A new family of iron(II)-cyclopentadienyl compounds shows strong activity against colorectal and triple negative breast cancer cells
Autor(a) principal: | |
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Data de Publicação: | 2020 |
Outros Autores: | , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/1822/64877 |
Resumo: | The following is available online, Figure S1—1H NMR spectrum of complexes 6, in acetone-d6, Table S1. Bond lengths [Å] and angles [°] for [Fe(η5-Cp)(CO)(PhCN)(PPh3)][CF3SO3] 1, [Fe(η5-Cp)(CO)(p-NCPhNH2)(PPh3)][CF3SO3] 4 and [Fe(η5-Cp)(CO)(p-NCPhBr)(PPh3)][CF3SO3] 5, Table S2. Relevant TD-DFT (PBE0) excitation energies (λ), oscillator strengths (f) and compositions (only those > 5% are shown), for complexes 1–6, compared with experimental data (λexp). Both calculated and experimental values were obtained in dichloromethane, Figure S2—UV-Vis spectra of complexes 1–6 in DMSO along the 24 h study, Figure S3—UV-Vis spectra of complexes 1–6 in DMSO/DMEM mixture along the 24 h study and its variation plot (%) (bottom), Figure S4. ‘FeCp’ compounds affect the colony formation ability of SW480 cell line. Analysis of the colony formation ability, after 48 h of incubation with 1/4 IC50 and IC50, in SW480 cell line. Representative images of colony formation assay in SW480 cell line, Figure S5. ‘FeCp’ compounds induce apoptosis colorectal cancer-derived cell line. Apoptotic cell death was analyzed by Annexin V fluorescein isothiocyanate (AV-FITC) and propidium iodide (PI) assay in SW480 cells, after incubation with IC50 and 2×IC50 concentrations for 48 h. Representative histograms of SW480 cell line double stained with AV and PI, Table S4. Crystal data and structure refinement for [Fe(η5-Cp)(CO)(PhCN)(PPh3)][CF3SO3] 1, [Fe(η5-Cp)(CO)(p-NCPhNH2)(PPh3)][CF3SO3] 4 and [Fe(η5-Cp)(CO)(p-NCPhBr)(PPh3)][CF3SO3] 5. |
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A new family of iron(II)-cyclopentadienyl compounds shows strong activity against colorectal and triple negative breast cancer cellsiron(II)-cyclopentadienylnitrile-based ligandscolorectal cancertriple negative breast cancerScience & TechnologyThe following is available online, Figure S1—1H NMR spectrum of complexes 6, in acetone-d6, Table S1. Bond lengths [Å] and angles [°] for [Fe(η5-Cp)(CO)(PhCN)(PPh3)][CF3SO3] 1, [Fe(η5-Cp)(CO)(p-NCPhNH2)(PPh3)][CF3SO3] 4 and [Fe(η5-Cp)(CO)(p-NCPhBr)(PPh3)][CF3SO3] 5, Table S2. Relevant TD-DFT (PBE0) excitation energies (λ), oscillator strengths (f) and compositions (only those > 5% are shown), for complexes 1–6, compared with experimental data (λexp). Both calculated and experimental values were obtained in dichloromethane, Figure S2—UV-Vis spectra of complexes 1–6 in DMSO along the 24 h study, Figure S3—UV-Vis spectra of complexes 1–6 in DMSO/DMEM mixture along the 24 h study and its variation plot (%) (bottom), Figure S4. ‘FeCp’ compounds affect the colony formation ability of SW480 cell line. Analysis of the colony formation ability, after 48 h of incubation with 1/4 IC50 and IC50, in SW480 cell line. Representative images of colony formation assay in SW480 cell line, Figure S5. ‘FeCp’ compounds induce apoptosis colorectal cancer-derived cell line. Apoptotic cell death was analyzed by Annexin V fluorescein isothiocyanate (AV-FITC) and propidium iodide (PI) assay in SW480 cells, after incubation with IC50 and 2×IC50 concentrations for 48 h. Representative histograms of SW480 cell line double stained with AV and PI, Table S4. Crystal data and structure refinement for [Fe(η5-Cp)(CO)(PhCN)(PPh3)][CF3SO3] 1, [Fe(η5-Cp)(CO)(p-NCPhNH2)(PPh3)][CF3SO3] 4 and [Fe(η5-Cp)(CO)(p-NCPhBr)(PPh3)][CF3SO3] 5.A family of compounds with the general formula [Fe(η<sup>5</sup>-C<sub>5</sub>H<sub>5</sub>)(CO)(PPh<sub>3</sub>)(NCR)]<sup>+</sup> has been synthesized (NCR = benzonitrile (<b>1</b>); 4-hydroxybenzonitrile (<b>2</b>); 4-hydroxymethylbenzonitrile (<b>3</b>); 4-aminobenzonitrile (<b>4</b>); 4-bromobenzonitrile (<b>5</b>); and, 4-chlorocinnamonitrile (<b>6</b>)). All of the compounds were obtained in good yields and were completely characterized by standard spectroscopic and analytical techniques. Compounds <b>1</b>, <b>4</b>, and <b>5</b> crystallize in the monoclinc P21/c space group and packing is determined by short contacts between the phosphane phenyl rings and cyclopentadienyl (compounds <b>1</b> and <b>4</b>) or π-π lateral interactions between the benzonitrile molecules (complex <b>5</b>). DFT and TD-DFT calculations were performed to help in the interpretation of the experimental UV-Vis. data and assign the electronic transitions. Cytotoxicity studies in MDA-MB-231 breast and SW480 colorectal cancer-derived cell lines showed IC<sub>50</sub> values at a low micromolar range for all of the compounds in both cell lines. The determination of the selectivity index for colorectal cells (SW480 vs. NCM460, a normal colon-derived cell line) indicates that the compounds have some inherent selectivity. Further studies on the SW480 cell line demonstrated that the compounds induce cell death by apoptosis, inhibit proliferation by inhibiting the formation of colonies, and affect the actin-cytoskeleton of the cells. These results are not observed for the hydroxylated compounds <b>2</b> and <b>3</b>, where an alternative mode of action might be present. Overall, the results indicate that the substituent at the nitrile-based ligand is associated to the biological activity of the compounds.Centro de Química Estrutural acknowledges Fundação para a Ciência e Tecnologia (FCT) for the Project UIDB/00100/2020. This work was also funded in the scope of the project PTDC/QUI-QIN/28662/2017 (FCT) and by the strategic program UID/BIA/04050/2019 (FCT). A. Pilon and Ana Rita Brás thank FCT for their Ph.D. Grants (SFRH/BD/139412/2018 and SFRH/BD/139271/2018, respectively). A. Valente acknowledges the CEECIND 2017 Initiative (CEECIND/01974/2017). P. J Costa thank FCT for Investigador FCT Program IF/00069/2014, exploratory project IF/00069/2014/CP1216/CT0006, and strategic project UID/MULTI/04046/2019. P. J. Costa also acknowledges FCT, Programa Operacional Regional de Lisboa (Lisboa 2020), Portugal 2020, FEDER/FN, and the European Union for project LISBOA-01-0145-FEDER-028455 / PTDC/QUI-QFI/28455/2017.Multidisciplinary Digital Publishing InstituteUniversidade do MinhoPilon, AdhanBrás, Ana RitaCôrte-Real, LeonorAvecilla, FernandoCosta, Paulo J.Preto, AnaGarcia, M. HelenaValente, Andreia2020-03-302020-03-30T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/64877engPilon, A.; Brás, A.R.; Côrte-Real, L.; Avecilla, F.; Costa, P.J.; Preto, A.; Garcia, M.H.; Valente, A. A New Family of Iron(II)-Cyclopentadienyl Compounds Shows Strong Activity against Colorectal and Triple Negative Breast Cancer Cells. Molecules 2020, 25, 1592.1420-304910.3390/molecules2507159232235674https://www.mdpi.com/1420-3049/25/7/1592info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-21T12:44:07Zoai:repositorium.sdum.uminho.pt:1822/64877Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:41:44.580840Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
A new family of iron(II)-cyclopentadienyl compounds shows strong activity against colorectal and triple negative breast cancer cells |
title |
A new family of iron(II)-cyclopentadienyl compounds shows strong activity against colorectal and triple negative breast cancer cells |
spellingShingle |
A new family of iron(II)-cyclopentadienyl compounds shows strong activity against colorectal and triple negative breast cancer cells Pilon, Adhan iron(II)-cyclopentadienyl nitrile-based ligands colorectal cancer triple negative breast cancer Science & Technology |
title_short |
A new family of iron(II)-cyclopentadienyl compounds shows strong activity against colorectal and triple negative breast cancer cells |
title_full |
A new family of iron(II)-cyclopentadienyl compounds shows strong activity against colorectal and triple negative breast cancer cells |
title_fullStr |
A new family of iron(II)-cyclopentadienyl compounds shows strong activity against colorectal and triple negative breast cancer cells |
title_full_unstemmed |
A new family of iron(II)-cyclopentadienyl compounds shows strong activity against colorectal and triple negative breast cancer cells |
title_sort |
A new family of iron(II)-cyclopentadienyl compounds shows strong activity against colorectal and triple negative breast cancer cells |
author |
Pilon, Adhan |
author_facet |
Pilon, Adhan Brás, Ana Rita Côrte-Real, Leonor Avecilla, Fernando Costa, Paulo J. Preto, Ana Garcia, M. Helena Valente, Andreia |
author_role |
author |
author2 |
Brás, Ana Rita Côrte-Real, Leonor Avecilla, Fernando Costa, Paulo J. Preto, Ana Garcia, M. Helena Valente, Andreia |
author2_role |
author author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Pilon, Adhan Brás, Ana Rita Côrte-Real, Leonor Avecilla, Fernando Costa, Paulo J. Preto, Ana Garcia, M. Helena Valente, Andreia |
dc.subject.por.fl_str_mv |
iron(II)-cyclopentadienyl nitrile-based ligands colorectal cancer triple negative breast cancer Science & Technology |
topic |
iron(II)-cyclopentadienyl nitrile-based ligands colorectal cancer triple negative breast cancer Science & Technology |
description |
The following is available online, Figure S1—1H NMR spectrum of complexes 6, in acetone-d6, Table S1. Bond lengths [Å] and angles [°] for [Fe(η5-Cp)(CO)(PhCN)(PPh3)][CF3SO3] 1, [Fe(η5-Cp)(CO)(p-NCPhNH2)(PPh3)][CF3SO3] 4 and [Fe(η5-Cp)(CO)(p-NCPhBr)(PPh3)][CF3SO3] 5, Table S2. Relevant TD-DFT (PBE0) excitation energies (λ), oscillator strengths (f) and compositions (only those > 5% are shown), for complexes 1–6, compared with experimental data (λexp). Both calculated and experimental values were obtained in dichloromethane, Figure S2—UV-Vis spectra of complexes 1–6 in DMSO along the 24 h study, Figure S3—UV-Vis spectra of complexes 1–6 in DMSO/DMEM mixture along the 24 h study and its variation plot (%) (bottom), Figure S4. ‘FeCp’ compounds affect the colony formation ability of SW480 cell line. Analysis of the colony formation ability, after 48 h of incubation with 1/4 IC50 and IC50, in SW480 cell line. Representative images of colony formation assay in SW480 cell line, Figure S5. ‘FeCp’ compounds induce apoptosis colorectal cancer-derived cell line. Apoptotic cell death was analyzed by Annexin V fluorescein isothiocyanate (AV-FITC) and propidium iodide (PI) assay in SW480 cells, after incubation with IC50 and 2×IC50 concentrations for 48 h. Representative histograms of SW480 cell line double stained with AV and PI, Table S4. Crystal data and structure refinement for [Fe(η5-Cp)(CO)(PhCN)(PPh3)][CF3SO3] 1, [Fe(η5-Cp)(CO)(p-NCPhNH2)(PPh3)][CF3SO3] 4 and [Fe(η5-Cp)(CO)(p-NCPhBr)(PPh3)][CF3SO3] 5. |
publishDate |
2020 |
dc.date.none.fl_str_mv |
2020-03-30 2020-03-30T00:00:00Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/1822/64877 |
url |
http://hdl.handle.net/1822/64877 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Pilon, A.; Brás, A.R.; Côrte-Real, L.; Avecilla, F.; Costa, P.J.; Preto, A.; Garcia, M.H.; Valente, A. A New Family of Iron(II)-Cyclopentadienyl Compounds Shows Strong Activity against Colorectal and Triple Negative Breast Cancer Cells. Molecules 2020, 25, 1592. 1420-3049 10.3390/molecules25071592 32235674 https://www.mdpi.com/1420-3049/25/7/1592 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Multidisciplinary Digital Publishing Institute |
publisher.none.fl_str_mv |
Multidisciplinary Digital Publishing Institute |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
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RCAAP |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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