Luminescent cyclometalated platinum compounds with N, P, and O^O ligands: Density-functional theory studies and analysis of the anticancer potential

Luminescent platinum cyclometalated complexes are species of interest mainly due to their applications in the optoelectronic and biological fields, especially with regard to their anticancer activity. Given this level of interest, a series of cyclometalated (2-[2′-thienyl]pyridinate, thpy and 2-[2,4...

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Autores: Leal, Jorge, Durá, Gema, Jalón, Félix A., Zafon, Elisenda, Massaguer i Vall-llovera, Anna, Cuevas-Vicario, José Vicente, Santos Peinado, Lucía, Rodríguez, Ana María Blanco, Manzano, Blanca R.
Tipo de documento: artigo
Estado:Versão publicada
Data de publicação:2023
País:España
Recursos:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositório:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:10256/27495
Acesso em linha:http://hdl.handle.net/10256/27495
Access Level:Acceso aberto
Palavra-chave:Patí -- Ús terapèutic
Platinum -- Therapeutic use
Fotoquimioteràpia
Photochemotherapy
Càncer -- Tractament
Cancer -- Treatment
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spelling Luminescent cyclometalated platinum compounds with N, P, and O^O ligands: Density-functional theory studies and analysis of the anticancer potentialLeal, JorgeDurá, GemaJalón, Félix A.Zafon, ElisendaMassaguer i Vall-llovera, AnnaCuevas-Vicario, José VicenteSantos Peinado, LucíaRodríguez, Ana María BlancoManzano, Blanca R.Patí -- Ús terapèuticPlatinum -- Therapeutic useFotoquimioteràpiaPhotochemotherapyCàncer -- TractamentCancer -- TreatmentLuminescent platinum cyclometalated complexes are species of interest mainly due to their applications in the optoelectronic and biological fields, especially with regard to their anticancer activity. Given this level of interest, a series of cyclometalated (2-[2′-thienyl]pyridinate, thpy and 2-[2,4-difluorophenyl]pyridinate, dfppy) platinum complexes with N-donor, PTA (1,3,5-triaza-7-phosphaadamantane) or chrysin-derived ligands (incorporating piperidine, HL1, or morpholine, HL2, fragments) were synthesized. The complexes are luminescent with tunable emission wavelengths. Aggregation in solution was observed for [Pt(dfppy)L1], 5. Density-functional theory (DFT) studies provided descriptions of the highest occupied molecular orbital (HOMO) and least unoccupied molecular orbital (LUMO) characteristics and their influence on the photophysical properties. The orbitals of 5–6 were different in nature to those of 1–4. Time-dependent DFT (TD-DFT) calculations showed that for 1–4 the excited states S<inf>1</inf> and T<inf>1</inf> reflect metal-to-ligand charge transfer (MLCT) and ligand-centered (LC) (C^N) contributions while for 5–6 these states are an LC transition centered on L1 or L2. The speciation in DMSO and DMSO/H<inf>2</inf>O was evaluated. Biological studies showed that [Pt(thpy)Cl(Hthpy)], 1, [Pt(dfppy)Cl(Hdfppy)], 2, and 5 exert significant cytotoxic activity against human cervical (HeLa) and lung (A549) carcinoma cells. The cytotoxicity of 1 increased 2.84-fold upon irradiation (blue). Microscopy assays on 5 showed that this compound accumulates in cytoplasmic organelles, preferentially in mitochondria. Mitochondrial metabolism was disrupted by the activity of the complexes, leading to a decline in the adenosine triphosphate (ATP) cellular content. Overall, the results show an alternative anticancer activity for complexes 1, 2, and 5, which could be of great interest for the treatment of tumors with acquired resistance to conventional DNA-targeted anticancer drugsResearch funding: Spanish Ministerio de Ciencia, Innovación y Universidades (MCIU), Agencia Estatal de Investigación (AEI), and Fondo Europeo de Desarrollo Regional (FEDER). Grant Numbers: RTI2018-100709-B-C21, RTI2018-100709-B-C22; Junta de Comunidades de Castilla-La Mancha-FEDER (JCCM). Grant Number: SBPLY/19/180501/000260 UCLM-FEDER. Grant Numbers: 2020-GRIN-29093, 2021-GRIN-30981; European Regional Development Fund. Grant Number: SBPLY/19/180501/000191 and Generalitat de Catalunya. Grant Number: 2021 FI_B 01036WileyAgencia Estatal de Investigación2023info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionpeer-reviewedapplication/pdfhttp://hdl.handle.net/10256/27495http://hdl.handle.net/10256/27495Applied Organometallic Chemistry, 2023, vol. 37, núm. 3, p. e6983Articles publicats (D-B)reponame: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/10.1002/aoc.6983info:eu-repo/semantics/altIdentifier/issn/0268-2605info:eu-repo/semantics/altIdentifier/eissn/1099-0739RTI2018-100709-B-C22info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/RTI2018-100709-B-C22Attribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:recercat.cat:10256/274952026-05-29T05:05:01Z
dc.title.none.fl_str_mv Luminescent cyclometalated platinum compounds with N, P, and O^O ligands: Density-functional theory studies and analysis of the anticancer potential
title Luminescent cyclometalated platinum compounds with N, P, and O^O ligands: Density-functional theory studies and analysis of the anticancer potential
spellingShingle Luminescent cyclometalated platinum compounds with N, P, and O^O ligands: Density-functional theory studies and analysis of the anticancer potential
Leal, Jorge
Patí -- Ús terapèutic
Platinum -- Therapeutic use
Fotoquimioteràpia
Photochemotherapy
Càncer -- Tractament
Cancer -- Treatment
title_short Luminescent cyclometalated platinum compounds with N, P, and O^O ligands: Density-functional theory studies and analysis of the anticancer potential
title_full Luminescent cyclometalated platinum compounds with N, P, and O^O ligands: Density-functional theory studies and analysis of the anticancer potential
title_fullStr Luminescent cyclometalated platinum compounds with N, P, and O^O ligands: Density-functional theory studies and analysis of the anticancer potential
title_full_unstemmed Luminescent cyclometalated platinum compounds with N, P, and O^O ligands: Density-functional theory studies and analysis of the anticancer potential
title_sort Luminescent cyclometalated platinum compounds with N, P, and O^O ligands: Density-functional theory studies and analysis of the anticancer potential
dc.creator.none.fl_str_mv Leal, Jorge
Durá, Gema
Jalón, Félix A.
Zafon, Elisenda
Massaguer i Vall-llovera, Anna
Cuevas-Vicario, José Vicente
Santos Peinado, Lucía
Rodríguez, Ana María Blanco
Manzano, Blanca R.
author Leal, Jorge
author_facet Leal, Jorge
Durá, Gema
Jalón, Félix A.
Zafon, Elisenda
Massaguer i Vall-llovera, Anna
Cuevas-Vicario, José Vicente
Santos Peinado, Lucía
Rodríguez, Ana María Blanco
Manzano, Blanca R.
author_role author
author2 Durá, Gema
Jalón, Félix A.
Zafon, Elisenda
Massaguer i Vall-llovera, Anna
Cuevas-Vicario, José Vicente
Santos Peinado, Lucía
Rodríguez, Ana María Blanco
Manzano, Blanca R.
author2_role author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Agencia Estatal de Investigación
dc.subject.none.fl_str_mv Patí -- Ús terapèutic
Platinum -- Therapeutic use
Fotoquimioteràpia
Photochemotherapy
Càncer -- Tractament
Cancer -- Treatment
topic Patí -- Ús terapèutic
Platinum -- Therapeutic use
Fotoquimioteràpia
Photochemotherapy
Càncer -- Tractament
Cancer -- Treatment
description Luminescent platinum cyclometalated complexes are species of interest mainly due to their applications in the optoelectronic and biological fields, especially with regard to their anticancer activity. Given this level of interest, a series of cyclometalated (2-[2′-thienyl]pyridinate, thpy and 2-[2,4-difluorophenyl]pyridinate, dfppy) platinum complexes with N-donor, PTA (1,3,5-triaza-7-phosphaadamantane) or chrysin-derived ligands (incorporating piperidine, HL1, or morpholine, HL2, fragments) were synthesized. The complexes are luminescent with tunable emission wavelengths. Aggregation in solution was observed for [Pt(dfppy)L1], 5. Density-functional theory (DFT) studies provided descriptions of the highest occupied molecular orbital (HOMO) and least unoccupied molecular orbital (LUMO) characteristics and their influence on the photophysical properties. The orbitals of 5–6 were different in nature to those of 1–4. Time-dependent DFT (TD-DFT) calculations showed that for 1–4 the excited states S<inf>1</inf> and T<inf>1</inf> reflect metal-to-ligand charge transfer (MLCT) and ligand-centered (LC) (C^N) contributions while for 5–6 these states are an LC transition centered on L1 or L2. The speciation in DMSO and DMSO/H<inf>2</inf>O was evaluated. Biological studies showed that [Pt(thpy)Cl(Hthpy)], 1, [Pt(dfppy)Cl(Hdfppy)], 2, and 5 exert significant cytotoxic activity against human cervical (HeLa) and lung (A549) carcinoma cells. The cytotoxicity of 1 increased 2.84-fold upon irradiation (blue). Microscopy assays on 5 showed that this compound accumulates in cytoplasmic organelles, preferentially in mitochondria. Mitochondrial metabolism was disrupted by the activity of the complexes, leading to a decline in the adenosine triphosphate (ATP) cellular content. Overall, the results show an alternative anticancer activity for complexes 1, 2, and 5, which could be of great interest for the treatment of tumors with acquired resistance to conventional DNA-targeted anticancer drugs
publishDate 2023
dc.date.none.fl_str_mv 2023
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
peer-reviewed
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10256/27495
http://hdl.handle.net/10256/27495
url http://hdl.handle.net/10256/27495
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/aoc.6983
info:eu-repo/semantics/altIdentifier/issn/0268-2605
info:eu-repo/semantics/altIdentifier/eissn/1099-0739
RTI2018-100709-B-C22
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/RTI2018-100709-B-C22
dc.rights.none.fl_str_mv Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution-NonCommercial-NoDerivatives 4.0 International
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 Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv Applied Organometallic Chemistry, 2023, vol. 37, núm. 3, p. e6983
Articles publicats (D-B)
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
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