Stereospecific ligands and their complexes. Part VII. Synthesis, characterization and in vitro antitumoral activity of platinum(II) complexes with O,O′-dialkyl esters of ( S,S)-ethylenediamine- N,N′-di-2-(4-methyl)pentanoic acid
Platinum(II) complexes ( 1–4) with bidentate N,N′-ligands, O,O′-dialkyl esters (alkyl = ethyl, n-propyl, n-butyl and n-pentyl), of ( S,S)-ethylenediamine- N,N′-di-2-(4-methyl)pentanoic acid were synthesized and characterized by IR, 1H NMR and 13C NMR spectroscopy and elemental analysis. DFT calculat...
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| Veröffentlicht in: | European journal of medicinal chemistry 2011-09, Vol.46 (9), p.4559-4565 |
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| creator | Vujić, Jelena M. Kaluđerović, Goran N. Milovanović, Marija Zmejkovski, Bojana B. Volarević, Vladislav Živić, Danijela Đurđević, Predrag Arsenijević, Nebojša Trifunović, Srećko R. |
| description | Platinum(II) complexes (
1–4) with bidentate
N,N′-ligands,
O,O′-dialkyl esters (alkyl = ethyl,
n-propyl,
n-butyl and
n-pentyl), of (
S,S)-ethylenediamine-
N,N′-di-2-(4-methyl)pentanoic acid were synthesized and characterized by IR,
1H NMR and
13C NMR spectroscopy and elemental analysis. DFT calculations were performed for the complexes and it was found that only one diastereoisomer could be formed. Cytotoxic activity of complexes
1–4 was determined against chronic lymphocytic leukemia cells (CLL) and compared to the activity of ligand precursors
L1·2HCl–
L4·2HCl and corresponding palladium(II) complexes, [PdCl
2
L] (
L =
L1–
L4). The complexes were found to exhibit significantly higher antitumor activities than cisplatin on CLL cells. Cytotoxic effect of platinum(II) complexes on CLL cells was higher compared to corresponding palladium(II) complexes. In addition the mode of cell death induced by platinum(II) complexes was determined.
Platinum(II) complexes (
1–
4) exhibited higher antitumoral activity than ligand precursors, corresponding palladium(II) complexes and cisplatin on chronic lymphocytic leukemia cells (CLL).
[Display omitted]
► Platinum(II) complexes from this study are more active than corresponding palladium(II) complexes and ligand precursors. ► Platinum(II) complexes expressed higher activity than cisplatin. ► Investigated complexes induced apoptotic mode of cell death on CLL cells. |
| doi_str_mv | 10.1016/j.ejmech.2011.07.034 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_886916201</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0223523411005472</els_id><sourcerecordid>886916201</sourcerecordid><originalsourceid>FETCH-LOGICAL-c391t-b527369875ce93a87958597bfe27ae538c223d1534f03ae41a4b0619a25927ae3</originalsourceid><addsrcrecordid>eNp9kUuOEzEURUsIRIeGHSDkCSKR4sKf-k6QUItPpFYHKcDUclyviIPLVdhOQzFiKayBJbAUZuwC5wM9Y2LL9rn3Pb-bJA8pSSmhxdNtCtsO1CZlhNKUlCnh2a1kQsuiwpzl2e1kQhjjOGc8O0vueb8lhOQFIXeTM0arjBScTJLfqwAOej-A0q1WyOgP0jYexQWFDWiHVN8NBr6AT9Eb6QJ6v1ikaDXa-Oq1nyO1kU6q6KK_yqB7e5Bq-_P7tQ6uj6egw67rnTQoYjrejqhv0WAibXfddLGY3dRAn3XYoOV8-evbD9xoaT6OBoGP7n4vmqLVfDXDEDajAQsR6LQFjK7mV0cBZnia4e4AzAawQdo-_koq3dxP7rTSeHhw2s-Tdy9fvL14jS-XrxYXzy-x4jUNeJ2zkhd1VeYKai6rss6rvC7XLbBSQs4rFYfa0JxnLeESMiqzNSloLVle7wl-njw5-g6u_7SLvYtOewXGSAv9zouqKmpaxNAimR1J5XrvHbRicLqTbhSUiH3GYiuOGYt9xoKUImYcZY9OBXbrDpp_or-hRuDxCZBeSdM6aZX2N1yWs6w81H925CCO41qDE15psCrO1YEKoun1_zv5AyfUy50</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>886916201</pqid></control><display><type>article</type><title>Stereospecific ligands and their complexes. Part VII. Synthesis, characterization and in vitro antitumoral activity of platinum(II) complexes with O,O′-dialkyl esters of ( S,S)-ethylenediamine- N,N′-di-2-(4-methyl)pentanoic acid</title><source>MEDLINE</source><source>Access via ScienceDirect (Elsevier)</source><creator>Vujić, Jelena M. ; Kaluđerović, Goran N. ; Milovanović, Marija ; Zmejkovski, Bojana B. ; Volarević, Vladislav ; Živić, Danijela ; Đurđević, Predrag ; Arsenijević, Nebojša ; Trifunović, Srećko R.</creator><creatorcontrib>Vujić, Jelena M. ; Kaluđerović, Goran N. ; Milovanović, Marija ; Zmejkovski, Bojana B. ; Volarević, Vladislav ; Živić, Danijela ; Đurđević, Predrag ; Arsenijević, Nebojša ; Trifunović, Srećko R.</creatorcontrib><description>Platinum(II) complexes (
1–4) with bidentate
N,N′-ligands,
O,O′-dialkyl esters (alkyl = ethyl,
n-propyl,
n-butyl and
n-pentyl), of (
S,S)-ethylenediamine-
N,N′-di-2-(4-methyl)pentanoic acid were synthesized and characterized by IR,
1H NMR and
13C NMR spectroscopy and elemental analysis. DFT calculations were performed for the complexes and it was found that only one diastereoisomer could be formed. Cytotoxic activity of complexes
1–4 was determined against chronic lymphocytic leukemia cells (CLL) and compared to the activity of ligand precursors
L1·2HCl–
L4·2HCl and corresponding palladium(II) complexes, [PdCl
2
L] (
L =
L1–
L4). The complexes were found to exhibit significantly higher antitumor activities than cisplatin on CLL cells. Cytotoxic effect of platinum(II) complexes on CLL cells was higher compared to corresponding palladium(II) complexes. In addition the mode of cell death induced by platinum(II) complexes was determined.
Platinum(II) complexes (
1–
4) exhibited higher antitumoral activity than ligand precursors, corresponding palladium(II) complexes and cisplatin on chronic lymphocytic leukemia cells (CLL).
[Display omitted]
► Platinum(II) complexes from this study are more active than corresponding palladium(II) complexes and ligand precursors. ► Platinum(II) complexes expressed higher activity than cisplatin. ► Investigated complexes induced apoptotic mode of cell death on CLL cells.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2011.07.034</identifier><identifier>PMID: 21840630</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Kidlington: Elsevier Masson SAS</publisher><subject>Antineoplastic agents ; Antitumoral activity ; Biological and medical sciences ; Chronic lymphocytic leukemia cells ; Edda-type ligands ; Esters ; Ethylenediamines - chemistry ; General aspects ; Humans ; Ligands ; Magnetic Resonance Spectroscopy ; Medical sciences ; Models, Molecular ; Pentanoic Acids - chemistry ; Pharmacology. Drug treatments ; Platinum Compounds - chemical synthesis ; Platinum Compounds - pharmacology ; Platinum(II) complexes ; Quantum Theory ; Spectrophotometry, Infrared ; Stereoisomerism ; Thermodynamics ; Tumor Cells, Cultured</subject><ispartof>European journal of medicinal chemistry, 2011-09, Vol.46 (9), p.4559-4565</ispartof><rights>2011 Elsevier Masson SAS</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Elsevier Masson SAS. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c391t-b527369875ce93a87958597bfe27ae538c223d1534f03ae41a4b0619a25927ae3</citedby><cites>FETCH-LOGICAL-c391t-b527369875ce93a87958597bfe27ae538c223d1534f03ae41a4b0619a25927ae3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ejmech.2011.07.034$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24524701$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21840630$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Vujić, Jelena M.</creatorcontrib><creatorcontrib>Kaluđerović, Goran N.</creatorcontrib><creatorcontrib>Milovanović, Marija</creatorcontrib><creatorcontrib>Zmejkovski, Bojana B.</creatorcontrib><creatorcontrib>Volarević, Vladislav</creatorcontrib><creatorcontrib>Živić, Danijela</creatorcontrib><creatorcontrib>Đurđević, Predrag</creatorcontrib><creatorcontrib>Arsenijević, Nebojša</creatorcontrib><creatorcontrib>Trifunović, Srećko R.</creatorcontrib><title>Stereospecific ligands and their complexes. Part VII. Synthesis, characterization and in vitro antitumoral activity of platinum(II) complexes with O,O′-dialkyl esters of ( S,S)-ethylenediamine- N,N′-di-2-(4-methyl)pentanoic acid</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>Platinum(II) complexes (
1–4) with bidentate
N,N′-ligands,
O,O′-dialkyl esters (alkyl = ethyl,
n-propyl,
n-butyl and
n-pentyl), of (
S,S)-ethylenediamine-
N,N′-di-2-(4-methyl)pentanoic acid were synthesized and characterized by IR,
1H NMR and
13C NMR spectroscopy and elemental analysis. DFT calculations were performed for the complexes and it was found that only one diastereoisomer could be formed. Cytotoxic activity of complexes
1–4 was determined against chronic lymphocytic leukemia cells (CLL) and compared to the activity of ligand precursors
L1·2HCl–
L4·2HCl and corresponding palladium(II) complexes, [PdCl
2
L] (
L =
L1–
L4). The complexes were found to exhibit significantly higher antitumor activities than cisplatin on CLL cells. Cytotoxic effect of platinum(II) complexes on CLL cells was higher compared to corresponding palladium(II) complexes. In addition the mode of cell death induced by platinum(II) complexes was determined.
Platinum(II) complexes (
1–
4) exhibited higher antitumoral activity than ligand precursors, corresponding palladium(II) complexes and cisplatin on chronic lymphocytic leukemia cells (CLL).
[Display omitted]
► Platinum(II) complexes from this study are more active than corresponding palladium(II) complexes and ligand precursors. ► Platinum(II) complexes expressed higher activity than cisplatin. ► Investigated complexes induced apoptotic mode of cell death on CLL cells.</description><subject>Antineoplastic agents</subject><subject>Antitumoral activity</subject><subject>Biological and medical sciences</subject><subject>Chronic lymphocytic leukemia cells</subject><subject>Edda-type ligands</subject><subject>Esters</subject><subject>Ethylenediamines - chemistry</subject><subject>General aspects</subject><subject>Humans</subject><subject>Ligands</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Pentanoic Acids - chemistry</subject><subject>Pharmacology. Drug treatments</subject><subject>Platinum Compounds - chemical synthesis</subject><subject>Platinum Compounds - pharmacology</subject><subject>Platinum(II) complexes</subject><subject>Quantum Theory</subject><subject>Spectrophotometry, Infrared</subject><subject>Stereoisomerism</subject><subject>Thermodynamics</subject><subject>Tumor Cells, Cultured</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kUuOEzEURUsIRIeGHSDkCSKR4sKf-k6QUItPpFYHKcDUclyviIPLVdhOQzFiKayBJbAUZuwC5wM9Y2LL9rn3Pb-bJA8pSSmhxdNtCtsO1CZlhNKUlCnh2a1kQsuiwpzl2e1kQhjjOGc8O0vueb8lhOQFIXeTM0arjBScTJLfqwAOej-A0q1WyOgP0jYexQWFDWiHVN8NBr6AT9Eb6QJ6v1ikaDXa-Oq1nyO1kU6q6KK_yqB7e5Bq-_P7tQ6uj6egw67rnTQoYjrejqhv0WAibXfddLGY3dRAn3XYoOV8-evbD9xoaT6OBoGP7n4vmqLVfDXDEDajAQsR6LQFjK7mV0cBZnia4e4AzAawQdo-_koq3dxP7rTSeHhw2s-Tdy9fvL14jS-XrxYXzy-x4jUNeJ2zkhd1VeYKai6rss6rvC7XLbBSQs4rFYfa0JxnLeESMiqzNSloLVle7wl-njw5-g6u_7SLvYtOewXGSAv9zouqKmpaxNAimR1J5XrvHbRicLqTbhSUiH3GYiuOGYt9xoKUImYcZY9OBXbrDpp_or-hRuDxCZBeSdM6aZX2N1yWs6w81H925CCO41qDE15psCrO1YEKoun1_zv5AyfUy50</recordid><startdate>20110901</startdate><enddate>20110901</enddate><creator>Vujić, Jelena M.</creator><creator>Kaluđerović, Goran N.</creator><creator>Milovanović, Marija</creator><creator>Zmejkovski, Bojana B.</creator><creator>Volarević, Vladislav</creator><creator>Živić, Danijela</creator><creator>Đurđević, Predrag</creator><creator>Arsenijević, Nebojša</creator><creator>Trifunović, Srećko R.</creator><general>Elsevier Masson SAS</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20110901</creationdate><title>Stereospecific ligands and their complexes. Part VII. Synthesis, characterization and in vitro antitumoral activity of platinum(II) complexes with O,O′-dialkyl esters of ( S,S)-ethylenediamine- N,N′-di-2-(4-methyl)pentanoic acid</title><author>Vujić, Jelena M. ; Kaluđerović, Goran N. ; Milovanović, Marija ; Zmejkovski, Bojana B. ; Volarević, Vladislav ; Živić, Danijela ; Đurđević, Predrag ; Arsenijević, Nebojša ; Trifunović, Srećko R.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c391t-b527369875ce93a87958597bfe27ae538c223d1534f03ae41a4b0619a25927ae3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Antineoplastic agents</topic><topic>Antitumoral activity</topic><topic>Biological and medical sciences</topic><topic>Chronic lymphocytic leukemia cells</topic><topic>Edda-type ligands</topic><topic>Esters</topic><topic>Ethylenediamines - chemistry</topic><topic>General aspects</topic><topic>Humans</topic><topic>Ligands</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Models, Molecular</topic><topic>Pentanoic Acids - chemistry</topic><topic>Pharmacology. Drug treatments</topic><topic>Platinum Compounds - chemical synthesis</topic><topic>Platinum Compounds - pharmacology</topic><topic>Platinum(II) complexes</topic><topic>Quantum Theory</topic><topic>Spectrophotometry, Infrared</topic><topic>Stereoisomerism</topic><topic>Thermodynamics</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vujić, Jelena M.</creatorcontrib><creatorcontrib>Kaluđerović, Goran N.</creatorcontrib><creatorcontrib>Milovanović, Marija</creatorcontrib><creatorcontrib>Zmejkovski, Bojana B.</creatorcontrib><creatorcontrib>Volarević, Vladislav</creatorcontrib><creatorcontrib>Živić, Danijela</creatorcontrib><creatorcontrib>Đurđević, Predrag</creatorcontrib><creatorcontrib>Arsenijević, Nebojša</creatorcontrib><creatorcontrib>Trifunović, Srećko R.</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Vujić, Jelena M.</au><au>Kaluđerović, Goran N.</au><au>Milovanović, Marija</au><au>Zmejkovski, Bojana B.</au><au>Volarević, Vladislav</au><au>Živić, Danijela</au><au>Đurđević, Predrag</au><au>Arsenijević, Nebojša</au><au>Trifunović, Srećko R.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereospecific ligands and their complexes. Part VII. Synthesis, characterization and in vitro antitumoral activity of platinum(II) complexes with O,O′-dialkyl esters of ( S,S)-ethylenediamine- N,N′-di-2-(4-methyl)pentanoic acid</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2011-09-01</date><risdate>2011</risdate><volume>46</volume><issue>9</issue><spage>4559</spage><epage>4565</epage><pages>4559-4565</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>Platinum(II) complexes (
1–4) with bidentate
N,N′-ligands,
O,O′-dialkyl esters (alkyl = ethyl,
n-propyl,
n-butyl and
n-pentyl), of (
S,S)-ethylenediamine-
N,N′-di-2-(4-methyl)pentanoic acid were synthesized and characterized by IR,
1H NMR and
13C NMR spectroscopy and elemental analysis. DFT calculations were performed for the complexes and it was found that only one diastereoisomer could be formed. Cytotoxic activity of complexes
1–4 was determined against chronic lymphocytic leukemia cells (CLL) and compared to the activity of ligand precursors
L1·2HCl–
L4·2HCl and corresponding palladium(II) complexes, [PdCl
2
L] (
L =
L1–
L4). The complexes were found to exhibit significantly higher antitumor activities than cisplatin on CLL cells. Cytotoxic effect of platinum(II) complexes on CLL cells was higher compared to corresponding palladium(II) complexes. In addition the mode of cell death induced by platinum(II) complexes was determined.
Platinum(II) complexes (
1–
4) exhibited higher antitumoral activity than ligand precursors, corresponding palladium(II) complexes and cisplatin on chronic lymphocytic leukemia cells (CLL).
[Display omitted]
► Platinum(II) complexes from this study are more active than corresponding palladium(II) complexes and ligand precursors. ► Platinum(II) complexes expressed higher activity than cisplatin. ► Investigated complexes induced apoptotic mode of cell death on CLL cells.</abstract><cop>Kidlington</cop><pub>Elsevier Masson SAS</pub><pmid>21840630</pmid><doi>10.1016/j.ejmech.2011.07.034</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0223-5234 |
| ispartof | European journal of medicinal chemistry, 2011-09, Vol.46 (9), p.4559-4565 |
| issn | 0223-5234 1768-3254 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_886916201 |
| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Antineoplastic agents Antitumoral activity Biological and medical sciences Chronic lymphocytic leukemia cells Edda-type ligands Esters Ethylenediamines - chemistry General aspects Humans Ligands Magnetic Resonance Spectroscopy Medical sciences Models, Molecular Pentanoic Acids - chemistry Pharmacology. Drug treatments Platinum Compounds - chemical synthesis Platinum Compounds - pharmacology Platinum(II) complexes Quantum Theory Spectrophotometry, Infrared Stereoisomerism Thermodynamics Tumor Cells, Cultured |
| title | Stereospecific ligands and their complexes. Part VII. Synthesis, characterization and in vitro antitumoral activity of platinum(II) complexes with O,O′-dialkyl esters of ( S,S)-ethylenediamine- N,N′-di-2-(4-methyl)pentanoic acid |
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