{"@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/1360004233129543936.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1021/acs.jmedchem.7b01468"}},{"identifier":{"@type":"URI","@value":"https://pubs.acs.org/doi/pdf/10.1021/acs.jmedchem.7b01468"}},{"identifier":{"@type":"PMID","@value":"29290115"}}],"resourceType":"学術雑誌論文(journal article)","dc:title":[{"@value":"Lipidated Brartemicin Analogues Are Potent Th1-Stimulating Vaccine Adjuvants"}],"description":[{"notation":[{"@value":"Effective Th1-stimulating vaccine adjuvants typically activate antigen presenting cells (APCs) through pattern recognition receptors (PRRs). Macrophage inducible C-type lectin (Mincle) is a PRR expressed on APCs and has been identified as a target for Th1-stimulating adjuvants. Herein, we report on the synthesis and adjuvanticity of rationally designed brartemicin analogues containing long-chain lipids and demonstrate that they are potent Mincle agonists that activate APCs to produce inflammatory cytokines in a Mincle-dependent fashion. Mincle binding, however, does not directly correlate to a functional immune response. Mutation studies indicated that the aromatic residue of lead compound 9a has an important interaction with Mincle Arg183. In vivo assessment of 9a highlighted the capability of this analogue to augment the Th1 response to a model vaccine antigen. Taken together, our results show that lipophilic brartemicin analogues are potent Mincle agonists and that 9a has superior in vivo adjuvant activity compared to TDB."}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1380004233129543939","@type":"Researcher","foaf:name":[{"@value":"Amy J. Foster"}],"jpcoar:affiliationName":[{"@value":"School of Chemical and Physical Sciences, Victoria University of Wellington, P.O. Box 600, Wellington 6140, New Zealand"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004233129543943","@type":"Researcher","foaf:name":[{"@value":"Masahiro Nagata"}],"jpcoar:affiliationName":[{"@value":"Department of Molecular Immunology, Research\rInstitute for Microbial Diseases, Osaka University, Suita 565-0871, Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004233129543941","@type":"Researcher","foaf:name":[{"@value":"Xiuyuan Lu"}],"jpcoar:affiliationName":[{"@value":"Department of Molecular Immunology, Research\rInstitute for Microbial Diseases, Osaka University, Suita 565-0871, Japan"},{"@value":"Division of Molecular\rImmunology, Medical Institute of Bioregulation, Kyushu University, Fukuoka 812-8582, Japan"},{"@value":"Laboratory\rof Molecular Immunology, Immunology Frontier Research Center, Osaka University, Suita 565-0871, Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004233129543938","@type":"Researcher","foaf:name":[{"@value":"Amy T. Lynch"}],"jpcoar:affiliationName":[{"@value":"School of Chemical and Physical Sciences, Victoria University of Wellington, P.O. Box 600, Wellington 6140, New Zealand"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004233129543942","@type":"Researcher","foaf:name":[{"@value":"Zakaria Omahdi"}],"jpcoar:affiliationName":[{"@value":"Department of Molecular Immunology, Research\rInstitute for Microbial Diseases, Osaka University, Suita 565-0871, Japan"},{"@value":"Division of Molecular\rImmunology, Medical Institute of Bioregulation, Kyushu University, Fukuoka 812-8582, Japan"},{"@value":"Laboratory\rof Molecular Immunology, Immunology Frontier Research Center, Osaka University, Suita 565-0871, Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004233129543936","@type":"Researcher","foaf:name":[{"@value":"Eri Ishikawa"}],"jpcoar:affiliationName":[{"@value":"Department of Molecular Immunology, Research\rInstitute for Microbial Diseases, Osaka University, Suita 565-0871, Japan"},{"@value":"Laboratory\rof Molecular Immunology, Immunology Frontier Research Center, Osaka University, Suita 565-0871, Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1420845751161626496","@type":"Researcher","personIdentifier":[{"@type":"KAKEN_RESEARCHERS","@value":"40312946"},{"@type":"NRID","@value":"1000040312946"},{"@type":"NRID","@value":"9000010064257"},{"@type":"NRID","@value":"9000260205605"},{"@type":"NRID","@value":"9000414491152"},{"@type":"NRID","@value":"9000413474472"},{"@type":"NRID","@value":"9000014204917"},{"@type":"NRID","@value":"9000014197178"},{"@type":"NRID","@value":"9000412104442"},{"@type":"NRID","@value":"9000402297865"},{"@type":"NRID","@value":"9000410649592"},{"@type":"NRID","@value":"9000010203371"},{"@type":"NRID","@value":"9000303638521"},{"@type":"NRID","@value":"9000309578004"},{"@type":"NRID","@value":"9000405928853"},{"@type":"NRID","@value":"9000001589333"},{"@type":"NRID","@value":"9000398802209"},{"@type":"NRID","@value":"9000009096778"},{"@type":"NRID","@value":"9000411542716"},{"@type":"NRID","@value":"9000378109025"},{"@type":"NRID","@value":"9000398138309"},{"@type":"NRID","@value":"9000408573040"},{"@type":"NRID","@value":"9000003766213"},{"@type":"NRID","@value":"9000367428927"},{"@type":"NRID","@value":"9000375852910"},{"@type":"NRID","@value":"9000016430030"},{"@type":"NRID","@value":"9000252741224"},{"@type":"NRID","@value":"9000386383845"},{"@type":"NRID","@value":"9000412086441"},{"@type":"NRID","@value":"9000259832865"},{"@type":"RESEARCHMAP","@value":"https://researchmap.jp/read0117961"}],"foaf:name":[{"@value":"Sho Yamasaki"}],"jpcoar:affiliationName":[{"@value":"Department of Molecular Immunology, Research\rInstitute for Microbial Diseases, Osaka University, Suita 565-0871, Japan"},{"@value":"Division of Molecular\rImmunology, Medical Institute of Bioregulation, Kyushu University, Fukuoka 812-8582, Japan"},{"@value":"Laboratory\rof Molecular Immunology, Immunology Frontier Research Center, Osaka University, Suita 565-0871, Japan"},{"@value":"Division of Molecular Immunology, Medical Mycology Research Center, Chiba University, Chiba 260-8673, Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004233129543937","@type":"Researcher","foaf:name":[{"@value":"Mattie S. M. Timmer"}],"jpcoar:affiliationName":[{"@value":"School of Chemical and Physical Sciences, Victoria University of Wellington, P.O. Box 600, Wellington 6140, New Zealand"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004233129543940","@type":"Researcher","foaf:name":[{"@value":"Bridget L. Stocker"}],"jpcoar:affiliationName":[{"@value":"School of Chemical and Physical Sciences, Victoria University of Wellington, P.O. Box 600, Wellington 6140, New Zealand"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"00222623"},{"@type":"EISSN","@value":"15204804"}],"prism:publicationName":[{"@value":"Journal of Medicinal Chemistry"}],"dc:publisher":[{"@value":"American Chemical Society (ACS)"}],"prism:publicationDate":"2018-01-18","prism:volume":"61","prism:number":"3","prism:startingPage":"1045","prism:endingPage":"1060"},"reviewed":"false","dcterms:accessRights":"http://purl.org/coar/access_right/c_abf2","url":[{"@id":"https://pubs.acs.org/doi/pdf/10.1021/acs.jmedchem.7b01468"}],"createdAt":"2017-12-30","modifiedAt":"2023-04-14","foaf:topic":[{"@id":"https://cir.nii.ac.jp/all?q=Vaccines","dc:title":"Vaccines"},{"@id":"https://cir.nii.ac.jp/all?q=Protein%20Conformation","dc:title":"Protein Conformation"},{"@id":"https://cir.nii.ac.jp/all?q=Antigen-Presenting%20Cells","dc:title":"Antigen-Presenting Cells"},{"@id":"https://cir.nii.ac.jp/all?q=Trehalose","dc:title":"Trehalose"},{"@id":"https://cir.nii.ac.jp/all?q=Th1%20Cells","dc:title":"Th1 Cells"},{"@id":"https://cir.nii.ac.jp/all?q=Molecular%20Docking%20Simulation","dc:title":"Molecular Docking Simulation"},{"@id":"https://cir.nii.ac.jp/all?q=Mice","dc:title":"Mice"},{"@id":"https://cir.nii.ac.jp/all?q=Adjuvants,%20Immunologic","dc:title":"Adjuvants, Immunologic"},{"@id":"https://cir.nii.ac.jp/all?q=Animals","dc:title":"Animals"},{"@id":"https://cir.nii.ac.jp/all?q=Lectins,%20C-Type","dc:title":"Lectins, C-Type"},{"@id":"https://cir.nii.ac.jp/all?q=Glycolipids","dc:title":"Glycolipids"},{"@id":"https://cir.nii.ac.jp/all?q=Receptors,%20Immunologic","dc:title":"Receptors, Immunologic"}],"project":[{"@id":"https://cir.nii.ac.jp/crid/1040282257256014720","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"26110009"},{"@type":"JGN","@value":"JP26110009"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PLANNED-26110009/"}],"notation":[{"@language":"ja","@value":"細胞死に伴って放出される内因性糖脂質アジュバントの同定"},{"@language":"en","@value":"Identification of endogenous glycolipids that activate immune responses via lectin receptors"}]}],"relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1050018506568522880","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Ligand-Controlled Stereoselective Synthesis and Biological Activity of 2-Exomethylene Pseudo-glycoconjugates: Discovery of Mincle-Selective Ligands"},{"@value":"Ligand‐Controlled Stereoselective Synthesis and Biological Activity of 2‐Exomethylene Pseudo‐glycoconjugates: Discovery of Mincle‐Selective 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Vaccination"}]},{"@id":"https://cir.nii.ac.jp/crid/1362825895146276352","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Cationic liposomes as vaccine adjuvants"}]},{"@id":"https://cir.nii.ac.jp/crid/1362825895622546688","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"The Mincle ligand trehalose dibehenate differentially modulates M1‐like and M2‐like macrophage phenotype and function via Syk signaling"}]},{"@id":"https://cir.nii.ac.jp/crid/1362825895823012480","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Macrophage Inducible C-Type Lectin As a Multifunctional Player in Immunity"}]},{"@id":"https://cir.nii.ac.jp/crid/1362825895905981056","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Mechanism for Recognition of an Unusual Mycobacterial Glycolipid by the Macrophage Receptor Mincle"}]},{"@id":"https://cir.nii.ac.jp/crid/1363107368538214656","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Immunostimulatory DNA Prepriming: A Novel Approach for Prolonged Th1-Biased Immunity"}]},{"@id":"https://cir.nii.ac.jp/crid/1363107369389288448","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Tuberculosis Subunit Vaccination Provides Long-Term Protective Immunity Characterized by Multifunctional CD4 Memory T Cells"}]},{"@id":"https://cir.nii.ac.jp/crid/1363107369839369344","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Vaccine Adjuvants: Putting Innate Immunity to Work"}]},{"@id":"https://cir.nii.ac.jp/crid/1363107371201197568","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Direct recognition of the mycobacterial glycolipid, trehalose dimycolate, by C-type lectin 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