Synthesis, characterization and biological activity of Pt(II) and Pt(IV) complexes with 5-methyl-5(4-pyridyl)-2,4-imidazolidenedione
New platinum(II) and platinum(IV) complexes with 5-methyl-5(4-pyridyl)-2,4-imidazolidenedione and various halogen ions with general formula [PtL 2X 2] and [PtL 2Cl 4], where L is the organic ligand and X is Cl −, Br −, J −, were synthesized. The molecular formulae of all the complexes were confirmed...
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| Veröffentlicht in: | European journal of medicinal chemistry 2008-05, Vol.43 (5), p.958-965 |
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| container_title | European journal of medicinal chemistry |
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| creator | Bakalova, Adriana Varbanov, Hristo Buyukliev, Rossen Momekov, Georgi Ferdinandov, Dilyan Konstantinov, Spiro Ivanov, Darvin |
| description | New platinum(II) and platinum(IV) complexes with 5-methyl-5(4-pyridyl)-2,4-imidazolidenedione and various halogen ions with general formula [PtL
2X
2] and [PtL
2Cl
4], where L is the organic ligand and X is Cl
−, Br
−, J
−, were synthesized. The molecular formulae of all the complexes were confirmed by elemental analysis, IR,
1H,
13C NMR spectral analyses and molar conductivity. The cytotoxic effects of these complexes were examined on some human tumor cell lines. The newly synthesized
cis-[PtL
2Cl
2] exerted cytotoxic activity against SKW-3, MCF-7, EJ, U-266 tumor cell lines, while
cis-[PtL
2Br
2],
trans-[PtL
2I
2] were less active. The higher oxidation state complex
cis-[PtL
2Cl
4] was inactive in all cell lines but in SKW-3 some augmentation of the cytotoxicity was seen after co-administration of ascorbic acid but not when treated in combination with reduced glutathione or
N-acetylcysteine. A DNA-fragmentation analysis revealed that the cytotoxicity of the dichloro analogue, characterized with superior activity compared to the other complexes, is mediated by induction of apoptotic cell death.
Three Pt(II) and one Pt(IV) complexes with 5-methyl-5(4-pyridyl)-2,4-imidazolidenedione and halogen ions were synthesized. Complex
1 showed superior cytotoxicity, as compared to the other complexes and was found to induce apoptosis.
[Display omitted] |
| doi_str_mv | 10.1016/j.ejmech.2007.06.025 |
| format | Article |
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2X
2] and [PtL
2Cl
4], where L is the organic ligand and X is Cl
−, Br
−, J
−, were synthesized. The molecular formulae of all the complexes were confirmed by elemental analysis, IR,
1H,
13C NMR spectral analyses and molar conductivity. The cytotoxic effects of these complexes were examined on some human tumor cell lines. The newly synthesized
cis-[PtL
2Cl
2] exerted cytotoxic activity against SKW-3, MCF-7, EJ, U-266 tumor cell lines, while
cis-[PtL
2Br
2],
trans-[PtL
2I
2] were less active. The higher oxidation state complex
cis-[PtL
2Cl
4] was inactive in all cell lines but in SKW-3 some augmentation of the cytotoxicity was seen after co-administration of ascorbic acid but not when treated in combination with reduced glutathione or
N-acetylcysteine. A DNA-fragmentation analysis revealed that the cytotoxicity of the dichloro analogue, characterized with superior activity compared to the other complexes, is mediated by induction of apoptotic cell death.
Three Pt(II) and one Pt(IV) complexes with 5-methyl-5(4-pyridyl)-2,4-imidazolidenedione and halogen ions were synthesized. Complex
1 showed superior cytotoxicity, as compared to the other complexes and was found to induce apoptosis.
[Display omitted]</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2007.06.025</identifier><identifier>PMID: 17707952</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Oxford: Elsevier Masson SAS</publisher><subject>2,4-Imidazolidenedione ; Adult ; Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Biological and medical sciences ; Cell Line, Tumor ; Chelating Agents - chemical synthesis ; Chelating Agents - chemistry ; Child ; cis/ trans Pt(II) and Pt(IV) complexes ; Cytotoxicity ; Drug Screening Assays, Antitumor ; Female ; General aspects ; Humans ; Imidazolines - chemical synthesis ; Imidazolines - chemistry ; Imidazolines - pharmacology ; Male ; Medical sciences ; Middle Aged ; Pharmacology. Drug treatments ; Platinum ; Pyridines - chemical synthesis ; Pyridines - chemistry ; Pyridines - pharmacology ; Structure-Activity Relationship</subject><ispartof>European journal of medicinal chemistry, 2008-05, Vol.43 (5), p.958-965</ispartof><rights>2007 Elsevier Masson SAS</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c390t-f1374a6f613ab35c8ab5ceda0f97037a7b736a1db8bc78ea613d01bc8fbeb35f3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ejmech.2007.06.025$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27923,27924,45994</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20375050$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17707952$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bakalova, Adriana</creatorcontrib><creatorcontrib>Varbanov, Hristo</creatorcontrib><creatorcontrib>Buyukliev, Rossen</creatorcontrib><creatorcontrib>Momekov, Georgi</creatorcontrib><creatorcontrib>Ferdinandov, Dilyan</creatorcontrib><creatorcontrib>Konstantinov, Spiro</creatorcontrib><creatorcontrib>Ivanov, Darvin</creatorcontrib><title>Synthesis, characterization and biological activity of Pt(II) and Pt(IV) complexes with 5-methyl-5(4-pyridyl)-2,4-imidazolidenedione</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>New platinum(II) and platinum(IV) complexes with 5-methyl-5(4-pyridyl)-2,4-imidazolidenedione and various halogen ions with general formula [PtL
2X
2] and [PtL
2Cl
4], where L is the organic ligand and X is Cl
−, Br
−, J
−, were synthesized. The molecular formulae of all the complexes were confirmed by elemental analysis, IR,
1H,
13C NMR spectral analyses and molar conductivity. The cytotoxic effects of these complexes were examined on some human tumor cell lines. The newly synthesized
cis-[PtL
2Cl
2] exerted cytotoxic activity against SKW-3, MCF-7, EJ, U-266 tumor cell lines, while
cis-[PtL
2Br
2],
trans-[PtL
2I
2] were less active. The higher oxidation state complex
cis-[PtL
2Cl
4] was inactive in all cell lines but in SKW-3 some augmentation of the cytotoxicity was seen after co-administration of ascorbic acid but not when treated in combination with reduced glutathione or
N-acetylcysteine. A DNA-fragmentation analysis revealed that the cytotoxicity of the dichloro analogue, characterized with superior activity compared to the other complexes, is mediated by induction of apoptotic cell death.
Three Pt(II) and one Pt(IV) complexes with 5-methyl-5(4-pyridyl)-2,4-imidazolidenedione and halogen ions were synthesized. Complex
1 showed superior cytotoxicity, as compared to the other complexes and was found to induce apoptosis.
[Display omitted]</description><subject>2,4-Imidazolidenedione</subject><subject>Adult</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor</subject><subject>Chelating Agents - chemical synthesis</subject><subject>Chelating Agents - chemistry</subject><subject>Child</subject><subject>cis/ trans Pt(II) and Pt(IV) complexes</subject><subject>Cytotoxicity</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Female</subject><subject>General aspects</subject><subject>Humans</subject><subject>Imidazolines - chemical synthesis</subject><subject>Imidazolines - chemistry</subject><subject>Imidazolines - pharmacology</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Middle Aged</subject><subject>Pharmacology. Drug treatments</subject><subject>Platinum</subject><subject>Pyridines - chemical synthesis</subject><subject>Pyridines - chemistry</subject><subject>Pyridines - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kEuLFDEQgIMo7rj6D0T6ouzApq0knaT7Isji6sCCgo9rSKer7Qz9GJOe1d6zP3wzzqA3T1VQX70-Qp4zyBkw9Xqb43ZA1-UcQOegcuDyAVkxrUoquCwekhVwLqjkojgjT2LcAoBUAI_JGdMadCX5ivz-vIxzh9HHy8x1Nlg3Y_B3dvbTmNmxyWo_9dN372yfpZq_9fOSTW32ab7YbNZ_iEP6bZ25adj1-Atj9tPPXSbpgHO39FReFHS3BN8s_Zryy4L6wTf2bup9gyM2aQ8-JY9a20d8dorn5Ov1uy9XH-jNx_ebq7c31IkKZtoyoQurWsWErYV0pa2lw8ZCW2kQ2upaC2VZU5e10yXaxDXAale2NSa-Fefk1XHuLkw_9hhnM_josO_tiNM-GlWxSijOElgcQRemGAO2Zhf8YMNiGJiDfbM1R_vmYN-AMsl-antxmr-vB2z-NZ10J-DlCbAxGW2DHZ2PfzmevpAgIXFvjhwmG7ceg4nO45ie9QHdbJrJ__-Se-PdpZ0</recordid><startdate>20080501</startdate><enddate>20080501</enddate><creator>Bakalova, Adriana</creator><creator>Varbanov, Hristo</creator><creator>Buyukliev, Rossen</creator><creator>Momekov, Georgi</creator><creator>Ferdinandov, Dilyan</creator><creator>Konstantinov, Spiro</creator><creator>Ivanov, Darvin</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>20080501</creationdate><title>Synthesis, characterization and biological activity of Pt(II) and Pt(IV) complexes with 5-methyl-5(4-pyridyl)-2,4-imidazolidenedione</title><author>Bakalova, Adriana ; Varbanov, Hristo ; Buyukliev, Rossen ; Momekov, Georgi ; Ferdinandov, Dilyan ; Konstantinov, Spiro ; Ivanov, Darvin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c390t-f1374a6f613ab35c8ab5ceda0f97037a7b736a1db8bc78ea613d01bc8fbeb35f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>2,4-Imidazolidenedione</topic><topic>Adult</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor</topic><topic>Chelating Agents - chemical synthesis</topic><topic>Chelating Agents - chemistry</topic><topic>Child</topic><topic>cis/ trans Pt(II) and Pt(IV) complexes</topic><topic>Cytotoxicity</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Female</topic><topic>General aspects</topic><topic>Humans</topic><topic>Imidazolines - chemical synthesis</topic><topic>Imidazolines - chemistry</topic><topic>Imidazolines - pharmacology</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Middle Aged</topic><topic>Pharmacology. Drug treatments</topic><topic>Platinum</topic><topic>Pyridines - chemical synthesis</topic><topic>Pyridines - chemistry</topic><topic>Pyridines - pharmacology</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bakalova, Adriana</creatorcontrib><creatorcontrib>Varbanov, Hristo</creatorcontrib><creatorcontrib>Buyukliev, Rossen</creatorcontrib><creatorcontrib>Momekov, Georgi</creatorcontrib><creatorcontrib>Ferdinandov, Dilyan</creatorcontrib><creatorcontrib>Konstantinov, Spiro</creatorcontrib><creatorcontrib>Ivanov, Darvin</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>Bakalova, Adriana</au><au>Varbanov, Hristo</au><au>Buyukliev, Rossen</au><au>Momekov, Georgi</au><au>Ferdinandov, Dilyan</au><au>Konstantinov, Spiro</au><au>Ivanov, Darvin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, characterization and biological activity of Pt(II) and Pt(IV) complexes with 5-methyl-5(4-pyridyl)-2,4-imidazolidenedione</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2008-05-01</date><risdate>2008</risdate><volume>43</volume><issue>5</issue><spage>958</spage><epage>965</epage><pages>958-965</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>New platinum(II) and platinum(IV) complexes with 5-methyl-5(4-pyridyl)-2,4-imidazolidenedione and various halogen ions with general formula [PtL
2X
2] and [PtL
2Cl
4], where L is the organic ligand and X is Cl
−, Br
−, J
−, were synthesized. The molecular formulae of all the complexes were confirmed by elemental analysis, IR,
1H,
13C NMR spectral analyses and molar conductivity. The cytotoxic effects of these complexes were examined on some human tumor cell lines. The newly synthesized
cis-[PtL
2Cl
2] exerted cytotoxic activity against SKW-3, MCF-7, EJ, U-266 tumor cell lines, while
cis-[PtL
2Br
2],
trans-[PtL
2I
2] were less active. The higher oxidation state complex
cis-[PtL
2Cl
4] was inactive in all cell lines but in SKW-3 some augmentation of the cytotoxicity was seen after co-administration of ascorbic acid but not when treated in combination with reduced glutathione or
N-acetylcysteine. A DNA-fragmentation analysis revealed that the cytotoxicity of the dichloro analogue, characterized with superior activity compared to the other complexes, is mediated by induction of apoptotic cell death.
Three Pt(II) and one Pt(IV) complexes with 5-methyl-5(4-pyridyl)-2,4-imidazolidenedione and halogen ions were synthesized. Complex
1 showed superior cytotoxicity, as compared to the other complexes and was found to induce apoptosis.
[Display omitted]</abstract><cop>Oxford</cop><pub>Elsevier Masson SAS</pub><pmid>17707952</pmid><doi>10.1016/j.ejmech.2007.06.025</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0223-5234 |
| ispartof | European journal of medicinal chemistry, 2008-05, Vol.43 (5), p.958-965 |
| issn | 0223-5234 1768-3254 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_69193621 |
| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | 2,4-Imidazolidenedione Adult Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biological and medical sciences Cell Line, Tumor Chelating Agents - chemical synthesis Chelating Agents - chemistry Child cis/ trans Pt(II) and Pt(IV) complexes Cytotoxicity Drug Screening Assays, Antitumor Female General aspects Humans Imidazolines - chemical synthesis Imidazolines - chemistry Imidazolines - pharmacology Male Medical sciences Middle Aged Pharmacology. Drug treatments Platinum Pyridines - chemical synthesis Pyridines - chemistry Pyridines - pharmacology Structure-Activity Relationship |
| title | Synthesis, characterization and biological activity of Pt(II) and Pt(IV) complexes with 5-methyl-5(4-pyridyl)-2,4-imidazolidenedione |
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