Synthesis, structural characterization and biological evaluation of dinuclear gold(III) complexes with aromatic nitrogen-containing ligands: antimicrobial activity in relation to the complex nuclearity
Samo za registrovane korisnike
2016
Autori
Glišić, BiljanaSavić, Nada D.
Warzajtis, Beata
Đokić, Lidija
Ilić-Tomić, Tatjana
Antić, Marija
Radenković, Slavko
Nikodinović-Runić, Jasmina
Rychlewska, Urszula
Djuran, Milos I.
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Izvor:
Medchemcomm, 2016, 7, 7, 1356-1366Izdavač:
- Royal Soc Chemistry, Cambridge
Finansiranje / projekti:
- PL-Grid infrastructure
- 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)
- Teorija grafova i matematičko programiranje sa primenama u hemiji i računarstvu (RS-MESTD-Basic Research (BR or ON)-174033)
DOI: 10.1039/c6md00214e
ISSN: 2040-2503
WoS: 000379431300010
Scopus: 2-s2.0-84978924683
Institucija/grupa
Institut za molekularnu genetiku i genetičko inženjerstvoTY - JOUR AU - Glišić, Biljana AU - Savić, Nada D. AU - Warzajtis, Beata AU - Đokić, Lidija AU - Ilić-Tomić, Tatjana AU - Antić, Marija AU - Radenković, Slavko AU - Nikodinović-Runić, Jasmina AU - Rychlewska, Urszula AU - Djuran, Milos I. PY - 2016 UR - https://imagine.imgge.bg.ac.rs/handle/123456789/913 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 EP - 1366 IS - 7 SP - 1356 VL - 7 DO - 10.1039/c6md00214e ER -
@article{ author = "Glišić, Biljana and Savić, Nada D. and Warzajtis, Beata and Đokić, Lidija and Ilić-Tomić, Tatjana and Antić, Marija and Radenković, Slavko and Nikodinović-Runić, Jasmina and Rychlewska, Urszula and Djuran, Milos 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", pages = "1366-1356", number = "7", volume = "7", doi = "10.1039/c6md00214e" }
Glišić, B., Savić, N. D., Warzajtis, B., Đokić, L., Ilić-Tomić, T., Antić, M., Radenković, S., Nikodinović-Runić, J., Rychlewska, U.,& Djuran, 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 B, Savić ND, Warzajtis B, Đokić L, Ilić-Tomić T, Antić M, Radenković S, Nikodinović-Runić J, Rychlewska U, Djuran 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, Savić, Nada D., Warzajtis, Beata, Đokić, Lidija, Ilić-Tomić, Tatjana, Antić, Marija, Radenković, Slavko, Nikodinović-Runić, Jasmina, Rychlewska, Urszula, Djuran, Milos 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 . .