting (2018)

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