Synthesis and Evaluation of Cytotoxic Activity of RuCp(II) Complexes Bearing (Iso)nicotinic Acid Based Ligands
Background/Objectives: Cancer remains one of the major challenges of our century. Organometallic ruthenium complexes are gaining recognition as a highly promising group of compounds in the development of cancer treatments. Methods: Building on the auspicious results obtained for [Ru(η<sup>5<...
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2025-01-01
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| author | Bárbara Marques Diogo M. Engrácia João Franco Machado Jaime A. S. Coelho Filipa Mendes Tânia S. Morais |
| author_facet | Bárbara Marques Diogo M. Engrácia João Franco Machado Jaime A. S. Coelho Filipa Mendes Tânia S. Morais |
| author_sort | Bárbara Marques |
| collection | DOAJ |
| description | Background/Objectives: Cancer remains one of the major challenges of our century. Organometallic ruthenium complexes are gaining recognition as a highly promising group of compounds in the development of cancer treatments. Methods: Building on the auspicious results obtained for [Ru(η<sup>5</sup>-C<sub>5</sub>H<sub>5</sub>)(PPh<sub>3</sub>)(bipy)][CF<sub>3</sub>SO<sub>3</sub>] (TM34), our focus has shifted to examining the effects of incorporating bioactive ligands into the TM34 framework, particularly within the cyclopentadienyl ring. Results: In this study, we report the synthesis and characterization of two new ruthenium(II) complexes with the general formula [Ru(η<sup>5</sup>-C<sub>5</sub>H<sub>4</sub>CCH<sub>3</sub>=R)(PPh<sub>3</sub>)(bipy)][CF<sub>3</sub>SO<sub>3</sub>], where R represents a nicotinic acid derivative (NNHCO(py-3-yl)) (1) or an isoniazid derivative (NNHCO(py-4-yl)) (2). The complexes were fully characterized using a combination of spectroscopic techniques and computational analysis, revealing the presence of <i>E/Z</i>-hydrazone isomerism. Stability studies confirmed the robustness of both complexes in biological media, with compound 1 maintaining good stability in buffer solutions mimicking physiological (pH 7.4) and tumor-like (pH 6.8) environments. The cytotoxicity of the complexes was evaluated in vitro in several human cancer cell lines, namely melanoma (A375), alveolar adenocarcinoma (A549), epidermoid carcinoma (A431), and breast cancer (MDA-MB 231). Conclusions: Both compounds exhibited moderate to high cytotoxic activity, with complex 1 showing a greater propensity to induce cell death, particularly in the A431 and MDA-MB 231 cell lines. |
| format | Article |
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| institution | Kabale University |
| issn | 1424-8247 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | MDPI AG |
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| spelling | doaj-art-bce9ca598ec945dc9a4c12c224d6c9c72025-01-24T13:45:23ZengMDPI AGPharmaceuticals1424-82472025-01-011819710.3390/ph18010097Synthesis and Evaluation of Cytotoxic Activity of RuCp(II) Complexes Bearing (Iso)nicotinic Acid Based LigandsBárbara Marques0Diogo M. Engrácia1João Franco Machado2Jaime A. S. Coelho3Filipa Mendes4Tânia S. Morais5Centro de Química Estrutural, Institute of Molecular Sciences, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, 1749-016 Lisboa, PortugalCentro de Ciências e Tecnologias Nucleares, Instituto Superior Técnico, Universidade de Lisboa, 2695-066 Bobadela LRS, PortugalCentro de Química Estrutural, Institute of Molecular Sciences, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, 1749-016 Lisboa, PortugalCentro de Química Estrutural, Institute of Molecular Sciences, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, 1749-016 Lisboa, PortugalCentro de Ciências e Tecnologias Nucleares, Instituto Superior Técnico, Universidade de Lisboa, 2695-066 Bobadela LRS, PortugalCentro de Química Estrutural, Institute of Molecular Sciences, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, 1749-016 Lisboa, PortugalBackground/Objectives: Cancer remains one of the major challenges of our century. Organometallic ruthenium complexes are gaining recognition as a highly promising group of compounds in the development of cancer treatments. Methods: Building on the auspicious results obtained for [Ru(η<sup>5</sup>-C<sub>5</sub>H<sub>5</sub>)(PPh<sub>3</sub>)(bipy)][CF<sub>3</sub>SO<sub>3</sub>] (TM34), our focus has shifted to examining the effects of incorporating bioactive ligands into the TM34 framework, particularly within the cyclopentadienyl ring. Results: In this study, we report the synthesis and characterization of two new ruthenium(II) complexes with the general formula [Ru(η<sup>5</sup>-C<sub>5</sub>H<sub>4</sub>CCH<sub>3</sub>=R)(PPh<sub>3</sub>)(bipy)][CF<sub>3</sub>SO<sub>3</sub>], where R represents a nicotinic acid derivative (NNHCO(py-3-yl)) (1) or an isoniazid derivative (NNHCO(py-4-yl)) (2). The complexes were fully characterized using a combination of spectroscopic techniques and computational analysis, revealing the presence of <i>E/Z</i>-hydrazone isomerism. Stability studies confirmed the robustness of both complexes in biological media, with compound 1 maintaining good stability in buffer solutions mimicking physiological (pH 7.4) and tumor-like (pH 6.8) environments. The cytotoxicity of the complexes was evaluated in vitro in several human cancer cell lines, namely melanoma (A375), alveolar adenocarcinoma (A549), epidermoid carcinoma (A431), and breast cancer (MDA-MB 231). Conclusions: Both compounds exhibited moderate to high cytotoxic activity, with complex 1 showing a greater propensity to induce cell death, particularly in the A431 and MDA-MB 231 cell lines.https://www.mdpi.com/1424-8247/18/1/97ruthenium–cyclopentadienylorganometallic(iso)nicotinic acidDFTanticancer |
| spellingShingle | Bárbara Marques Diogo M. Engrácia João Franco Machado Jaime A. S. Coelho Filipa Mendes Tânia S. Morais Synthesis and Evaluation of Cytotoxic Activity of RuCp(II) Complexes Bearing (Iso)nicotinic Acid Based Ligands Pharmaceuticals ruthenium–cyclopentadienyl organometallic (iso)nicotinic acid DFT anticancer |
| title | Synthesis and Evaluation of Cytotoxic Activity of RuCp(II) Complexes Bearing (Iso)nicotinic Acid Based Ligands |
| title_full | Synthesis and Evaluation of Cytotoxic Activity of RuCp(II) Complexes Bearing (Iso)nicotinic Acid Based Ligands |
| title_fullStr | Synthesis and Evaluation of Cytotoxic Activity of RuCp(II) Complexes Bearing (Iso)nicotinic Acid Based Ligands |
| title_full_unstemmed | Synthesis and Evaluation of Cytotoxic Activity of RuCp(II) Complexes Bearing (Iso)nicotinic Acid Based Ligands |
| title_short | Synthesis and Evaluation of Cytotoxic Activity of RuCp(II) Complexes Bearing (Iso)nicotinic Acid Based Ligands |
| title_sort | synthesis and evaluation of cytotoxic activity of rucp ii complexes bearing iso nicotinic acid based ligands |
| topic | ruthenium–cyclopentadienyl organometallic (iso)nicotinic acid DFT anticancer |
| url | https://www.mdpi.com/1424-8247/18/1/97 |
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