Synthesis, Structure and Biological Activity of Indole–Imidazole Complexes with ZnCl<sub>2</sub>: Can Coordination Enhance the Functionality of Bioactive Ligands?
The ability of the indole–imidazole hybrid ligands to coordinate with the Zn(II) ion and the resulting structures of this new class of coordination compounds were analyzed in order to determine their structural properties and biological functionalities. For this purpose, six novel Zn(II) complexes,...
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MDPI AG
2023-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/10/4132 |
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| author | Karolina Babijczuk Beata Warżajtis Justyna Starzyk Lucyna Mrówczyńska Beata Jasiewicz Urszula Rychlewska |
| author_facet | Karolina Babijczuk Beata Warżajtis Justyna Starzyk Lucyna Mrówczyńska Beata Jasiewicz Urszula Rychlewska |
| author_sort | Karolina Babijczuk |
| collection | DOAJ |
| description | The ability of the indole–imidazole hybrid ligands to coordinate with the Zn(II) ion and the resulting structures of this new class of coordination compounds were analyzed in order to determine their structural properties and biological functionalities. For this purpose, six novel Zn(II) complexes, [Zn(InIm)<sub>2</sub>Cl<sub>2</sub>] (<b>1</b>), [Zn(InMeIm)<sub>2</sub>Cl<sub>2</sub>] (<b>2</b>), [Zn(IniPrIm)<sub>2</sub>Cl<sub>2</sub>] (<b>3</b>), [Zn(InEtMeIm)<sub>2</sub>Cl<sub>2</sub>] (<b>4</b>), [Zn(InPhIm)<sub>2</sub>Cl<sub>2</sub>] (<b>5</b>) and [Zn<sub>2</sub>(InBzIm)<sub>2</sub>Cl<sub>2</sub>] (<b>6</b>) (where InIm is 3-((1H-imidazol-1-yl)methyl)-1H-indole), were synthesized by the reactions of ZnCl<sub>2</sub> and the corresponding ligand in a 1:2 molar ratio in methanol solvent at an ambient temperature. The structural and spectral characterization of these complexes was performed using NMR, FT–IR and ESI–MS spectrometry and elemental analysis, and the crystal structures of <b>1</b>–<b>5</b> were determined using single-crystal X-ray diffraction. Complexes <b>1</b>–<b>5</b> form polar supramolecular aggregates by utilizing, for this purpose, the N-H(indole)∙∙∙Cl(chloride) intermolecular hydrogen bonds. The assemblies thus formed differ depending on the distinctive molecular shape, which can be either compact or extended. All complexes were screened for their hemolytic, cytoprotective, antifungal, and antibacterial activities. The results show that the cytoprotective activity of the indole/imidazole ligand significantly increases upon its complexation with ZnCl<sub>2</sub> up to a value comparable with the standard antioxidant Trolox, while the response of its substituted analogues is diverse and less pronounced. |
| first_indexed | 2024-03-11T03:27:46Z |
| format | Article |
| id | doaj.art-d3a782070bf3422b83893f8a31ef26f4 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T03:27:46Z |
| publishDate | 2023-05-01 |
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| spelling | doaj.art-d3a782070bf3422b83893f8a31ef26f42023-11-18T02:39:44ZengMDPI AGMolecules1420-30492023-05-012810413210.3390/molecules28104132Synthesis, Structure and Biological Activity of Indole–Imidazole Complexes with ZnCl<sub>2</sub>: Can Coordination Enhance the Functionality of Bioactive Ligands?Karolina Babijczuk0Beata Warżajtis1Justyna Starzyk2Lucyna Mrówczyńska3Beata Jasiewicz4Urszula Rychlewska5Department of Bioactive Products, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznań, PolandDepartment of Crystallography, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznań, PolandDepartment of Soil Science and Microbiology, Faculty of Agronomy, Horticulture, and Bioengineering, University of Life Science, Szydłowska 50, 60-656 Poznań, PolandDepartment of Cell Biology, Faculty of Biology, Adam Mickiewicz University, Uniwersytetu Poznańskiego 6, 61-614 Poznań, PolandDepartment of Bioactive Products, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznań, PolandDepartment of Crystallography, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznań, PolandThe ability of the indole–imidazole hybrid ligands to coordinate with the Zn(II) ion and the resulting structures of this new class of coordination compounds were analyzed in order to determine their structural properties and biological functionalities. For this purpose, six novel Zn(II) complexes, [Zn(InIm)<sub>2</sub>Cl<sub>2</sub>] (<b>1</b>), [Zn(InMeIm)<sub>2</sub>Cl<sub>2</sub>] (<b>2</b>), [Zn(IniPrIm)<sub>2</sub>Cl<sub>2</sub>] (<b>3</b>), [Zn(InEtMeIm)<sub>2</sub>Cl<sub>2</sub>] (<b>4</b>), [Zn(InPhIm)<sub>2</sub>Cl<sub>2</sub>] (<b>5</b>) and [Zn<sub>2</sub>(InBzIm)<sub>2</sub>Cl<sub>2</sub>] (<b>6</b>) (where InIm is 3-((1H-imidazol-1-yl)methyl)-1H-indole), were synthesized by the reactions of ZnCl<sub>2</sub> and the corresponding ligand in a 1:2 molar ratio in methanol solvent at an ambient temperature. The structural and spectral characterization of these complexes was performed using NMR, FT–IR and ESI–MS spectrometry and elemental analysis, and the crystal structures of <b>1</b>–<b>5</b> were determined using single-crystal X-ray diffraction. Complexes <b>1</b>–<b>5</b> form polar supramolecular aggregates by utilizing, for this purpose, the N-H(indole)∙∙∙Cl(chloride) intermolecular hydrogen bonds. The assemblies thus formed differ depending on the distinctive molecular shape, which can be either compact or extended. All complexes were screened for their hemolytic, cytoprotective, antifungal, and antibacterial activities. The results show that the cytoprotective activity of the indole/imidazole ligand significantly increases upon its complexation with ZnCl<sub>2</sub> up to a value comparable with the standard antioxidant Trolox, while the response of its substituted analogues is diverse and less pronounced.https://www.mdpi.com/1420-3049/28/10/4132indole derivativesZn(II) complexeshuman erythrocytesoxidative hemolysisantibacterial activityfungicidal properties |
| spellingShingle | Karolina Babijczuk Beata Warżajtis Justyna Starzyk Lucyna Mrówczyńska Beata Jasiewicz Urszula Rychlewska Synthesis, Structure and Biological Activity of Indole–Imidazole Complexes with ZnCl<sub>2</sub>: Can Coordination Enhance the Functionality of Bioactive Ligands? Molecules indole derivatives Zn(II) complexes human erythrocytes oxidative hemolysis antibacterial activity fungicidal properties |
| title | Synthesis, Structure and Biological Activity of Indole–Imidazole Complexes with ZnCl<sub>2</sub>: Can Coordination Enhance the Functionality of Bioactive Ligands? |
| title_full | Synthesis, Structure and Biological Activity of Indole–Imidazole Complexes with ZnCl<sub>2</sub>: Can Coordination Enhance the Functionality of Bioactive Ligands? |
| title_fullStr | Synthesis, Structure and Biological Activity of Indole–Imidazole Complexes with ZnCl<sub>2</sub>: Can Coordination Enhance the Functionality of Bioactive Ligands? |
| title_full_unstemmed | Synthesis, Structure and Biological Activity of Indole–Imidazole Complexes with ZnCl<sub>2</sub>: Can Coordination Enhance the Functionality of Bioactive Ligands? |
| title_short | Synthesis, Structure and Biological Activity of Indole–Imidazole Complexes with ZnCl<sub>2</sub>: Can Coordination Enhance the Functionality of Bioactive Ligands? |
| title_sort | synthesis structure and biological activity of indole imidazole complexes with zncl sub 2 sub can coordination enhance the functionality of bioactive ligands |
| topic | indole derivatives Zn(II) complexes human erythrocytes oxidative hemolysis antibacterial activity fungicidal properties |
| url | https://www.mdpi.com/1420-3049/28/10/4132 |
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