{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T18:33:28Z","timestamp":1790015608755,"version":"4.0.1"},"reference-count":51,"publisher":"American Chemical Society (ACS)","issue":"3","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Org. Chem."],"published-print":{"date-parts":[[2008,2,1]]},"DOI":"10.1021\/jo701667u","type":"journal-article","created":{"date-parts":[[2008,1,9]],"date-time":"2008-01-09T10:01:23Z","timestamp":1199872883000},"page":"992-1003","source":"Crossref","is-referenced-by-count":15,"title":["Strategies for Synthesis of Adducts of <i>o<\/i>-Quinone Metabolites of Carcinogenic Polycyclic Aromatic Hydrocarbons with 2\u2018-Deoxyribonucleosides"],"prefix":"10.1021","volume":"73","author":[{"given":"Chongzhao","family":"Ran","sequence":"first","affiliation":[{"name":"The Ben May Department for Cancer Research, The University of Chicago, Chicago, Illinois 60637, and The Centers for Cancer Pharmacology and Excellence in Environmental Toxicology, University of Pennsylvania School of Medicine, Philadelphia, Pennsylvania 19104"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qing","family":"Dai","sequence":"additional","affiliation":[{"name":"The Ben May Department for Cancer Research, The University of Chicago, Chicago, Illinois 60637, and The Centers for Cancer Pharmacology and Excellence in Environmental Toxicology, University of Pennsylvania School of Medicine, Philadelphia, Pennsylvania 19104"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qian","family":"Ruan","sequence":"additional","affiliation":[{"name":"The Ben May Department for Cancer Research, The University of Chicago, Chicago, Illinois 60637, and The Centers for Cancer Pharmacology and Excellence in Environmental Toxicology, University of Pennsylvania School of Medicine, Philadelphia, Pennsylvania 19104"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Trevor M.","family":"Penning","sequence":"additional","affiliation":[{"name":"The Ben May Department for Cancer Research, The University of Chicago, Chicago, Illinois 60637, and The Centers for Cancer Pharmacology and Excellence in Environmental Toxicology, University of Pennsylvania School of Medicine, Philadelphia, Pennsylvania 19104"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ian A.","family":"Blair","sequence":"additional","affiliation":[{"name":"The Ben May Department for Cancer Research, The University of Chicago, Chicago, Illinois 60637, and The Centers for Cancer Pharmacology and Excellence in Environmental Toxicology, University of Pennsylvania School of Medicine, Philadelphia, Pennsylvania 19104"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ronald G.","family":"Harvey","sequence":"additional","affiliation":[{"name":"The Ben May Department for Cancer Research, The University of Chicago, Chicago, Illinois 60637, and The Centers for Cancer Pharmacology and Excellence in Environmental Toxicology, University of Pennsylvania School of Medicine, Philadelphia, Pennsylvania 19104"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2008,1,9]]},"reference":[{"key":"jo701667ub00001\/jo701667ub00001_1","volume-title":"Chemical, Environmental and Experimental Data","volume":"32","author":"International Agency for Research on Cancer.","year":"1983"},{"key":"jo701667ub00002\/jo701667ub00002_1","volume-title":"Polycyclic Aromatic Hydrocarbons:\u2009 Chemistry and Carcinogenicity","author":"Harvey R. G.","year":"1991"},{"key":"jo701667ub00003\/jo701667ub00003_1","first-page":"46","volume-title":"Chemical Carcinogens","volume":"1","author":"Dipple A.","year":"1984","edition":"2"},{"key":"jo701667ub00004\/jo701667ub00004_1","first-page":"932","volume":"6","author":"Straif K.","year":"2005","journal-title":"Nat. Oncol."},{"key":"jo701667ub00005\/jo701667ub00005_1","doi-asserted-by":"crossref","first-page":"878","DOI":"10.1093\/carcin\/14.5.875","volume":"14","author":"Higginbotham S.","year":"1993","journal-title":"Carcinogenesis"},{"key":"jo701667ub00005\/jo701667ub00005_2","doi-asserted-by":"crossref","first-page":"1944","DOI":"10.1093\/carcin\/12.10.1939","volume":"12","author":"Cavalieri E. L.","year":"1991","journal-title":"Carcinogenesis"},{"key":"jo701667ub00006\/jo701667ub00006_1","volume-title":"Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Tobacco Smoke and Involuntary Smoking","volume":"83","author":"International Agency for Research on Cancer.","year":"2004"},{"key":"jo701667ub00007\/jo701667ub00007_1","doi-asserted-by":"crossref","first-page":"771","DOI":"10.1080\/10406630490472527","volume":"24","author":"Seidel A.","year":"2004","journal-title":"Polycyclic Aromat. Compd."},{"key":"jo701667ub00008\/jo701667ub00008_1","first-page":"7451","volume":"21","author":"Pfiefer G. P.","year":"2002","journal-title":"Oncogene"},{"key":"jo701667ub00009\/jo701667ub00009_1","unstructured":"World Health Organization.Tobacco or Health:\u2009 A Global StatusReport; WHO:\u2009 Geneva 1997; pp 10\u221248."},{"key":"jo701667ub00010\/jo701667ub00010_1","first-page":"4917","volume":"42","author":"Conney A. H.","year":"1982","journal-title":"Cancer Res."},{"key":"jo701667ub00011\/jo701667ub00011_1","doi-asserted-by":"crossref","first-page":"350","DOI":"10.1038\/269348a0","volume":"269","author":"Jeffrey A. M.","year":"1977","journal-title":"Nature (London)"},{"key":"jo701667ub00012\/jo701667ub00012_1","volume-title":"DNA Adducts:\u2009 Identification and Biological Significance","author":"Dipple","year":"1994"},{"key":"jo701667ub00013\/jo701667ub00013_1","doi-asserted-by":"crossref","first-page":"6191","DOI":"10.1016\/S0021-9258(19)84546-5","volume":"261","author":"Smithgall T. E.","year":"1986","journal-title":"J. Biol. Chem."},{"key":"jo701667ub00014\/jo701667ub00014_1","doi-asserted-by":"crossref","first-page":"92","DOI":"10.1021\/tx950055s","volume":"9","author":"Penning T. M.","year":"1996","journal-title":"Chem. Res. Toxicol."},{"key":"jo701667ub00015\/jo701667ub00015_1","doi-asserted-by":"crossref","first-page":"482","DOI":"10.1093\/carcin\/14.3.475","volume":"14","author":"Shou M.","year":"1993","journal-title":"Carcinogenesis"},{"key":"jo701667ub00015\/jo701667ub00015_2","doi-asserted-by":"crossref","first-page":"246","DOI":"10.1021\/tx980182z","volume":"12","author":"McCoull K. D.","year":"1999","journal-title":"Chem. Res. Toxicol."},{"key":"jo701667ub00015\/jo701667ub00015_3","doi-asserted-by":"crossref","first-page":"18","DOI":"10.1021\/tx980143n","volume":"12","author":"Penning T. M.","year":"1999","journal-title":"Chem. Res. Toxicol."},{"key":"jo701667ub00017\/jo701667ub00017_1","doi-asserted-by":"crossref","first-page":"160","DOI":"10.1021\/tx9902082","volume":"13","author":"Bolton J. I.","year":"2000","journal-title":"J. Chem. Res. Toxicol."},{"key":"jo701667ub00018\/jo701667ub00018_1","doi-asserted-by":"crossref","first-page":"677","DOI":"10.3109\/00498259509061885","volume":"25","author":"Cavalieri E. L.","year":"1995","journal-title":"Xenobiotica"},{"key":"jo701667ub00019\/jo701667ub00019_1","doi-asserted-by":"crossref","first-page":"6377","DOI":"10.1002\/anie.200460782","volume":"43","author":"Gunda P.","year":"2004","journal-title":"Angew. Chem. Int. Ed."},{"key":"jo701667ub00020\/jo701667ub00020_1","first-page":"1001","volume":"5","author":"Dai Q.","year":"2005","journal-title":"Org. Lett."},{"key":"jo701667ub00021\/jo701667ub00021_1","first-page":"2032","volume":"69","author":"Harvey R. G.","year":"2004","journal-title":"J. Org. Chem."},{"key":"jo701667ub00022\/jo701667ub00022_1","doi-asserted-by":"crossref","first-page":"2260","DOI":"10.1073\/pnas.58.6.2253","volume":"58","author":"Huggins C. B.","year":"1967","journal-title":"Proc. Natl. Acad. Sci. U.S.A."},{"key":"jo701667ub00023\/jo701667ub00023_1","doi-asserted-by":"crossref","first-page":"222","DOI":"10.1007\/BF00809595","volume":"119","author":"Husu B.","year":"1988","journal-title":"Monatsh. Chem."},{"key":"jo701667ub00024\/jo701667ub00024_1","doi-asserted-by":"crossref","first-page":"669","DOI":"10.1021\/jo020625a","volume":"68","author":"Francom P.","year":"2003","journal-title":"J. Org. Chem."},{"key":"jo701667ub00024\/jo701667ub00024_2","doi-asserted-by":"crossref","first-page":"7195","DOI":"10.1021\/jo050847j","volume":"70","author":"Pottabathini N.","year":"2005","journal-title":"J. Org. Chem."},{"key":"jo701667ub00025\/jo701667ub00025_1","first-page":"2067","volume":"37","author":"Hartwig J. F.","year":"1998","journal-title":"Angew. Chem., Int. Ed."},{"key":"jo701667ub00025\/jo701667ub00025_2","doi-asserted-by":"crossref","first-page":"7195","DOI":"10.1021\/jo0513764","volume":"70","author":"Lakshman M. K.","year":"2005","journal-title":"J. Org. Chem."},{"key":"jo701667ub00025\/jo701667ub00025_3","doi-asserted-by":"crossref","first-page":"7284","DOI":"10.1016\/S0040-4039(00)01196-5","volume":"41","author":"Bonala R. R.","year":"2000","journal-title":"Tetrahedron Lett."},{"key":"jo701667ub00025\/jo701667ub00025_4","doi-asserted-by":"crossref","first-page":"6091","DOI":"10.1021\/ja9908671","volume":"121","author":"Lakshman M. K.","year":"1999","journal-title":"J. Am. Chem. Soc."},{"key":"jo701667ub00025\/jo701667ub00025_5","doi-asserted-by":"crossref","first-page":"6030","DOI":"10.1021\/jo030113b","volume":"68","author":"Lakshman M. K.","year":"2003","journal-title":"J. Org. Chem."},{"key":"jo701667ub00025\/jo701667ub00025_6","doi-asserted-by":"crossref","first-page":"1494","DOI":"10.1021\/tx0256174","volume":"15","author":"Johnson F.","year":"2002","journal-title":"Chem. Res. Toxicol."},{"key":"jo701667ub00026\/jo701667ub00026_1","doi-asserted-by":"crossref","first-page":"5045","DOI":"10.1021\/jo070204z","volume":"72","author":"Champeil E.","year":"2007","journal-title":"J. Org. Chem. Soc."},{"key":"jo701667ub00027\/jo701667ub00027_1","first-page":"62","volume-title":"Polycyclic Hydrocarbons and Carcinogenesis","author":"Glusker J.","year":"1985"},{"key":"jo701667ub00028\/jo701667ub00028_1","volume-title":"Polycyclic Aromatic Hydrocarbons","author":"Harvey R. G.","year":"1997"},{"key":"jo701667ub00029\/jo701667ub00029_1","doi-asserted-by":"crossref","first-page":"1145","DOI":"10.1021\/ja00838a031","volume":"97","author":"Cho H.","year":"1975","journal-title":"J. Am. Chem. Soc."},{"key":"jo701667ub00030\/jo701667ub00030_1","first-page":"347","volume":"339","author":"Wood J. L.","year":"1979","journal-title":"J. Chem.-Biol. Interact."},{"key":"jo701667ub00031\/jo701667ub00031_1","doi-asserted-by":"crossref","first-page":"4196","DOI":"10.1021\/jo00415a045","volume":"43","author":"Felix A. M.","year":"1978","journal-title":"J. Org. Chem."},{"key":"jo701667ub00032\/jo701667ub00032_1","first-page":"2964","volume":"72","author":"Harwood E. A.","year":"2000","journal-title":"J. Org. Chem."},{"key":"jo701667ub00033\/jo701667ub00033_1","doi-asserted-by":"crossref","first-page":"1341","DOI":"10.1021\/tx700107z","volume":"20","author":"Jiang H.","year":"2007","journal-title":"Chem. Res. Toxicol."},{"key":"jo701667ub00034\/jo701667ub00034_1","doi-asserted-by":"crossref","first-page":"431","DOI":"10.1021\/tx060180b","volume":"20","author":"Ruan Q.","year":"2007","journal-title":"Chem. Res. Toxicol."},{"key":"jo701667ub00035\/jo701667ub00035_1","doi-asserted-by":"crossref","first-page":"1380","DOI":"10.1002\/rcm.2457","volume":"20","author":"Ruan Q.","year":"2006","journal-title":"Rapid Commun. Mass Spectrom."},{"key":"jo701667ub00036\/jo701667ub00036_1","first-page":"884","volume":"4","author":"Kwong F. Y.","year":"2003","journal-title":"Org. Lett."},{"key":"jo701667ub00037\/jo701667ub00037_1","first-page":"3726","volume":"70","author":"Ran C.","year":"2005","journal-title":"J. Org. Chem."},{"key":"jo701667ub00038\/jo701667ub00038_1","first-page":"1771","volume":"62","author":"Dai C.","year":"2005","journal-title":"Tetrahedron"},{"key":"jo701667ub00039\/jo701667ub00039_1","unstructured":"Benzo[a]pyrene is commonly employed as a standard for PAHs in the environment. It is also implicated as a cancer-causative agents in tobacco smoke.6-9"},{"key":"jo701667ub00040\/jo701667ub00040_1","first-page":"311","volume":"21","author":"Dibenzo","year":"1987","journal-title":"Environ. Sci. Technol."},{"key":"jo701667ub00041\/jo701667ub00041_1","first-page":"2737","volume":"20","author":"Masuda Y.","year":"1972","journal-title":"Chem. Pharm. Bull."},{"key":"jo701667ub00041\/jo701667ub00041_2","doi-asserted-by":"crossref","first-page":"43","DOI":"10.1007\/BF00593423","volume":"55","author":"Lacassagne A.","year":"1968","journal-title":"Naturwissenschaften"},{"key":"jo701667ub00043\/jo701667ub00043_1","first-page":"3914","volume":"3910","author":"Although","year":"1980","journal-title":"Cancer Res."}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jo701667u","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,5]],"date-time":"2023-03-05T19:22:56Z","timestamp":1678044176000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/jo701667u"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2008,1,9]]},"references-count":51,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2008,2,1]]}},"alternative-id":["10.1021\/jo701667u"],"URL":"https:\/\/doi.org\/10.1021\/jo701667u","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2008,1,9]]}}}