Effect of the aniline fragment in Pt(II) and Pt(IV) complexes as anti-proliferative agents. Standard reduction potential as a more reliable parameter for Pt(IV) compounds than peak reduction potential
The problems of resistance and side effects associated with cisplatin and other chemotherapeutic drugs have boosted research aimed at finding new compounds with improved properties. The use of platinum(IV) prodrugs is one alternative, although there is some controversy regarding the predictive abili...
| Autores: | , , , , , , , , , , , , , , |
|---|---|
| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2021 |
| País: | España |
| Institución: | Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
| Repositorio: | Recercat. Dipósit de la Recerca de Catalunya |
| OAI Identifier: | oai:recercat.cat:10256/26257 |
| Acceso en línea: | http://hdl.handle.net/10256/26257 |
| Access Level: | acceso abierto |
| Palabra clave: | Càncer Quimioteràpia del càncer Cancer Cancer chemotherapy Patí -- Ús terapèutic Platinum -- Therapeutic use |
| id |
ES_aa0bbdd3a9fb7792fdc67384fb2adb07 |
|---|---|
| oai_identifier_str |
oai:recercat.cat:10256/26257 |
| network_acronym_str |
ES |
| network_name_str |
España |
| repository_id_str |
|
| spelling |
Effect of the aniline fragment in Pt(II) and Pt(IV) complexes as anti-proliferative agents. Standard reduction potential as a more reliable parameter for Pt(IV) compounds than peak reduction potentialLeal, JorgeSantos Peinado, LucíaFernández-Aroca, Diego M.Cuevas-Vicario, José VicenteMartínez Lorente, Mª ÁngelesMassaguer i Vall-llovera, AnnaJalón, Félix A.Ruiz-Hidalgo, María JoséSánchez-Prieto, RicardoRodríguez, Ana María BlancoCastañeda Peñalvo, GregorioDurá, GemaCarriõn, María CarmenBarrabés Vera, SílviaManzano, Blanca R.CàncerQuimioteràpia del càncerCancerCancer chemotherapyPatí -- Ús terapèuticPlatinum -- Therapeutic useThe problems of resistance and side effects associated with cisplatin and other chemotherapeutic drugs have boosted research aimed at finding new compounds with improved properties. The use of platinum(IV) prodrugs is one alternative, although there is some controversy regarding the predictive ability of the peak reduction potentials. In the work described here a series of fourteen chloride Pt(II) and Pt(IV) compounds was synthesised and fully characterised. The compounds contain different bidentate arylazole heterocyclic ligands. Their cytotoxic properties against human lung carcinoma (A549), human breast carcinoma (MCF7) and human colon carcinoma (HCT116 and HT29) cell lines were studied. A clear relationship between the type of ligand and the anti-proliferative properties was found, with the best results obtained for the Pt(II) compound that contains an aniline fragment, (13), thus evidencing a positive effect of the NH2 group. Stability and aquation studies in DMSO, DMF and DMSO/water mixtures were carried out on the active complexes and an in-depth analysis of the two aquation processes, including DFT analysis, of 13 was undertaken. It was verified that DNA was the target and that cell death occurred by apoptosis in the case of 13. Furthermore, the cytotoxic derivatives did not exhibit haemolytic activity. The reduction of the Pt(IV) compounds whose Pt(II) congeners were active was studied by several techniques. It was concluded that the peak reduction potential was not useful to predict the ability for reduction. However, a correlation between the cytotoxic activity and the standard reduction potential was foundElsevier2021info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionpeer-reviewedapplication/pdfhttp://hdl.handle.net/10256/26257© Journal of Inorganic Biochemistry, 2021, vol. 218, art.núm.111403Articles publicats (D-B)Leal, Jorge Santos, Lúcia H.M.L.M. Fernández-Aroca, Diego M. Cuevas-Vicario, José Vicente Martínez, Ma Ángeles Massaguer i Vall-llovera, Anna Jalón, Félix A. Ruiz-Hidalgo, María José Sánchez-Prieto, Ricardo Rodríguez, Ana maría Blanco Castañeda Peñalvo, Gregorio Dura, Gema Carriõn, María Carmen Barrabés Vera, Sílvia Manzano, Blanca R. 2021 Effect of the aniline fragment in Pt(II) and Pt(IV) complexes as anti-proliferative agents. Standard reduction potential as a more reliable parameter for Pt(IV) compounds than peak reduction potential. Journal of Inorganic Biochemistry 218 art.núm.111403reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jinorgbio.2021.111403info:eu-repo/semantics/altIdentifier/issn/0162-0134info:eu-repo/semantics/altIdentifier/eissn/1873-3344Reconeixement-NoComercial-SenseObraDerivada 4.0 Internacionalhttp://creativecommons.org/licenses/by-nc-nd/4.0info:eu-repo/semantics/openAccessoai:recercat.cat:10256/262572026-05-29T05:05:01Z |
| dc.title.none.fl_str_mv |
Effect of the aniline fragment in Pt(II) and Pt(IV) complexes as anti-proliferative agents. Standard reduction potential as a more reliable parameter for Pt(IV) compounds than peak reduction potential |
| title |
Effect of the aniline fragment in Pt(II) and Pt(IV) complexes as anti-proliferative agents. Standard reduction potential as a more reliable parameter for Pt(IV) compounds than peak reduction potential |
| spellingShingle |
Effect of the aniline fragment in Pt(II) and Pt(IV) complexes as anti-proliferative agents. Standard reduction potential as a more reliable parameter for Pt(IV) compounds than peak reduction potential Leal, Jorge Càncer Quimioteràpia del càncer Cancer Cancer chemotherapy Patí -- Ús terapèutic Platinum -- Therapeutic use |
| title_short |
Effect of the aniline fragment in Pt(II) and Pt(IV) complexes as anti-proliferative agents. Standard reduction potential as a more reliable parameter for Pt(IV) compounds than peak reduction potential |
| title_full |
Effect of the aniline fragment in Pt(II) and Pt(IV) complexes as anti-proliferative agents. Standard reduction potential as a more reliable parameter for Pt(IV) compounds than peak reduction potential |
| title_fullStr |
Effect of the aniline fragment in Pt(II) and Pt(IV) complexes as anti-proliferative agents. Standard reduction potential as a more reliable parameter for Pt(IV) compounds than peak reduction potential |
| title_full_unstemmed |
Effect of the aniline fragment in Pt(II) and Pt(IV) complexes as anti-proliferative agents. Standard reduction potential as a more reliable parameter for Pt(IV) compounds than peak reduction potential |
| title_sort |
Effect of the aniline fragment in Pt(II) and Pt(IV) complexes as anti-proliferative agents. Standard reduction potential as a more reliable parameter for Pt(IV) compounds than peak reduction potential |
| dc.creator.none.fl_str_mv |
Leal, Jorge Santos Peinado, Lucía Fernández-Aroca, Diego M. Cuevas-Vicario, José Vicente Martínez Lorente, Mª Ángeles Massaguer i Vall-llovera, Anna Jalón, Félix A. Ruiz-Hidalgo, María José Sánchez-Prieto, Ricardo Rodríguez, Ana María Blanco Castañeda Peñalvo, Gregorio Durá, Gema Carriõn, María Carmen Barrabés Vera, Sílvia Manzano, Blanca R. |
| author |
Leal, Jorge |
| author_facet |
Leal, Jorge Santos Peinado, Lucía Fernández-Aroca, Diego M. Cuevas-Vicario, José Vicente Martínez Lorente, Mª Ángeles Massaguer i Vall-llovera, Anna Jalón, Félix A. Ruiz-Hidalgo, María José Sánchez-Prieto, Ricardo Rodríguez, Ana María Blanco Castañeda Peñalvo, Gregorio Durá, Gema Carriõn, María Carmen Barrabés Vera, Sílvia Manzano, Blanca R. |
| author_role |
author |
| author2 |
Santos Peinado, Lucía Fernández-Aroca, Diego M. Cuevas-Vicario, José Vicente Martínez Lorente, Mª Ángeles Massaguer i Vall-llovera, Anna Jalón, Félix A. Ruiz-Hidalgo, María José Sánchez-Prieto, Ricardo Rodríguez, Ana María Blanco Castañeda Peñalvo, Gregorio Durá, Gema Carriõn, María Carmen Barrabés Vera, Sílvia Manzano, Blanca R. |
| author2_role |
author author author author author author author author author author author author author author |
| dc.subject.none.fl_str_mv |
Càncer Quimioteràpia del càncer Cancer Cancer chemotherapy Patí -- Ús terapèutic Platinum -- Therapeutic use |
| topic |
Càncer Quimioteràpia del càncer Cancer Cancer chemotherapy Patí -- Ús terapèutic Platinum -- Therapeutic use |
| description |
The problems of resistance and side effects associated with cisplatin and other chemotherapeutic drugs have boosted research aimed at finding new compounds with improved properties. The use of platinum(IV) prodrugs is one alternative, although there is some controversy regarding the predictive ability of the peak reduction potentials. In the work described here a series of fourteen chloride Pt(II) and Pt(IV) compounds was synthesised and fully characterised. The compounds contain different bidentate arylazole heterocyclic ligands. Their cytotoxic properties against human lung carcinoma (A549), human breast carcinoma (MCF7) and human colon carcinoma (HCT116 and HT29) cell lines were studied. A clear relationship between the type of ligand and the anti-proliferative properties was found, with the best results obtained for the Pt(II) compound that contains an aniline fragment, (13), thus evidencing a positive effect of the NH2 group. Stability and aquation studies in DMSO, DMF and DMSO/water mixtures were carried out on the active complexes and an in-depth analysis of the two aquation processes, including DFT analysis, of 13 was undertaken. It was verified that DNA was the target and that cell death occurred by apoptosis in the case of 13. Furthermore, the cytotoxic derivatives did not exhibit haemolytic activity. The reduction of the Pt(IV) compounds whose Pt(II) congeners were active was studied by several techniques. It was concluded that the peak reduction potential was not useful to predict the ability for reduction. However, a correlation between the cytotoxic activity and the standard reduction potential was found |
| publishDate |
2021 |
| dc.date.none.fl_str_mv |
2021 |
| dc.type.none.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion peer-reviewed |
| format |
article |
| status_str |
acceptedVersion |
| dc.identifier.none.fl_str_mv |
http://hdl.handle.net/10256/26257 |
| url |
http://hdl.handle.net/10256/26257 |
| dc.language.none.fl_str_mv |
Inglés |
| language_invalid_str_mv |
Inglés |
| dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jinorgbio.2021.111403 info:eu-repo/semantics/altIdentifier/issn/0162-0134 info:eu-repo/semantics/altIdentifier/eissn/1873-3344 |
| dc.rights.none.fl_str_mv |
Reconeixement-NoComercial-SenseObraDerivada 4.0 Internacional http://creativecommons.org/licenses/by-nc-nd/4.0 info:eu-repo/semantics/openAccess |
| rights_invalid_str_mv |
Reconeixement-NoComercial-SenseObraDerivada 4.0 Internacional http://creativecommons.org/licenses/by-nc-nd/4.0 |
| eu_rights_str_mv |
openAccess |
| dc.format.none.fl_str_mv |
application/pdf |
| dc.publisher.none.fl_str_mv |
Elsevier |
| publisher.none.fl_str_mv |
Elsevier |
| dc.source.none.fl_str_mv |
© Journal of Inorganic Biochemistry, 2021, vol. 218, art.núm.111403 Articles publicats (D-B) Leal, Jorge Santos, Lúcia H.M.L.M. Fernández-Aroca, Diego M. Cuevas-Vicario, José Vicente Martínez, Ma Ángeles Massaguer i Vall-llovera, Anna Jalón, Félix A. Ruiz-Hidalgo, María José Sánchez-Prieto, Ricardo Rodríguez, Ana maría Blanco Castañeda Peñalvo, Gregorio Dura, Gema Carriõn, María Carmen Barrabés Vera, Sílvia Manzano, Blanca R. 2021 Effect of the aniline fragment in Pt(II) and Pt(IV) complexes as anti-proliferative agents. Standard reduction potential as a more reliable parameter for Pt(IV) compounds than peak reduction potential. Journal of Inorganic Biochemistry 218 art.núm.111403 reponame:Recercat. Dipósit de la Recerca de Catalunya instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
| instname_str |
Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
| reponame_str |
Recercat. Dipósit de la Recerca de Catalunya |
| collection |
Recercat. Dipósit de la Recerca de Catalunya |
| repository.name.fl_str_mv |
|
| repository.mail.fl_str_mv |
|
| _version_ |
1869416110823047168 |
| score |
15,81155 |