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Title: Zirconacyclopentadiene-Annulated Polycyclic Aromatic Hydrocarbons

ORCiD logo [1]; ORCiD logo [1];  [1]
  1. Department of Chemistry, University of California, Berkeley CA 94720 USA
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Journal Article: Publisher's Accepted Manuscript
Journal Name:
Angewandte Chemie (International Edition)
Additional Journal Information:
Journal Name: Angewandte Chemie (International Edition); Journal Volume: 56; Journal Issue: 17; Related Information: CHORUS Timestamp: 2017-11-02 07:12:30; Journal ID: ISSN 1433-7851
Wiley Blackwell (John Wiley & Sons)
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Citation Formats

Kiel, Gavin R., Ziegler, Micah S., and Tilley, T. Don. Zirconacyclopentadiene-Annulated Polycyclic Aromatic Hydrocarbons. Germany: N. p., 2017. Web. doi:10.1002/anie.201700818.
Kiel, Gavin R., Ziegler, Micah S., & Tilley, T. Don. Zirconacyclopentadiene-Annulated Polycyclic Aromatic Hydrocarbons. Germany. doi:10.1002/anie.201700818.
Kiel, Gavin R., Ziegler, Micah S., and Tilley, T. Don. Thu . "Zirconacyclopentadiene-Annulated Polycyclic Aromatic Hydrocarbons". Germany. doi:10.1002/anie.201700818.
title = {Zirconacyclopentadiene-Annulated Polycyclic Aromatic Hydrocarbons},
author = {Kiel, Gavin R. and Ziegler, Micah S. and Tilley, T. Don},
abstractNote = {},
doi = {10.1002/anie.201700818},
journal = {Angewandte Chemie (International Edition)},
number = 17,
volume = 56,
place = {Germany},
year = {Thu Mar 23 00:00:00 EDT 2017},
month = {Thu Mar 23 00:00:00 EDT 2017}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record at 10.1002/anie.201700818

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Cited by: 2works
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  • Workers in coke oven plants have a higher incidence of lung cancer than the general population. They are exposed to a variety of chemicals, in particular the polycyclic aromatic hydrocarbons (PAH), including benzo(a)pyrene. To evaluate the genotoxic effects of PAH exposure, air samples and urine samples were analyzed for PAH by capillary gas chromatography and high-performance liquid chromatography, respectively. Since benzo(a)pyrene is activated to 7 beta,8 alpha-dihydroxy-(9 alpha,10 alpha)-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene (BPDE) and binds to DNA, we have used ultrasensitive enzymatic radioimmunoassay and synchronous fluorescence spectrophotometry to measure BPDE-DNA adducts in lymphocyte DNA. The results show that workers were exposed to highmore » concentrations of atmospheric PAH. However, the mean PAH exposure levels are reduced 60% when the workers wore masks during work. When compared to exposure levels, the urinary excretion of PAH was relatively low. Approximately one-third of the workers had detectable putative BPDE-DNA adducts in lymphocytes by ultrasensitive enzymatic radioimmunoassay, and 10% of the samples had emission peaks at 379 nm by synchronous fluorescence spectrophotometry. The four most positive samples were the same in both of the assays. Antibodies to an epitope(s) on BPDE-DNA were found in the sera of approximately one-third of the workers. Detection of DNA adducts and antibodies to these adducts are internal indicators of exposure to benzo(a)pyrene.« less
  • The {sup 32}P-postlabeling assay, thin-layer chromatography, and reverse-phase high-pressure liquid chromatography (HPLC) were used to separate DNA adducts formed from 10 polycyclic aromatic hydrocarbons (PAHs) and 6 nitrated polycyclic aromatic hydrocarbons (NO{sub 2}-PAHs). The PAHs included benzo[j]fluoranthene, benzo[k]fluoranthene, indeno[1,2,3-cd]pyrene, benzo[a]pyrene, chrysene, 6-methylchrysene, 5-methylchrysene, and benz[a]anthracene. The NO{sub 2}-PAHs included 1-nitropyrene, 2-nitrofluoranthene, 3-nitrofluoranthene, 1,6-dinitropyrene, 1,3-dinitropyrene, and 1,8-dinitropyrene. Separation of seven of the major PAH-DNA adducts was achieved by an initial PAH HPLC gradient system. The major NO{sub 2}-PAH-DNA adducts were not all separated from each other using the initial PAH HPLC gradient but were clearly separated from the PAH-DNA adducts. Amore » second NO{sub 2}-PAH HPLC gradient system was developed to separate NO{sub 2}-PAH-DNA adducts following one-dimensional TLC and HPLC analysis. HPLC profiles of NO{sub 2}-PAH-DNA adducts were compared using both adduct enhancement versions of the {sup 32}P-postlabeling assay to evaluate the use of this technique on HPLC to screen for the presence of NO{sub 2}-PAH-DNA adducts. To demonstrate the application of these separation methods to a complex mixture of DNA adducts, the chromatographic mobilities of the {sup 32}P-postlabeled DNA adduct standards (PAHs and NO{sub 2}-PAHs) were compared with those produced by a complex mixture of polycyclic organic matter (POM) extracted from diesel emission particles. The diesel-derived adducts did not elute with the identical retention time of any of the PAH or NO{sub 2}-PAH standards used in this study. HPLC analyses of the NO{sub 2}-PAH-derived adducts (butanol extracted) revealed the presence of multiple DNA adducts.« less
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