PMID- 28848957 OWN - NLM STAT- MEDLINE DCOM- 20180223 LR - 20181202 IS - 2050-7895 (Electronic) IS - 2050-7887 (Linking) VI - 19 IP - 10 DP - 2017 Oct 18 TI - Epoxide formation from heterogeneous oxidation of benzo[a]pyrene with gas-phase ozone and indoor air. PG - 1292-1299 LID - 10.1039/c7em00181a [doi] AB - The formation of two classes of epoxide products from the heterogeneous reaction of benzo[a]pyrene (BaP) with gas-phase ozone was demonstrated. BaP was coated on a Pyrex glass tube and oxidized with different concentrations of ozone. After oxidation, the epoxide products were derivatized by N-acetylcystein (NAC) and then analyzed by liquid chromatography-tandem mass spectrometry (LC-MS/MS). The results show that in addition to mono-epoxides, diol-epoxides were also formed. BaP exposed to genuine indoor air also produces mono- and diol-epoxides, having similar chromatograms to those produced by oxidation of BaP by low concentrations of ozone. Although it is well recognized that diol-epoxides are formed from BaP oxidation in the human body and that they exhibit carcinogenicity via formation of adducts with DNA, this is the first demonstration that such classes of compounds can be formed by abiotic heterogeneous oxidation. FAU - Zhou, Shouming AU - Zhou S AD - Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON M5S 3H6, Canada. szhou@chem.utoronto.ca leo.yeung@oru.se. FAU - Yeung, Leo W Y AU - Yeung LWY FAU - Forbes, Matthew W AU - Forbes MW FAU - Mabury, Scott AU - Mabury S FAU - Abbatt, Jonathan P D AU - Abbatt JPD LA - eng PT - Journal Article PL - England TA - Environ Sci Process Impacts JT - Environmental science. Processes & impacts JID - 101601576 RN - 0 (DNA Adducts) RN - 0 (Epoxy Compounds) RN - 3417WMA06D (Benzo(a)pyrene) RN - 66H7ZZK23N (Ozone) SB - IM MH - Air Pollution, Indoor/*analysis MH - Animals MH - Benzo(a)pyrene/*chemistry MH - Chromatography, High Pressure Liquid MH - DNA Adducts/analysis MH - Epoxy Compounds/*analysis MH - Humans MH - *Models, Theoretical MH - Molecular Structure MH - Oxidation-Reduction MH - Ozone/*chemistry MH - Tandem Mass Spectrometry EDAT- 2017/08/30 06:00 MHDA- 2018/02/24 06:00 CRDT- 2017/08/30 06:00 PHST- 2017/08/30 06:00 [pubmed] PHST- 2018/02/24 06:00 [medline] PHST- 2017/08/30 06:00 [entrez] AID - 10.1039/c7em00181a [doi] PST - ppublish SO - Environ Sci Process Impacts. 2017 Oct 18;19(10):1292-1299. doi: 10.1039/c7em00181a.