{"@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/1360004230067541376.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1002/cmdc.201200390"}},{"identifier":{"@type":"URI","@value":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fcmdc.201200390"}},{"identifier":{"@type":"URI","@value":"https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/cmdc.201200390"}},{"identifier":{"@type":"PMID","@value":"23086703"}}],"resourceType":"学術雑誌論文(journal article)","dc:title":[{"@value":"Low‐Molecular‐Weight CXCR4 Ligands with Variable Spacers"}],"description":[{"type":"abstract","notation":[{"@value":"<jats:title>Abstract</jats:title><jats:p>Low‐molecular‐weight CXCR4 ligands based on known lead compounds including the 14‐mer peptide T140, the cyclic pentapeptide FC131, peptide mimetics, and dipicolylamine‐containing compounds were designed and synthesized. Three types of aromatic spacers, 1,4‐phenylenedimethanamine, naphthalene‐2,6‐diyldimethanamine, and [1,1′‐biphenyl]‐4,4′‐diyldimethanamine, were used to build four pharmacophore groups. As pharmacophore groups, 2‐pyridylmethyl and 1‐naphthylmethyl are present in all of the compounds, and several aromatic groups and a cationic group from 1‐propylguanidine and 1,1,3,3‐tetramethyl‐2‐propylguanidine were also used. Several compounds showed significant CXCR4 binding affinity, and zinc(II) complexation of bis(pyridin‐2‐ylmethyl)amine moieties resulted in a remarkable increase in CXCR4 binding affinity.</jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1380004230067541123","@type":"Researcher","foaf:name":[{"@value":"Tetsuo Narumi"}]},{"@id":"https://cir.nii.ac.jp/crid/1420570853390836224","@type":"Researcher","personIdentifier":[{"@type":"KAKEN_RESEARCHERS","@value":"70547322"},{"@type":"NRID","@value":"1000070547322"},{"@type":"NRID","@value":"9000264866240"},{"@type":"NRID","@value":"9000018990039"},{"@type":"NRID","@value":"9000391962702"},{"@type":"NRID","@value":"9000261652847"},{"@type":"NRID","@value":"9000391962694"}],"foaf:name":[{"@value":"Haruo Aikawa"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004230067541384","@type":"Researcher","foaf:name":[{"@value":"Tomohiro Tanaka"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004230067541130","@type":"Researcher","foaf:name":[{"@value":"Chie Hashimoto"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004230067541504","@type":"Researcher","foaf:name":[{"@value":"Nami Ohashi"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004230067541381","@type":"Researcher","foaf:name":[{"@value":"Wataru Nomura"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004230067541383","@type":"Researcher","foaf:name":[{"@value":"Takuya Kobayakawa"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004230067541515","@type":"Researcher","foaf:name":[{"@value":"Hikaru Takano"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004230067541256","@type":"Researcher","foaf:name":[{"@value":"Yuki Hirota"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004230067541260","@type":"Researcher","foaf:name":[{"@value":"Tsutomu Murakami"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004230067541257","@type":"Researcher","foaf:name":[{"@value":"Naoki Yamamoto"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004230067541516","@type":"Researcher","foaf:name":[{"@value":"Hirokazu Tamamura"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"18607179"},{"@type":"EISSN","@value":"18607187"}],"prism:publicationName":[{"@value":"ChemMedChem"}],"dc:publisher":[{"@value":"Wiley"}],"prism:publicationDate":"2012-10-19","prism:volume":"8","prism:number":"1","prism:startingPage":"118","prism:endingPage":"124"},"reviewed":"false","dc:rights":["http://onlinelibrary.wiley.com/termsAndConditions#vor"],"url":[{"@id":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fcmdc.201200390"},{"@id":"https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/cmdc.201200390"}],"createdAt":"2012-10-19","modifiedAt":"2025-10-12","foaf:topic":[{"@id":"https://cir.nii.ac.jp/all?q=Receptors,%20CXCR4","dc:title":"Receptors, CXCR4"},{"@id":"https://cir.nii.ac.jp/all?q=Ligands","dc:title":"Ligands"},{"@id":"https://cir.nii.ac.jp/all?q=Peptides,%20Cyclic","dc:title":"Peptides, Cyclic"},{"@id":"https://cir.nii.ac.jp/all?q=Small%20Molecule%20Libraries","dc:title":"Small Molecule Libraries"},{"@id":"https://cir.nii.ac.jp/all?q=Jurkat%20Cells","dc:title":"Jurkat Cells"},{"@id":"https://cir.nii.ac.jp/all?q=Zinc","dc:title":"Zinc"},{"@id":"https://cir.nii.ac.jp/all?q=Coordination%20Complexes","dc:title":"Coordination Complexes"},{"@id":"https://cir.nii.ac.jp/all?q=Humans","dc:title":"Humans"},{"@id":"https://cir.nii.ac.jp/all?q=Peptidomimetics","dc:title":"Peptidomimetics"},{"@id":"https://cir.nii.ac.jp/all?q=Oligopeptides","dc:title":"Oligopeptides"}],"project":[{"@id":"https://cir.nii.ac.jp/crid/1040000782189426560","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"24105507"},{"@type":"JGN","@value":"JP24105507"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PUBLICLY-24105507/"}],"notation":[{"@language":"ja","@value":"複合型高活性アゾリウム塩の創製と不斉合成への応用"}]},{"@id":"https://cir.nii.ac.jp/crid/1040000782191094272","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"24119506"},{"@type":"JGN","@value":"JP24119506"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PUBLICLY-24119506/"}],"notation":[{"@language":"ja","@value":"新規トランスジェニック細胞樹立の基盤技術確立と合成生物学への応用"}]},{"@id":"https://cir.nii.ac.jp/crid/1040000782199742848","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"24390024"},{"@type":"JGN","@value":"JP24390024"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-24390024/"}],"notation":[{"@language":"ja","@value":"ＧＰＣＲの２価型リガンドによるがん組織・転移の早期診断技術の開発"},{"@language":"en","@value":"Development of early diagnostic methods for cancer tissue and metastasis  utilizing bivalent  GPCR ligands"}]},{"@id":"https://cir.nii.ac.jp/crid/1040282257157231488","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"23710251"},{"@type":"JGN","@value":"JP23710251"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-23710251/"}],"notation":[{"@language":"ja","@value":"化学修飾型基質を特異的に取り込むDNAメチル化酵素を用いたメチル基継承機構の研究"},{"@language":"en","@value":"Development of orthogonal combinations of artificial DNA methyltrasferases and their substrates for study of heritable patterns of DNA methylation."}]},{"@id":"https://cir.nii.ac.jp/crid/1040282257198913664","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"24659043"},{"@type":"JGN","@value":"JP24659043"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-24659043/"}],"notation":[{"@language":"ja","@value":"ニ量体化した膜型受容体検出のためのスイッチオン・オフ型プローブの創出"},{"@language":"en","@value":"Development of swich on-off type probes for detection of GPCR dimers"}]},{"@id":"https://cir.nii.ac.jp/crid/1040282257468785408","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"11J05127"},{"@type":"JGN","@value":"JP11J05127"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-11J05127/"}],"notation":[{"@language":"ja","@value":"HIV－1第二受容体CXCR4の細胞外ドメインを再構築した戦略的抗原分子の創製"}]}],"relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1360011144603821568","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Inhibition of T-tropic HIV Strains by Selective Antagonization of the Chemokine Receptor CXCR4"}]},{"@id":"https://cir.nii.ac.jp/crid/1360011145685334912","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Acute versus chronic NMDA receptor blockade and synaptic AMPA receptor delivery"}]},{"@id":"https://cir.nii.ac.jp/crid/1360011146592139520","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Development of a linear type of low molecular weight CXCR4 antagonists based on T140 analogs"}]},{"@id":"https://cir.nii.ac.jp/crid/1360292619014640640","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"The chemokine receptor CXCR4 is essential for vascularization of the gastrointestinal tract"}]},{"@id":"https://cir.nii.ac.jp/crid/1360292620752928128","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"The lymphocyte chemoattractant SDF-1 is a ligand for LESTR/fusin and blocks HIV-1 entry"}]},{"@id":"https://cir.nii.ac.jp/crid/1360565164472699264","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Azamacrocyclic Metal Complexes as CXCR4 Antagonists"}]},{"@id":"https://cir.nii.ac.jp/crid/1360565165787162752","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Pharmacophore-based small molecule CXCR4 ligands"}]},{"@id":"https://cir.nii.ac.jp/crid/1360574093984395776","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Stereoselective Synthesis of [<scp>l</scp>-Arg-<scp>l</scp>/<scp>d</scp>-3-(2-naphthyl)alanine]-Type (<i>E</i>)-Alkene Dipeptide Isosteres and Its Application to the Synthesis and Biological Evaluation of Pseudopeptide Analogues of the CXCR4 Antagonist FC131"}]},{"@id":"https://cir.nii.ac.jp/crid/1360848656945431808","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"CXCR4-derived synthetic peptides inducing anti-HIV-1 antibodies"}]},{"@id":"https://cir.nii.ac.jp/crid/1360848662808985856","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"The successes and failures of HIV drug discovery"}]},{"@id":"https://cir.nii.ac.jp/crid/1360855569393605376","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Highly potent and selective inhibition of human immunodeficiency virus by the bicyclam derivative JM3100"}]},{"@id":"https://cir.nii.ac.jp/crid/1361137044326854784","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Identification of Novel Low Molecular Weight CXCR4 Antagonists by Structural Tuning of Cyclic Tetrapeptide Scaffolds"}]},{"@id":"https://cir.nii.ac.jp/crid/1361137044358721024","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Metal Ion Enhanced Binding of AMD3100 to Asp<sup>262</sup> in the CXCR4 Receptor"}]},{"@id":"https://cir.nii.ac.jp/crid/1361137044916811264","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"The CXC chemokine SDF-1 is the ligand for LESTR/fusin and prevents infection by T-cell-line-adapted HIV-1"}]},{"@id":"https://cir.nii.ac.jp/crid/1361418520720565760","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Defects of B-cell lymphopoiesis and bone-marrow myelopoiesis in mice lacking the CXC chemokine PBSF/SDF-1"}]},{"@id":"https://cir.nii.ac.jp/crid/1361699994063127808","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"A Low-Molecular-Weight Inhibitor against the Chemokine Receptor CXCR4: A Strong Anti-HIV Peptide T140"}]},{"@id":"https://cir.nii.ac.jp/crid/1361699994986994304","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"A highly efficacious lymphocyte chemoattractant, stromal cell-derived factor 1 (SDF-1)"}]},{"@id":"https://cir.nii.ac.jp/crid/1361699996075283328","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"HIV-1 Entry Cofactor: Functional cDNA Cloning of a Seven-Transmembrane, G Protein-Coupled Receptor"}]},{"@id":"https://cir.nii.ac.jp/crid/1361699996206738048","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"CXCR4 Regulates Interneuron Migration in the Developing Neocortex"}]},{"@id":"https://cir.nii.ac.jp/crid/1361981469828315648","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Identification of a New Class of Low Molecular Weight Antagonists against the Chemokine Receptor CXCR4 Having the Dipicolylamine−Zinc(II) Complex Structure"}]},{"@id":"https://cir.nii.ac.jp/crid/1361981470592270720","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Identification of a major co-receptor for primary isolates of HIV-1"}]},{"@id":"https://cir.nii.ac.jp/crid/1361981470637755904","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"A Small Molecule CXCR4 Inhibitor that Blocks T Cell Line–tropic HIV-1 Infection"}]},{"@id":"https://cir.nii.ac.jp/crid/1362262944447143936","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Bivalent Ligands of CXCR4 with Rigid Linkers for Elucidation of the Dimerization State in Cells"}]},{"@id":"https://cir.nii.ac.jp/crid/1362262945976486144","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Dimerization of CXCR4 in living malignant cells: control of cell migration by a synthetic peptide that reduces homologous CXCR4 interactions"}]},{"@id":"https://cir.nii.ac.jp/crid/1362262946307743232","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Involvement of chemokine receptors in breast cancer metastasis"}]},{"@id":"https://cir.nii.ac.jp/crid/1362544418322179456","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Effects of inhibitors of the chemokine receptor CXCR4 on acute lymphoblastic leukemia cells in vitro"}]},{"@id":"https://cir.nii.ac.jp/crid/1362544419969067392","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Development of a Unique Small Molecule Modulator of CXCR4"}]},{"@id":"https://cir.nii.ac.jp/crid/1362825895537623936","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Molecular‐Size Reduction of a Potent CXCR4‐Chemokine Antagonist Using Orthogonal Combination of Conformation‐ and Sequence‐Based Libraries"}]},{"@id":"https://cir.nii.ac.jp/crid/1363107369369148544","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"T140 analogs as CXCR4 antagonists identified as anti‐metastatic agents in the treatment of breast cancer"}]},{"@id":"https://cir.nii.ac.jp/crid/1363107370974248064","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Molecular cloning and structure of a pre-B-cell growth-stimulating factor."}]},{"@id":"https://cir.nii.ac.jp/crid/1363388845361264512","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Pharmacophore identification of a specific CXCR4 inhibitor, T140, leads to development of effective anti-HIV agents with very high selectivity indexes"}]},{"@id":"https://cir.nii.ac.jp/crid/1363388846242430080","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Discovery of Novel Non‐Cyclam Polynitrogenated CXCR4 Coreceptor Inhibitors"}]},{"@id":"https://cir.nii.ac.jp/crid/1363670318659548800","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Distinctive features of “nurselike” cells that differentiate in the context of chronic lymphocytic leukemia"}]},{"@id":"https://cir.nii.ac.jp/crid/1363670319193132032","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Structure-activity relationship study of CXCR4 antagonists bearing the cyclic pentapeptide scaffold: identification of the new pharmacophore"}]},{"@id":"https://cir.nii.ac.jp/crid/1363670320390751616","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Stromal Cell-Derived Factor-1-CXC Chemokine Receptor 4 Interactions Play a Central Role in CD4+ T Cell Accumulation in Rheumatoid Arthritis Synovium"}]},{"@id":"https://cir.nii.ac.jp/crid/1363951794365961088","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Signal Sequence Trap: a Cloning Strategy for Secreted Proteins and Type I Membrane Proteins"}]},{"@id":"https://cir.nii.ac.jp/crid/1363951794470588288","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Identification of a CXCR4 antagonist, a T140 analog, as an anti‐rheumatoid arthritis agent"}]},{"@id":"https://cir.nii.ac.jp/crid/1363951795715234432","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"AMD3465, a monomacrocyclic CXCR4 antagonist and potent HIV entry inhibitor"}]},{"@id":"https://cir.nii.ac.jp/crid/1364233269346184320","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"A duodenally absorbable CXC chemokine receptor 4 antagonist, KRH-1636, exhibits a potent and selective anti-HIV-1 activity"}]},{"@id":"https://cir.nii.ac.jp/crid/1364233270990286976","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Molecular Mechanism of AMD3100 Antagonism in the CXCR4 Receptor"}]}],"dataSourceIdentifier":[{"@type":"CROSSREF","@value":"10.1002/cmdc.201200390"},{"@type":"KAKEN","@value":"PRODUCT-21362131"},{"@type":"KAKEN","@value":"PRODUCT-21368638"},{"@type":"KAKEN","@value":"PRODUCT-14568480"},{"@type":"KAKEN","@value":"PRODUCT-14340600"},{"@type":"KAKEN","@value":"PRODUCT-14781712"},{"@type":"KAKEN","@value":"PRODUCT-14781716"},{"@type":"KAKEN","@value":"PRODUCT-9351979"},{"@type":"OPENAIRE","@value":"doi_dedup___::ea5107af50dbeeab9eaafe29664fca10"},{"@type":"CROSSREF","@value":"10.1016/j.bmc.2013.09.037_references_DOI_9xFS2p6lWrtnmpttb4oYtjYRtGY"}]}