{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,16]],"date-time":"2026-04-16T22:15:49Z","timestamp":1776377749392,"version":"3.51.2"},"reference-count":60,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2021,12,2]],"date-time":"2021-12-02T00:00:00Z","timestamp":1638403200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000054","name":"National Cancer Institute","doi-asserted-by":"publisher","award":["R01 CA-100670"],"award-info":[{"award-number":["R01 CA-100670"]}],"id":[{"id":"10.13039\/100000054","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2022,1,13]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Metabolic activation of the human carcinogen 1,3\u2010butadiene (BD) by cytochrome 450 monooxygenases gives rise to a genotoxic diepoxide, 1,2,3,4\u2010diepoxybutane (DEB). This reactive electrophile alkylates guanine bases in DNA to produce N7\u2010(2\u2010hydroxy\u20103,4\u2010epoxy\u20101\u2010yl)\u2010dG (N7\u2010DE\u2010dG) adducts. Because of the positive charge at the N7 position of the purine heterocycle, N7\u2010DEB\u2010dG adducts are inherently unstable and can undergo spontaneous depurination or base\u2010catalyzed imidazole ring opening to give <jats:italic>N<\/jats:italic><jats:sup><jats:italic>6<\/jats:italic><\/jats:sup>\u2010[2\u2010deoxy\u2010D\u2010<jats:italic>erythro<\/jats:italic>\u2010pentofuranosyl]\u20102,6\u2010diamino\u20103,4\u2010dihydro\u20104\u2010oxo\u20105\u2010<jats:italic>N<\/jats:italic>\u20101\u2010(oxiran\u20102\u2010yl)propan\u20101\u2010ol\u2010formamidopyrimidine (DEB\u2010FAPy\u2010dG) adducts. Here we report the first synthesis and structural characterization of DEB\u2010FAPy\u2010dG adducts. Authentic standards of DEB\u2010FAPy\u2010dG and its <jats:sup>15<\/jats:sup>N<jats:sub>3<\/jats:sub>\u2010labeled analogue were used for the development of a quantitative nanoLC\u2010ESI<jats:sup>+<\/jats:sup>\u2010HRMS\/MS method, allowing for adduct detection in DEB\u2010treated calf thymus DNA. DEB\u2010FAPy\u2010dG formation in DNA was dependent on DEB concentration and pH, with higher numbers observed under alkaline conditions.<\/jats:p>","DOI":"10.1002\/chem.202103245","type":"journal-article","created":{"date-parts":[[2021,11,12]],"date-time":"2021-11-12T11:38:25Z","timestamp":1636717105000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["DEB\u2010FAPy\u2010dG Adducts of 1,3\u2010Butadiene: Synthesis, Structural Characterization, and Formation in 1,2,3,4\u2010Diepoxybutane Treated DNA**"],"prefix":"10.1002","volume":"28","author":[{"given":"Suresh S.","family":"Pujari","sequence":"first","affiliation":[{"name":"Department of Medicinal Chemistry College of Pharmacy Cancer and Cardiovascular Research Building University of Minnesota  2231 6th Street SE Minneapolis MN 55455 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Caitlin C.","family":"Jokipii Krueger","sequence":"additional","affiliation":[{"name":"Department of Medicinal Chemistry College of Pharmacy Cancer and Cardiovascular Research Building University of Minnesota  2231 6th Street SE Minneapolis MN 55455 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Christopher","family":"Chao","sequence":"additional","affiliation":[{"name":"Department of Medicinal Chemistry College of Pharmacy Cancer and Cardiovascular Research Building University of Minnesota  2231 6th Street SE Minneapolis MN 55455 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Spencer","family":"Hutchins","sequence":"additional","affiliation":[{"name":"Department of Medicinal Chemistry College of Pharmacy Cancer and Cardiovascular Research Building University of Minnesota  2231 6th Street SE Minneapolis MN 55455 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alexander K.","family":"Hurben","sequence":"additional","affiliation":[{"name":"Department of Medicinal Chemistry College of Pharmacy Cancer and Cardiovascular Research Building University of Minnesota  2231 6th Street SE Minneapolis MN 55455 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gunnar","family":"Boysen","sequence":"additional","affiliation":[{"name":"Department of Environmental and Occupational Health and the Winthrop P Rockefeller Cancer Institute University of Arkansas for Medical Sciences  4301 West Markham St., Slot 820 Little Rock AR 72205 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0621-6860","authenticated-orcid":false,"given":"Natalia","family":"Tretyakova","sequence":"additional","affiliation":[{"name":"Department of Medicinal Chemistry College of Pharmacy Cancer and Cardiovascular Research Building University of Minnesota  2231 6th Street SE Minneapolis MN 55455 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2021,12,2]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1093\/chromsci\/28.5.230"},{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/B614142K"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbi.2006.10.004"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrc1190"},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.3109\/10408449709037482"},{"key":"e_1_2_2_6_1","unstructured":"\u00a0"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/0300-483X(96)03443-9"},{"key":"e_1_2_2_8_2","first-page":"1","author":"Delzell E.","year":"2006","journal-title":"Res. Rep. Health Eff. Inst."},{"key":"e_1_2_2_9_1","unstructured":"\u00a0"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1006\/abbi.1994.1246"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/0300-483X(96)03423-3"},{"key":"e_1_2_2_12_1","doi-asserted-by":"publisher","DOI":"10.1006\/abbi.1994.1246"},{"key":"e_1_2_2_13_1","unstructured":"\u00a0"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1093\/carcin\/15.4.719"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1093\/carcin\/15.4.713"},{"key":"e_1_2_2_16_1","first-page":"151","author":"Blair I. A.","year":"2000","journal-title":"Res. Rep. Health Eff. Inst."},{"key":"e_1_2_2_17_1","unstructured":"\u00a0"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrestox.5b00166"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1098-2280(2000)35:1<48::AID-EM7>3.0.CO;2-C"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1093\/mutage\/12.2.61"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1383-5742(00)00047-8"},{"key":"e_1_2_2_22_1","unstructured":"\u00a0"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/tx049965c"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/tx900242k"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrestox.8b00123"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrestox.6b00392"},{"key":"e_1_2_2_27_1","unstructured":"\u00a0"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1038\/171737a0"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.mrgentox.2009.05.006"},{"key":"e_1_2_2_30_1","unstructured":"\u00a0"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/20.12.3079"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1016\/0006-291X(83)91185-3"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M200316200"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/tx300113e"},{"key":"e_1_2_2_35_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.mrrev.2003.11.001"},{"key":"e_1_2_2_36_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.102167699"},{"key":"e_1_2_2_37_1","unstructured":"\u00a0"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar2002182"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.freeradbiomed.2008.07.004"},{"key":"e_1_2_2_40_1","unstructured":"\u00a0"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1620932114"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.062053799"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.C200355200"},{"key":"e_1_2_2_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi00771a017"},{"key":"e_1_2_2_45_1","unstructured":"\u00a0"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja063781y"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/tx5002354"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/tx800352a"},{"key":"e_1_2_2_49_1","doi-asserted-by":"publisher","DOI":"10.1016\/0300-483X(96)03423-3"},{"key":"e_1_2_2_50_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrestox.5b00297"},{"key":"e_1_2_2_51_1","unstructured":"\u00a0"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0891-5849(99)00208-7"},{"key":"e_1_2_2_53_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0921-8777(99)00012-9"},{"key":"e_1_2_2_54_2","doi-asserted-by":"publisher","DOI":"10.18388\/abp.1999_4151"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.5483\/BMBRep.2003.36.1.012"},{"key":"e_1_2_2_56_1","unstructured":"\u00a0"},{"key":"e_1_2_2_57_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.87.3.1104"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/mc.2940040206"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1038\/350427a0"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1038\/350429a0"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202103245","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.202103245","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202103245","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T19:36:34Z","timestamp":1760297794000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202103245"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,12,2]]},"references-count":60,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2022,1,13]]}},"alternative-id":["10.1002\/chem.202103245"],"URL":"https:\/\/doi.org\/10.1002\/chem.202103245","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,12,2]]},"assertion":[{"value":"2021-09-07","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-12-02","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202103245"}}