EXAFS structural study of platinum-based anticancer drugs degradation in presence of sulfur nucleophilic species
Three platinum complexes, cisplatin, carboplatin and oxaliplatin are currently used worldwide. Investigation of their main structural modifications in presence of sulfur nucleophiles is of particular interest because of the implication of thiol and thioether groups in biochemical mechanism of action...
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| Veröffentlicht in: | Biochimie 2009-10, Vol.91 (10), p.1301-1306 |
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| creator | Provost, Karine Bouvet-Muller, Diane Crauste-Manciet, Sylvie Moscovici, Jacques Olivi, Luca Vlaic, Gilberto Michalowicz, Alain |
| description | Three platinum complexes, cisplatin, carboplatin and oxaliplatin are currently used worldwide. Investigation of their main structural modifications in presence of sulfur nucleophiles is of particular interest because of the implication of thiol and thioether groups in biochemical mechanism of action, resistance mechanism and
in vivo or
in vitro detoxification. We present the main structural results we have obtained concerning the reaction of these drugs with diverse sulfur nucleophiles (cysteine, glutathione, methionine, thiosulfate and thiocyanate), monitored in solution or as precipitates by EXAFS spectroscopy. The reactivities of the carboxylate and amine ligands of both carboplatin and oxaliplatin are compared, on the basis of first-coordination sphere modeling. Among the new results of this EXAFS study, we present the first observation of oxaliplatin diaminocyclohexane ligand displacement by sulfur nucleophiles. |
| doi_str_mv | 10.1016/j.biochi.2009.07.005 |
| format | Article |
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in vivo or
in vitro detoxification. We present the main structural results we have obtained concerning the reaction of these drugs with diverse sulfur nucleophiles (cysteine, glutathione, methionine, thiosulfate and thiocyanate), monitored in solution or as precipitates by EXAFS spectroscopy. The reactivities of the carboxylate and amine ligands of both carboplatin and oxaliplatin are compared, on the basis of first-coordination sphere modeling. Among the new results of this EXAFS study, we present the first observation of oxaliplatin diaminocyclohexane ligand displacement by sulfur nucleophiles.</description><identifier>ISSN: 0300-9084</identifier><identifier>EISSN: 1638-6183</identifier><identifier>DOI: 10.1016/j.biochi.2009.07.005</identifier><identifier>PMID: 19607872</identifier><language>eng</language><publisher>France: Elsevier Masson SAS</publisher><subject>Antineoplastic Agents - chemistry ; Drug reactivity ; EXAFS structure ; Organoplatinum Compounds - chemistry ; Platinum antitumoral drugs ; Spectrometry, X-Ray Emission ; Sulfur - chemistry ; Sulfur nucleophiles</subject><ispartof>Biochimie, 2009-10, Vol.91 (10), p.1301-1306</ispartof><rights>2009 Elsevier Masson SAS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c392t-8a09a790c4cd6b5bb431689db0bd0d279dc5b9545d7da4267ba7c3299cc149383</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.biochi.2009.07.005$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19607872$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Provost, Karine</creatorcontrib><creatorcontrib>Bouvet-Muller, Diane</creatorcontrib><creatorcontrib>Crauste-Manciet, Sylvie</creatorcontrib><creatorcontrib>Moscovici, Jacques</creatorcontrib><creatorcontrib>Olivi, Luca</creatorcontrib><creatorcontrib>Vlaic, Gilberto</creatorcontrib><creatorcontrib>Michalowicz, Alain</creatorcontrib><title>EXAFS structural study of platinum-based anticancer drugs degradation in presence of sulfur nucleophilic species</title><title>Biochimie</title><addtitle>Biochimie</addtitle><description>Three platinum complexes, cisplatin, carboplatin and oxaliplatin are currently used worldwide. Investigation of their main structural modifications in presence of sulfur nucleophiles is of particular interest because of the implication of thiol and thioether groups in biochemical mechanism of action, resistance mechanism and
in vivo or
in vitro detoxification. We present the main structural results we have obtained concerning the reaction of these drugs with diverse sulfur nucleophiles (cysteine, glutathione, methionine, thiosulfate and thiocyanate), monitored in solution or as precipitates by EXAFS spectroscopy. The reactivities of the carboxylate and amine ligands of both carboplatin and oxaliplatin are compared, on the basis of first-coordination sphere modeling. Among the new results of this EXAFS study, we present the first observation of oxaliplatin diaminocyclohexane ligand displacement by sulfur nucleophiles.</description><subject>Antineoplastic Agents - chemistry</subject><subject>Drug reactivity</subject><subject>EXAFS structure</subject><subject>Organoplatinum Compounds - chemistry</subject><subject>Platinum antitumoral drugs</subject><subject>Spectrometry, X-Ray Emission</subject><subject>Sulfur - chemistry</subject><subject>Sulfur nucleophiles</subject><issn>0300-9084</issn><issn>1638-6183</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kU9r3DAQxUVpSbZpvkEpOrUnu6M_tqxLIYSkLQR6aAK9CWmkTbR4bVeyAvn21bILveU0A_N7b-A9Qj4yaBmw_uuudXHGp9hyAN2CagG6N2TDejE0PRvEW7IBAdBoGOQ5eZ_zDioBXJ-Rc6Z7UIPiG7Lc_Lm6_U3zmgquJdmxrsW_0HlLl9GucSr7xtkcPLXTGtFOGBL1qTxm6sNjsr4y80TjRJcUcqjngzSXcVsSnQqOYV6e4hiR5iVgDPkDebe1Yw6Xp3lBHm5v7q9_NHe_vv-8vrprUGi-NoMFbZUGlOh71zknBesH7R04D54r7bFzupOdV95K3itnFQquNSKTWgzignw5-i5p_ltCXs0-ZgzjaKcwl2yUkCCFZAfy86skZzAwyaGC8ghimnNOYWuWFPc2vRgG5tCJ2ZljJ-bQiQFlauJV9unkX9w--P-iUwkV-HYEQs3jOYZkck2qRuljCrgaP8fXP_wDvGugqg</recordid><startdate>20091001</startdate><enddate>20091001</enddate><creator>Provost, Karine</creator><creator>Bouvet-Muller, Diane</creator><creator>Crauste-Manciet, Sylvie</creator><creator>Moscovici, Jacques</creator><creator>Olivi, Luca</creator><creator>Vlaic, Gilberto</creator><creator>Michalowicz, Alain</creator><general>Elsevier Masson SAS</general><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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20091001</creationdate><title>EXAFS structural study of platinum-based anticancer drugs degradation in presence of sulfur nucleophilic species</title><author>Provost, Karine ; Bouvet-Muller, Diane ; Crauste-Manciet, Sylvie ; Moscovici, Jacques ; Olivi, Luca ; Vlaic, Gilberto ; Michalowicz, Alain</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c392t-8a09a790c4cd6b5bb431689db0bd0d279dc5b9545d7da4267ba7c3299cc149383</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Antineoplastic Agents - chemistry</topic><topic>Drug reactivity</topic><topic>EXAFS structure</topic><topic>Organoplatinum Compounds - chemistry</topic><topic>Platinum antitumoral drugs</topic><topic>Spectrometry, X-Ray Emission</topic><topic>Sulfur - chemistry</topic><topic>Sulfur nucleophiles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Provost, Karine</creatorcontrib><creatorcontrib>Bouvet-Muller, Diane</creatorcontrib><creatorcontrib>Crauste-Manciet, Sylvie</creatorcontrib><creatorcontrib>Moscovici, Jacques</creatorcontrib><creatorcontrib>Olivi, Luca</creatorcontrib><creatorcontrib>Vlaic, Gilberto</creatorcontrib><creatorcontrib>Michalowicz, Alain</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Biochimie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Provost, Karine</au><au>Bouvet-Muller, Diane</au><au>Crauste-Manciet, Sylvie</au><au>Moscovici, Jacques</au><au>Olivi, Luca</au><au>Vlaic, Gilberto</au><au>Michalowicz, Alain</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>EXAFS structural study of platinum-based anticancer drugs degradation in presence of sulfur nucleophilic species</atitle><jtitle>Biochimie</jtitle><addtitle>Biochimie</addtitle><date>2009-10-01</date><risdate>2009</risdate><volume>91</volume><issue>10</issue><spage>1301</spage><epage>1306</epage><pages>1301-1306</pages><issn>0300-9084</issn><eissn>1638-6183</eissn><abstract>Three platinum complexes, cisplatin, carboplatin and oxaliplatin are currently used worldwide. Investigation of their main structural modifications in presence of sulfur nucleophiles is of particular interest because of the implication of thiol and thioether groups in biochemical mechanism of action, resistance mechanism and
in vivo or
in vitro detoxification. We present the main structural results we have obtained concerning the reaction of these drugs with diverse sulfur nucleophiles (cysteine, glutathione, methionine, thiosulfate and thiocyanate), monitored in solution or as precipitates by EXAFS spectroscopy. The reactivities of the carboxylate and amine ligands of both carboplatin and oxaliplatin are compared, on the basis of first-coordination sphere modeling. Among the new results of this EXAFS study, we present the first observation of oxaliplatin diaminocyclohexane ligand displacement by sulfur nucleophiles.</abstract><cop>France</cop><pub>Elsevier Masson SAS</pub><pmid>19607872</pmid><doi>10.1016/j.biochi.2009.07.005</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0300-9084 |
| ispartof | Biochimie, 2009-10, Vol.91 (10), p.1301-1306 |
| issn | 0300-9084 1638-6183 |
| language | eng |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Antineoplastic Agents - chemistry Drug reactivity EXAFS structure Organoplatinum Compounds - chemistry Platinum antitumoral drugs Spectrometry, X-Ray Emission Sulfur - chemistry Sulfur nucleophiles |
| title | EXAFS structural study of platinum-based anticancer drugs degradation in presence of sulfur nucleophilic species |
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