Analogues of cis- and transplatin with a rich solutionchemistry: Cis-[PtCl2(NH3)(1-MeC-N3)] and trans-[PtI2(NH3)(1-MeC-N3)]
Mono(nucleobase) complexes of the general composition cis-[PtCl(NH)L] with L=1-methylcytosine, 1-MeC (1 a) and L=1-ethyl-5-methylcytosine, as well as trans-[PtX(NH)(1-MeC)] with X=I (5 a) and X=Br (5 b) have been isolated and were characterized by X-ray crystallography. The Pt coordination occurs th...
| Autores: | , , , , , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2015 |
| País: | España |
| Institución: | Consejo Superior de Investigaciones Científicas (CSIC) |
| Repositorio: | DIGITAL.CSIC. Repositorio Institucional del CSIC |
| OAI Identifier: | oai:digital.csic.es:10261/154617 |
| Acceso en línea: | http://hdl.handle.net/10261/154617 |
| Access Level: | acceso abierto |
| Palabra clave: | 1-methylcytosine Diplatinum(III) Mass spectrometry Platinum Condensation reactions |
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Analogues of cis- and transplatin with a rich solutionchemistry: Cis-[PtCl2(NH3)(1-MeC-N3)] and trans-[PtI2(NH3)(1-MeC-N3)]Siebel, SabineDammann, ClaudiaSanz Miguel, Pablo J.Drewello, ThomasKampf, GunnarTeubner, NataschaBednarski, Patrick J.Freisinger, EvaLippert, Bernhard1-methylcytosineDiplatinum(III)Mass spectrometryPlatinumCondensation reactionsMono(nucleobase) complexes of the general composition cis-[PtCl(NH)L] with L=1-methylcytosine, 1-MeC (1 a) and L=1-ethyl-5-methylcytosine, as well as trans-[PtX(NH)(1-MeC)] with X=I (5 a) and X=Br (5 b) have been isolated and were characterized by X-ray crystallography. The Pt coordination occurs through the N3 atom of the cytosine in all cases. The diaqua complexes of compounds 1 a and 5 a, cis-[Pt(HO)(NH)(1-MeC)] and trans-[Pt(HO)(NH)(1-MeC)], display a rich chemistry in aqueous solution, which is dominated by extensive condensation reactions leading to μ-OH- and μ-(1-MeC-N3,N4)-bridged species and ready oxidation of Pt to mixed-valence state complexes as well as diplatinum(III) compounds, one of which was characterized by X-ray crystallography: h,t-[{Pt(NH)(OH)(1-MeC-N3,N4)}](NO).2 [NH](NO).2 HO. A combination of H NMR spectroscopy and ESI mass spectrometry was applied to identify some of the various species present in solution and the gas phase, respectively. As it turned out, mass spectrometry did not permit an unambiguous assignment of the structures of +1 cations due to the possibilities of realizing multiple bridging patterns in isomeric species, the occurrence of different tautomers, and uncertainties regarding the Pt oxidation states. Additionally, compound 1 a was found to have selective and moderate antiproliferative activity for a human cervix cancer line (SISO) compared to six other human cancer cell lines.This work was supported by the Deutsche Forschungsgemeinschaft. P.J.S.M. thanks the Spanish Ministry of Economy and Competitiveness for funding through the Ramón y Cajal program.Peer ReviewedWiley-VCHGerman Research FoundationMinisterio de Economía y Competitividad (España)Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2017201720152017info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/154617reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Ingléshttps://doi.org/10.1002/chem.201502691Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1546172026-05-22T06:33:51Z |
| dc.title.none.fl_str_mv |
Analogues of cis- and transplatin with a rich solutionchemistry: Cis-[PtCl2(NH3)(1-MeC-N3)] and trans-[PtI2(NH3)(1-MeC-N3)] |
| title |
Analogues of cis- and transplatin with a rich solutionchemistry: Cis-[PtCl2(NH3)(1-MeC-N3)] and trans-[PtI2(NH3)(1-MeC-N3)] |
| spellingShingle |
Analogues of cis- and transplatin with a rich solutionchemistry: Cis-[PtCl2(NH3)(1-MeC-N3)] and trans-[PtI2(NH3)(1-MeC-N3)] Siebel, Sabine 1-methylcytosine Diplatinum(III) Mass spectrometry Platinum Condensation reactions |
| title_short |
Analogues of cis- and transplatin with a rich solutionchemistry: Cis-[PtCl2(NH3)(1-MeC-N3)] and trans-[PtI2(NH3)(1-MeC-N3)] |
| title_full |
Analogues of cis- and transplatin with a rich solutionchemistry: Cis-[PtCl2(NH3)(1-MeC-N3)] and trans-[PtI2(NH3)(1-MeC-N3)] |
| title_fullStr |
Analogues of cis- and transplatin with a rich solutionchemistry: Cis-[PtCl2(NH3)(1-MeC-N3)] and trans-[PtI2(NH3)(1-MeC-N3)] |
| title_full_unstemmed |
Analogues of cis- and transplatin with a rich solutionchemistry: Cis-[PtCl2(NH3)(1-MeC-N3)] and trans-[PtI2(NH3)(1-MeC-N3)] |
| title_sort |
Analogues of cis- and transplatin with a rich solutionchemistry: Cis-[PtCl2(NH3)(1-MeC-N3)] and trans-[PtI2(NH3)(1-MeC-N3)] |
| dc.creator.none.fl_str_mv |
Siebel, Sabine Dammann, Claudia Sanz Miguel, Pablo J. Drewello, Thomas Kampf, Gunnar Teubner, Natascha Bednarski, Patrick J. Freisinger, Eva Lippert, Bernhard |
| author |
Siebel, Sabine |
| author_facet |
Siebel, Sabine Dammann, Claudia Sanz Miguel, Pablo J. Drewello, Thomas Kampf, Gunnar Teubner, Natascha Bednarski, Patrick J. Freisinger, Eva Lippert, Bernhard |
| author_role |
author |
| author2 |
Dammann, Claudia Sanz Miguel, Pablo J. Drewello, Thomas Kampf, Gunnar Teubner, Natascha Bednarski, Patrick J. Freisinger, Eva Lippert, Bernhard |
| author2_role |
author author author author author author author author |
| dc.contributor.none.fl_str_mv |
German Research Foundation Ministerio de Economía y Competitividad (España) Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72] |
| dc.subject.none.fl_str_mv |
1-methylcytosine Diplatinum(III) Mass spectrometry Platinum Condensation reactions |
| topic |
1-methylcytosine Diplatinum(III) Mass spectrometry Platinum Condensation reactions |
| description |
Mono(nucleobase) complexes of the general composition cis-[PtCl(NH)L] with L=1-methylcytosine, 1-MeC (1 a) and L=1-ethyl-5-methylcytosine, as well as trans-[PtX(NH)(1-MeC)] with X=I (5 a) and X=Br (5 b) have been isolated and were characterized by X-ray crystallography. The Pt coordination occurs through the N3 atom of the cytosine in all cases. The diaqua complexes of compounds 1 a and 5 a, cis-[Pt(HO)(NH)(1-MeC)] and trans-[Pt(HO)(NH)(1-MeC)], display a rich chemistry in aqueous solution, which is dominated by extensive condensation reactions leading to μ-OH- and μ-(1-MeC-N3,N4)-bridged species and ready oxidation of Pt to mixed-valence state complexes as well as diplatinum(III) compounds, one of which was characterized by X-ray crystallography: h,t-[{Pt(NH)(OH)(1-MeC-N3,N4)}](NO).2 [NH](NO).2 HO. A combination of H NMR spectroscopy and ESI mass spectrometry was applied to identify some of the various species present in solution and the gas phase, respectively. As it turned out, mass spectrometry did not permit an unambiguous assignment of the structures of +1 cations due to the possibilities of realizing multiple bridging patterns in isomeric species, the occurrence of different tautomers, and uncertainties regarding the Pt oxidation states. Additionally, compound 1 a was found to have selective and moderate antiproliferative activity for a human cervix cancer line (SISO) compared to six other human cancer cell lines. |
| publishDate |
2015 |
| dc.date.none.fl_str_mv |
2015 2017 2017 2017 |
| dc.type.none.fl_str_mv |
info:eu-repo/semantics/article http://purl.org/coar/resource_type/c_6501 Postprint info:eu-repo/semantics/acceptedVersion |
| format |
article |
| status_str |
acceptedVersion |
| dc.identifier.none.fl_str_mv |
http://hdl.handle.net/10261/154617 |
| url |
http://hdl.handle.net/10261/154617 |
| dc.language.none.fl_str_mv |
Inglés |
| language_invalid_str_mv |
Inglés |
| dc.relation.none.fl_str_mv |
https://doi.org/10.1002/chem.201502691 Sí |
| dc.rights.none.fl_str_mv |
info:eu-repo/semantics/openAccess |
| eu_rights_str_mv |
openAccess |
| dc.publisher.none.fl_str_mv |
Wiley-VCH |
| publisher.none.fl_str_mv |
Wiley-VCH |
| dc.source.none.fl_str_mv |
reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC instname:Consejo Superior de Investigaciones Científicas (CSIC) |
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Consejo Superior de Investigaciones Científicas (CSIC) |
| reponame_str |
DIGITAL.CSIC. Repositorio Institucional del CSIC |
| collection |
DIGITAL.CSIC. Repositorio Institucional del CSIC |
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1869412066534621184 |
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15.228081 |