Mononuclear silver(I) complexes with 1,7-phenanthroline as potent inhibitors of Candida growth
2018
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Authors
Savić, Nada D.Vojnović, Sandra
Glišić, Biljana Đ.
Crochet, Aurelien
Pavić, Aleksandar
Janjić, Goran V.
Pekmezović, Marina
Opsenica, Igor
Fromm, Katharina M.
Nikodinović-Runić, Jasmina
Đuran, Miloš I.
Article (Accepted Version)
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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. (C) 2018 Elsevier Masson SAS. All rights reserved.
Keywords:
Silver(I) complexes / Antimicrobial activity / Cytotoxicity / Candida / Danio rerioSource:
European Journal of Medicinal Chemistry, 2018, 156, 760-773Publisher:
- Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux
Funding / projects:
- Synthesis of new metal complexes and investigation of their reactions with peptides (RS-MESTD-Basic Research (BR or ON)-172036)
- Microbial diversity study and characterization of beneficial environmental microorganisms (RS-MESTD-Basic Research (BR or ON)-173048)
- European Unions Horizon 2020 research and innovation programme under the Marie Sklodowska-Curie [642095]
- 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]
Note:
- This is peer-reviewed version of the following article: Savić, N. D.; Vojnovic, S.; Glišić, B. Đ.; Crochet, A.; Pavic, A.; Janjić, G. V.; Pekmezović, M.; Opsenica, I. M.; Fromm, K. M.; Nikodinovic-Runic, J.; et al. Mononuclear Silver(I) Complexes with 1,7-Phenanthroline as Potent Inhibitors of Candida Growth. Eur. J. Med. Chem. 2018, 156, 760–773. https://doi.org/10.1016/j.ejmech.2018.07.049
- Supplementary material: https://imagine.imgge.bg.ac.rs/handle/123456789/2229
DOI: 10.1016/j.ejmech.2018.07.049
ISSN: 0223-5234
PubMed: 30053719
WoS: 000443663200056
Scopus: 2-s2.0-85050292358
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Institution/Community
Institut za molekularnu genetiku i genetičko inženjerstvoTY - JOUR AU - Savić, Nada D. AU - Vojnović, Sandra AU - Glišić, Biljana Đ. AU - Crochet, Aurelien AU - Pavić, Aleksandar AU - Janjić, Goran V. AU - Pekmezović, Marina AU - Opsenica, Igor AU - Fromm, Katharina M. AU - Nikodinović-Runić, Jasmina AU - Đuran, Miloš I. PY - 2018 UR - https://imagine.imgge.bg.ac.rs/handle/123456789/2228 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. (C) 2018 Elsevier Masson SAS. All rights reserved. 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 EP - 773 SP - 760 VL - 156 DO - 10.1016/j.ejmech.2018.07.049 ER -
@article{ author = "Savić, Nada D. and Vojnović, Sandra and Glišić, Biljana Đ. and Crochet, Aurelien and Pavić, Aleksandar and Janjić, Goran V. and Pekmezović, Marina and Opsenica, Igor and Fromm, Katharina M. and Nikodinović-Runić, Jasmina and Đuran, Miloš I.", 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. (C) 2018 Elsevier Masson SAS. All rights reserved.", 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", pages = "773-760", volume = "156", doi = "10.1016/j.ejmech.2018.07.049" }
Savić, N. D., Vojnović, S., Glišić, B. Đ., Crochet, A., Pavić, A., Janjić, G. V., Pekmezović, M., Opsenica, I., Fromm, K. M., Nikodinović-Runić, J.,& Đuran, M. I.. (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
Savić ND, Vojnović S, Glišić BĐ, Crochet A, Pavić A, Janjić GV, Pekmezović M, Opsenica I, Fromm KM, Nikodinović-Runić J, Đuran MI. 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 .
Savić, Nada D., Vojnović, Sandra, Glišić, Biljana Đ., Crochet, Aurelien, Pavić, Aleksandar, Janjić, Goran V., Pekmezović, Marina, Opsenica, Igor, Fromm, Katharina M., Nikodinović-Runić, Jasmina, Đuran, Miloš I., "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 . .