Synthesis, structural characterization and antimicrobial activity of silver(I) complexes with 1-benzyl-1H-tetrazoles
Аутори
Andrejević, Tina P.Nikolić, Andrea M.
Glišić, Biljana
Wadepohl, Hubert
Vojnović, Sandra
Zlatović, Mario
Petković, Milos
Nikodinović-Runić, Jasmina
Opsenica, Igor M.
Djuran, Milos
Чланак у часопису (Рецензирана верзија)
Метаподаци
Приказ свих података о документуАпстракт
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).
Кључне речи:
Structural characterization / Silver(I) complexes / Cytotoxicity / Antimicrobial activity / 1-Benzyl-1H-tetrazolesИзвор:
Polyhedron, 2018, 154, 325-333Издавач:
- Pergamon-Elsevier Science Ltd, Oxford
Финансирање / пројекти:
- SupraMedChem"Balkans.Net SCOPES Institutional Partnership [IZ74Z0_160515]
- Serbian Academy of Sciences and Arts [F128]
- 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)
- Синтеза аминохинолина и њихових деривата као антималарика и инхибитора ботулинум неуротоксина А (RS-MESTD-Basic Research (BR or ON)-172008)
- Синтеза нових комплекса метала и испитивање њихових реакција са пептидима (RS-MESTD-Basic Research (BR or ON)-172036)
- Изучавање микробиолошког диверзитета и карактеризација корисних срединских микроорганизама (RS-MESTD-Basic Research (BR or ON)-173048)
Напомена:
- Related to published version: https://imagine.imgge.bg.ac.rs/handle/123456789/1144
- This is the peer-reviewed version of the article: Andrejević, T. P., Nikolić, A. M., Glišić, B., Wadepohl, H., Vojnović, S., Zlatović, M., Petković, M., Nikodinović-Runić, J., Opsenica, I. M., & Djuran, M. (2018). Synthesis, structural characterization and antimicrobial activity of silver(I) complexes with 1-benzyl-1H-tetrazoles. Polyhedron, 154, 325–333. https://doi.org/10.1016/j.poly.2018.08.001
Повезане информације:
- Друга верзија
https://imagine.imgge.bg.ac.rs/handle/123456789/1144 - Друга верзија
https://doi.org/10.1016/j.poly.2018.08.001
DOI: 10.1016/j.poly.2018.08.001
ISSN: 0277-5387
WoS: 000446286300034
Scopus: 2-s2.0-85051984920
Институција/група
Institut za molekularnu genetiku i genetičko inženjerstvoTY - JOUR AU - Andrejević, Tina P. AU - Nikolić, Andrea M. AU - Glišić, Biljana AU - Wadepohl, Hubert AU - Vojnović, Sandra AU - Zlatović, Mario AU - Petković, Milos AU - Nikodinović-Runić, Jasmina AU - Opsenica, Igor M. AU - Djuran, Milos PY - 2018 UR - https://imagine.imgge.bg.ac.rs/handle/123456789/1759 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). PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Polyhedron T1 - Synthesis, structural characterization and antimicrobial activity of silver(I) complexes with 1-benzyl-1H-tetrazoles EP - 333 SP - 325 VL - 154 DO - 10.1016/j.poly.2018.08.001 ER -
@article{ author = "Andrejević, Tina P. and Nikolić, Andrea M. and Glišić, Biljana and Wadepohl, Hubert and Vojnović, Sandra and Zlatović, Mario and Petković, Milos and Nikodinović-Runić, Jasmina and Opsenica, Igor M. and Djuran, Milos", 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).", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Polyhedron", title = "Synthesis, structural characterization and antimicrobial activity of silver(I) complexes with 1-benzyl-1H-tetrazoles", pages = "333-325", volume = "154", doi = "10.1016/j.poly.2018.08.001" }
Andrejević, T. P., Nikolić, A. M., Glišić, B., Wadepohl, H., Vojnović, S., Zlatović, M., Petković, M., Nikodinović-Runić, J., Opsenica, I. M.,& Djuran, M.. (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 AM, Glišić B, Wadepohl H, Vojnović S, Zlatović M, Petković M, Nikodinović-Runić J, Opsenica IM, Djuran M. 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 M., Glišić, Biljana, Wadepohl, Hubert, Vojnović, Sandra, Zlatović, Mario, Petković, Milos, Nikodinović-Runić, Jasmina, Opsenica, Igor M., Djuran, Milos, "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 . .