Silver(I) Complexes with Clinically Used Azoles: Synthesis, Structural Characterization and Antimicrobial Evaluation
Authors
Stevanović, NevenaLazić, Jelena
Kljun, Jakob
Stanković, Mia
Nikodinović-Runić, Jasmina
Turel, Iztok
Djuran, Miloš
Glišić, Biljana
Article (Published version)
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Recently, we synthesized silver(I) complex with the antifungal agent itraconazole, which showed improved anti-Candida potential and therapeutic safety in comparison to itraconazole and rescued zebrafish embryos affected by lethal C. albicans infection, when used in safe doses. Inspired by these results, in the present study, three new silver(I) complexes with clinically used azoles, econazole (ecz), clotrimazole (ctz) and voriconazole (vcz), [Ag(ecz)2]SbF6 (Ag1), [Ag(ctz)2]SbF6 (Ag2) and {[Ag(vcz)2]SbF6}n (Ag3) were synthesized and structurally characterized by elemental microanalysis, mass spectrometry, spectroscopy (1H NMR, IR and UV-Vis), cyclic voltammetry, molar conductivity measurements, and single crystal X-ray diffraction analysis. The spectroscopic and crystallographic results revealed that, in the synthesized silver(I) complexes, azole ligands are monodentately coordinated to the Ag(I) ion through the nitrogen atom forming [Ag(azole)2]+ complex cation. The antimicrobial effec...t of complexes and azole ligands was evaluated against different Candida species, as well as Gram-positive and Gram-negative bacteria. The synthesized complexes Ag1-3 exhibited good to moderate antimicrobial activity being, in most cases, more active than the corresponding azole ligands. Complexes Ag2 and Ag3 also showed strong inhibitory activity against C. albicans biofilm formation and strong inhibition of C. albicans filamentation at subinhibitory concentrations.
Keywords:
antifungal azoles / antimicrobials / biofilms / silver(I) complexesSource:
Medical Sciences Forum, 2022, 14, 1, 102-Funding / projects:
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200042 (University of Belgrade, Institute of Molecular Genetics and Genetic Engineering) (RS-MESTD-inst-2020-200042)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200122 (University of Kragujevac, Faculty of Science) (RS-MESTD-inst-2020-200122)
- Slovenian Research Agency (grant P1-0175). The EN!FIST Centre of Excellence, Trg OF 13, SI-1000 Ljubljana, Slovenia, is acknowledged for the use of the SuperNova diffractometer
- This research has also received funding from the Serbian Academy of Sciences and Arts under project No. F128.
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Institut za molekularnu genetiku i genetičko inženjerstvoTY - JOUR AU - Stevanović, Nevena AU - Lazić, Jelena AU - Kljun, Jakob AU - Stanković, Mia AU - Nikodinović-Runić, Jasmina AU - Turel, Iztok AU - Djuran, Miloš AU - Glišić, Biljana PY - 2022 UR - https://www.mdpi.com/2673-9992/14/1/102 UR - https://imagine.imgge.bg.ac.rs/handle/123456789/1844 AB - Recently, we synthesized silver(I) complex with the antifungal agent itraconazole, which showed improved anti-Candida potential and therapeutic safety in comparison to itraconazole and rescued zebrafish embryos affected by lethal C. albicans infection, when used in safe doses. Inspired by these results, in the present study, three new silver(I) complexes with clinically used azoles, econazole (ecz), clotrimazole (ctz) and voriconazole (vcz), [Ag(ecz)2]SbF6 (Ag1), [Ag(ctz)2]SbF6 (Ag2) and {[Ag(vcz)2]SbF6}n (Ag3) were synthesized and structurally characterized by elemental microanalysis, mass spectrometry, spectroscopy (1H NMR, IR and UV-Vis), cyclic voltammetry, molar conductivity measurements, and single crystal X-ray diffraction analysis. The spectroscopic and crystallographic results revealed that, in the synthesized silver(I) complexes, azole ligands are monodentately coordinated to the Ag(I) ion through the nitrogen atom forming [Ag(azole)2]+ complex cation. The antimicrobial effect of complexes and azole ligands was evaluated against different Candida species, as well as Gram-positive and Gram-negative bacteria. The synthesized complexes Ag1-3 exhibited good to moderate antimicrobial activity being, in most cases, more active than the corresponding azole ligands. Complexes Ag2 and Ag3 also showed strong inhibitory activity against C. albicans biofilm formation and strong inhibition of C. albicans filamentation at subinhibitory concentrations. T2 - Medical Sciences Forum T2 - Medical Sciences Forum T1 - Silver(I) Complexes with Clinically Used Azoles: Synthesis, Structural Characterization and Antimicrobial Evaluation IS - 1 SP - 102 VL - 14 DO - 10.3390/ECMC2022-13249 ER -
@article{ author = "Stevanović, Nevena and Lazić, Jelena and Kljun, Jakob and Stanković, Mia and Nikodinović-Runić, Jasmina and Turel, Iztok and Djuran, Miloš and Glišić, Biljana", year = "2022", abstract = "Recently, we synthesized silver(I) complex with the antifungal agent itraconazole, which showed improved anti-Candida potential and therapeutic safety in comparison to itraconazole and rescued zebrafish embryos affected by lethal C. albicans infection, when used in safe doses. Inspired by these results, in the present study, three new silver(I) complexes with clinically used azoles, econazole (ecz), clotrimazole (ctz) and voriconazole (vcz), [Ag(ecz)2]SbF6 (Ag1), [Ag(ctz)2]SbF6 (Ag2) and {[Ag(vcz)2]SbF6}n (Ag3) were synthesized and structurally characterized by elemental microanalysis, mass spectrometry, spectroscopy (1H NMR, IR and UV-Vis), cyclic voltammetry, molar conductivity measurements, and single crystal X-ray diffraction analysis. The spectroscopic and crystallographic results revealed that, in the synthesized silver(I) complexes, azole ligands are monodentately coordinated to the Ag(I) ion through the nitrogen atom forming [Ag(azole)2]+ complex cation. The antimicrobial effect of complexes and azole ligands was evaluated against different Candida species, as well as Gram-positive and Gram-negative bacteria. The synthesized complexes Ag1-3 exhibited good to moderate antimicrobial activity being, in most cases, more active than the corresponding azole ligands. Complexes Ag2 and Ag3 also showed strong inhibitory activity against C. albicans biofilm formation and strong inhibition of C. albicans filamentation at subinhibitory concentrations.", journal = "Medical Sciences Forum, Medical Sciences Forum", title = "Silver(I) Complexes with Clinically Used Azoles: Synthesis, Structural Characterization and Antimicrobial Evaluation", number = "1", pages = "102", volume = "14", doi = "10.3390/ECMC2022-13249" }
Stevanović, N., Lazić, J., Kljun, J., Stanković, M., Nikodinović-Runić, J., Turel, I., Djuran, M.,& Glišić, B.. (2022). Silver(I) Complexes with Clinically Used Azoles: Synthesis, Structural Characterization and Antimicrobial Evaluation. in Medical Sciences Forum, 14(1), 102. https://doi.org/10.3390/ECMC2022-13249
Stevanović N, Lazić J, Kljun J, Stanković M, Nikodinović-Runić J, Turel I, Djuran M, Glišić B. Silver(I) Complexes with Clinically Used Azoles: Synthesis, Structural Characterization and Antimicrobial Evaluation. in Medical Sciences Forum. 2022;14(1):102. doi:10.3390/ECMC2022-13249 .
Stevanović, Nevena, Lazić, Jelena, Kljun, Jakob, Stanković, Mia, Nikodinović-Runić, Jasmina, Turel, Iztok, Djuran, Miloš, Glišić, Biljana, "Silver(I) Complexes with Clinically Used Azoles: Synthesis, Structural Characterization and Antimicrobial Evaluation" in Medical Sciences Forum, 14, no. 1 (2022):102, https://doi.org/10.3390/ECMC2022-13249 . .