Low-Dimensional Compounds Containing Bioactive Ligands. Part XIX: Crystal Structures and Biological Properties of Copper Complexes with Halogen and Nitro Derivatives of 8-Hydroxyquinoline
Six new copper(II) complexes were prepared: [Cu(ClBrQ)<sub>2</sub>] (<b>1a</b>, <b>1b</b>), [Cu(ClBrQ)<sub>2</sub>]·1/2 diox (<b>2</b>) (diox = 1,4-dioxane), [Cu(BrQ)<sub>2</sub>] (<b>3</b>), [Cu(dNQ)<sub>2<...
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MDPI AG
2022-11-01
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| Online Access: | https://www.mdpi.com/2304-6740/10/12/223 |
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| author | Martina Kepeňová Martin Kello Romana Smolková Michal Goga Richard Frenák Ľudmila Tkáčiková Miroslava Litecká Jan Šubrt Ivan Potočňák |
| author_facet | Martina Kepeňová Martin Kello Romana Smolková Michal Goga Richard Frenák Ľudmila Tkáčiková Miroslava Litecká Jan Šubrt Ivan Potočňák |
| author_sort | Martina Kepeňová |
| collection | DOAJ |
| description | Six new copper(II) complexes were prepared: [Cu(ClBrQ)<sub>2</sub>] (<b>1a</b>, <b>1b</b>), [Cu(ClBrQ)<sub>2</sub>]·1/2 diox (<b>2</b>) (diox = 1,4-dioxane), [Cu(BrQ)<sub>2</sub>] (<b>3</b>), [Cu(dNQ)<sub>2</sub>] (<b>4</b>), [Cu(dNQ)<sub>2</sub>(DMF)<sub>2</sub>] (<b>5</b>) and [Cu(ClNQ)<sub>2</sub>] (<b>6</b>), where HClBrQ is 5-chloro-7-bromo-8-hydroxyquinoline, HBrQ is 7-bromo-8-hydroxyquinoline, HClNQ is 5-chloro-7-nitro-8-hydroxyquinoline and HdNQ is 5,7-dinitro-8-hydroxyquinoline. Prepared compounds were characterised by infrared spectroscopy, elemental analysis and by X-ray structural analysis. Structural analysis revealed that all complexes are molecular. Square planar coordination of copper atoms in [Cu(XQ)<sub>2</sub>] (XQ = ClBrQ (<b>1a</b>, <b>1b</b>), BrQ (<b>3</b>) and ClNQ (<b>6</b>)) and tetragonal bipyramidal coordination in [Cu(dNQ)<sub>2</sub>(DMF)<sub>2</sub>] (<b>5</b>) complexes were observed. In these four complexes, bidentate chelate coordination of XQ ligands via oxygen and nitrogen atoms was found. Hydrogen bonds stabilizing the structure were observed in [Cu(dNQ)<sub>2</sub>(DMF)<sub>2</sub>] (<b>5</b>) and [Cu(ClNQ)<sub>2</sub>] (<b>6</b>), no other nonbonding interactions were noticed in all five structures. The stability of the complexes in DMSO and DMSO/water was evaluated by UV-Vis spectroscopy. Cytotoxic activity of the complexes and ligands was tested against MCF-7, MDA-MB-231, HCT116, CaCo2, HeLa, A549 and Jurkat cancer cell lines. The selectivity of the complexes was verified on a noncancerous Cos-7 cell line. Antiproliferative activity of the prepared complexes was very low in comparison with cisplatin, except complex <b>3</b>; however, its activity was not selective and was similar to the activity of its ligand HBrQ. Antibacterial potential was observed only with ligand HClNQ. Radical scavenging experiments revealed relatively high antioxidant activity of complex <b>3</b> against ABTS radical. |
| first_indexed | 2024-03-09T16:17:34Z |
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| issn | 2304-6740 |
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| spelling | doaj.art-3fbde945d0d54fc189d80febf3f1ff002023-11-24T15:38:00ZengMDPI AGInorganics2304-67402022-11-01101222310.3390/inorganics10120223Low-Dimensional Compounds Containing Bioactive Ligands. Part XIX: Crystal Structures and Biological Properties of Copper Complexes with Halogen and Nitro Derivatives of 8-HydroxyquinolineMartina Kepeňová0Martin Kello1Romana Smolková2Michal Goga3Richard Frenák4Ľudmila Tkáčiková5Miroslava Litecká6Jan Šubrt7Ivan Potočňák8Institute of Chemistry, P. J. Šafárik University in Košice, Moyzesova 11, 041 54 Košice, SlovakiaDepartment of Pharmacology, P. J. Šafárik University in Košice, Trieda SNP 1, 040 11 Košice, SlovakiaDepartment of Ecology, Faculty of Humanities and Natural Sciences, University of Prešov, Ulica 17. Novembra 1, 081 16 Prešov, SlovakiaDepartment of Botany, Faculty of Science, Institute of Biology and Ecology, P. J. Šafárik University in Košice, Mánesova 23, 040 01 Košice, SlovakiaDepartment of Botany, Faculty of Science, Institute of Biology and Ecology, P. J. Šafárik University in Košice, Mánesova 23, 040 01 Košice, SlovakiaDepartment of Microbiology and Immunology, University of Veterinary Medicine and Pharmacy, Komenského 73, 041 81 Košice, SlovakiaCentre of Instrumental Techniques, Institute of Inorganic Chemistry of the CAS, Husinec-Řež č.p. 1001, CZ-25068 Řež, Czech RepublicCentre of Instrumental Techniques, Institute of Inorganic Chemistry of the CAS, Husinec-Řež č.p. 1001, CZ-25068 Řež, Czech RepublicInstitute of Chemistry, P. J. Šafárik University in Košice, Moyzesova 11, 041 54 Košice, SlovakiaSix new copper(II) complexes were prepared: [Cu(ClBrQ)<sub>2</sub>] (<b>1a</b>, <b>1b</b>), [Cu(ClBrQ)<sub>2</sub>]·1/2 diox (<b>2</b>) (diox = 1,4-dioxane), [Cu(BrQ)<sub>2</sub>] (<b>3</b>), [Cu(dNQ)<sub>2</sub>] (<b>4</b>), [Cu(dNQ)<sub>2</sub>(DMF)<sub>2</sub>] (<b>5</b>) and [Cu(ClNQ)<sub>2</sub>] (<b>6</b>), where HClBrQ is 5-chloro-7-bromo-8-hydroxyquinoline, HBrQ is 7-bromo-8-hydroxyquinoline, HClNQ is 5-chloro-7-nitro-8-hydroxyquinoline and HdNQ is 5,7-dinitro-8-hydroxyquinoline. Prepared compounds were characterised by infrared spectroscopy, elemental analysis and by X-ray structural analysis. Structural analysis revealed that all complexes are molecular. Square planar coordination of copper atoms in [Cu(XQ)<sub>2</sub>] (XQ = ClBrQ (<b>1a</b>, <b>1b</b>), BrQ (<b>3</b>) and ClNQ (<b>6</b>)) and tetragonal bipyramidal coordination in [Cu(dNQ)<sub>2</sub>(DMF)<sub>2</sub>] (<b>5</b>) complexes were observed. In these four complexes, bidentate chelate coordination of XQ ligands via oxygen and nitrogen atoms was found. Hydrogen bonds stabilizing the structure were observed in [Cu(dNQ)<sub>2</sub>(DMF)<sub>2</sub>] (<b>5</b>) and [Cu(ClNQ)<sub>2</sub>] (<b>6</b>), no other nonbonding interactions were noticed in all five structures. The stability of the complexes in DMSO and DMSO/water was evaluated by UV-Vis spectroscopy. Cytotoxic activity of the complexes and ligands was tested against MCF-7, MDA-MB-231, HCT116, CaCo2, HeLa, A549 and Jurkat cancer cell lines. The selectivity of the complexes was verified on a noncancerous Cos-7 cell line. Antiproliferative activity of the prepared complexes was very low in comparison with cisplatin, except complex <b>3</b>; however, its activity was not selective and was similar to the activity of its ligand HBrQ. Antibacterial potential was observed only with ligand HClNQ. Radical scavenging experiments revealed relatively high antioxidant activity of complex <b>3</b> against ABTS radical.https://www.mdpi.com/2304-6740/10/12/223copper complexesderivatives of 8-hydroxyquinolinecrystal structurebrominationbiological properties |
| spellingShingle | Martina Kepeňová Martin Kello Romana Smolková Michal Goga Richard Frenák Ľudmila Tkáčiková Miroslava Litecká Jan Šubrt Ivan Potočňák Low-Dimensional Compounds Containing Bioactive Ligands. Part XIX: Crystal Structures and Biological Properties of Copper Complexes with Halogen and Nitro Derivatives of 8-Hydroxyquinoline Inorganics copper complexes derivatives of 8-hydroxyquinoline crystal structure bromination biological properties |
| title | Low-Dimensional Compounds Containing Bioactive Ligands. Part XIX: Crystal Structures and Biological Properties of Copper Complexes with Halogen and Nitro Derivatives of 8-Hydroxyquinoline |
| title_full | Low-Dimensional Compounds Containing Bioactive Ligands. Part XIX: Crystal Structures and Biological Properties of Copper Complexes with Halogen and Nitro Derivatives of 8-Hydroxyquinoline |
| title_fullStr | Low-Dimensional Compounds Containing Bioactive Ligands. Part XIX: Crystal Structures and Biological Properties of Copper Complexes with Halogen and Nitro Derivatives of 8-Hydroxyquinoline |
| title_full_unstemmed | Low-Dimensional Compounds Containing Bioactive Ligands. Part XIX: Crystal Structures and Biological Properties of Copper Complexes with Halogen and Nitro Derivatives of 8-Hydroxyquinoline |
| title_short | Low-Dimensional Compounds Containing Bioactive Ligands. Part XIX: Crystal Structures and Biological Properties of Copper Complexes with Halogen and Nitro Derivatives of 8-Hydroxyquinoline |
| title_sort | low dimensional compounds containing bioactive ligands part xix crystal structures and biological properties of copper complexes with halogen and nitro derivatives of 8 hydroxyquinoline |
| topic | copper complexes derivatives of 8-hydroxyquinoline crystal structure bromination biological properties |
| url | https://www.mdpi.com/2304-6740/10/12/223 |
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