{"id":"https://openalex.org/W2016239673","doi":"https://doi.org/10.1093/carcin/8.2.209","title":"Covalent binding of estrogen metabolites to hamster liver microsomal proteins: inhibition by ascorbic acid and catechol-O-methyl transferase","display_name":"Covalent binding of estrogen metabolites to hamster liver microsomal proteins: inhibition by ascorbic acid and catechol-O-methyl transferase","publication_year":1987,"publication_date":"1987-01-01","ids":{"openalex":"https://openalex.org/W2016239673","doi":"https://doi.org/10.1093/carcin/8.2.209","mag":"2016239673","pmid":"https://pubmed.ncbi.nlm.nih.gov/3802402"},"language":"en","primary_location":{"id":"doi:10.1093/carcin/8.2.209","doi":"https://doi.org/10.1093/carcin/8.2.209","is_oa":false,"landing_page_url":"https://doi.org/10.1093/carcin/8.2.209","pdf_url":null,"source":{"id":"https://openalex.org/S184620562","display_name":"Carcinogenesis","issn_l":"0143-3334","issn":["0143-3334","1460-2180"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-c","jufo-1","ki-jl-1","medline","norway-1","poland-140","russia-white-list-1"],"host_organization":"https://openalex.org/P4310311648","host_organization_name":"Oxford University Press","host_organization_lineage":["https://openalex.org/P4310311648","https://openalex.org/P4310311647"],"host_organization_lineage_names":["Oxford University Press","University of Oxford"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Carcinogenesis","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","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/A5078543866","display_name":"Heidemarie Haaf","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I130238516","display_name":"University of Minnesota","ror":"https://ror.org/017zqws13","country_code":"US","type":"education","lineage":["https://openalex.org/I130238516"]},{"id":"https://openalex.org/I4210140408","display_name":"Minneapolis VA Medical Center","ror":"https://ror.org/032b8d361","country_code":"US","type":"healthcare","lineage":["https://openalex.org/I1322918889","https://openalex.org/I2799886695","https://openalex.org/I4210117246","https://openalex.org/I4210117924","https://openalex.org/I4210140408"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Heidemarie Haaf","raw_affiliation_strings":["Medical Research Laboratories, V.A. Medical Center, and Department of Urological Surgery, University of Minnesota Medical School Minneapolis, MN 55417, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Medical Research Laboratories, V.A. Medical Center, and Department of Urological Surgery, University of Minnesota Medical School Minneapolis, MN 55417, USA","institution_ids":["https://openalex.org/I130238516","https://openalex.org/I4210140408"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5081062639","display_name":"Sara Antonia Li","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I130238516","display_name":"University of Minnesota","ror":"https://ror.org/017zqws13","country_code":"US","type":"education","lineage":["https://openalex.org/I130238516"]},{"id":"https://openalex.org/I4210140408","display_name":"Minneapolis VA Medical Center","ror":"https://ror.org/032b8d361","country_code":"US","type":"healthcare","lineage":["https://openalex.org/I1322918889","https://openalex.org/I2799886695","https://openalex.org/I4210117246","https://openalex.org/I4210117924","https://openalex.org/I4210140408"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Sara Antonia Li","raw_affiliation_strings":["Medical Research Laboratories, V.A. Medical Center, and Department of Urological Surgery, University of Minnesota Medical School Minneapolis, MN 55417, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Medical Research Laboratories, V.A. Medical Center, and Department of Urological Surgery, University of Minnesota Medical School Minneapolis, MN 55417, USA","institution_ids":["https://openalex.org/I130238516","https://openalex.org/I4210140408"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5113666712","display_name":"Jonathan J. Li","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I130238516","display_name":"University of Minnesota","ror":"https://ror.org/017zqws13","country_code":"US","type":"education","lineage":["https://openalex.org/I130238516"]},{"id":"https://openalex.org/I4210140408","display_name":"Minneapolis VA Medical Center","ror":"https://ror.org/032b8d361","country_code":"US","type":"healthcare","lineage":["https://openalex.org/I1322918889","https://openalex.org/I2799886695","https://openalex.org/I4210117246","https://openalex.org/I4210117924","https://openalex.org/I4210140408"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Jonathan J. Li","raw_affiliation_strings":["Medical Research Laboratories, V.A. Medical Center, and Department of Urological Surgery, University of Minnesota Medical SchoolMinneapolis, MN 55417, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Medical Research Laboratories, V.A. Medical Center, and Department of Urological Surgery, University of Minnesota Medical SchoolMinneapolis, MN 55417, USA","institution_ids":["https://openalex.org/I130238516","https://openalex.org/I4210140408"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":4835,"currency":"USD","value_usd":4835},"apc_paid":null,"fwci":0.921,"has_fulltext":false,"cited_by_count":25,"citation_normalized_percentile":{"value":0.74612517,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":94},"biblio":{"volume":"8","issue":"2","first_page":"209","last_page":"215"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10756","display_name":"Estrogen and related hormone effects","score":0.5820000171661377,"subfield":{"id":"https://openalex.org/subfields/1311","display_name":"Genetics"},"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/T10756","display_name":"Estrogen and related hormone effects","score":0.5820000171661377,"subfield":{"id":"https://openalex.org/subfields/1311","display_name":"Genetics"},"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/T10375","display_name":"Pharmacogenetics and Drug Metabolism","score":0.3366999924182892,"subfield":{"id":"https://openalex.org/subfields/3004","display_name":"Pharmacology"},"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/T11908","display_name":"Protein Interaction Studies and Fluorescence Analysis","score":0.05490000173449516,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"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"}}],"keywords":[{"id":"https://openalex.org/keywords/estrogen-metabolites","display_name":"estrogen metabolites","score":0.6899999976158142},{"id":"https://openalex.org/keywords/covalent-attachment","display_name":"covalent binding","score":0.9440000057220459},{"id":"https://openalex.org/keywords/liver-microsomal-proteins","display_name":"liver microsomal proteins","score":0.8100000023841858},{"id":"https://openalex.org/keywords/vitamin-c","display_name":"vitamin C","score":0.9309999942779541},{"id":"https://openalex.org/keywords/s-adenosylmethionine","display_name":"S-adenosylmethionine","score":0.847000002861023},{"id":"https://openalex.org/keywords/nadph","display_name":"NADPH","score":0.5929999947547913},{"id":"https://openalex.org/keywords/steroidal-estrogens","display_name":"steroidal estrogens","score":0.8489999771118164},{"id":"https://openalex.org/keywords/diethylstilbestrol","display_name":"diethylstilbestrol","score":0.8069999814033508}],"concepts":[{"id":"https://openalex.org/C87644729","wikidata":"https://www.wikidata.org/wiki/Q547502","display_name":"Microsome","level":3,"score":0.8451031446456909},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.6392780542373657},{"id":"https://openalex.org/C2781397067","wikidata":"https://www.wikidata.org/wiki/Q423989","display_name":"Diethylstilbestrol","level":3,"score":0.6299893856048584},{"id":"https://openalex.org/C2986274086","wikidata":"https://www.wikidata.org/wiki/Q199678","display_name":"Ascorbic acid","level":2,"score":0.6247707605361938},{"id":"https://openalex.org/C2777335581","wikidata":"https://www.wikidata.org/wiki/Q409721","display_name":"Estriol","level":3,"score":0.5206345915794373},{"id":"https://openalex.org/C2778575167","wikidata":"https://www.wikidata.org/wiki/Q6573","display_name":"Hamster","level":2,"score":0.5164063572883606},{"id":"https://openalex.org/C62231903","wikidata":"https://www.wikidata.org/wiki/Q1057","display_name":"Metabolism","level":2,"score":0.4770490527153015},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.46934592723846436},{"id":"https://openalex.org/C126322002","wikidata":"https://www.wikidata.org/wiki/Q11180","display_name":"Internal medicine","level":1,"score":0.4627106189727783},{"id":"https://openalex.org/C2777164284","wikidata":"https://www.wikidata.org/wiki/Q277954","display_name":"Estrogen","level":2,"score":0.449873149394989},{"id":"https://openalex.org/C134018914","wikidata":"https://www.wikidata.org/wiki/Q162606","display_name":"Endocrinology","level":1,"score":0.43240344524383545},{"id":"https://openalex.org/C2776524530","wikidata":"https://www.wikidata.org/wiki/Q4119721","display_name":"Microsoma","level":4,"score":0.42130813002586365},{"id":"https://openalex.org/C71315377","wikidata":"https://www.wikidata.org/wiki/Q11364","display_name":"Hormone","level":2,"score":0.29122060537338257},{"id":"https://openalex.org/C181199279","wikidata":"https://www.wikidata.org/wiki/Q8047","display_name":"Enzyme","level":2,"score":0.23392269015312195},{"id":"https://openalex.org/C86803240","wikidata":"https://www.wikidata.org/wiki/Q420","display_name":"Biology","level":0,"score":0.23334038257598877},{"id":"https://openalex.org/C31903555","wikidata":"https://www.wikidata.org/wiki/Q1637030","display_name":"Food science","level":1,"score":0.0},{"id":"https://openalex.org/C71924100","wikidata":"https://www.wikidata.org/wiki/Q11190","display_name":"Medicine","level":0,"score":0.0}],"mesh":[{"descriptor_ui":"D000818","descriptor_name":"Animals","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D001205","descriptor_name":"Ascorbic Acid","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":true},{"descriptor_ui":"D002394","descriptor_name":"Catechol O-Methyltransferase","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D002396","descriptor_name":"Catechols","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D004054","descriptor_name":"Diethylstilbestrol","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D004958","descriptor_name":"Estradiol","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D004967","descriptor_name":"Estrogens","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D006224","descriptor_name":"Cricetinae","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D007668","descriptor_name":"Kidney","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D008862","descriptor_name":"Microsomes, Liver","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D009249","descriptor_name":"NADP","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D010084","descriptor_name":"Oxidation-Reduction","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D011485","descriptor_name":"Protein Binding","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D013267","descriptor_name":"Stilbenes","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D013329","descriptor_name":"Structure-Activity Relationship","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1093/carcin/8.2.209","doi":"https://doi.org/10.1093/carcin/8.2.209","is_oa":false,"landing_page_url":"https://doi.org/10.1093/carcin/8.2.209","pdf_url":null,"source":{"id":"https://openalex.org/S184620562","display_name":"Carcinogenesis","issn_l":"0143-3334","issn":["0143-3334","1460-2180"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-c","jufo-1","ki-jl-1","medline","norway-1","poland-140","russia-white-list-1"],"host_organization":"https://openalex.org/P4310311648","host_organization_name":"Oxford University Press","host_organization_lineage":["https://openalex.org/P4310311648","https://openalex.org/P4310311647"],"host_organization_lineage_names":["Oxford University Press","University of Oxford"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Carcinogenesis","raw_type":"journal-article"},{"id":"pmid:3802402","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/3802402","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":"Carcinogenesis","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[{"id":"https://metadata.un.org/sdg/3","score":0.6240000128746033,"display_name":"Good health and well-being"}],"sustainable_development_goals_aurora":[{"id":"https://metadata.un.org/sdg/6","score":0.4099999964237213,"display_name":"Clean water and sanitation"}],"study_designs":[],"awards":[{"id":"https://openalex.org/G2151373064","display_name":null,"funder_award_id":"22008","funder_id":"https://openalex.org/F4320332505","funder_display_name":"U.S. Public Health Service"},{"id":"https://openalex.org/G8969176385","display_name":null,"funder_award_id":"41387","funder_id":"https://openalex.org/F4320332505","funder_display_name":"U.S. Public Health Service"}],"funders":[{"id":"https://openalex.org/F4320332505","display_name":"U.S. Public Health Service","ror":"https://ror.org/05xf94514"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":0,"referenced_works":[],"related_works":["https://openalex.org/W2018124505","https://openalex.org/W2047389924","https://openalex.org/W1608518618","https://openalex.org/W2021256385","https://openalex.org/W2045693925","https://openalex.org/W2412908931","https://openalex.org/W2414567946","https://openalex.org/W2046520700","https://openalex.org/W2092024825","https://openalex.org/W152404513"],"abstract_inverted_index":{"We":[0],"have":[1],"studied":[2,151],"the":[3,59,66,94,108,148,153,176,221,235,256,272,278,286,326,330,341],"irreversible":[4,51,75],"binding":[5,18,76,95,111,156,294,343],"of":[6,14,19,61,68,83,112,147,178,220,274,295],"[14C]estradiol":[7],"to":[8,22,63,96,106,134,161,182,189,238,259,276,335],"hamster":[9,331],"liver":[10,33,159,208,240],"and":[11,35,87,115,144,180,197,214,247,269,298],"kidney":[12,23,323,332],"microsomes":[13,24],"castrated":[15],"hamsters.":[16],"The":[17,74],"estradiol":[20,166,206,213,231,313],"metabolites":[21,290],"was":[25,36,77,173],"approximately":[26],"25":[27],"times":[28],"lower":[29],"than":[30,131,165,218],"seen":[31],"for":[32,142,265,292,311,319,329],"microsomes,":[34],"not":[37,322],"affected":[38],"by":[39,81],"increases":[40],"in":[41,54,98,175,203,308],"protein":[42],"or":[43],"substrate":[44,264,318],"concentration.":[45],"Our":[46],"results":[47],"indicate":[48],"that":[49,124,194,285],"this":[50,72],"binding,":[52],"covalent":[53,110,293,342],"nature,":[55],"is":[56,315,338],"dependent":[57],"on":[58],"metabolism":[60,273],"estrogens":[62,117,150,188,300,337],"catechols":[64,305],"since":[65],"absence":[67],"NADPH":[69],"markedly":[70],"reduces":[71],"binding.":[73],"inhibited":[78,93,271],"nearly":[79],"70%":[80],"addition":[82],"catechol-O-methyl":[84],"transferase":[85],"(COMT)":[86],"S-adenosylmethionine":[88],"(SAM).":[89],"Ascorbic":[90],"acid":[91],"also":[92],"85%":[97],"a":[99,103,162,263,316],"dose-dependent":[100],"manner.":[101],"Utilizing":[102],"displacement":[104],"assay":[105],"assess":[107],"relative":[109],"different":[113],"stilbene":[114,149,297],"steroidal":[116,187,299],"with":[118,333,340],"homologous":[119],"radiolabeled":[120,205],"hormones,":[121],"we":[122,192,254],"found":[123,255],"only":[125],"indenestrol":[126],"B":[127],"exhibited":[128,233],"greater":[129,163,217],"ability":[130,177,237],"diethylstilbestrol":[132],"(DES)":[133],"displace":[135,183,190],"[14C]DES":[136],"from":[137,157,207,304],"hepatic":[138],"microsomal":[139,209,241,324],"proteins.":[140,210],"Except":[141,310],"hydroxypropiophenone":[143],"beta-dienestrol,":[145],"all":[146],"displaced":[152,216],"radioactive":[154,222],"DES":[155],"these":[158,336],"proteins":[160,242],"extent":[164],"at":[167,224],"comparable":[168],"concentrations.":[169,227],"A":[170],"marked":[171],"difference":[172],"observed":[174,193],"alpha-":[179],"beta-dienestrol":[181],"[14C]DES.":[184],"Using":[185],"radioinert":[186],"[14C]estradiol,":[191],"both":[195,296],"estriol":[196],"deoxoestrone":[198],"were":[199,249],"significantly":[200],"less":[201],"effective":[202],"displacing":[204],"Only":[211],"ethinyl":[212,312],"2-hydroxyestradiol":[215],"50%":[219],"hormone":[223],"1-fold":[225],"excess":[226],"Interestingly,":[228],"11":[229],"beta-methoxyethinyl":[230],"(Moxestrol)":[232],"essentially":[234],"same":[236],"bind":[239],"as":[243,251,262],"estradiol.":[244],"When":[245],"estrone":[246,275],"2,4-dibromoestradiol":[248],"used":[250],"substrates":[252],"together,":[253],"latter":[257],"compound":[258],"be":[260],"inactive":[261],"estrogen":[266,289],"hydroxylase":[267],"(ESH)":[268],"additionally":[270],"form":[277],"catechol":[279],"metabolite.":[280],"Data":[281],"presented":[282],"herein":[283],"suggest":[284],"chemically":[287],"reactive":[288],"responsible":[291],"are":[301],"quinoids":[302],"derived":[303],"formed":[306],"earlier":[307],"metabolism.":[309],"which":[314],"good":[317],"liver,":[320],"but":[321],"ESH,":[325],"carcinogenicity":[327],"data":[328,344],"respect":[334],"consistent":[339],"presented.":[345]},"counts_by_year":[{"year":2023,"cited_by_count":1},{"year":2020,"cited_by_count":1},{"year":2018,"cited_by_count":1},{"year":2016,"cited_by_count":1},{"year":2015,"cited_by_count":1},{"year":2012,"cited_by_count":1}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}
