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Mononuclear silver(I) complexes with 1,7-phenanthroline as potent inhibitors of Candida growth

Authorized Users Only
2018
Authors
Savic, Nada D.
Vojnovic, Sandra
Glišić, Biljana
Crochet, Aurélien
Pavić, Aleksandar
Janjić, Goran
Pekmezovic, Marina
Opsenica, Igor
Fromm, Katharina M.
Nikodinović-Runić, Jasmina
Đuran, Miloš
Article (Published version)
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Abstract
Mononuclear silver(I) complexes with 1,7-phenanthroline (1,7-phen), [Ag(NO3-O,O') (1,7-phen-N7)(2)] (1) and [Ag(1,7-phen-N7)(2)]X, X = ClO4- (2), CF3SO3- (3), BF4- (4) and SbF6- (5) were synthesized and structurally characterized by NMR (H-1 and C-13), IR and UV-Vis spectroscopy and ESI mass spectrometry. The crystal structures of 1, 3 and 4 were determined by single-crystal X-ray diffraction analysis. In all these complexes, 1,7-phen coordinates to the Ag(I) ion in a monodentate fashion via the less sterically hindered N7 nitrogen atom. The investigation of the solution stability of 1-5 in DMSO revealed that they are sufficiently stable in this solvent at room temperature. Complexes 1-5 showed selectivity towards Candida spp. in comparison to bacteria, effectively inhibiting the growth of four different Candida species with minimal inhibitory concentrations (MIC) between 1.2 and 11.3 mu M. Based on the lowest MIC values and the lowest cytotoxicity against healthy human fibroblasts wit...h selectivity index of more than 30, the antifungal potential was examined in detail for the complex 1. It had the ability to attenuate C. albicans virulence and to reduce epithelial cell damage in the cell infection model. Induction of reactive oxygen species (ROS) response has been detected in C. albicans, with fungal DNA being one of the possible target biomolecules. The toxicity profile of 1 in the zebrafish model (Danio rerio) revealed improved safety and activity in comparison to that of clinically utilized silver(I) sulfadiazine.

Keywords:
Silver(I) complexes / Antimicrobial activity / Cytotoxicity / Candida / Danio rerio
Source:
European Journal of Medicinal Chemistry, 2018, 156, 760-773
Publisher:
  • Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux
Funding / projects:
  • Synthesis of new metal complexes and investigation of their reactions with peptides (RS-172036)
  • Microbial diversity study and characterization of beneficial environmental microorganisms (RS-173048)
  • European Union's Horizon 2020 research and innovation programme under the Marie Sklodowska-Curie
  • Supra-MedChem"Balkans.Net SCOPES Institutional Partnership [IZ74Z0_160515]
  • European Unions Horizon 2020 research and innovation programme under the Marie Sklodowska-Curie [642095]
  • Serbian Academy of Sciences and Arts [F128]

DOI: 10.1016/j.ejmech.2018.07.049

ISSN: 0223-5234

PubMed: 30053719

WoS: 000443663200056

Scopus: 2-s2.0-85050292358
[ Google Scholar ]
30
26
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/2429
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Savic, Nada D.
AU  - Vojnovic, Sandra
AU  - Glišić, Biljana
AU  - Crochet, Aurélien
AU  - Pavić, Aleksandar
AU  - Janjić, Goran
AU  - Pekmezovic, Marina
AU  - Opsenica, Igor
AU  - Fromm, Katharina M.
AU  - Nikodinović-Runić, Jasmina
AU  - Đuran, Miloš
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2429
AB  - Mononuclear silver(I) complexes with 1,7-phenanthroline (1,7-phen), [Ag(NO3-O,O') (1,7-phen-N7)(2)] (1) and [Ag(1,7-phen-N7)(2)]X, X = ClO4- (2), CF3SO3- (3), BF4- (4) and SbF6- (5) were synthesized and structurally characterized by NMR (H-1 and C-13), IR and UV-Vis spectroscopy and ESI mass spectrometry. The crystal structures of 1, 3 and 4 were determined by single-crystal X-ray diffraction analysis. In all these complexes, 1,7-phen coordinates to the Ag(I) ion in a monodentate fashion via the less sterically hindered N7 nitrogen atom. The investigation of the solution stability of 1-5 in DMSO revealed that they are sufficiently stable in this solvent at room temperature. Complexes 1-5 showed selectivity towards Candida spp. in comparison to bacteria, effectively inhibiting the growth of four different Candida species with minimal inhibitory concentrations (MIC) between 1.2 and 11.3 mu M. Based on the lowest MIC values and the lowest cytotoxicity against healthy human fibroblasts with selectivity index of more than 30, the antifungal potential was examined in detail for the complex 1. It had the ability to attenuate C. albicans virulence and to reduce epithelial cell damage in the cell infection model. Induction of reactive oxygen species (ROS) response has been detected in C. albicans, with fungal DNA being one of the possible target biomolecules. The toxicity profile of 1 in the zebrafish model (Danio rerio) revealed improved safety and activity in comparison to that of clinically utilized silver(I) sulfadiazine.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux
T2  - European Journal of Medicinal Chemistry
T1  - Mononuclear silver(I) complexes with 1,7-phenanthroline as potent inhibitors of Candida growth
VL  - 156
SP  - 760
EP  - 773
DO  - 10.1016/j.ejmech.2018.07.049
ER  - 
@article{
author = "Savic, Nada D. and Vojnovic, Sandra and Glišić, Biljana and Crochet, Aurélien and Pavić, Aleksandar and Janjić, Goran and Pekmezovic, Marina and Opsenica, Igor and Fromm, Katharina M. and Nikodinović-Runić, Jasmina and Đuran, Miloš",
year = "2018",
abstract = "Mononuclear silver(I) complexes with 1,7-phenanthroline (1,7-phen), [Ag(NO3-O,O') (1,7-phen-N7)(2)] (1) and [Ag(1,7-phen-N7)(2)]X, X = ClO4- (2), CF3SO3- (3), BF4- (4) and SbF6- (5) were synthesized and structurally characterized by NMR (H-1 and C-13), IR and UV-Vis spectroscopy and ESI mass spectrometry. The crystal structures of 1, 3 and 4 were determined by single-crystal X-ray diffraction analysis. In all these complexes, 1,7-phen coordinates to the Ag(I) ion in a monodentate fashion via the less sterically hindered N7 nitrogen atom. The investigation of the solution stability of 1-5 in DMSO revealed that they are sufficiently stable in this solvent at room temperature. Complexes 1-5 showed selectivity towards Candida spp. in comparison to bacteria, effectively inhibiting the growth of four different Candida species with minimal inhibitory concentrations (MIC) between 1.2 and 11.3 mu M. Based on the lowest MIC values and the lowest cytotoxicity against healthy human fibroblasts with selectivity index of more than 30, the antifungal potential was examined in detail for the complex 1. It had the ability to attenuate C. albicans virulence and to reduce epithelial cell damage in the cell infection model. Induction of reactive oxygen species (ROS) response has been detected in C. albicans, with fungal DNA being one of the possible target biomolecules. The toxicity profile of 1 in the zebrafish model (Danio rerio) revealed improved safety and activity in comparison to that of clinically utilized silver(I) sulfadiazine.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux",
journal = "European Journal of Medicinal Chemistry",
title = "Mononuclear silver(I) complexes with 1,7-phenanthroline as potent inhibitors of Candida growth",
volume = "156",
pages = "760-773",
doi = "10.1016/j.ejmech.2018.07.049"
}
Savic, N. D., Vojnovic, S., Glišić, B., Crochet, A., Pavić, A., Janjić, G., Pekmezovic, M., Opsenica, I., Fromm, K. M., Nikodinović-Runić, J.,& Đuran, M.. (2018). Mononuclear silver(I) complexes with 1,7-phenanthroline as potent inhibitors of Candida growth. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux., 156, 760-773.
https://doi.org/10.1016/j.ejmech.2018.07.049
Savic ND, Vojnovic S, Glišić B, Crochet A, Pavić A, Janjić G, Pekmezovic M, Opsenica I, Fromm KM, Nikodinović-Runić J, Đuran M. Mononuclear silver(I) complexes with 1,7-phenanthroline as potent inhibitors of Candida growth. in European Journal of Medicinal Chemistry. 2018;156:760-773.
doi:10.1016/j.ejmech.2018.07.049 .
Savic, Nada D., Vojnovic, Sandra, Glišić, Biljana, Crochet, Aurélien, Pavić, Aleksandar, Janjić, Goran, Pekmezovic, Marina, Opsenica, Igor, Fromm, Katharina M., Nikodinović-Runić, Jasmina, Đuran, Miloš, "Mononuclear silver(I) complexes with 1,7-phenanthroline as potent inhibitors of Candida growth" in European Journal of Medicinal Chemistry, 156 (2018):760-773,
https://doi.org/10.1016/j.ejmech.2018.07.049 . .

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