Synthesis, Spectroscopy, Single-Crystal Structure Analysis and Antibacterial Activity of Two Novel Complexes of Silver(I) with Miconazole Drug
In a previous article, we reported on the higher toxicity of silver(I) complexes of miconazole [Ag(MCZ)<sub>2</sub>NO<sub>3</sub> (<b>1</b>)] and [Ag(MCZ)<sub>2</sub>ClO<sub>4</sub> (<b>2</b>)] in HepG2 tumor cells compared to t...
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2021-02-01
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| author | Karolina Stryjska Izabela Korona-Glowniak Lilianna Chęcińska Joachim Kusz Justyn Ochocki |
| author_facet | Karolina Stryjska Izabela Korona-Glowniak Lilianna Chęcińska Joachim Kusz Justyn Ochocki |
| author_sort | Karolina Stryjska |
| collection | DOAJ |
| description | In a previous article, we reported on the higher toxicity of silver(I) complexes of miconazole [Ag(MCZ)<sub>2</sub>NO<sub>3</sub> (<b>1</b>)] and [Ag(MCZ)<sub>2</sub>ClO<sub>4</sub> (<b>2</b>)] in HepG2 tumor cells compared to the corresponding salts of silver, miconazole and cisplatin. Here, we present the synthesis of two silver(I) complexes of miconazole containing two new counter ions in the form of Ag(MCZ)<sub>2</sub>X (MCZ = 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole]; X = BF<sub>4</sub><sup>−</sup> (<b>3</b>), SbF<sub>6</sub><sup>−</sup> (<b>4</b>)). The novel silver(I) complexes were characterized by elemental analysis, <sup>1</sup>H NMR, <sup>13</sup>C NMR and infrared (IR) spectroscopy, electrospray ionization (ESI)-MS spectrometry and X-ray-crystallography. In the present study, the antimicrobial activity of all obtained silver(I) complexes of miconazole against six strains of Gram-positive bacteria, five strains of Gram-negative bacteria and yeasts was evaluated. The results were compared with those of a silver sulfadiazine drug, the corresponding silver salts and the free ligand. Silver(I) complexes exhibited significant activity against Gram-positive bacteria, which was much better than that of silver sulfadiazine and silver salts. The highest antimicrobial activity was observed for the complex containing the nitrate counter ion. All Ag(I) complexes of miconazole resulted in much better inhibition of yeast growth than silver sulfadiazine, silver salts and miconazole. Moreover, the synthesized silver(I) complexes showed good or moderate activity against Gram-negative bacteria compared to the free ligand. |
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| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-09T05:58:13Z |
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| spelling | doaj.art-5c8df5d297de4ce89c35b2468e7e6df72023-12-03T12:11:56ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672021-02-01224151010.3390/ijms22041510Synthesis, Spectroscopy, Single-Crystal Structure Analysis and Antibacterial Activity of Two Novel Complexes of Silver(I) with Miconazole DrugKarolina Stryjska0Izabela Korona-Glowniak1Lilianna Chęcińska2Joachim Kusz3Justyn Ochocki4Department of Bioinorganic Chemistry, Chair of Medicinal Chemistry, Medical University of Lodz, Muszyńskiego 1, 90-151 Łódź, PolandDepartment of Pharmaceutical Microbiology, Medical University of Lublin, Chodźki 1, 20-093 Lublin, PolandFaculty of Chemistry, University of Lodz, Pomorska 163/165, 90-236 Łódź, PolandInstitute of Physics, University of Silesia, 75 Pułku Piechoty 1, 41-500 Chorzów, PolandDepartment of Bioinorganic Chemistry, Chair of Medicinal Chemistry, Medical University of Lodz, Muszyńskiego 1, 90-151 Łódź, PolandIn a previous article, we reported on the higher toxicity of silver(I) complexes of miconazole [Ag(MCZ)<sub>2</sub>NO<sub>3</sub> (<b>1</b>)] and [Ag(MCZ)<sub>2</sub>ClO<sub>4</sub> (<b>2</b>)] in HepG2 tumor cells compared to the corresponding salts of silver, miconazole and cisplatin. Here, we present the synthesis of two silver(I) complexes of miconazole containing two new counter ions in the form of Ag(MCZ)<sub>2</sub>X (MCZ = 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole]; X = BF<sub>4</sub><sup>−</sup> (<b>3</b>), SbF<sub>6</sub><sup>−</sup> (<b>4</b>)). The novel silver(I) complexes were characterized by elemental analysis, <sup>1</sup>H NMR, <sup>13</sup>C NMR and infrared (IR) spectroscopy, electrospray ionization (ESI)-MS spectrometry and X-ray-crystallography. In the present study, the antimicrobial activity of all obtained silver(I) complexes of miconazole against six strains of Gram-positive bacteria, five strains of Gram-negative bacteria and yeasts was evaluated. The results were compared with those of a silver sulfadiazine drug, the corresponding silver salts and the free ligand. Silver(I) complexes exhibited significant activity against Gram-positive bacteria, which was much better than that of silver sulfadiazine and silver salts. The highest antimicrobial activity was observed for the complex containing the nitrate counter ion. All Ag(I) complexes of miconazole resulted in much better inhibition of yeast growth than silver sulfadiazine, silver salts and miconazole. Moreover, the synthesized silver(I) complexes showed good or moderate activity against Gram-negative bacteria compared to the free ligand.https://www.mdpi.com/1422-0067/22/4/1510synthesissilver(I) complexesNMR spectroscopyIR spectroscopyX-ray crystallographyantimicrobial activity |
| spellingShingle | Karolina Stryjska Izabela Korona-Glowniak Lilianna Chęcińska Joachim Kusz Justyn Ochocki Synthesis, Spectroscopy, Single-Crystal Structure Analysis and Antibacterial Activity of Two Novel Complexes of Silver(I) with Miconazole Drug International Journal of Molecular Sciences synthesis silver(I) complexes NMR spectroscopy IR spectroscopy X-ray crystallography antimicrobial activity |
| title | Synthesis, Spectroscopy, Single-Crystal Structure Analysis and Antibacterial Activity of Two Novel Complexes of Silver(I) with Miconazole Drug |
| title_full | Synthesis, Spectroscopy, Single-Crystal Structure Analysis and Antibacterial Activity of Two Novel Complexes of Silver(I) with Miconazole Drug |
| title_fullStr | Synthesis, Spectroscopy, Single-Crystal Structure Analysis and Antibacterial Activity of Two Novel Complexes of Silver(I) with Miconazole Drug |
| title_full_unstemmed | Synthesis, Spectroscopy, Single-Crystal Structure Analysis and Antibacterial Activity of Two Novel Complexes of Silver(I) with Miconazole Drug |
| title_short | Synthesis, Spectroscopy, Single-Crystal Structure Analysis and Antibacterial Activity of Two Novel Complexes of Silver(I) with Miconazole Drug |
| title_sort | synthesis spectroscopy single crystal structure analysis and antibacterial activity of two novel complexes of silver i with miconazole drug |
| topic | synthesis silver(I) complexes NMR spectroscopy IR spectroscopy X-ray crystallography antimicrobial activity |
| url | https://www.mdpi.com/1422-0067/22/4/1510 |
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