Synthesis, structural characterization and antimicrobial activity of silver(I) complexes with 1-benzyl-1H-tetrazoles
Autori
Andrejević, Tina P.Nikolić, Andrea
Glišić, Biljana Đ.
Wadepohl, Hubert
Vojnović, Sandra
Zlatović, Mario
Petković, Miloš
Nikodinović-Runić, Jasmina
Opsenica, Igor
Đuran, Miloš I.
Članak u časopisu (Recenzirana verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
Herein, we report the synthesis and structural characteristics of three tetrazole-containing compounds, 1-benzyl-1H-tetrazole (bntz), 1-benzyl-1H-tetrazol-5-amine (bntza) and 1-(4-methoxybenzyl)-1H-tetrazol-5-amine (mbntza) and the corresponding silver(I) complexes of the general formula [Ag(NO3-O)(L-N4)(2)](n), L = bntz (1), bntza (2) and mbntza (3). Silver(I) complexes 1-3 and 1-benzyl-1H-tetrazoles have been studied in detail by NMR, IR and UV-Vis spectroscopic methods and the structures of 1 and 2 have been determined by single-crystal X-ray diffraction analysis. The results of these analyses revealed a monodentate coordination of the ligands to Ag(I) ion via the N4 tetrazole nitrogen. The antimicrobial potential of silver(I) complexes 1-3 was evaluated against the broad panel of Gram-positive and Gram-negative bacteria and fungi, displaying their remarkable inhibiting activity with MIC (minimal inhibitory concentration) values in the range 2-8 and 0.16-1.25 mu g/mL (3.8-16.3 and 0....31-2.15 mu M), respectively. On the other hand, 1-benzyl-1H-tetrazoles used for the synthesis of the silver(I) complexes were not active against the investigated strains, suggesting that the activity of the complexes originates from the Ag(I) ion exclusively. Moreover, silver(I) complexes 1-3 have good therapeutic potential, which can be deduced from their moderate cytotoxicity on the human fibroblast cell line MRC5, with IC50 values falling in the range 30-60 mu g/mL (57.7-103.4 mu M). (C) 2018 Elsevier Ltd. All rights reserved.
Ključne reči:
1-Benzyl-1H-tetrazoles / Silver(I) complexes / Structural characterization / Antimicrobial activity / CytotoxicityIzvor:
Polyhedron, 2018, 154, 325-333Izdavač:
- Pergamon-Elsevier Science Ltd, Oxford
Finansiranje / projekti:
- Sinteza aminohinolina i njihovih derivata kao antimalarika i inhibitora botulinum neurotoksina A (RS-MESTD-Basic Research (BR or ON)-172008)
- Sinteza novih kompleksa metala i ispitivanje njihovih reakcija sa peptidima (RS-MESTD-Basic Research (BR or ON)-172036)
- Izučavanje mikrobiološkog diverziteta i karakterizacija korisnih sredinskih mikroorganizama (RS-MESTD-Basic Research (BR or ON)-173048)
- Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research (EU-FP7-256716)
- Serbian Academy of Sciences and Arts [F128]
- SupraMedChem'Balkans.Net SCOPES Institutional Partnership [IZ74Z0_160515]
Napomena:
- This is peer-reviewed version of the following article: Andrejević, T. P.; Nikolić, A. M.; Glišić, B. Đ.; Wadepohl, H.; Vojnovic, S.; Zlatović, M.; Petković, M.; Nikodinovic-Runic, J.; Opsenica, I. M.; Djuran, M. I. Synthesis, Structural Characterization and Antimicrobial Activity of Silver(I) Complexes with 1-Benzyl-1H-Tetrazoles. Polyhedron 2018, 154, 325–333. https://doi.org/10.1016/j.poly.2018.08.001
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/2992
DOI: 10.1016/j.poly.2018.08.001
ISSN: 0277-5387
WoS: 000446286300034
Scopus: 2-s2.0-85051984920
Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Andrejević, Tina P. AU - Nikolić, Andrea AU - Glišić, Biljana Đ. AU - Wadepohl, Hubert AU - Vojnović, Sandra AU - Zlatović, Mario AU - Petković, Miloš AU - Nikodinović-Runić, Jasmina AU - Opsenica, Igor AU - Đuran, Miloš I. PY - 2018 UR - https://cherry.chem.bg.ac.rs/handle/123456789/2991 AB - Herein, we report the synthesis and structural characteristics of three tetrazole-containing compounds, 1-benzyl-1H-tetrazole (bntz), 1-benzyl-1H-tetrazol-5-amine (bntza) and 1-(4-methoxybenzyl)-1H-tetrazol-5-amine (mbntza) and the corresponding silver(I) complexes of the general formula [Ag(NO3-O)(L-N4)(2)](n), L = bntz (1), bntza (2) and mbntza (3). Silver(I) complexes 1-3 and 1-benzyl-1H-tetrazoles have been studied in detail by NMR, IR and UV-Vis spectroscopic methods and the structures of 1 and 2 have been determined by single-crystal X-ray diffraction analysis. The results of these analyses revealed a monodentate coordination of the ligands to Ag(I) ion via the N4 tetrazole nitrogen. The antimicrobial potential of silver(I) complexes 1-3 was evaluated against the broad panel of Gram-positive and Gram-negative bacteria and fungi, displaying their remarkable inhibiting activity with MIC (minimal inhibitory concentration) values in the range 2-8 and 0.16-1.25 mu g/mL (3.8-16.3 and 0.31-2.15 mu M), respectively. On the other hand, 1-benzyl-1H-tetrazoles used for the synthesis of the silver(I) complexes were not active against the investigated strains, suggesting that the activity of the complexes originates from the Ag(I) ion exclusively. Moreover, silver(I) complexes 1-3 have good therapeutic potential, which can be deduced from their moderate cytotoxicity on the human fibroblast cell line MRC5, with IC50 values falling in the range 30-60 mu g/mL (57.7-103.4 mu M). (C) 2018 Elsevier Ltd. All rights reserved. PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Polyhedron T1 - Synthesis, structural characterization and antimicrobial activity of silver(I) complexes with 1-benzyl-1H-tetrazoles VL - 154 SP - 325 EP - 333 DO - 10.1016/j.poly.2018.08.001 ER -
@article{ author = "Andrejević, Tina P. and Nikolić, Andrea and Glišić, Biljana Đ. and Wadepohl, Hubert and Vojnović, Sandra and Zlatović, Mario and Petković, Miloš and Nikodinović-Runić, Jasmina and Opsenica, Igor and Đuran, Miloš I.", year = "2018", abstract = "Herein, we report the synthesis and structural characteristics of three tetrazole-containing compounds, 1-benzyl-1H-tetrazole (bntz), 1-benzyl-1H-tetrazol-5-amine (bntza) and 1-(4-methoxybenzyl)-1H-tetrazol-5-amine (mbntza) and the corresponding silver(I) complexes of the general formula [Ag(NO3-O)(L-N4)(2)](n), L = bntz (1), bntza (2) and mbntza (3). Silver(I) complexes 1-3 and 1-benzyl-1H-tetrazoles have been studied in detail by NMR, IR and UV-Vis spectroscopic methods and the structures of 1 and 2 have been determined by single-crystal X-ray diffraction analysis. The results of these analyses revealed a monodentate coordination of the ligands to Ag(I) ion via the N4 tetrazole nitrogen. The antimicrobial potential of silver(I) complexes 1-3 was evaluated against the broad panel of Gram-positive and Gram-negative bacteria and fungi, displaying their remarkable inhibiting activity with MIC (minimal inhibitory concentration) values in the range 2-8 and 0.16-1.25 mu g/mL (3.8-16.3 and 0.31-2.15 mu M), respectively. On the other hand, 1-benzyl-1H-tetrazoles used for the synthesis of the silver(I) complexes were not active against the investigated strains, suggesting that the activity of the complexes originates from the Ag(I) ion exclusively. Moreover, silver(I) complexes 1-3 have good therapeutic potential, which can be deduced from their moderate cytotoxicity on the human fibroblast cell line MRC5, with IC50 values falling in the range 30-60 mu g/mL (57.7-103.4 mu M). (C) 2018 Elsevier Ltd. All rights reserved.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Polyhedron", title = "Synthesis, structural characterization and antimicrobial activity of silver(I) complexes with 1-benzyl-1H-tetrazoles", volume = "154", pages = "325-333", doi = "10.1016/j.poly.2018.08.001" }
Andrejević, T. P., Nikolić, A., Glišić, B. Đ., Wadepohl, H., Vojnović, S., Zlatović, M., Petković, M., Nikodinović-Runić, J., Opsenica, I.,& Đuran, M. I.. (2018). Synthesis, structural characterization and antimicrobial activity of silver(I) complexes with 1-benzyl-1H-tetrazoles. in Polyhedron Pergamon-Elsevier Science Ltd, Oxford., 154, 325-333. https://doi.org/10.1016/j.poly.2018.08.001
Andrejević TP, Nikolić A, Glišić BĐ, Wadepohl H, Vojnović S, Zlatović M, Petković M, Nikodinović-Runić J, Opsenica I, Đuran MI. Synthesis, structural characterization and antimicrobial activity of silver(I) complexes with 1-benzyl-1H-tetrazoles. in Polyhedron. 2018;154:325-333. doi:10.1016/j.poly.2018.08.001 .
Andrejević, Tina P., Nikolić, Andrea, Glišić, Biljana Đ., Wadepohl, Hubert, Vojnović, Sandra, Zlatović, Mario, Petković, Miloš, Nikodinović-Runić, Jasmina, Opsenica, Igor, Đuran, Miloš I., "Synthesis, structural characterization and antimicrobial activity of silver(I) complexes with 1-benzyl-1H-tetrazoles" in Polyhedron, 154 (2018):325-333, https://doi.org/10.1016/j.poly.2018.08.001 . .