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Bioactivation of Cyclopenta- and Cyclohexa-fused Polycyclic Aromatic Hydrocarbons via the Formation of Benzylic Sulfuric Acid Esters

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Authors
Surh, Young-Joon; Tannenbaum, Steven R.
Issue Date
1994
Citation
Polycyclic Aromatic Compounds, Vol.7 No.1-3, pp.83-90
Keywords
benzylic sulfate esterscyclopenta-fused PAHmetabolic activationmutagenicitysulfate conjugationsulfotransferases
Abstract
There has been accumulated evidence that sulfo-conjugation plays an important role in the formation of electrophilic, mutagenic, and tumorigenic sulfuric acid ester metabolites from some hydroxymethyl aromatic hydrocarbons. In the present study, we have investigated whether sulfotransferases can also activate cyclopenta- and cyclohexa-fused polycyclic aromatic hydrocarbons containing secondary benzylic hydroxyl group(s). Thus, 3,4-dihydroxy-3,4-dihydrocyclopenta[cd]pyrene, as well as its monohydroxy analogs, covalently bound to DNA when incubated with rat liver cytosol and the sulfo-group donor, 3-phosphoadenosine-5-phosphosulfate. Likewise, 7-hydroxy-7,8,9,10-tetrahydrobcnzo[a]pyrene was activated to form an electrophilic and mutagenic species through sulfuric acid esterification. However, neither benzo[a]pyrene-7,8-dihydrodiol nor 7,8,9,10-tetrahydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene produced reactive species in the presence of sulfotransferase activity. © 1994, Taylor & Francis Group, LLC. All rights reserved.
ISSN
1040-6638
URI
https://hdl.handle.net/10371/172892
DOI
https://doi.org/10.1080/10406639408014716
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Graduate School of Convergence Science and Technology (융합과학기술대학원)Dept. of Molecular and Biopharmaceutical Sciences (분자의학 및 바이오제약학과)Journal Papers (저널논문_분자의학 및 바이오제약학과)
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