Synthesis, Spectroscopy, Single-Crystal Structure Analysis and Antibacterial Activity of Two Novel Complexes of Silver(I) with Miconazole Drug

• Published in: International journal of molecular sciences Vol. 22; no. 4; p. 1510
• Main Authors: Stryjska, Karolina, Korona-Glowniak, Izabela, Chęcińska, Lilianna, Kusz, Joachim, Ochocki, Justyn
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 03-02-2021; MDPI
• Subjects: Anti-Bacterial Agents - pharmacology; Antibacterial activity; Antibiotics; Antifungal agents; Antifungal Agents - pharmacology; Antimicrobial activity; Antimicrobial agents; Bacteria; Bacterial infections; Catalytic oxidation; Cisplatin; Coordination Complexes - chemical synthesis; Coordination Complexes - chemistry; Coordination Complexes - pharmacology; Crystal structure; Crystallography; Drug resistance; Gonorrhea; Gram-negative bacteria; Gram-Negative Bacteria - drug effects; Gram-positive bacteria; Gram-Positive Bacteria - drug effects; Imidazole; Infections; Infrared analysis; Infrared spectroscopy; Ionization; IR spectroscopy; Ligands; Medicine; Miconazole; Miconazole - chemistry; Nitrates; NMR; NMR spectroscopy; Nuclear magnetic resonance; Salts; Silver; Silver - chemistry; silver(I) complexes; Single crystals; Spectrum analysis; Strains (organisms); Structural analysis; Sulfadiazine; synthesis; Toxicity; Tumor cells; Ulcers; X-ray crystallography; Yeast; Yeasts - drug effects; X-ray crystallography; synthesis; silver(I) complexes; antimicrobial activity; NMR spectroscopy; IR spectroscopy
• ISSN: 1422-0067; 1661-6596; 1422-0067
• DOI: 10.3390/ijms22041510

In a previous article, we reported on the higher toxicity of silver(I) complexes of miconazole [Ag(MCZ)
NO
(
)] and [Ag(MCZ)
ClO
(
)] 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)
X (MCZ = 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole]; X = BF
(
), SbF
(
)). The novel silver(I) complexes were characterized by elemental analysis,
H NMR,
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.