{"id":"https://openalex.org/W2104309844","doi":null,"title":"Further characterization of the DNA adducts formed by electrophilic esters of the hepatocarcinogens 1'-hydroxysafrole and 1'-hydroxyestragole in vitro and in mouse liver in vivo, including new adducts at C-8 and N-7 of guanine residues.","display_name":"Further characterization of the DNA adducts formed by electrophilic esters of the hepatocarcinogens 1'-hydroxysafrole and 1'-hydroxyestragole in vitro and in mouse liver in vivo, including new adducts at C-8 and N-7 of guanine residues.","publication_year":1985,"publication_date":"1985-07-01","ids":{"openalex":"https://openalex.org/W2104309844","mag":"2104309844","pmid":"https://pubmed.ncbi.nlm.nih.gov/4005847"},"language":"en","primary_location":{"id":"pmid:4005847","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/4005847","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Cancer research","raw_type":"Journal Article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["pubmed"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5006462740","display_name":"Roger W. Wiseman","orcid":"https://orcid.org/0000-0002-7682-7085","observed_orcids":["https://orcid.org/0000-0002-7682-7085"]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"R W Wiseman","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5018262531","display_name":"Timothy R. Fennell","orcid":"https://orcid.org/0000-0001-5632-0159","observed_orcids":["https://orcid.org/0000-0001-5632-0159"]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"T R Fennell","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5046704046","display_name":"JAMES ALEXANDER MILLER","orcid":"https://orcid.org/0000-0002-4023-4296","observed_orcids":["https://orcid.org/0000-0002-4023-4296"]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"J A Miller","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"last","author":{"id":"https://openalex.org/A5030586479","display_name":"Elizabeth C. Miller","orcid":"https://orcid.org/0000-0002-1278-9219","observed_orcids":["https://orcid.org/0000-0002-1278-9219"]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"E C Miller","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]}],"institutions":[],"countries_distinct_count":0,"institutions_distinct_count":0,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":null,"apc_paid":null,"fwci":1.7712,"has_fulltext":false,"cited_by_count":79,"citation_normalized_percentile":{"value":0.81408012,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":99},"biblio":{"volume":"45","issue":"7","first_page":"3096","last_page":"105"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10433","display_name":"Carcinogens and Genotoxicity Assessment","score":0.9970999956130981,"subfield":{"id":"https://openalex.org/subfields/1306","display_name":"Cancer Research"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},"topics":[{"id":"https://openalex.org/T10433","display_name":"Carcinogens and Genotoxicity Assessment","score":0.9970999956130981,"subfield":{"id":"https://openalex.org/subfields/1306","display_name":"Cancer Research"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T12356","display_name":"Bioactive Compounds and Antitumor Agents","score":0.0003000000142492354,"subfield":{"id":"https://openalex.org/subfields/3005","display_name":"Toxicology"},"field":{"id":"https://openalex.org/fields/30","display_name":"Pharmacology, Toxicology and Pharmaceutics"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T12756","display_name":"Plant Toxicity and Pharmacological Properties","score":0.00019999999494757503,"subfield":{"id":"https://openalex.org/subfields/3005","display_name":"Toxicology"},"field":{"id":"https://openalex.org/fields/30","display_name":"Pharmacology, Toxicology and Pharmaceutics"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/dna-adducts","display_name":"DNA adducts","score":0.9599999785423279},{"id":"https://openalex.org/keywords/hepatocarcinogens","display_name":"hepatocarcinogens","score":0.9300000071525574},{"id":"https://openalex.org/keywords/deoxyguanosine-adducts","display_name":"deoxyguanosine adducts","score":0.8450000286102295},{"id":"https://openalex.org/keywords/diastereomers","display_name":"diastereomers","score":0.8220000267028809},{"id":"https://openalex.org/keywords/mouse-liver","display_name":"mouse liver","score":0.6439999938011169}],"concepts":[{"id":"https://openalex.org/C2780441211","wikidata":"https://www.wikidata.org/wiki/Q422488","display_name":"Deoxyguanosine","level":3,"score":0.9268465042114258},{"id":"https://openalex.org/C108204754","wikidata":"https://www.wikidata.org/wiki/Q353392","display_name":"Adduct","level":2,"score":0.8535813689231873},{"id":"https://openalex.org/C138716334","wikidata":"https://www.wikidata.org/wiki/Q268477","display_name":"Diastereomer","level":2,"score":0.8375651836395264},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8042879104614258},{"id":"https://openalex.org/C50027330","wikidata":"https://www.wikidata.org/wiki/Q908086","display_name":"Electrophile","level":3,"score":0.5854365825653076},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.5670637488365173},{"id":"https://openalex.org/C207001950","wikidata":"https://www.wikidata.org/wiki/Q141124","display_name":"In vivo","level":2,"score":0.5538738965988159},{"id":"https://openalex.org/C133571119","wikidata":"https://www.wikidata.org/wiki/Q899102","display_name":"Circular dichroism","level":2,"score":0.4937196671962738},{"id":"https://openalex.org/C2780636463","wikidata":"https://www.wikidata.org/wiki/Q422457","display_name":"Deoxyadenosine","level":3,"score":0.47782209515571594},{"id":"https://openalex.org/C66974803","wikidata":"https://www.wikidata.org/wiki/Q10359898","display_name":"Nuclear magnetic resonance spectroscopy","level":2,"score":0.46705639362335205},{"id":"https://openalex.org/C202751555","wikidata":"https://www.wikidata.org/wiki/Q221681","display_name":"In vitro","level":2,"score":0.4214223027229309},{"id":"https://openalex.org/C552990157","wikidata":"https://www.wikidata.org/wiki/Q7430","display_name":"DNA","level":2,"score":0.39953547716140747},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.2144860327243805},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.13383620977401733},{"id":"https://openalex.org/C86803240","wikidata":"https://www.wikidata.org/wiki/Q420","display_name":"Biology","level":0,"score":0.08903199434280396},{"id":"https://openalex.org/C54355233","wikidata":"https://www.wikidata.org/wiki/Q7162","display_name":"Genetics","level":1,"score":0.06660637259483337},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.0}],"mesh":[{"descriptor_ui":"D000818","descriptor_name":"Animals","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D000840","descriptor_name":"Anisoles","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D002273","descriptor_name":"Carcinogens","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D002851","descriptor_name":"Chromatography, High Pressure Liquid","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D004149","descriptor_name":"Dioxoles","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D004247","descriptor_name":"DNA","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D006147","descriptor_name":"Guanine","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D008099","descriptor_name":"Liver","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D008113","descriptor_name":"Liver Neoplasms","qualifier_ui":"Q000139","qualifier_name":"chemically induced","is_major_topic":false},{"descriptor_ui":"D008297","descriptor_name":"Male","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D008809","descriptor_name":"Mice, Inbred C3H","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D008810","descriptor_name":"Mice, Inbred C57BL","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D009682","descriptor_name":"Magnetic Resonance Spectroscopy","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D012451","descriptor_name":"Safrole","qualifier_ui":"Q000031","qualifier_name":"analogs & derivatives","is_major_topic":false},{"descriptor_ui":"D012451","descriptor_name":"Safrole","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D051379","descriptor_name":"Mice","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D066298","descriptor_name":"In Vitro Techniques","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"pmid:4005847","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/4005847","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Cancer research","raw_type":"Journal Article"},{"id":"mag:2104309844","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/4005847","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":null,"is_accepted":false,"is_published":false,"raw_source_name":"PubMed","raw_type":null}],"best_oa_location":null,"sustainable_development_goals":[{"display_name":"Good health and well-being","id":"https://metadata.un.org/sdg/3","score":0.766700029373169}],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":42,"referenced_works":["https://openalex.org/W85996255","https://openalex.org/W1259363667","https://openalex.org/W1489532275","https://openalex.org/W1496485738","https://openalex.org/W1501368690","https://openalex.org/W1516224401","https://openalex.org/W1542868541","https://openalex.org/W1545342976","https://openalex.org/W1554112810","https://openalex.org/W1578468861","https://openalex.org/W1649900618","https://openalex.org/W1824864124","https://openalex.org/W1964752188","https://openalex.org/W1965446350","https://openalex.org/W1970375585","https://openalex.org/W1982167643","https://openalex.org/W1982566674","https://openalex.org/W1982574781","https://openalex.org/W1984367999","https://openalex.org/W1985561532","https://openalex.org/W1993634692","https://openalex.org/W1998986687","https://openalex.org/W2012643983","https://openalex.org/W2012997912","https://openalex.org/W2018869043","https://openalex.org/W2019981881","https://openalex.org/W2028229747","https://openalex.org/W2032736194","https://openalex.org/W2054693456","https://openalex.org/W2071402193","https://openalex.org/W2095619460","https://openalex.org/W2107753038","https://openalex.org/W2107936532","https://openalex.org/W2116390732","https://openalex.org/W2119751348","https://openalex.org/W2121288020","https://openalex.org/W2124767862","https://openalex.org/W2125292738","https://openalex.org/W2148481538","https://openalex.org/W2169136570","https://openalex.org/W2337620995","https://openalex.org/W2801777644"],"related_works":["https://openalex.org/W2169136570","https://openalex.org/W1592187749","https://openalex.org/W2031534611","https://openalex.org/W2148481538","https://openalex.org/W2032723120","https://openalex.org/W3080848322","https://openalex.org/W2108278096","https://openalex.org/W7144170556","https://openalex.org/W6964577007","https://openalex.org/W2412607370"],"abstract_inverted_index":{"The":[0,60,136],"identities":[1],"of":[2,8,31,66,134,168,173,179,236,238,242,258,282,295,306,310],"the":[3,9,28,64,77,101,109,166,223,230,239,301,307],"adducts":[4,61,297],"formed":[5,24,62],"on":[6],"reaction":[7,163],"model":[10],"electrophilic":[11],"and":[12,22,73,80,100,116,148,157,183,191,197,202,212,217,275,288],"carcinogenic":[13],"esters":[14],"1'-acetoxysafrole":[15,46,67],"or":[16,45,68,126],"1'-acetoxyestragole":[17,69],"with":[18,43,50,111],"deoxyguanosine":[19],"in":[20,25,27,206,222,229,300],"vitro":[21],"those":[23],"vivo":[26],"hepatic":[29,240,302],"DNA":[30,241,303],"12-day-old":[32,244],"male":[33,243],"C57BL/6":[34],"X":[35],"C3H/He":[36],"F1":[37],"(hereafter":[38],"called":[39],"B6C3F1)":[40],"mice":[41,246],"treated":[42],"1'-hydroxysafrole":[44],"were":[47,128,142,159,193,204,226,277,298],"investigated":[48],"further":[49],"more":[51],"discriminating":[52],"high-performance":[53],"liquid":[54,234],"chromatography":[55,235],"systems":[56],"than":[57],"previously":[58],"used.":[59],"from":[63,108,161,175,181],"reactions":[65,110],"are":[70,74],"strictly":[71],"analogous":[72,102],"distinguished":[75],"by":[76,88,120,144,268],"prefixes":[78],"S":[79],"E,":[81],"respectively.":[82,199,214,292],"Five":[83],"adducts,":[84,154],"including":[85],"S(E)-II":[86],"identified":[87,119],"Phillips":[89,121,269],"et":[90,122,270],"al.":[91,123,271],"(Cancer":[92],"Res.,":[93],"41:":[94],"176-186,":[95],"2664-2671,":[96],"1981)":[97],"as":[98,124,195,210,272],"N2-(trans-isosafrol-3'-yl)deoxyguanosine":[99],"isoestragole":[103],"derivative,":[104],"have":[105],"been":[106],"characterized":[107,194,205],"each":[112,129,140,162],"ester.":[113],"Adducts":[114,189,200,215,262],"S-I":[115],"E-I,":[117],"tentatively":[118],"N2-(safrol-1'-yl)-":[125],"N2-(estragol-1'-yl)deoxyguanosine,":[127],"resolved":[130],"into":[131],"a":[132,207,251],"pair":[133],"diastereomers.":[135],"proposed":[137],"structures":[138],"for":[139],"diastereomer":[141],"confirmed":[143],"nuclear":[145,185],"magnetic":[146,186],"resonance":[147,187],"circular":[149],"dichroism":[150],"spectroscopy.":[151],"Two":[152],"new":[153],"i.e.,":[155],"S(E)-V":[156],"S(E)-VI,":[158],"isolated":[160],"mixture.":[164],"On":[165],"basis":[167],"their":[169,171,177,184],"pKas,":[170],"loss":[172],"3H":[174,180],"[8-3H]deoxyguanosine,":[176],"retention":[178],"[1',2'-3H]deoxyguanosine,":[182],"spectra,":[188],"S-V":[190],"E-V":[192],"8-(trans-isosafrol-3'-yl)-":[196],"8-(trans-isoestragol-3'-yl)deoxyguanosine,":[198],"S-VI":[201,276],"E-VI":[203],"similar":[208],"manner":[209],"7-(trans-isosafrol-3'-yl)-":[211],"7-(trans-isoestragol-3'-yl)guanine,":[213],"S-III":[216],"E-III,":[218],"minor":[219],"components":[220],"described":[221],"earlier":[224],"studies,":[225],"not":[227],"observed":[228],"present":[231,278],"work.":[232],"High-performance":[233],"hydrolysates":[237],"B6C3F1":[245],"killed":[247],"9":[248],"h":[249],"after":[250,304],"single":[252],"dose":[253,309],"(0.1":[254],"mumol/g":[255],"body":[256],"weight)":[257],"[2',3'-3H]-1'-hydroxysafrole":[259],"showed":[260],"that":[261],"S-Ia,":[263],"S-Ib,":[264],"S-II,":[265],"S-IV":[266],"(identified":[267],"N6-(trans-isosafrol-3'-yl)deoxyadenosine),":[273],"S-V,":[274],"at":[279],"average":[280],"levels":[281,294],"3.5,":[283],"7.0,":[284],"24.4,":[285],"2.9,":[286],"1.2,":[287],"3.6":[289],"pmol/mg":[290],"DNA,":[291],"Similar":[293],"these":[296],"found":[299],"administration":[305],"same":[308],"[2',3'-3H]-1'-acetoxysafrole":[311],"under":[312],"identical":[313],"conditions.":[314]},"counts_by_year":[{"year":2024,"cited_by_count":1},{"year":2023,"cited_by_count":4},{"year":2020,"cited_by_count":4},{"year":2019,"cited_by_count":1},{"year":2018,"cited_by_count":4},{"year":2017,"cited_by_count":6},{"year":2016,"cited_by_count":4},{"year":2014,"cited_by_count":2},{"year":2013,"cited_by_count":4},{"year":2012,"cited_by_count":8}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}