Antitumor and DNA-binding properties of a group of oligomeric complexes of Pt(II) and Pt(IV)
The antitumor and DNA-binding properties of a group of oligomeric platinum(II) and platinum(IV) complexes are described. The compounds, having the stoichiometry [cis-PtII(X)2(mu-OH)]2(NO3)2, where X is NH3, NH2CH2CH3, and NH2CH(CH3)2, were found to be inactive or only weakly active against L-1210 le...
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| Veröffentlicht in: | Journal of medicinal chemistry 1990-08, Vol.33 (8), p.2184-2188 |
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| container_title | Journal of medicinal chemistry |
| container_volume | 33 |
| creator | PERITZ, A AL-BAKER, S VOLLANO, J. F SCHURIG, J. E BRADNER, W. T DABROWIAK, J. C |
| description | The antitumor and DNA-binding properties of a group of oligomeric platinum(II) and platinum(IV) complexes are described. The compounds, having the stoichiometry [cis-PtII(X)2(mu-OH)]2(NO3)2, where X is NH3, NH2CH2CH3, and NH2CH(CH3)2, were found to be inactive or only weakly active against L-1210 leukemia. In vitro studies involving PM2-DNA show that these compounds bind to and unwind closed circular DNA in a manner similar to cis-PtII-(NH3)2Cl2. The Pt(IV) complexes produced by hydrogen peroxide oxidation of the Pt(II) dimers are inactive as antitumor agents and are incapable of unwinding PM2-DNA. The cyclotrimer [cis-PtII(RR-DACH)(mu-OH)]3(NO3)3, where RR-DACH is (R,R)-1,2 diaminocyclohexane, exhibits potent antitumor activity against L-1210 leukemia and modest activities with B-16 and M5076 tumor lines. This compound platinates DNA, causing DNA unwinding and mobility shifts. |
| doi_str_mv | 10.1021/jm00170a022 |
| format | Article |
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F ; SCHURIG, J. E ; BRADNER, W. T ; DABROWIAK, J. C</creator><creatorcontrib>PERITZ, A ; AL-BAKER, S ; VOLLANO, J. F ; SCHURIG, J. E ; BRADNER, W. T ; DABROWIAK, J. C</creatorcontrib><description>The antitumor and DNA-binding properties of a group of oligomeric platinum(II) and platinum(IV) complexes are described. The compounds, having the stoichiometry [cis-PtII(X)2(mu-OH)]2(NO3)2, where X is NH3, NH2CH2CH3, and NH2CH(CH3)2, were found to be inactive or only weakly active against L-1210 leukemia. In vitro studies involving PM2-DNA show that these compounds bind to and unwind closed circular DNA in a manner similar to cis-PtII-(NH3)2Cl2. The Pt(IV) complexes produced by hydrogen peroxide oxidation of the Pt(II) dimers are inactive as antitumor agents and are incapable of unwinding PM2-DNA. The cyclotrimer [cis-PtII(RR-DACH)(mu-OH)]3(NO3)3, where RR-DACH is (R,R)-1,2 diaminocyclohexane, exhibits potent antitumor activity against L-1210 leukemia and modest activities with B-16 and M5076 tumor lines. This compound platinates DNA, causing DNA unwinding and mobility shifts.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00170a022</identifier><identifier>PMID: 2374144</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Antineoplastic Agents - metabolism ; Antineoplastic Agents - therapeutic use ; Chemistry ; DNA - metabolism ; DNA, Circular - metabolism ; Exact sciences and technology ; Free radicals chemistry ; Hydrogen Peroxide ; Leukemia L1210 - drug therapy ; Macromolecular Substances ; Mice ; Organic chemistry ; Organoplatinum Compounds - metabolism ; Organoplatinum Compounds - therapeutic use ; Oxidation-Reduction ; Prodrugs ; Reactivity and mechanisms ; Tumor Cells, Cultured</subject><ispartof>Journal of medicinal chemistry, 1990-08, Vol.33 (8), p.2184-2188</ispartof><rights>1991 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=19457241$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/2374144$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>PERITZ, A</creatorcontrib><creatorcontrib>AL-BAKER, S</creatorcontrib><creatorcontrib>VOLLANO, J. F</creatorcontrib><creatorcontrib>SCHURIG, J. E</creatorcontrib><creatorcontrib>BRADNER, W. T</creatorcontrib><creatorcontrib>DABROWIAK, J. C</creatorcontrib><title>Antitumor and DNA-binding properties of a group of oligomeric complexes of Pt(II) and Pt(IV)</title><title>Journal of medicinal chemistry</title><addtitle>J Med Chem</addtitle><description>The antitumor and DNA-binding properties of a group of oligomeric platinum(II) and platinum(IV) complexes are described. The compounds, having the stoichiometry [cis-PtII(X)2(mu-OH)]2(NO3)2, where X is NH3, NH2CH2CH3, and NH2CH(CH3)2, were found to be inactive or only weakly active against L-1210 leukemia. In vitro studies involving PM2-DNA show that these compounds bind to and unwind closed circular DNA in a manner similar to cis-PtII-(NH3)2Cl2. The Pt(IV) complexes produced by hydrogen peroxide oxidation of the Pt(II) dimers are inactive as antitumor agents and are incapable of unwinding PM2-DNA. The cyclotrimer [cis-PtII(RR-DACH)(mu-OH)]3(NO3)3, where RR-DACH is (R,R)-1,2 diaminocyclohexane, exhibits potent antitumor activity against L-1210 leukemia and modest activities with B-16 and M5076 tumor lines. This compound platinates DNA, causing DNA unwinding and mobility shifts.</description><subject>Animals</subject><subject>Antineoplastic Agents - metabolism</subject><subject>Antineoplastic Agents - therapeutic use</subject><subject>Chemistry</subject><subject>DNA - metabolism</subject><subject>DNA, Circular - metabolism</subject><subject>Exact sciences and technology</subject><subject>Free radicals chemistry</subject><subject>Hydrogen Peroxide</subject><subject>Leukemia L1210 - drug therapy</subject><subject>Macromolecular Substances</subject><subject>Mice</subject><subject>Organic chemistry</subject><subject>Organoplatinum Compounds - metabolism</subject><subject>Organoplatinum Compounds - therapeutic use</subject><subject>Oxidation-Reduction</subject><subject>Prodrugs</subject><subject>Reactivity and mechanisms</subject><subject>Tumor Cells, Cultured</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1990</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMtLw0AYxBdRaq2ePAu5KPYQ3Wd2cyz1VSjqQT0JYV8pK0k27iag_72pDV49fcM3P4ZhADhF8ApBjK4_aggRhxJivAemiGGYUgHpPpjC4ZXiDJNDcBTjB4SQIEwmYIIJp4jSKXhfNJ3r-tqHRDYmuXlcpMo1xjWbpA2-taFzNia-TGSyCb5vt9JXbuNrG5xOtK_byn7tkOfucrWa_-Zs5dv8GByUsor2ZLwz8Hp3-7J8SNdP96vlYp22OONdSrXEBinMOWNKMzY0k4aXlCmcMal0Rm3JhRFYSEOU4UrrkmWG5EgrKKAhM3Cxyx0qf_Y2dkXtorZVJRvr-1jwXOQZJfm_IGK5ICJHA3g2gr2qrSna4GoZvotxt8E_H30ZtazKIBvt4h-Gcso4poj8AFzjems</recordid><startdate>19900801</startdate><enddate>19900801</enddate><creator>PERITZ, A</creator><creator>AL-BAKER, S</creator><creator>VOLLANO, J. F</creator><creator>SCHURIG, J. E</creator><creator>BRADNER, W. T</creator><creator>DABROWIAK, J. C</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7TM</scope><scope>7X8</scope></search><sort><creationdate>19900801</creationdate><title>Antitumor and DNA-binding properties of a group of oligomeric complexes of Pt(II) and Pt(IV)</title><author>PERITZ, A ; AL-BAKER, S ; VOLLANO, J. F ; SCHURIG, J. E ; BRADNER, W. T ; DABROWIAK, J. C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p267t-4ca2d1b27755bc55414ad7f45b265abc64ef78d828ad3bd7bccf56d391cb080d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1990</creationdate><topic>Animals</topic><topic>Antineoplastic Agents - metabolism</topic><topic>Antineoplastic Agents - therapeutic use</topic><topic>Chemistry</topic><topic>DNA - metabolism</topic><topic>DNA, Circular - metabolism</topic><topic>Exact sciences and technology</topic><topic>Free radicals chemistry</topic><topic>Hydrogen Peroxide</topic><topic>Leukemia L1210 - drug therapy</topic><topic>Macromolecular Substances</topic><topic>Mice</topic><topic>Organic chemistry</topic><topic>Organoplatinum Compounds - metabolism</topic><topic>Organoplatinum Compounds - therapeutic use</topic><topic>Oxidation-Reduction</topic><topic>Prodrugs</topic><topic>Reactivity and mechanisms</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>PERITZ, A</creatorcontrib><creatorcontrib>AL-BAKER, S</creatorcontrib><creatorcontrib>VOLLANO, J. F</creatorcontrib><creatorcontrib>SCHURIG, J. E</creatorcontrib><creatorcontrib>BRADNER, W. T</creatorcontrib><creatorcontrib>DABROWIAK, J. C</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>Nucleic Acids Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>PERITZ, A</au><au>AL-BAKER, S</au><au>VOLLANO, J. F</au><au>SCHURIG, J. E</au><au>BRADNER, W. T</au><au>DABROWIAK, J. C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antitumor and DNA-binding properties of a group of oligomeric complexes of Pt(II) and Pt(IV)</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J Med Chem</addtitle><date>1990-08-01</date><risdate>1990</risdate><volume>33</volume><issue>8</issue><spage>2184</spage><epage>2188</epage><pages>2184-2188</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>The antitumor and DNA-binding properties of a group of oligomeric platinum(II) and platinum(IV) complexes are described. The compounds, having the stoichiometry [cis-PtII(X)2(mu-OH)]2(NO3)2, where X is NH3, NH2CH2CH3, and NH2CH(CH3)2, were found to be inactive or only weakly active against L-1210 leukemia. In vitro studies involving PM2-DNA show that these compounds bind to and unwind closed circular DNA in a manner similar to cis-PtII-(NH3)2Cl2. The Pt(IV) complexes produced by hydrogen peroxide oxidation of the Pt(II) dimers are inactive as antitumor agents and are incapable of unwinding PM2-DNA. The cyclotrimer [cis-PtII(RR-DACH)(mu-OH)]3(NO3)3, where RR-DACH is (R,R)-1,2 diaminocyclohexane, exhibits potent antitumor activity against L-1210 leukemia and modest activities with B-16 and M5076 tumor lines. This compound platinates DNA, causing DNA unwinding and mobility shifts.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>2374144</pmid><doi>10.1021/jm00170a022</doi><tpages>5</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 1990-08, Vol.33 (8), p.2184-2188 |
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| subjects | Animals Antineoplastic Agents - metabolism Antineoplastic Agents - therapeutic use Chemistry DNA - metabolism DNA, Circular - metabolism Exact sciences and technology Free radicals chemistry Hydrogen Peroxide Leukemia L1210 - drug therapy Macromolecular Substances Mice Organic chemistry Organoplatinum Compounds - metabolism Organoplatinum Compounds - therapeutic use Oxidation-Reduction Prodrugs Reactivity and mechanisms Tumor Cells, Cultured |
| title | Antitumor and DNA-binding properties of a group of oligomeric complexes of Pt(II) and Pt(IV) |
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