Novel Copper(II) Coordination Compounds Containing Pyridine Derivatives of <i>N</i><sup>4</sup>-Methoxyphenyl-Thiosemicarbazones with Selective Anticancer Activity
Ten coordination compounds, [Cu(L<sup>1</sup>)Cl] (<b>C1</b>), [Cu(L<sup>1</sup>)NO<sub>3</sub>] (<b>C2</b>), [Cu(L<sup>2</sup>)Cl] (C3), [Cu(L<sup>2</sup>)NO<sub>3</sub>] (<b>C4</b>), [Cu(L&l...
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2024-12-01
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| author | Roman Rusnac Olga Garbuz Victor Kravtsov Elena Melnic Dorin Istrati Victor Tsapkov Donald Poirier Aurelian Gulea |
| author_facet | Roman Rusnac Olga Garbuz Victor Kravtsov Elena Melnic Dorin Istrati Victor Tsapkov Donald Poirier Aurelian Gulea |
| author_sort | Roman Rusnac |
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| description | Ten coordination compounds, [Cu(L<sup>1</sup>)Cl] (<b>C1</b>), [Cu(L<sup>1</sup>)NO<sub>3</sub>] (<b>C2</b>), [Cu(L<sup>2</sup>)Cl] (C3), [Cu(L<sup>2</sup>)NO<sub>3</sub>] (<b>C4</b>), [Cu(L<sup>3</sup>)Cl] (<b>C5</b>), [Cu(L<sup>3</sup>)NO<sub>3</sub>] (<b>C6</b>), [Cu(L<sup>4</sup>)NO<sub>3</sub>] (<b>C7</b>), [Cu(L<sup>4</sup>)Cl] (<b>C8</b>), [Cu(L<sup>5</sup>)Cl] (<b>C9</b>), and [Cu(L<sup>5</sup>)NO<sub>3</sub>] (<b>C10</b>), containing pyridine derivatives of <i>N</i><sup>4</sup>-methoxyphenyl-thiosemicarbazones were synthesized and characterized. The molecular structure of four compounds was investigated using single crystal X-ray diffraction. Spectral analysis techniques such as FT-IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, elemental analysis, and molar conductivity were used for all the synthesized compounds. The tested synthesized compounds were evaluated for their anticancer activity and selectivity against a variety of cancer cell lines, including HL-60, LNCaP, MCF-7, HepG-2, K-562, HeLa, BxPC-3, RD, and MDCK normal cell line. Most compounds demonstrated selective anticancer activity superior to doxorubicin. Notably, all ligands showed high antiproliferative activity against HL-60 cells, with IC<sub>50</sub> values between 0.01 and 0.06 µM and a selectivity index as high as 5000. Coordination of copper(II) with ligands <b>HL<sup>1</sup></b> and <b>HL<sup>3</sup></b> notably enhanced antiproliferative activity, lowering the IC<sub>50</sub> to 0.03 µM. Additionally, the antioxidant activity of these compounds was assessed, revealing that all tested ligands and most coordination compounds exhibited greater antioxidant activity compared to Trolox, with some ligands showing activity up to 12.3 times higher. Toxicity studies on <i>Daphnia magna</i> indicated low toxicity for the ligands, generally less than doxorubicin, with LC<sub>50</sub> values ranging from 13 to 90 µM, suggesting moderate toxicity. Conversely, the coordination complexes were more toxic, with LC<sub>50</sub> values between 0.5 and 13 µM. |
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| spelling | doaj-art-d2c32cb6535c40a1a3c8b1145c0e64b72024-12-27T14:42:54ZengMDPI AGMolecules1420-30492024-12-012924600210.3390/molecules29246002Novel Copper(II) Coordination Compounds Containing Pyridine Derivatives of <i>N</i><sup>4</sup>-Methoxyphenyl-Thiosemicarbazones with Selective Anticancer ActivityRoman Rusnac0Olga Garbuz1Victor Kravtsov2Elena Melnic3Dorin Istrati4Victor Tsapkov5Donald Poirier6Aurelian Gulea7Laboratory of Advanced Materials in Biopharmaceutics and Technics, Institute of Chemistry, Moldova State University, MD-2009 Chisinau, MoldovaLaboratory of Systematics and Molecular Phylogenetics, Institute of Zoology, Moldova State University, MD-2028 Chisinau, MoldovaLaboratory of Physical Methods of Solid State Investigation “Tadeusz Malinowski”, Institute of Applied Physics, Moldova State University, MD-2028 Chisinau, MoldovaLaboratory of Physical Methods of Solid State Investigation “Tadeusz Malinowski”, Institute of Applied Physics, Moldova State University, MD-2028 Chisinau, MoldovaDepartment of Dentistry, University of Medicine and Pharmacy “Nicolae Testemitanu”, MD-2004 Chisinau, MoldovaLaboratory of Advanced Materials in Biopharmaceutics and Technics, Institute of Chemistry, Moldova State University, MD-2009 Chisinau, MoldovaLaboratory of Medicinal Chemistry, CHU de Québec Research Center, Université Laval, Québec, QC G1V 4G2, CanadaLaboratory of Advanced Materials in Biopharmaceutics and Technics, Institute of Chemistry, Moldova State University, MD-2009 Chisinau, MoldovaTen coordination compounds, [Cu(L<sup>1</sup>)Cl] (<b>C1</b>), [Cu(L<sup>1</sup>)NO<sub>3</sub>] (<b>C2</b>), [Cu(L<sup>2</sup>)Cl] (C3), [Cu(L<sup>2</sup>)NO<sub>3</sub>] (<b>C4</b>), [Cu(L<sup>3</sup>)Cl] (<b>C5</b>), [Cu(L<sup>3</sup>)NO<sub>3</sub>] (<b>C6</b>), [Cu(L<sup>4</sup>)NO<sub>3</sub>] (<b>C7</b>), [Cu(L<sup>4</sup>)Cl] (<b>C8</b>), [Cu(L<sup>5</sup>)Cl] (<b>C9</b>), and [Cu(L<sup>5</sup>)NO<sub>3</sub>] (<b>C10</b>), containing pyridine derivatives of <i>N</i><sup>4</sup>-methoxyphenyl-thiosemicarbazones were synthesized and characterized. The molecular structure of four compounds was investigated using single crystal X-ray diffraction. Spectral analysis techniques such as FT-IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, elemental analysis, and molar conductivity were used for all the synthesized compounds. The tested synthesized compounds were evaluated for their anticancer activity and selectivity against a variety of cancer cell lines, including HL-60, LNCaP, MCF-7, HepG-2, K-562, HeLa, BxPC-3, RD, and MDCK normal cell line. Most compounds demonstrated selective anticancer activity superior to doxorubicin. Notably, all ligands showed high antiproliferative activity against HL-60 cells, with IC<sub>50</sub> values between 0.01 and 0.06 µM and a selectivity index as high as 5000. Coordination of copper(II) with ligands <b>HL<sup>1</sup></b> and <b>HL<sup>3</sup></b> notably enhanced antiproliferative activity, lowering the IC<sub>50</sub> to 0.03 µM. Additionally, the antioxidant activity of these compounds was assessed, revealing that all tested ligands and most coordination compounds exhibited greater antioxidant activity compared to Trolox, with some ligands showing activity up to 12.3 times higher. Toxicity studies on <i>Daphnia magna</i> indicated low toxicity for the ligands, generally less than doxorubicin, with LC<sub>50</sub> values ranging from 13 to 90 µM, suggesting moderate toxicity. Conversely, the coordination complexes were more toxic, with LC<sub>50</sub> values between 0.5 and 13 µM.https://www.mdpi.com/1420-3049/29/24/6002coordination compounds<i>N</i><sup>4</sup><i>-</i>methoxyphenyl thiosemicarbazonesanticancer agentsmolecular structureantioxidant activitytoxicity |
| spellingShingle | Roman Rusnac Olga Garbuz Victor Kravtsov Elena Melnic Dorin Istrati Victor Tsapkov Donald Poirier Aurelian Gulea Novel Copper(II) Coordination Compounds Containing Pyridine Derivatives of <i>N</i><sup>4</sup>-Methoxyphenyl-Thiosemicarbazones with Selective Anticancer Activity Molecules coordination compounds <i>N</i><sup>4</sup><i>-</i>methoxyphenyl thiosemicarbazones anticancer agents molecular structure antioxidant activity toxicity |
| title | Novel Copper(II) Coordination Compounds Containing Pyridine Derivatives of <i>N</i><sup>4</sup>-Methoxyphenyl-Thiosemicarbazones with Selective Anticancer Activity |
| title_full | Novel Copper(II) Coordination Compounds Containing Pyridine Derivatives of <i>N</i><sup>4</sup>-Methoxyphenyl-Thiosemicarbazones with Selective Anticancer Activity |
| title_fullStr | Novel Copper(II) Coordination Compounds Containing Pyridine Derivatives of <i>N</i><sup>4</sup>-Methoxyphenyl-Thiosemicarbazones with Selective Anticancer Activity |
| title_full_unstemmed | Novel Copper(II) Coordination Compounds Containing Pyridine Derivatives of <i>N</i><sup>4</sup>-Methoxyphenyl-Thiosemicarbazones with Selective Anticancer Activity |
| title_short | Novel Copper(II) Coordination Compounds Containing Pyridine Derivatives of <i>N</i><sup>4</sup>-Methoxyphenyl-Thiosemicarbazones with Selective Anticancer Activity |
| title_sort | novel copper ii coordination compounds containing pyridine derivatives of i n i sup 4 sup methoxyphenyl thiosemicarbazones with selective anticancer activity |
| topic | coordination compounds <i>N</i><sup>4</sup><i>-</i>methoxyphenyl thiosemicarbazones anticancer agents molecular structure antioxidant activity toxicity |
| url | https://www.mdpi.com/1420-3049/29/24/6002 |
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