Synthesis, structural characterization and biological evaluation of dinuclear gold(III) complexes with aromatic nitrogen-containing ligands: antimicrobial activity in relation to the complex nuclearity
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2016
Authors
Glišić, Biljana Đ.Savić, Nada D.
Warżajtis, Beata
Đokić, Lidija
Ilić-Tomić, Tatjana
Antić, Marija
Radenković, Slavko
Nikodinović-Runić, Jasmina
Rychlewska, Urszula
Đuran, Miloš I.
Article (Published version)
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Dinuclear gold(III) complexes {[AuCl3](2)(mu-4,4'-bipy)} (1) and {[AuCl3](2)(mu-bpe)} (2) with bridging aromatic nitrogen-containing heterocyclic ligands, 4,4'-bipyridine (4,4'-bipy) and 1,2-bis(4-pyridyl)ethane (bpe), were synthesized and characterized by NMR (H-1 and C-13), UV-vis and IR spectroscopic techniques. The crystal structure of 1 was determined by single-crystal X-ray diffraction analysis, while the DFT M06-2X method was applied in order to optimize the structures of 1 and 2. A detailed mechanistic study was performed using the same DFT approach in order to shed light on the disparate coordination modes of the presently investigated N-heterocyclic ligands and the monocyclic pyrazine, which contains two nitrogen atoms within one ring, toward the AuCl3 fragment. The investigation of the solution stability of 1 and 2 in DMSO revealed that both complexes were sufficiently stable in this solvent at room temperature. Complexes 1 and 2, along with K[AuCl4] and the N-heterocyclic l...igands used for their synthesis, were evaluated by in vitro antimicrobial studies against a panel of Gram-positive and Gram-negative bacteria and the fungus Candida albicans. In most cases, complexes 1 and 2 have higher antibacterial activity than K[AuCl4] (MICs for 1 and 2 were in the range 3.9-62.5 mu g mL(-1)), while both of the N-heterocycles did not affect the bacterial growth at concentrations up to 500 mu g mL(-1). On the other hand, the antifungal activity of these two complexes against C. albicans was moderate and lower than that of K[AuCl4]. In order to determine the therapeutic potential of 1 and 2, their antiproliferative effect on the normal human lung fibroblast cell line MRC5 and embryotoxicity on zebrafish (Danio rerio) have also been evaluated. To the best of our knowledge, complexes 1 and 2 are the first examples of dinuclear gold(III) complexes with aromatic six-membered heterocycles containing two nitrogen atoms as bridging ligands.
Source:
MedChemComm, 2016, 7, 7, 1356-1366Publisher:
- Royal Soc Chemistry, Cambridge
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)
- Graph theory and mathematical programming with applications in chemistry and computer science (RS-MESTD-Basic Research (BR or ON)-174033)
- PL-Grid infrastructure
DOI: 10.1039/c6md00214e
ISSN: 2040-2503
WoS: 000379431300010
Scopus: 2-s2.0-84978924683
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Inovacioni centar / Innovation CentreTY - JOUR AU - Glišić, Biljana Đ. AU - Savić, Nada D. AU - Warżajtis, Beata AU - Đokić, Lidija AU - Ilić-Tomić, Tatjana AU - Antić, Marija AU - Radenković, Slavko AU - Nikodinović-Runić, Jasmina AU - Rychlewska, Urszula AU - Đuran, Miloš I. PY - 2016 UR - https://cherry.chem.bg.ac.rs/handle/123456789/2275 AB - Dinuclear gold(III) complexes {[AuCl3](2)(mu-4,4'-bipy)} (1) and {[AuCl3](2)(mu-bpe)} (2) with bridging aromatic nitrogen-containing heterocyclic ligands, 4,4'-bipyridine (4,4'-bipy) and 1,2-bis(4-pyridyl)ethane (bpe), were synthesized and characterized by NMR (H-1 and C-13), UV-vis and IR spectroscopic techniques. The crystal structure of 1 was determined by single-crystal X-ray diffraction analysis, while the DFT M06-2X method was applied in order to optimize the structures of 1 and 2. A detailed mechanistic study was performed using the same DFT approach in order to shed light on the disparate coordination modes of the presently investigated N-heterocyclic ligands and the monocyclic pyrazine, which contains two nitrogen atoms within one ring, toward the AuCl3 fragment. The investigation of the solution stability of 1 and 2 in DMSO revealed that both complexes were sufficiently stable in this solvent at room temperature. Complexes 1 and 2, along with K[AuCl4] and the N-heterocyclic ligands used for their synthesis, were evaluated by in vitro antimicrobial studies against a panel of Gram-positive and Gram-negative bacteria and the fungus Candida albicans. In most cases, complexes 1 and 2 have higher antibacterial activity than K[AuCl4] (MICs for 1 and 2 were in the range 3.9-62.5 mu g mL(-1)), while both of the N-heterocycles did not affect the bacterial growth at concentrations up to 500 mu g mL(-1). On the other hand, the antifungal activity of these two complexes against C. albicans was moderate and lower than that of K[AuCl4]. In order to determine the therapeutic potential of 1 and 2, their antiproliferative effect on the normal human lung fibroblast cell line MRC5 and embryotoxicity on zebrafish (Danio rerio) have also been evaluated. To the best of our knowledge, complexes 1 and 2 are the first examples of dinuclear gold(III) complexes with aromatic six-membered heterocycles containing two nitrogen atoms as bridging ligands. PB - Royal Soc Chemistry, Cambridge T2 - MedChemComm T1 - Synthesis, structural characterization and biological evaluation of dinuclear gold(III) complexes with aromatic nitrogen-containing ligands: antimicrobial activity in relation to the complex nuclearity VL - 7 IS - 7 SP - 1356 EP - 1366 DO - 10.1039/c6md00214e ER -
@article{ author = "Glišić, Biljana Đ. and Savić, Nada D. and Warżajtis, Beata and Đokić, Lidija and Ilić-Tomić, Tatjana and Antić, Marija and Radenković, Slavko and Nikodinović-Runić, Jasmina and Rychlewska, Urszula and Đuran, Miloš I.", year = "2016", abstract = "Dinuclear gold(III) complexes {[AuCl3](2)(mu-4,4'-bipy)} (1) and {[AuCl3](2)(mu-bpe)} (2) with bridging aromatic nitrogen-containing heterocyclic ligands, 4,4'-bipyridine (4,4'-bipy) and 1,2-bis(4-pyridyl)ethane (bpe), were synthesized and characterized by NMR (H-1 and C-13), UV-vis and IR spectroscopic techniques. The crystal structure of 1 was determined by single-crystal X-ray diffraction analysis, while the DFT M06-2X method was applied in order to optimize the structures of 1 and 2. A detailed mechanistic study was performed using the same DFT approach in order to shed light on the disparate coordination modes of the presently investigated N-heterocyclic ligands and the monocyclic pyrazine, which contains two nitrogen atoms within one ring, toward the AuCl3 fragment. The investigation of the solution stability of 1 and 2 in DMSO revealed that both complexes were sufficiently stable in this solvent at room temperature. Complexes 1 and 2, along with K[AuCl4] and the N-heterocyclic ligands used for their synthesis, were evaluated by in vitro antimicrobial studies against a panel of Gram-positive and Gram-negative bacteria and the fungus Candida albicans. In most cases, complexes 1 and 2 have higher antibacterial activity than K[AuCl4] (MICs for 1 and 2 were in the range 3.9-62.5 mu g mL(-1)), while both of the N-heterocycles did not affect the bacterial growth at concentrations up to 500 mu g mL(-1). On the other hand, the antifungal activity of these two complexes against C. albicans was moderate and lower than that of K[AuCl4]. In order to determine the therapeutic potential of 1 and 2, their antiproliferative effect on the normal human lung fibroblast cell line MRC5 and embryotoxicity on zebrafish (Danio rerio) have also been evaluated. To the best of our knowledge, complexes 1 and 2 are the first examples of dinuclear gold(III) complexes with aromatic six-membered heterocycles containing two nitrogen atoms as bridging ligands.", publisher = "Royal Soc Chemistry, Cambridge", journal = "MedChemComm", title = "Synthesis, structural characterization and biological evaluation of dinuclear gold(III) complexes with aromatic nitrogen-containing ligands: antimicrobial activity in relation to the complex nuclearity", volume = "7", number = "7", pages = "1356-1366", doi = "10.1039/c6md00214e" }
Glišić, B. Đ., Savić, N. D., Warżajtis, B., Đokić, L., Ilić-Tomić, T., Antić, M., Radenković, S., Nikodinović-Runić, J., Rychlewska, U.,& Đuran, M. I.. (2016). Synthesis, structural characterization and biological evaluation of dinuclear gold(III) complexes with aromatic nitrogen-containing ligands: antimicrobial activity in relation to the complex nuclearity. in MedChemComm Royal Soc Chemistry, Cambridge., 7(7), 1356-1366. https://doi.org/10.1039/c6md00214e
Glišić BĐ, Savić ND, Warżajtis B, Đokić L, Ilić-Tomić T, Antić M, Radenković S, Nikodinović-Runić J, Rychlewska U, Đuran MI. Synthesis, structural characterization and biological evaluation of dinuclear gold(III) complexes with aromatic nitrogen-containing ligands: antimicrobial activity in relation to the complex nuclearity. in MedChemComm. 2016;7(7):1356-1366. doi:10.1039/c6md00214e .
Glišić, Biljana Đ., Savić, Nada D., Warżajtis, Beata, Đokić, Lidija, Ilić-Tomić, Tatjana, Antić, Marija, Radenković, Slavko, Nikodinović-Runić, Jasmina, Rychlewska, Urszula, Đuran, Miloš I., "Synthesis, structural characterization and biological evaluation of dinuclear gold(III) complexes with aromatic nitrogen-containing ligands: antimicrobial activity in relation to the complex nuclearity" in MedChemComm, 7, no. 7 (2016):1356-1366, https://doi.org/10.1039/c6md00214e . .