Cited 42 times in
Coordination modes vs. antitumor activity: synthesis and antitumor activity of novel platinum(II) complexes of N-substituted amino dicarboxylic acids
DC Field | Value | Language |
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dc.contributor.author | 정현철 | - |
dc.date.accessioned | 2020-09-04T02:05:19Z | - |
dc.date.available | 2020-09-04T02:05:19Z | - |
dc.date.issued | 2004-01 | - |
dc.identifier.issn | 0162-0134 | - |
dc.identifier.uri | https://ir.ymlib.yonsei.ac.kr/handle/22282913/178795 | - |
dc.description.abstract | The trans-(+/-)-1,2-diaminocyclohexaneplatinum(II) complexes of multidentate L-glutamate (Glu) and L-aspartate (Asp) were prepared and their antitumor activity was examined in relation with their coordination modes. All these complexes were obtained as a mixture of (O,O')- and (O,N)-chelate isomers due to rapid isomerization of the initially formed (O,O')-isomer to the thermodynamically more stable (O,N)-isomer. The (O,O')/(O,N)-isomeric mixture with the mole ratio of 80/20 exhibited excellent antitumor activity while the pure (O,N)-isomer was only marginally active. Therefore, in order to prevent the linkage isomerization of the active (O,O')-isomer to the inactive (O,N)-isomer, we have designed N-substituted amino dicarboxylic acids as a leaving group and prepared a new series of complexes, [Pt(dach)(RGlu)] and [Pt(dach)(RAsp)] (dach=trans-(+/-)-1,2-diaminocyclohexane; R=acetyl (Ac), propionyl (Pro), pivaloyl (Piv), carbobenzyloxy (Cbz) or phthaloyl (Phth)) and characterized by means of elemental analyses, and 1H NMR, 195Pt NMR and IR spectroscopies. The N-substituted amino dicarboxylate ligands were found to coordinate to platinum(II) ion through only the (O,O')-chelation mode, and their Pt(II) complexes were chemically stable in aqueous solution. The present Pt(II) complexes of N-substituted amino dicarboxylic acids showed excellent antitumor activity against both murine leukemia L1210 and human tumor cells. Especially, the highly hydrophobic N-phthaloylglutamate complex, [Pt(dach)(PhthGlu)], exhibited an outstanding in vitro activity (IC50=2.22 microM) on the human stomach cancer cells which are not responsive to cisplatin and carboplatin. | - |
dc.description.statementOfResponsibility | restriction | - |
dc.language | English | - |
dc.publisher | Elsevier | - |
dc.relation.isPartOf | JOURNAL OF INORGANIC BIOCHEMISTRY | - |
dc.rights | CC BY-NC-ND 2.0 KR | - |
dc.subject.MESH | Amino Acids, Dicarboxylic / chemical synthesis | - |
dc.subject.MESH | Amino Acids, Dicarboxylic / chemistry* | - |
dc.subject.MESH | Amino Acids, Dicarboxylic / pharmacology* | - |
dc.subject.MESH | Animals | - |
dc.subject.MESH | Antineoplastic Agents / chemical synthesis | - |
dc.subject.MESH | Antineoplastic Agents / chemistry* | - |
dc.subject.MESH | Antineoplastic Agents / pharmacology* | - |
dc.subject.MESH | Cell Line, Tumor | - |
dc.subject.MESH | Drug Screening Assays, Antitumor | - |
dc.subject.MESH | Humans | - |
dc.subject.MESH | Hydrophobic and Hydrophilic Interactions | - |
dc.subject.MESH | Inhibitory Concentration 50 | - |
dc.subject.MESH | Isomerism | - |
dc.subject.MESH | Leukemia L1210 / drug therapy | - |
dc.subject.MESH | Organoplatinum Compounds / chemical synthesis | - |
dc.subject.MESH | Organoplatinum Compounds / chemistry* | - |
dc.subject.MESH | Organoplatinum Compounds / pharmacology* | - |
dc.title | Coordination modes vs. antitumor activity: synthesis and antitumor activity of novel platinum(II) complexes of N-substituted amino dicarboxylic acids | - |
dc.type | Article | - |
dc.contributor.college | College of Medicine (의과대학) | - |
dc.contributor.department | Dept. of Internal Medicine (내과학교실) | - |
dc.contributor.googleauthor | Yeong-Sang Kim | - |
dc.contributor.googleauthor | Rita Song | - |
dc.contributor.googleauthor | Hyun Cheol Chung | - |
dc.contributor.googleauthor | Moo Jin Jun | - |
dc.contributor.googleauthor | Youn Soo Sohn | - |
dc.identifier.doi | 10.1016/j.jinorgbio.2003.09.004 | - |
dc.contributor.localId | A03773 | - |
dc.relation.journalcode | J01459 | - |
dc.identifier.eissn | 1873-3344 | - |
dc.identifier.pmid | 14659638 | - |
dc.identifier.url | https://www.sciencedirect.com/science/article/pii/S0162013403003763?via%3Dihub#! | - |
dc.contributor.alternativeName | Chung, Hyun Cheol | - |
dc.contributor.affiliatedAuthor | 정현철 | - |
dc.citation.volume | 98 | - |
dc.citation.number | 1 | - |
dc.citation.startPage | 98 | - |
dc.citation.endPage | 104 | - |
dc.identifier.bibliographicCitation | JOURNAL OF INORGANIC BIOCHEMISTRY, Vol.98(1) : 98-104, 2004-01 | - |
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