TY  - JOUR
AU  - Stanković, Mia
AU  - Kljun, Jakob
AU  - Stevanović, Nevena Lj.
AU  - Lazić, Jelena
AU  - Skaro Bogojevic, Sanja
AU  - Vojnović, Sandra
AU  - Zlatar, Matija
AU  - Nikodinović-Runić, Jasmina
AU  - Turel, Iztok
AU  - Đuran, Miloš
AU  - Glišić, Biljana
PY  - 2024
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7296
AB  - Inspired by the emergence of resistance to currently available antifungal therapy and by the great potential of metal complexes for the treatment of various diseases, we synthesized three new silver(I) complexes containing clinically used antifungal azoles as ligands, [Ag(ecz)2]SbF6 (1, ecz is econazole), {[Ag(vcz)2]SbF6}n (2, vcz is voriconazole), and [Ag(ctz)2]SbF6 (3, ctz is clotrimazole), and investigated their antimicrobial properties. The synthesized complexes were characterized by mass spectrometry, IR, UV-vis and 1H NMR spectroscopy, cyclic voltammetry, and single-crystal X-ray diffraction analysis. In the mononuclear complexes 1 and 3 with ecz and ctz, respectively, the silver(I) ion has the expected linear geometry, in which the azoles are monodentately coordinated to this metal center through the N3 imidazole nitrogen atom. In contrast, the vcz-containing complex 2 has a polymeric structure in the solid state in which the silver(I) ions are coordinated by four nitrogen atoms in a distorted tetrahedral geometry. DFT calculations were done to predict the most favorable structures of the studied complexes in DMSO solution. All the studied silver(I) complexes have shown excellent antifungal and good to moderate antibacterial activities with minimal inhibitory concentration (MIC) values in the ranges of 0.01–27.1 and 2.61–47.9 μM on the selected panel of fungi and bacteria, respectively. Importantly, the complexes 1–3 have exhibited a significantly improved antifungal activity compared to the free azoles, with the most pronounced effect observed in the case of complex 2 compared to the parent vcz against Candida glabrata with an increase of activity by five orders of magnitude. Moreover, the silver(I)-azole complexes 2 and 3 significantly inhibited the formation of C. albicans hyphae and biofilms at the subinhibitory concentration of 50% MIC. To investigate the impact of the complex 3 more thoroughly on Candida pathogenesis, its effect on the adherence of C. albicans to A549 cells (human adenocarcinoma alveolar basal epithelial cells), as an initial step of the invasion of host cells, was studied.
PB  - Royal Society of Chemistry (RSC)
T2  - Dalton Transactions
T1  - Silver(I) complexes containing antifungal azoles: significant improvement of the anti-Candida potential of the azole drug after its coordination to the silver(I) ion
VL  - 53
SP  - 2218
EP  - 2230
DO  - 10.1039/D3DT03010E
ER  - 

@article{
author = "Stanković, Mia and Kljun, Jakob and Stevanović, Nevena Lj. and Lazić, Jelena and Skaro Bogojevic, Sanja and Vojnović, Sandra and Zlatar, Matija and Nikodinović-Runić, Jasmina and Turel, Iztok and Đuran, Miloš and Glišić, Biljana",
year = "2024",
abstract = "Inspired by the emergence of resistance to currently available antifungal therapy and by the great potential of metal complexes for the treatment of various diseases, we synthesized three new silver(I) complexes containing clinically used antifungal azoles as ligands, [Ag(ecz)2]SbF6 (1, ecz is econazole), {[Ag(vcz)2]SbF6}n (2, vcz is voriconazole), and [Ag(ctz)2]SbF6 (3, ctz is clotrimazole), and investigated their antimicrobial properties. The synthesized complexes were characterized by mass spectrometry, IR, UV-vis and 1H NMR spectroscopy, cyclic voltammetry, and single-crystal X-ray diffraction analysis. In the mononuclear complexes 1 and 3 with ecz and ctz, respectively, the silver(I) ion has the expected linear geometry, in which the azoles are monodentately coordinated to this metal center through the N3 imidazole nitrogen atom. In contrast, the vcz-containing complex 2 has a polymeric structure in the solid state in which the silver(I) ions are coordinated by four nitrogen atoms in a distorted tetrahedral geometry. DFT calculations were done to predict the most favorable structures of the studied complexes in DMSO solution. All the studied silver(I) complexes have shown excellent antifungal and good to moderate antibacterial activities with minimal inhibitory concentration (MIC) values in the ranges of 0.01–27.1 and 2.61–47.9 μM on the selected panel of fungi and bacteria, respectively. Importantly, the complexes 1–3 have exhibited a significantly improved antifungal activity compared to the free azoles, with the most pronounced effect observed in the case of complex 2 compared to the parent vcz against Candida glabrata with an increase of activity by five orders of magnitude. Moreover, the silver(I)-azole complexes 2 and 3 significantly inhibited the formation of C. albicans hyphae and biofilms at the subinhibitory concentration of 50% MIC. To investigate the impact of the complex 3 more thoroughly on Candida pathogenesis, its effect on the adherence of C. albicans to A549 cells (human adenocarcinoma alveolar basal epithelial cells), as an initial step of the invasion of host cells, was studied.",
publisher = "Royal Society of Chemistry (RSC)",
journal = "Dalton Transactions",
title = "Silver(I) complexes containing antifungal azoles: significant improvement of the anti-Candida potential of the azole drug after its coordination to the silver(I) ion",
volume = "53",
pages = "2218-2230",
doi = "10.1039/D3DT03010E"
}

Stanković, M., Kljun, J., Stevanović, N. Lj., Lazić, J., Skaro Bogojevic, S., Vojnović, S., Zlatar, M., Nikodinović-Runić, J., Turel, I., Đuran, M.,& Glišić, B.. (2024). Silver(I) complexes containing antifungal azoles: significant improvement of the anti-Candida potential of the azole drug after its coordination to the silver(I) ion. in Dalton Transactions
Royal Society of Chemistry (RSC)., 53, 2218-2230.
https://doi.org/10.1039/D3DT03010E

Stanković M, Kljun J, Stevanović NL, Lazić J, Skaro Bogojevic S, Vojnović S, Zlatar M, Nikodinović-Runić J, Turel I, Đuran M, Glišić B. Silver(I) complexes containing antifungal azoles: significant improvement of the anti-Candida potential of the azole drug after its coordination to the silver(I) ion. in Dalton Transactions. 2024;53:2218-2230.
doi:10.1039/D3DT03010E .

Stanković, Mia, Kljun, Jakob, Stevanović, Nevena Lj., Lazić, Jelena, Skaro Bogojevic, Sanja, Vojnović, Sandra, Zlatar, Matija, Nikodinović-Runić, Jasmina, Turel, Iztok, Đuran, Miloš, Glišić, Biljana, "Silver(I) complexes containing antifungal azoles: significant improvement of the anti-Candida potential of the azole drug after its coordination to the silver(I) ion" in Dalton Transactions, 53 (2024):2218-2230,
https://doi.org/10.1039/D3DT03010E . .

TY  - JOUR
AU  - Andrejević, Tina P.
AU  - Aleksić, Ivana
AU  - Kljun, Jakob
AU  - Počkaj, Marta
AU  - Zlatar, Matija
AU  - Vojnović, Sandra
AU  - Nikodinović-Runić, Jasmina
AU  - Turel, Iztok
AU  - Đuran, Miloš
AU  - Glišić, Biljana
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5654
AB  - Dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz) was used as a ligand for the synthesis of new copper(II) and silver(I) complexes, [CuCl2(py-2pz)]2 (1), [Cu(CF3SO3)(H2O)(py-2pz)2]CF3SO3·2H2O (2), [Ag(py-2pz)2]PF6 (3) and {[Ag(NO3)(py-2pz)]·0.5H2O}n (4). The complexes were characterized by spectroscopic and electrochemical methods, while their structures were determined by single crystal X-ray diffraction analysis. The X-ray analysis revealed the bidentate coordination mode of py-2pz to the corresponding metal ion via its pyridine and pyrazine nitrogen atoms in all complexes, while in polynuclear complex 4, the heterocyclic pyrazine ring of one py-2pz additionally behaves as a bridging ligand between two Ag(I) ions. DFT calculations were performed to elucidate the structures of the investigated complexes in solution. The antimicrobial potential of the complexes 1–4 was evaluated against two bacterial (Pseudomonas aeruginosa and Staphylococcus aureus) and two Candida (C. albicans and C. parapsilosis) species. Silver(I) complexes 3 and 4 have shown good antibacterial and antifungal properties with minimal inhibitory concentration (MIC) values ranging from 4.9 to 39.0 μM (3.9–31.2 μg mL−1). All complexes inhibited the filamentation of C. albicans and hyphae formation, while silver(I) complexes 3 and 4 had also the ability to inhibit the biofilm formation process of this fungus. The binding affinity of the complexes 1–4 with calf thymus DNA (ct-DNA) and bovine serum albumin (BSA) was studied by fluorescence emission spectroscopy to clarify the mode of their antimicrobial activity. Catechol oxidase biomimetic catalytic activity of copper(II) complexes 1 and 2 was additionally investigated by using 3,5-di-tert-butylcatechol (3,5-DTBC) and o-aminophenol (OAP) as substrates.
PB  - Royal Society of Chemistry (RSC)
T2  - RSC Advances
T1  - Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex
VL  - 13
IS  - 7
SP  - 4376
EP  - 4393
DO  - 10.1039/D2RA07401J
ER  - 

@article{
author = "Andrejević, Tina P. and Aleksić, Ivana and Kljun, Jakob and Počkaj, Marta and Zlatar, Matija and Vojnović, Sandra and Nikodinović-Runić, Jasmina and Turel, Iztok and Đuran, Miloš and Glišić, Biljana",
year = "2023",
abstract = "Dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz) was used as a ligand for the synthesis of new copper(II) and silver(I) complexes, [CuCl2(py-2pz)]2 (1), [Cu(CF3SO3)(H2O)(py-2pz)2]CF3SO3·2H2O (2), [Ag(py-2pz)2]PF6 (3) and {[Ag(NO3)(py-2pz)]·0.5H2O}n (4). The complexes were characterized by spectroscopic and electrochemical methods, while their structures were determined by single crystal X-ray diffraction analysis. The X-ray analysis revealed the bidentate coordination mode of py-2pz to the corresponding metal ion via its pyridine and pyrazine nitrogen atoms in all complexes, while in polynuclear complex 4, the heterocyclic pyrazine ring of one py-2pz additionally behaves as a bridging ligand between two Ag(I) ions. DFT calculations were performed to elucidate the structures of the investigated complexes in solution. The antimicrobial potential of the complexes 1–4 was evaluated against two bacterial (Pseudomonas aeruginosa and Staphylococcus aureus) and two Candida (C. albicans and C. parapsilosis) species. Silver(I) complexes 3 and 4 have shown good antibacterial and antifungal properties with minimal inhibitory concentration (MIC) values ranging from 4.9 to 39.0 μM (3.9–31.2 μg mL−1). All complexes inhibited the filamentation of C. albicans and hyphae formation, while silver(I) complexes 3 and 4 had also the ability to inhibit the biofilm formation process of this fungus. The binding affinity of the complexes 1–4 with calf thymus DNA (ct-DNA) and bovine serum albumin (BSA) was studied by fluorescence emission spectroscopy to clarify the mode of their antimicrobial activity. Catechol oxidase biomimetic catalytic activity of copper(II) complexes 1 and 2 was additionally investigated by using 3,5-di-tert-butylcatechol (3,5-DTBC) and o-aminophenol (OAP) as substrates.",
publisher = "Royal Society of Chemistry (RSC)",
journal = "RSC Advances",
title = "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex",
volume = "13",
number = "7",
pages = "4376-4393",
doi = "10.1039/D2RA07401J"
}

Andrejević, T. P., Aleksić, I., Kljun, J., Počkaj, M., Zlatar, M., Vojnović, S., Nikodinović-Runić, J., Turel, I., Đuran, M.,& Glišić, B.. (2023). Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex. in RSC Advances
Royal Society of Chemistry (RSC)., 13(7), 4376-4393.
https://doi.org/10.1039/D2RA07401J

Andrejević TP, Aleksić I, Kljun J, Počkaj M, Zlatar M, Vojnović S, Nikodinović-Runić J, Turel I, Đuran M, Glišić B. Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex. in RSC Advances. 2023;13(7):4376-4393.
doi:10.1039/D2RA07401J .

Andrejević, Tina P., Aleksić, Ivana, Kljun, Jakob, Počkaj, Marta, Zlatar, Matija, Vojnović, Sandra, Nikodinović-Runić, Jasmina, Turel, Iztok, Đuran, Miloš, Glišić, Biljana, "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex" in RSC Advances, 13, no. 7 (2023):4376-4393,
https://doi.org/10.1039/D2RA07401J . .

TY  - DATA
AU  - Andrejević, Tina P.
AU  - Aleksić, Ivana
AU  - Kljun, Jakob
AU  - Počkaj, Marta
AU  - Zlatar, Matija
AU  - Vojnović, Sandra
AU  - Nikodinović-Runić, Jasmina
AU  - Turel, Iztok
AU  - Đuran, Miloš
AU  - Glišić, Biljana
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5669
AB  - TEZLOD : New Structure undergoing enhancement  Space Group: P 1 (2), Cell: a 7.7916(6)Å b 8.9848(6)Å c 11.9955(7)Å, α 104.394(6)° β 106.396(6)° γ 104.368(6)°
PB  - The Cambridge Crystallographic Data Centre (CCDC)
T1  - CCDC 2220146: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex"
DO  - 10.5517/ccdc.csd.cc2dj7mt
ER  - 

@misc{
author = "Andrejević, Tina P. and Aleksić, Ivana and Kljun, Jakob and Počkaj, Marta and Zlatar, Matija and Vojnović, Sandra and Nikodinović-Runić, Jasmina and Turel, Iztok and Đuran, Miloš and Glišić, Biljana",
year = "2023",
abstract = "TEZLOD : New Structure undergoing enhancement  Space Group: P 1 (2), Cell: a 7.7916(6)Å b 8.9848(6)Å c 11.9955(7)Å, α 104.394(6)° β 106.396(6)° γ 104.368(6)°",
publisher = "The Cambridge Crystallographic Data Centre (CCDC)",
title = "CCDC 2220146: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex"",
doi = "10.5517/ccdc.csd.cc2dj7mt"
}

Andrejević, T. P., Aleksić, I., Kljun, J., Počkaj, M., Zlatar, M., Vojnović, S., Nikodinović-Runić, J., Turel, I., Đuran, M.,& Glišić, B.. (2023). CCDC 2220146: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex". 
The Cambridge Crystallographic Data Centre (CCDC)..
https://doi.org/10.5517/ccdc.csd.cc2dj7mt

Andrejević TP, Aleksić I, Kljun J, Počkaj M, Zlatar M, Vojnović S, Nikodinović-Runić J, Turel I, Đuran M, Glišić B. CCDC 2220146: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex". 2023;.
doi:10.5517/ccdc.csd.cc2dj7mt .

Andrejević, Tina P., Aleksić, Ivana, Kljun, Jakob, Počkaj, Marta, Zlatar, Matija, Vojnović, Sandra, Nikodinović-Runić, Jasmina, Turel, Iztok, Đuran, Miloš, Glišić, Biljana, "CCDC 2220146: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex"" (2023),
https://doi.org/10.5517/ccdc.csd.cc2dj7mt . .

TY  - DATA
AU  - Andrejević, Tina P.
AU  - Aleksić, Ivana
AU  - Kljun, Jakob
AU  - Počkaj, Marta
AU  - Zlatar, Matija
AU  - Vojnović, Sandra
AU  - Nikodinović-Runić, Jasmina
AU  - Turel, Iztok
AU  - Đuran, Miloš
AU  - Glišić, Biljana
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5669
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5670
AB  - TEZLUJ : New Structure undergoing enhancement  Space Group: P 1 (2), Cell: a 8.2856(3)Å b 12.1191(5)Å c 19.2393(6)Å, α 82.105(3)° β 86.220(3)° γ 77.071(3)°
PB  - The Cambridge Crystallographic Data Centre (CCDC)
T1  - CCDC 2220147: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex"
DO  - 10.5517/ccdc.csd.cc2dj7nv
ER  - 

@misc{
author = "Andrejević, Tina P. and Aleksić, Ivana and Kljun, Jakob and Počkaj, Marta and Zlatar, Matija and Vojnović, Sandra and Nikodinović-Runić, Jasmina and Turel, Iztok and Đuran, Miloš and Glišić, Biljana",
year = "2023",
abstract = "TEZLUJ : New Structure undergoing enhancement  Space Group: P 1 (2), Cell: a 8.2856(3)Å b 12.1191(5)Å c 19.2393(6)Å, α 82.105(3)° β 86.220(3)° γ 77.071(3)°",
publisher = "The Cambridge Crystallographic Data Centre (CCDC)",
title = "CCDC 2220147: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex"",
doi = "10.5517/ccdc.csd.cc2dj7nv"
}

Andrejević, T. P., Aleksić, I., Kljun, J., Počkaj, M., Zlatar, M., Vojnović, S., Nikodinović-Runić, J., Turel, I., Đuran, M.,& Glišić, B.. (2023). CCDC 2220147: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex". 
The Cambridge Crystallographic Data Centre (CCDC)..
https://doi.org/10.5517/ccdc.csd.cc2dj7nv

Andrejević TP, Aleksić I, Kljun J, Počkaj M, Zlatar M, Vojnović S, Nikodinović-Runić J, Turel I, Đuran M, Glišić B. CCDC 2220147: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex". 2023;.
doi:10.5517/ccdc.csd.cc2dj7nv .

Andrejević, Tina P., Aleksić, Ivana, Kljun, Jakob, Počkaj, Marta, Zlatar, Matija, Vojnović, Sandra, Nikodinović-Runić, Jasmina, Turel, Iztok, Đuran, Miloš, Glišić, Biljana, "CCDC 2220147: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex"" (2023),
https://doi.org/10.5517/ccdc.csd.cc2dj7nv . .

TY  - DATA
AU  - Andrejević, Tina P.
AU  - Aleksić, Ivana
AU  - Kljun, Jakob
AU  - Počkaj, Marta
AU  - Zlatar, Matija
AU  - Vojnović, Sandra
AU  - Nikodinović-Runić, Jasmina
AU  - Turel, Iztok
AU  - Đuran, Miloš
AU  - Glišić, Biljana
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5671
AB  - TEZMAQ; Space Group: P 1 (2), Cell: a 8.2856(3)Å b 12.1191(5)Å c 19.2393(6)Å, α 82.105(3)° β 86.220(3)° γ 77.071(3)°
PB  - The Cambridge Crystallographic Data Centre (CCDC)
T1  - CCDC 2220148: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex"
DO  - 10.5517/ccdc.csd.cc2dj7pw
ER  - 

@misc{
author = "Andrejević, Tina P. and Aleksić, Ivana and Kljun, Jakob and Počkaj, Marta and Zlatar, Matija and Vojnović, Sandra and Nikodinović-Runić, Jasmina and Turel, Iztok and Đuran, Miloš and Glišić, Biljana",
year = "2023",
abstract = "TEZMAQ; Space Group: P 1 (2), Cell: a 8.2856(3)Å b 12.1191(5)Å c 19.2393(6)Å, α 82.105(3)° β 86.220(3)° γ 77.071(3)°",
publisher = "The Cambridge Crystallographic Data Centre (CCDC)",
title = "CCDC 2220148: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex"",
doi = "10.5517/ccdc.csd.cc2dj7pw"
}

Andrejević, T. P., Aleksić, I., Kljun, J., Počkaj, M., Zlatar, M., Vojnović, S., Nikodinović-Runić, J., Turel, I., Đuran, M.,& Glišić, B.. (2023). CCDC 2220148: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex". 
The Cambridge Crystallographic Data Centre (CCDC)..
https://doi.org/10.5517/ccdc.csd.cc2dj7pw

Andrejević TP, Aleksić I, Kljun J, Počkaj M, Zlatar M, Vojnović S, Nikodinović-Runić J, Turel I, Đuran M, Glišić B. CCDC 2220148: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex". 2023;.
doi:10.5517/ccdc.csd.cc2dj7pw .

Andrejević, Tina P., Aleksić, Ivana, Kljun, Jakob, Počkaj, Marta, Zlatar, Matija, Vojnović, Sandra, Nikodinović-Runić, Jasmina, Turel, Iztok, Đuran, Miloš, Glišić, Biljana, "CCDC 2220148: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex"" (2023),
https://doi.org/10.5517/ccdc.csd.cc2dj7pw . .

TY  - DATA
AU  - Andrejević, Tina P.
AU  - Aleksić, Ivana
AU  - Kljun, Jakob
AU  - Počkaj, Marta
AU  - Zlatar, Matija
AU  - Vojnović, Sandra
AU  - Nikodinović-Runić, Jasmina
AU  - Turel, Iztok
AU  - Đuran, Miloš
AU  - Glišić, Biljana
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5672
AB  - TEZMEU: Space Group: P 1 (2), Cell: a 7.4731(4)Å b 11.7049(4)Å c 17.6092(8)Å, α 97.285(4)° β 96.617(4)° γ 102.781(4)°
PB  - The Cambridge Crystallographic Data Centre (CCDC)
T1  - CCDC 2220149: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex"
DO  - 10.5517/ccdc.csd.cc2dj7qx
ER  - 

@misc{
author = "Andrejević, Tina P. and Aleksić, Ivana and Kljun, Jakob and Počkaj, Marta and Zlatar, Matija and Vojnović, Sandra and Nikodinović-Runić, Jasmina and Turel, Iztok and Đuran, Miloš and Glišić, Biljana",
year = "2023",
abstract = "TEZMEU: Space Group: P 1 (2), Cell: a 7.4731(4)Å b 11.7049(4)Å c 17.6092(8)Å, α 97.285(4)° β 96.617(4)° γ 102.781(4)°",
publisher = "The Cambridge Crystallographic Data Centre (CCDC)",
title = "CCDC 2220149: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex"",
doi = "10.5517/ccdc.csd.cc2dj7qx"
}

Andrejević, T. P., Aleksić, I., Kljun, J., Počkaj, M., Zlatar, M., Vojnović, S., Nikodinović-Runić, J., Turel, I., Đuran, M.,& Glišić, B.. (2023). CCDC 2220149: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex". 
The Cambridge Crystallographic Data Centre (CCDC)..
https://doi.org/10.5517/ccdc.csd.cc2dj7qx

Andrejević TP, Aleksić I, Kljun J, Počkaj M, Zlatar M, Vojnović S, Nikodinović-Runić J, Turel I, Đuran M, Glišić B. CCDC 2220149: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex". 2023;.
doi:10.5517/ccdc.csd.cc2dj7qx .

Andrejević, Tina P., Aleksić, Ivana, Kljun, Jakob, Počkaj, Marta, Zlatar, Matija, Vojnović, Sandra, Nikodinović-Runić, Jasmina, Turel, Iztok, Đuran, Miloš, Glišić, Biljana, "CCDC 2220149: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex"" (2023),
https://doi.org/10.5517/ccdc.csd.cc2dj7qx . .

TY  - DATA
AU  - Andrejević, Tina P.
AU  - Aleksić, Ivana
AU  - Kljun, Jakob
AU  - Počkaj, Marta
AU  - Zlatar, Matija
AU  - Vojnović, Sandra
AU  - Nikodinović-Runić, Jasmina
AU  - Turel, Iztok
AU  - Đuran, Miloš
AU  - Glišić, Biljana
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5673
AB  - TEZMIY: Space Group: P 21/n (14), Cell: a 11.0042(12)Å b 12.8657(8)Å c 12.5820(12)Å, α 90° β 115.436(13)° γ 90°
PB  - The Cambridge Crystallographic Data Centre (CCDC)
T1  - CCDC 2220150: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex"
DO  - 10.5517/ccdc.csd.cc2dj7ry
ER  - 

@misc{
author = "Andrejević, Tina P. and Aleksić, Ivana and Kljun, Jakob and Počkaj, Marta and Zlatar, Matija and Vojnović, Sandra and Nikodinović-Runić, Jasmina and Turel, Iztok and Đuran, Miloš and Glišić, Biljana",
year = "2023",
abstract = "TEZMIY: Space Group: P 21/n (14), Cell: a 11.0042(12)Å b 12.8657(8)Å c 12.5820(12)Å, α 90° β 115.436(13)° γ 90°",
publisher = "The Cambridge Crystallographic Data Centre (CCDC)",
title = "CCDC 2220150: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex"",
doi = "10.5517/ccdc.csd.cc2dj7ry"
}

Andrejević, T. P., Aleksić, I., Kljun, J., Počkaj, M., Zlatar, M., Vojnović, S., Nikodinović-Runić, J., Turel, I., Đuran, M.,& Glišić, B.. (2023). CCDC 2220150: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex". 
The Cambridge Crystallographic Data Centre (CCDC)..
https://doi.org/10.5517/ccdc.csd.cc2dj7ry

Andrejević TP, Aleksić I, Kljun J, Počkaj M, Zlatar M, Vojnović S, Nikodinović-Runić J, Turel I, Đuran M, Glišić B. CCDC 2220150: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex". 2023;.
doi:10.5517/ccdc.csd.cc2dj7ry .

Andrejević, Tina P., Aleksić, Ivana, Kljun, Jakob, Počkaj, Marta, Zlatar, Matija, Vojnović, Sandra, Nikodinović-Runić, Jasmina, Turel, Iztok, Đuran, Miloš, Glišić, Biljana, "CCDC 2220150: Experimental Crystal Structure Determination. Crystallographic data for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex"" (2023),
https://doi.org/10.5517/ccdc.csd.cc2dj7ry . .

TY  - DATA
AU  - Andrejević, Tina P.
AU  - Aleksić, Ivana
AU  - Kljun, Jakob
AU  - Počkaj, Marta
AU  - Zlatar, Matija
AU  - Vojnović, Sandra
AU  - Nikodinović-Runić, Jasmina
AU  - Turel, Iztok
AU  - Đuran, Miloš
AU  - Glišić, Biljana
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5674
AB  - Dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz) was used as a ligand for the synthesis of new copper(II) and silver(I) complexes, [CuCl2(py-2pz)]2 (1), [Cu(CF3SO3)(H2O)(py-2pz)2]CF3SO3·2H2O (2), [Ag(py-2pz)2]PF6 (3) and {[Ag(NO3)(py-2pz)]·0.5H2O}n (4). The complexes were characterized by spectroscopic and electrochemical methods, while their structures were determined by single crystal X-ray diffraction analysis. The X-ray analysis revealed the bidentate coordination mode of py-2pz to the corresponding metal ion via its pyridine and pyrazine nitrogen atoms in all complexes, while in polynuclear complex 4, the heterocyclic pyrazine ring of one py-2pz additionally behaves as a bridging ligand between two Ag(I) ions. DFT calculations were performed to elucidate the structures of the investigated complexes in solution. The antimicrobial potential of the complexes 1–4 was evaluated against two bacterial (Pseudomonas aeruginosa and Staphylococcus aureus) and two Candida (C. albicans and C. parapsilosis) species. Silver(I) complexes 3 and 4 have shown good antibacterial and antifungal properties with minimal inhibitory concentration (MIC) values ranging from 4.9 to 39.0 μM (3.9–31.2 μg mL−1). All complexes inhibited the filamentation of C. albicans and hyphae formation, while silver(I) complexes 3 and 4 had also the ability to inhibit the biofilm formation process of this fungus. The binding affinity of the complexes 1–4 with calf thymus DNA (ct-DNA) and bovine serum albumin (BSA) was studied by fluorescence emission spectroscopy to clarify the mode of their antimicrobial activity. Catechol oxidase biomimetic catalytic activity of copper(II) complexes 1 and 2 was additionally investigated by using 3,5-di-tert-butylcatechol (3,5-DTBC) and o-aminophenol (OAP) as substrates.
AB  - 1H NMR spectrum of py-2pz S5 1H NMR spectrum of complex 3 S6 1H NMR spectrum of complex 4 S7 Fig. S1 UV-Vis spectra of copper(II) complexes 1 and 2 recorded in DMSO at room  temperature. S8 Fig. S2 UV-Vis spectra of silver(I) complexes 3 and 4 in respect to the spectrum of  uncoordinated py-2pz recorded in DMSO at room temperature. S9 Fig. S3 Time-dependant UV-Vis spectra of copper(II) complex 2 and silver(I)  complex 3 recorded in DMSO/PBS (v/v 2 : 1 and 1 : 42.9 for 2 and 3, respectively)  at room temperature. S10 Fig. S4 Cyclic voltammogram of py-2pz ligand at GC electrode in DMSO (c = 1 ×  10-3 M) and 0.1 M TBAHP as a supporting electrolyte with a scan rate of 50  mV s-1 . S11 Fig. S5 Graphical representation of the spin density of the high-spin state of 1.  Isosurfaces were drawn at 0.003 a.u. with α-spin depicted by blue surfaces. S12 Fig. S6 Inhibition of violacein and prodigiosin production in the presence of  complexes 1 – 4 and py-2pz ligand tested on Chromobacterium violaceum CV026  and Serratia marcescens at 100 µg per disc concentration. DMSO was used as a  control. S13 Scheme S1 Catechol oxidase (CAO) and phenoxazinone synthase (PHS) activity. S14 Table S1 C. albicans ATCC10231 biofilm inhibition (%) in the presence of silver(I)  complexes 3 and 4 in range of subinhibitory concentrations. Table S2 Details of the crystal structure determination for copper(II) complexes  1 and 2 S16 Table S3 Details of the crystal structure determination for silver(I) complexes  3 and 4 S17 Cartesian coordinates of all DFT optimized structures S18.
PB  - Royal Society of Chemistry (RSC)
T2  - RSC Advances
T1  - Electronic Supplementary Information for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex"
DO  - 10.1039/D2RA07401J
ER  - 

@misc{
author = "Andrejević, Tina P. and Aleksić, Ivana and Kljun, Jakob and Počkaj, Marta and Zlatar, Matija and Vojnović, Sandra and Nikodinović-Runić, Jasmina and Turel, Iztok and Đuran, Miloš and Glišić, Biljana",
year = "2023",
abstract = "Dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz) was used as a ligand for the synthesis of new copper(II) and silver(I) complexes, [CuCl2(py-2pz)]2 (1), [Cu(CF3SO3)(H2O)(py-2pz)2]CF3SO3·2H2O (2), [Ag(py-2pz)2]PF6 (3) and {[Ag(NO3)(py-2pz)]·0.5H2O}n (4). The complexes were characterized by spectroscopic and electrochemical methods, while their structures were determined by single crystal X-ray diffraction analysis. The X-ray analysis revealed the bidentate coordination mode of py-2pz to the corresponding metal ion via its pyridine and pyrazine nitrogen atoms in all complexes, while in polynuclear complex 4, the heterocyclic pyrazine ring of one py-2pz additionally behaves as a bridging ligand between two Ag(I) ions. DFT calculations were performed to elucidate the structures of the investigated complexes in solution. The antimicrobial potential of the complexes 1–4 was evaluated against two bacterial (Pseudomonas aeruginosa and Staphylococcus aureus) and two Candida (C. albicans and C. parapsilosis) species. Silver(I) complexes 3 and 4 have shown good antibacterial and antifungal properties with minimal inhibitory concentration (MIC) values ranging from 4.9 to 39.0 μM (3.9–31.2 μg mL−1). All complexes inhibited the filamentation of C. albicans and hyphae formation, while silver(I) complexes 3 and 4 had also the ability to inhibit the biofilm formation process of this fungus. The binding affinity of the complexes 1–4 with calf thymus DNA (ct-DNA) and bovine serum albumin (BSA) was studied by fluorescence emission spectroscopy to clarify the mode of their antimicrobial activity. Catechol oxidase biomimetic catalytic activity of copper(II) complexes 1 and 2 was additionally investigated by using 3,5-di-tert-butylcatechol (3,5-DTBC) and o-aminophenol (OAP) as substrates., 1H NMR spectrum of py-2pz S5 1H NMR spectrum of complex 3 S6 1H NMR spectrum of complex 4 S7 Fig. S1 UV-Vis spectra of copper(II) complexes 1 and 2 recorded in DMSO at room  temperature. S8 Fig. S2 UV-Vis spectra of silver(I) complexes 3 and 4 in respect to the spectrum of  uncoordinated py-2pz recorded in DMSO at room temperature. S9 Fig. S3 Time-dependant UV-Vis spectra of copper(II) complex 2 and silver(I)  complex 3 recorded in DMSO/PBS (v/v 2 : 1 and 1 : 42.9 for 2 and 3, respectively)  at room temperature. S10 Fig. S4 Cyclic voltammogram of py-2pz ligand at GC electrode in DMSO (c = 1 ×  10-3 M) and 0.1 M TBAHP as a supporting electrolyte with a scan rate of 50  mV s-1 . S11 Fig. S5 Graphical representation of the spin density of the high-spin state of 1.  Isosurfaces were drawn at 0.003 a.u. with α-spin depicted by blue surfaces. S12 Fig. S6 Inhibition of violacein and prodigiosin production in the presence of  complexes 1 – 4 and py-2pz ligand tested on Chromobacterium violaceum CV026  and Serratia marcescens at 100 µg per disc concentration. DMSO was used as a  control. S13 Scheme S1 Catechol oxidase (CAO) and phenoxazinone synthase (PHS) activity. S14 Table S1 C. albicans ATCC10231 biofilm inhibition (%) in the presence of silver(I)  complexes 3 and 4 in range of subinhibitory concentrations. Table S2 Details of the crystal structure determination for copper(II) complexes  1 and 2 S16 Table S3 Details of the crystal structure determination for silver(I) complexes  3 and 4 S17 Cartesian coordinates of all DFT optimized structures S18.",
publisher = "Royal Society of Chemistry (RSC)",
journal = "RSC Advances",
title = "Electronic Supplementary Information for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex"",
doi = "10.1039/D2RA07401J"
}

Andrejević, T. P., Aleksić, I., Kljun, J., Počkaj, M., Zlatar, M., Vojnović, S., Nikodinović-Runić, J., Turel, I., Đuran, M.,& Glišić, B.. (2023). Electronic Supplementary Information for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex". in RSC Advances
Royal Society of Chemistry (RSC)..
https://doi.org/10.1039/D2RA07401J

Andrejević TP, Aleksić I, Kljun J, Počkaj M, Zlatar M, Vojnović S, Nikodinović-Runić J, Turel I, Đuran M, Glišić B. Electronic Supplementary Information for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex". in RSC Advances. 2023;.
doi:10.1039/D2RA07401J .

Andrejević, Tina P., Aleksić, Ivana, Kljun, Jakob, Počkaj, Marta, Zlatar, Matija, Vojnović, Sandra, Nikodinović-Runić, Jasmina, Turel, Iztok, Đuran, Miloš, Glišić, Biljana, "Electronic Supplementary Information for: "Copper(II) and silver(I) complexes with dimethyl 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of the metal ion on the antimicrobial potential of the complex"" in RSC Advances (2023),
https://doi.org/10.1039/D2RA07401J . .

TY  - JOUR
AU  - Gitarić, Jelena
AU  - Stanojević, Ivana
AU  - Radanović, Dušanka
AU  - Crochet, Aurélien
AU  - Ašanin, Darko
AU  - Janković, Vukašin
AU  - Skaro-Bogojević, Sanja
AU  - Đuran, Miloš
AU  - Glišić, Biljana
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5322
AB  - To investigate how modification in the structure of 1,3-propanediamine chain of 1,3-pdta (1,3-propanediamine-N,N,N′,N′-tetraacetate) ligand affects the structural and biological properties of the corresponding metal complexes, two new octahedral complexes, [Co(H2O)5Co(2,2-diMe-1,3-pdta)]·H2O (1) and [Mg(H2O)5Mg(2,2-diMe-1,3-pdta)]·1.5H2O (2) (2,2-diMe-1,3-pdta = 2,2-dimethyl-1,3-propanediamine-N,N,N′,N′-tetraacetate), were synthesized and characterized by IR spectroscopy and single-crystal X-ray diffraction analysis. Additionally, UV-Vis and NMR spectroscopic methods were applied for the characterization of 1 and 2, respectively. Crystallographic data indicate that these complexes contain 2,2-diMe-1,3-pdta coordinated to the metal ion through 2 N and 4 O atoms forming [M(H2O)5M′(2,2-diMe-1,3-pdta)] complex unit (M, M′ = Co(II), Co(II) (1) and M, M′ = Mg(II), Mg(II) (2)), which is composed of [M′(2,2-diMe-1,3-pdta)]2− and [M(H2O)5O]2+ octahedra bridged by one of the axial carboxylate groups. The antimicrobial activities of 1 and 2 were evaluated against different bacteria and Candida spp., while their cytotoxic effect was tested on the normal human lung fibroblasts (MRC-5). The ability of 1 and 2 to inhibit formation of C. glabrata biofilms was also assessed. The obtained structural parameters and biological properties of the two complexes were compared to Co(II) and Mg(II) complexes with 1,3-pdta ligand.
PB  - Taylor &Francis
T2  - Journal of Coordination Chemistry
T1  - Cobalt(II) and magnesium(II) complexes with 1,3-pdta-type of ligands: influence of an alkyl substituent at 1,3-propanediamine chain on the structural and antimicrobial properties of the complex
VL  - 75
IS  - 11-14
SP  - 1899
EP  - 1914
DO  - 10.1080/00958972.2022.2101365
ER  - 

@article{
author = "Gitarić, Jelena and Stanojević, Ivana and Radanović, Dušanka and Crochet, Aurélien and Ašanin, Darko and Janković, Vukašin and Skaro-Bogojević, Sanja and Đuran, Miloš and Glišić, Biljana",
year = "2022",
abstract = "To investigate how modification in the structure of 1,3-propanediamine chain of 1,3-pdta (1,3-propanediamine-N,N,N′,N′-tetraacetate) ligand affects the structural and biological properties of the corresponding metal complexes, two new octahedral complexes, [Co(H2O)5Co(2,2-diMe-1,3-pdta)]·H2O (1) and [Mg(H2O)5Mg(2,2-diMe-1,3-pdta)]·1.5H2O (2) (2,2-diMe-1,3-pdta = 2,2-dimethyl-1,3-propanediamine-N,N,N′,N′-tetraacetate), were synthesized and characterized by IR spectroscopy and single-crystal X-ray diffraction analysis. Additionally, UV-Vis and NMR spectroscopic methods were applied for the characterization of 1 and 2, respectively. Crystallographic data indicate that these complexes contain 2,2-diMe-1,3-pdta coordinated to the metal ion through 2 N and 4 O atoms forming [M(H2O)5M′(2,2-diMe-1,3-pdta)] complex unit (M, M′ = Co(II), Co(II) (1) and M, M′ = Mg(II), Mg(II) (2)), which is composed of [M′(2,2-diMe-1,3-pdta)]2− and [M(H2O)5O]2+ octahedra bridged by one of the axial carboxylate groups. The antimicrobial activities of 1 and 2 were evaluated against different bacteria and Candida spp., while their cytotoxic effect was tested on the normal human lung fibroblasts (MRC-5). The ability of 1 and 2 to inhibit formation of C. glabrata biofilms was also assessed. The obtained structural parameters and biological properties of the two complexes were compared to Co(II) and Mg(II) complexes with 1,3-pdta ligand.",
publisher = "Taylor &Francis",
journal = "Journal of Coordination Chemistry",
title = "Cobalt(II) and magnesium(II) complexes with 1,3-pdta-type of ligands: influence of an alkyl substituent at 1,3-propanediamine chain on the structural and antimicrobial properties of the complex",
volume = "75",
number = "11-14",
pages = "1899-1914",
doi = "10.1080/00958972.2022.2101365"
}

Gitarić, J., Stanojević, I., Radanović, D., Crochet, A., Ašanin, D., Janković, V., Skaro-Bogojević, S., Đuran, M.,& Glišić, B.. (2022). Cobalt(II) and magnesium(II) complexes with 1,3-pdta-type of ligands: influence of an alkyl substituent at 1,3-propanediamine chain on the structural and antimicrobial properties of the complex. in Journal of Coordination Chemistry
Taylor &Francis., 75(11-14), 1899-1914.
https://doi.org/10.1080/00958972.2022.2101365

Gitarić J, Stanojević I, Radanović D, Crochet A, Ašanin D, Janković V, Skaro-Bogojević S, Đuran M, Glišić B. Cobalt(II) and magnesium(II) complexes with 1,3-pdta-type of ligands: influence of an alkyl substituent at 1,3-propanediamine chain on the structural and antimicrobial properties of the complex. in Journal of Coordination Chemistry. 2022;75(11-14):1899-1914.
doi:10.1080/00958972.2022.2101365 .

Gitarić, Jelena, Stanojević, Ivana, Radanović, Dušanka, Crochet, Aurélien, Ašanin, Darko, Janković, Vukašin, Skaro-Bogojević, Sanja, Đuran, Miloš, Glišić, Biljana, "Cobalt(II) and magnesium(II) complexes with 1,3-pdta-type of ligands: influence of an alkyl substituent at 1,3-propanediamine chain on the structural and antimicrobial properties of the complex" in Journal of Coordination Chemistry, 75, no. 11-14 (2022):1899-1914,
https://doi.org/10.1080/00958972.2022.2101365 . .

TY  - JOUR
AU  - Stanojević, Ivana M.
AU  - Glišić, Biljana
AU  - Radanović, Dušanka
AU  - Đuran, Miloš
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4369
AB  - The article presents an overview of the results achieved during the last several decades on the synthesis and structural characterization of copper(II) complexes with different aminopolycarboxylates. Considering the structural varieties in designing aminopolycarboxylate ligands and significant stereochemical flexibility of the corresponding copper(II) complexes to adopt a wide range of coordination geometries, this review is mainly focused on the results related to the crystallographic characterization of the synthesized complexes. The ligands used for the synthesis of copper(II) complexes described in this article contain two amine nitrogen atoms and different number of the carboxylate oxygen donor atoms (N2O2, N2O3 and N2O4-type of ligands). Giving the importance to the biological relevance of the Cu(II) ion and broad aspects of potential application of aminopolycarboxylate ligands in human practice, the presented results could have some important implications for coordination chemists dealing with structural properties of aminopolycarboxylate-copper(II) complexes and their potential medicinal and biological applications.
PB  - Elsevier
T2  - Journal of Molecular Structure
T1  - Copper(II) complexes of aminopolycarboxylate ligands with N2O2, N2O3 and N2O4 donor sets. The relationship between the ligand structure and molecular geometry of the complex
VL  - 1232
SP  - 130001
DO  - 10.1016/j.molstruc.2021.130001
ER  - 

@article{
author = "Stanojević, Ivana M. and Glišić, Biljana and Radanović, Dušanka and Đuran, Miloš",
year = "2021",
abstract = "The article presents an overview of the results achieved during the last several decades on the synthesis and structural characterization of copper(II) complexes with different aminopolycarboxylates. Considering the structural varieties in designing aminopolycarboxylate ligands and significant stereochemical flexibility of the corresponding copper(II) complexes to adopt a wide range of coordination geometries, this review is mainly focused on the results related to the crystallographic characterization of the synthesized complexes. The ligands used for the synthesis of copper(II) complexes described in this article contain two amine nitrogen atoms and different number of the carboxylate oxygen donor atoms (N2O2, N2O3 and N2O4-type of ligands). Giving the importance to the biological relevance of the Cu(II) ion and broad aspects of potential application of aminopolycarboxylate ligands in human practice, the presented results could have some important implications for coordination chemists dealing with structural properties of aminopolycarboxylate-copper(II) complexes and their potential medicinal and biological applications.",
publisher = "Elsevier",
journal = "Journal of Molecular Structure",
title = "Copper(II) complexes of aminopolycarboxylate ligands with N2O2, N2O3 and N2O4 donor sets. The relationship between the ligand structure and molecular geometry of the complex",
volume = "1232",
pages = "130001",
doi = "10.1016/j.molstruc.2021.130001"
}

Stanojević, I. M., Glišić, B., Radanović, D.,& Đuran, M.. (2021). Copper(II) complexes of aminopolycarboxylate ligands with N2O2, N2O3 and N2O4 donor sets. The relationship between the ligand structure and molecular geometry of the complex. in Journal of Molecular Structure
Elsevier., 1232, 130001.
https://doi.org/10.1016/j.molstruc.2021.130001

Stanojević IM, Glišić B, Radanović D, Đuran M. Copper(II) complexes of aminopolycarboxylate ligands with N2O2, N2O3 and N2O4 donor sets. The relationship between the ligand structure and molecular geometry of the complex. in Journal of Molecular Structure. 2021;1232:130001.
doi:10.1016/j.molstruc.2021.130001 .

Stanojević, Ivana M., Glišić, Biljana, Radanović, Dušanka, Đuran, Miloš, "Copper(II) complexes of aminopolycarboxylate ligands with N2O2, N2O3 and N2O4 donor sets. The relationship between the ligand structure and molecular geometry of the complex" in Journal of Molecular Structure, 1232 (2021):130001,
https://doi.org/10.1016/j.molstruc.2021.130001 . .

TY  - JOUR
AU  - Savic, Nada D.
AU  - Vojnovic, Sandra
AU  - Glišić, Biljana
AU  - Crochet, Aurélien
AU  - Pavić, Aleksandar
AU  - Janjić, Goran
AU  - Pekmezovic, Marina
AU  - Opsenica, Igor
AU  - Fromm, Katharina M.
AU  - Nikodinović-Runić, Jasmina
AU  - Đuran, Miloš
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2429
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.
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
VL  - 156
SP  - 760
EP  - 773
DO  - 10.1016/j.ejmech.2018.07.049
ER  - 

@article{
author = "Savic, Nada D. and Vojnovic, Sandra and Glišić, Biljana and Crochet, Aurélien and Pavić, Aleksandar and Janjić, Goran and Pekmezovic, Marina and Opsenica, Igor and Fromm, Katharina M. and Nikodinović-Runić, Jasmina and Đuran, Miloš",
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.",
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",
volume = "156",
pages = "760-773",
doi = "10.1016/j.ejmech.2018.07.049"
}

Savic, N. D., Vojnovic, S., Glišić, B., Crochet, A., Pavić, A., Janjić, G., Pekmezovic, M., Opsenica, I., Fromm, K. M., Nikodinović-Runić, J.,& Đuran, M.. (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

Savic ND, Vojnovic S, Glišić B, Crochet A, Pavić A, Janjić G, Pekmezovic M, Opsenica I, Fromm KM, Nikodinović-Runić J, Đuran M. 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 .

Savic, Nada D., Vojnovic, Sandra, Glišić, Biljana, Crochet, Aurélien, Pavić, Aleksandar, Janjić, Goran, Pekmezovic, Marina, Opsenica, Igor, Fromm, Katharina M., Nikodinović-Runić, Jasmina, Đuran, Miloš, "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 . .

TY  - JOUR
AU  - Pavić, Aleksandar
AU  - Glišić, Biljana
AU  - Vojnovic, Sandra
AU  - Warzajtis, Beata
AU  - Savic, Nada D.
AU  - Antic, Marija
AU  - Radenković, Slavko
AU  - Janjić, Goran
AU  - Nikodinović-Runić, Jasmina
AU  - Rychlewska, Urszula
AU  - Đuran, Miloš
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2136
AB  - Gold(III) complexes with 1,7- and 4,7-phenanthroline ligands, [AuCl3(1,7-phen-kappa N7)] (1) and [AuCl3(4,7-phen-kappa N4)] (2) were synthesized and structurally characterized by spectroscopic (NMR, IR and UV-vis) and single crystal X-ray diffraction techniques. In these complexes, 1,7- and 4,7-phenanthrolines are monodentatedly coordinated to the Au(III) ion through the N7 and N4 nitrogen atoms, respectively. In comparison to the clinically relevant anti-angiogenic compounds auranofin and sunitinib, gold(III)-phenanthroline complexes showed from 1.5- to 20-fold higher anti-angiogenic potential, and 13- and 118-fold lower toxicity. Among the tested compounds, complex 1 was the most potent and may be an excellent anti-angiogenic drug candidate, since it showed strong anti-angiogenic activity in zebrafish embryos achieving IC50 value (concentration resulting in an anti-angiogenic phenotype at 50% of embryos) of 2.89 mu M, while had low toxicity with LC50 value (the concentration inducing the lethal effect of 50% embryos) of 128 mu M. Molecular docking study revealed that both complexes and ligands could suppress angiogenesis targeting the multiple major regulators of angiogenesis, such as the vascular endothelial growth factor receptor (VEGFR-2), the matrix metalloproteases (MMP-2 and MMP-9), and thioredoxin reductase (TrxR1), where the complexes showed higher binding affinity in comparison to ligands, and particularly to auranofin, but comparable to sunitinib, an anti-angiogenic drug of clinical relevance.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - Mononuclear gold(III) complexes with phenanthroline ligands as efficient inhibitors of angiogenesis: A comparative study with auranofin and sunitinib
VL  - 174
SP  - 156
EP  - 168
DO  - 10.1016/j.jinorgbio.2017.06.009
ER  - 

@article{
author = "Pavić, Aleksandar and Glišić, Biljana and Vojnovic, Sandra and Warzajtis, Beata and Savic, Nada D. and Antic, Marija and Radenković, Slavko and Janjić, Goran and Nikodinović-Runić, Jasmina and Rychlewska, Urszula and Đuran, Miloš",
year = "2017",
abstract = "Gold(III) complexes with 1,7- and 4,7-phenanthroline ligands, [AuCl3(1,7-phen-kappa N7)] (1) and [AuCl3(4,7-phen-kappa N4)] (2) were synthesized and structurally characterized by spectroscopic (NMR, IR and UV-vis) and single crystal X-ray diffraction techniques. In these complexes, 1,7- and 4,7-phenanthrolines are monodentatedly coordinated to the Au(III) ion through the N7 and N4 nitrogen atoms, respectively. In comparison to the clinically relevant anti-angiogenic compounds auranofin and sunitinib, gold(III)-phenanthroline complexes showed from 1.5- to 20-fold higher anti-angiogenic potential, and 13- and 118-fold lower toxicity. Among the tested compounds, complex 1 was the most potent and may be an excellent anti-angiogenic drug candidate, since it showed strong anti-angiogenic activity in zebrafish embryos achieving IC50 value (concentration resulting in an anti-angiogenic phenotype at 50% of embryos) of 2.89 mu M, while had low toxicity with LC50 value (the concentration inducing the lethal effect of 50% embryos) of 128 mu M. Molecular docking study revealed that both complexes and ligands could suppress angiogenesis targeting the multiple major regulators of angiogenesis, such as the vascular endothelial growth factor receptor (VEGFR-2), the matrix metalloproteases (MMP-2 and MMP-9), and thioredoxin reductase (TrxR1), where the complexes showed higher binding affinity in comparison to ligands, and particularly to auranofin, but comparable to sunitinib, an anti-angiogenic drug of clinical relevance.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "Mononuclear gold(III) complexes with phenanthroline ligands as efficient inhibitors of angiogenesis: A comparative study with auranofin and sunitinib",
volume = "174",
pages = "156-168",
doi = "10.1016/j.jinorgbio.2017.06.009"
}

Pavić, A., Glišić, B., Vojnovic, S., Warzajtis, B., Savic, N. D., Antic, M., Radenković, S., Janjić, G., Nikodinović-Runić, J., Rychlewska, U.,& Đuran, M.. (2017). Mononuclear gold(III) complexes with phenanthroline ligands as efficient inhibitors of angiogenesis: A comparative study with auranofin and sunitinib. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 174, 156-168.
https://doi.org/10.1016/j.jinorgbio.2017.06.009

Pavić A, Glišić B, Vojnovic S, Warzajtis B, Savic ND, Antic M, Radenković S, Janjić G, Nikodinović-Runić J, Rychlewska U, Đuran M. Mononuclear gold(III) complexes with phenanthroline ligands as efficient inhibitors of angiogenesis: A comparative study with auranofin and sunitinib. in Journal of Inorganic Biochemistry. 2017;174:156-168.
doi:10.1016/j.jinorgbio.2017.06.009 .

Pavić, Aleksandar, Glišić, Biljana, Vojnovic, Sandra, Warzajtis, Beata, Savic, Nada D., Antic, Marija, Radenković, Slavko, Janjić, Goran, Nikodinović-Runić, Jasmina, Rychlewska, Urszula, Đuran, Miloš, "Mononuclear gold(III) complexes with phenanthroline ligands as efficient inhibitors of angiogenesis: A comparative study with auranofin and sunitinib" in Journal of Inorganic Biochemistry, 174 (2017):156-168,
https://doi.org/10.1016/j.jinorgbio.2017.06.009 . .

TY  - JOUR
AU  - Pavić, Aleksandar
AU  - Glišić, Biljana
AU  - Vojnovic, Sandra
AU  - Warzajtis, Beata
AU  - Savic, Nada D.
AU  - Antic, Marija
AU  - Radenković, Slavko
AU  - Janjić, Goran
AU  - Nikodinović-Runić, Jasmina
AU  - Rychlewska, Urszula
AU  - Đuran, Miloš
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2939
AB  - Gold(III) complexes with 1,7- and 4,7-phenanthroline ligands, [AuCl3(1,7-phen-kappa N7)] (1) and [AuCl3(4,7-phen-kappa N4)] (2) were synthesized and structurally characterized by spectroscopic (NMR, IR and UV-vis) and single crystal X-ray diffraction techniques. In these complexes, 1,7- and 4,7-phenanthrolines are monodentatedly coordinated to the Au(III) ion through the N7 and N4 nitrogen atoms, respectively. In comparison to the clinically relevant anti-angiogenic compounds auranofin and sunitinib, gold(III)-phenanthroline complexes showed from 1.5- to 20-fold higher anti-angiogenic potential, and 13- and 118-fold lower toxicity. Among the tested compounds, complex 1 was the most potent and may be an excellent anti-angiogenic drug candidate, since it showed strong anti-angiogenic activity in zebrafish embryos achieving IC50 value (concentration resulting in an anti-angiogenic phenotype at 50% of embryos) of 2.89 mu M, while had low toxicity with LC50 value (the concentration inducing the lethal effect of 50% embryos) of 128 mu M. Molecular docking study revealed that both complexes and ligands could suppress angiogenesis targeting the multiple major regulators of angiogenesis, such as the vascular endothelial growth factor receptor (VEGFR-2), the matrix metalloproteases (MMP-2 and MMP-9), and thioredoxin reductase (TrxR1), where the complexes showed higher binding affinity in comparison to ligands, and particularly to auranofin, but comparable to sunitinib, an anti-angiogenic drug of clinical relevance.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - Mononuclear gold(III) complexes with phenanthroline ligands as efficient inhibitors of angiogenesis: A comparative study with auranofin and sunitinib
VL  - 174
SP  - 156
EP  - 168
DO  - 10.1016/j.jinorgbio.2017.06.009
ER  - 

@article{
author = "Pavić, Aleksandar and Glišić, Biljana and Vojnovic, Sandra and Warzajtis, Beata and Savic, Nada D. and Antic, Marija and Radenković, Slavko and Janjić, Goran and Nikodinović-Runić, Jasmina and Rychlewska, Urszula and Đuran, Miloš",
year = "2017",
abstract = "Gold(III) complexes with 1,7- and 4,7-phenanthroline ligands, [AuCl3(1,7-phen-kappa N7)] (1) and [AuCl3(4,7-phen-kappa N4)] (2) were synthesized and structurally characterized by spectroscopic (NMR, IR and UV-vis) and single crystal X-ray diffraction techniques. In these complexes, 1,7- and 4,7-phenanthrolines are monodentatedly coordinated to the Au(III) ion through the N7 and N4 nitrogen atoms, respectively. In comparison to the clinically relevant anti-angiogenic compounds auranofin and sunitinib, gold(III)-phenanthroline complexes showed from 1.5- to 20-fold higher anti-angiogenic potential, and 13- and 118-fold lower toxicity. Among the tested compounds, complex 1 was the most potent and may be an excellent anti-angiogenic drug candidate, since it showed strong anti-angiogenic activity in zebrafish embryos achieving IC50 value (concentration resulting in an anti-angiogenic phenotype at 50% of embryos) of 2.89 mu M, while had low toxicity with LC50 value (the concentration inducing the lethal effect of 50% embryos) of 128 mu M. Molecular docking study revealed that both complexes and ligands could suppress angiogenesis targeting the multiple major regulators of angiogenesis, such as the vascular endothelial growth factor receptor (VEGFR-2), the matrix metalloproteases (MMP-2 and MMP-9), and thioredoxin reductase (TrxR1), where the complexes showed higher binding affinity in comparison to ligands, and particularly to auranofin, but comparable to sunitinib, an anti-angiogenic drug of clinical relevance.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "Mononuclear gold(III) complexes with phenanthroline ligands as efficient inhibitors of angiogenesis: A comparative study with auranofin and sunitinib",
volume = "174",
pages = "156-168",
doi = "10.1016/j.jinorgbio.2017.06.009"
}

Pavić, A., Glišić, B., Vojnovic, S., Warzajtis, B., Savic, N. D., Antic, M., Radenković, S., Janjić, G., Nikodinović-Runić, J., Rychlewska, U.,& Đuran, M.. (2017). Mononuclear gold(III) complexes with phenanthroline ligands as efficient inhibitors of angiogenesis: A comparative study with auranofin and sunitinib. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 174, 156-168.
https://doi.org/10.1016/j.jinorgbio.2017.06.009

Pavić A, Glišić B, Vojnovic S, Warzajtis B, Savic ND, Antic M, Radenković S, Janjić G, Nikodinović-Runić J, Rychlewska U, Đuran M. Mononuclear gold(III) complexes with phenanthroline ligands as efficient inhibitors of angiogenesis: A comparative study with auranofin and sunitinib. in Journal of Inorganic Biochemistry. 2017;174:156-168.
doi:10.1016/j.jinorgbio.2017.06.009 .

Pavić, Aleksandar, Glišić, Biljana, Vojnovic, Sandra, Warzajtis, Beata, Savic, Nada D., Antic, Marija, Radenković, Slavko, Janjić, Goran, Nikodinović-Runić, Jasmina, Rychlewska, Urszula, Đuran, Miloš, "Mononuclear gold(III) complexes with phenanthroline ligands as efficient inhibitors of angiogenesis: A comparative study with auranofin and sunitinib" in Journal of Inorganic Biochemistry, 174 (2017):156-168,
https://doi.org/10.1016/j.jinorgbio.2017.06.009 . .