{"@context":{"@vocab":"https://cir.nii.ac.jp/schema/1.0/","rdfs":"http://www.w3.org/2000/01/rdf-schema#","dc":"http://purl.org/dc/elements/1.1/","dcterms":"http://purl.org/dc/terms/","foaf":"http://xmlns.com/foaf/0.1/","prism":"http://prismstandard.org/namespaces/basic/2.0/","cinii":"http://ci.nii.ac.jp/ns/1.0/","datacite":"https://schema.datacite.org/meta/kernel-4/","ndl":"http://ndl.go.jp/dcndl/terms/","jpcoar":"https://github.com/JPCOAR/schema/blob/master/2.0/"},"@id":"https://cir.nii.ac.jp/crid/1360580229808601728.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1016/j.bcp.2022.115243"}},{"identifier":{"@type":"URI","@value":"https://api.elsevier.com/content/article/PII:S0006295222003379?httpAccept=text/xml"}},{"identifier":{"@type":"URI","@value":"https://api.elsevier.com/content/article/PII:S0006295222003379?httpAccept=text/plain"}},{"identifier":{"@type":"PMID","@value":"36084709"}}],"resourceType":"学術雑誌論文(journal article)","dc:title":[{"@value":"Sulfation of 12-hydroxy-nevirapine by human SULTs and the effects of genetic polymorphisms of SULT1A1 and SULT2A1"}],"description":[{"notation":[{"@value":"Nevirapine (NVP) is an effective drug for the treatment of HIV infections, but its use is limited by a high incidence of severe skin rash and liver injury. 12-Hydroxynevirapine (12-OH-NVP) is the major metabolite of nevirapine. There is strong evidence that the sulfate of 12-OH-NVP is responsible for the skin rash. While several cytosolic sulfotransferases (SULTs) have been shown to be capable of sulfating 12-OH-NVP, the exact mechanism of sulfation in vivo is unclear. The current study aimed to clarify human SULT(s) and human organs that are capable of sulfating 12-OH-NVP and investigate the metabolic sulfation of 12-OH-NVP using cultured HepG2 human hepatoma cells. Enzymatic assays revealed that of the thirteen human SULTs, SULT1A1 and SULT2A1 displayed strong 12-OH-NVP-sulfating activity. 1-Phenyl-1-hexanol (PHHX), which applied topically prevents the skin rash in rats, inhibited 12-OH-NVP sulfation by SULT1A1 and SULT2A1, implying the involvement of these two enzymes in the sulfation of 12-OH-NVP in vivo. Among five human organ cytosols analyzed, liver cytosol displayed the strongest 12-OH-NVP-sulfating activity, while a low but significant activity was detected with skin cytosol. Cultured HepG2 cells were shown to be capable of sulfating 12-OH-NVP. The effects of genetic polymorphisms of SULT1A1 and SULT2A1 genes on the sulfation of 12-OH-NVP by SULT1A1 and SULT2A1 allozymes were investigated. Two SULT1A1 allozymes, Arg37Asp and Met223Val, showed no detectable 12-OH-NVP-sulfating activity, while a SULT2A1 allozyme, Met57Thr, displayed significantly higher 12-OH-NVP-sulfating activity compared with the wild-type enzyme. Collectively, these results contribute to a better understanding of the involvement of sulfation in NVP-induced skin rash and provide clues to the possible role of SULT genetic polymorphisms in the risk of this adverse reaction."}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1420282801206524928","@type":"Researcher","personIdentifier":[{"@type":"KAKEN_RESEARCHERS","@value":"20647036"},{"@type":"NRID","@value":"1000020647036"},{"@type":"ORCID","@value":"0000-0001-5405-693X"},{"@type":"NRID","@value":"9000017331216"},{"@type":"NRID","@value":"9000410514710"},{"@type":"NRID","@value":"9000361682740"},{"@type":"NRID","@value":"9000014587059"},{"@type":"NRID","@value":"9000415172546"},{"@type":"NRID","@value":"9000403273824"},{"@type":"NRID","@value":"9000410515414"},{"@type":"NRID","@value":"9000398611420"},{"@type":"NRID","@value":"9000326649409"},{"@type":"NRID","@value":"9000345392005"},{"@type":"NRID","@value":"9000347093295"},{"@type":"NRID","@value":"9000313190442"},{"@type":"NRID","@value":"9000379560117"},{"@type":"NRID","@value":"9000021423283"},{"@type":"NRID","@value":"9000384339923"},{"@type":"NRID","@value":"9000308731485"},{"@type":"NRID","@value":"9000399221465"},{"@type":"NRID","@value":"9000345255795"},{"@type":"NRID","@value":"9000345272232"},{"@type":"NRID","@value":"9000367045255"},{"@type":"NRID","@value":"9000408597167"},{"@type":"NRID","@value":"9000398607545"},{"@type":"RESEARCHMAP","@value":"https://researchmap.jp/7000027302"}],"foaf:name":[{"@value":"Katsuhisa Kurogi"}]},{"@id":"https://cir.nii.ac.jp/crid/1380580229808601861","@type":"Researcher","foaf:name":[{"@value":"Yanshan Cao"}]},{"@id":"https://cir.nii.ac.jp/crid/1380580229808601742","@type":"Researcher","foaf:name":[{"@value":"Koshi Segawa"}]},{"@id":"https://cir.nii.ac.jp/crid/1380580229808601856","@type":"Researcher","foaf:name":[{"@value":"Yoichi Sakakibara"}]},{"@id":"https://cir.nii.ac.jp/crid/1380580229808601729","@type":"Researcher","foaf:name":[{"@value":"Masahito Suiko"}]},{"@id":"https://cir.nii.ac.jp/crid/1380580229808601874","@type":"Researcher","foaf:name":[{"@value":"Jack Uetrecht"}]},{"@id":"https://cir.nii.ac.jp/crid/1380580229808601623","@type":"Researcher","foaf:name":[{"@value":"Ming-Cheh Liu"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"00062952"}],"prism:publicationName":[{"@value":"Biochemical Pharmacology"}],"dc:publisher":[{"@value":"Elsevier BV"}],"prism:publicationDate":"2022-10","prism:volume":"204","prism:startingPage":"115243"},"reviewed":"false","dc:rights":["https://www.elsevier.com/tdm/userlicense/1.0/","https://www.elsevier.com/legal/tdmrep-license","https://doi.org/10.15223/policy-017","https://doi.org/10.15223/policy-037","https://doi.org/10.15223/policy-012","https://doi.org/10.15223/policy-029","https://doi.org/10.15223/policy-004"],"url":[{"@id":"https://api.elsevier.com/content/article/PII:S0006295222003379?httpAccept=text/xml"},{"@id":"https://api.elsevier.com/content/article/PII:S0006295222003379?httpAccept=text/plain"}],"createdAt":"2022-09-06","modifiedAt":"2025-09-13","foaf:topic":[{"@id":"https://cir.nii.ac.jp/all?q=Polymorphism,%20Genetic","dc:title":"Polymorphism, Genetic"},{"@id":"https://cir.nii.ac.jp/all?q=Sulfates","dc:title":"Sulfates"},{"@id":"https://cir.nii.ac.jp/all?q=HIV%20Infections","dc:title":"HIV Infections"},{"@id":"https://cir.nii.ac.jp/all?q=Exanthema","dc:title":"Exanthema"},{"@id":"https://cir.nii.ac.jp/all?q=Arylsulfotransferase","dc:title":"Arylsulfotransferase"},{"@id":"https://cir.nii.ac.jp/all?q=Rats","dc:title":"Rats"},{"@id":"https://cir.nii.ac.jp/all?q=Isoenzymes","dc:title":"Isoenzymes"},{"@id":"https://cir.nii.ac.jp/all?q=Cytosol","dc:title":"Cytosol"},{"@id":"https://cir.nii.ac.jp/all?q=Animals","dc:title":"Animals"},{"@id":"https://cir.nii.ac.jp/all?q=Humans","dc:title":"Humans"},{"@id":"https://cir.nii.ac.jp/all?q=Nevirapine","dc:title":"Nevirapine"},{"@id":"https://cir.nii.ac.jp/all?q=Sulfotransferases","dc:title":"Sulfotransferases"}],"project":[{"@id":"https://cir.nii.ac.jp/crid/1040581301854690816","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"23K21173"},{"@type":"JGN","@value":"JP23K21173"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-23K21173/"}],"notation":[{"@language":"ja","@value":"酸化ストレス防御機構としてのα,β-不飽和カルボニル硫酸化の機能解明"},{"@language":"en","@value":"Functional elucidation of a,b-unsaturated carbonyl sulfation as a defense mechanism against oxidative stress"}]}],"relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1050866603021971968","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"A new type of sulfation reaction: C-sulfonation for α,β-unsaturated carbonyl groups by a novel sulfotransferase SULT7A1"},{"@value":"A new type of sulfation reaction: <i>C</i>-sulfonation for α,β-unsaturated carbonyl groups by a novel sulfotransferase SULT7A1"}]},{"@id":"https://cir.nii.ac.jp/crid/1360004234172774528","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Updated perspectives on the cytosolic sulfotransferases (SULTs) and SULT-mediated sulfation"}]},{"@id":"https://cir.nii.ac.jp/crid/1360004236112900224","@type":"Article","resourceType":"学術雑誌論文(journal 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sulfation"}]},{"@id":"https://cir.nii.ac.jp/crid/1364233270175841152","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"The identity of alcohol sulfotransferases with hydroxysteroid sulfotransferases"}]},{"@id":"https://cir.nii.ac.jp/crid/1370580229808601613","@type":"Product","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"α-Hydroxytamoxifen is a substrate of hydroxysteroid (alcohol) sulfotransferase, resulting in tamoxifen DNA adducts"}]},{"@id":"https://cir.nii.ac.jp/crid/1390001204633647744","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Ethanol Sulfation by the Human Cytosolic Sulfotransferases: A Systematic Analysis"}]},{"@id":"https://cir.nii.ac.jp/crid/1390001205179657856","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Tissue-Specific mRNA Expression Profiles of Human Phase I Metabolizing Enzymes Except for Cytochrome P450 and Phase II Metabolizing Enzymes"},{"@value":"Tissue-specific mRNA expression profiles of human phase I metabolizing enzymes except for cytochrome P450 and phase II etabolizing enzymes"}]},{"@id":"https://cir.nii.ac.jp/crid/1390282681450574080","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@language":"en","@value":"cDNA Cloning, Expression, and Characterization of the Human Bifunctional ATP Sulfurylase/Adenosine 5'-Phosphosulfate Kinase Enzyme."},{"@value":"cDNA Cloning,Expression,and Characterization of the Human Bifunctional ATP Sulfurylase/Adenosine 5′-Phosphosulfate Kinase Enzyme"},{"@language":"ja-Kana","@value":"cDNA CloningExpressionand Characterizat"},{"@value":"cDNA cloning, expression, and characterization of the human bifunctional ATP sulfurylase/adenosine 5ʹ-phosphosulfate kinase 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