Slovenian Research Agency [P1-0175]

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Slovenian Research Agency [P1-0175]

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Zinc(II) Complexes with Dimethyl 2,2 '-Bipyridine-4,5-dicarboxylate: Structure, Antimicrobial Activity and DNA/BSA Binding Study

Andrejević, Tina P.; Aleksić, Ivana; Kljun, Jakob; Pantović, Bojana, V; Milivojević, Dušan; Vojnović, Sandra; Turel, Iztok; Djuran, Milos; Glišić, Biljana

(MDPI, Basel, 2022)

TY  - JOUR
AU  - Andrejević, Tina P.
AU  - Aleksić, Ivana
AU  - Kljun, Jakob
AU  - Pantović, Bojana, V
AU  - Milivojević, Dušan
AU  - Vojnović, Sandra
AU  - Turel, Iztok
AU  - Djuran, Milos
AU  - Glišić, Biljana
PY  - 2022
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1589
AB  - Two zinc(II) complexes with dimethyl 2,2 '-bipyridine-4,5-dicarboxylate (py-2py) of the general formula [Zn(py-2py)X-2], X = Cl- (1) and Br- (2) were synthesized and characterized by NMR, IR and UV-Vis spectroscopy and single-crystal X-ray diffraction analysis. Complexes 1 and 2 are isostructural and adopt a slightly distorted tetrahedral geometry with values of tetrahedral indices tau(4) and tau'(4) in the range of 0.80-0.85. The complexes were evaluated for their in vitro antimicrobial activity against two bacterial (Pseudomonas aeruginosa and Staphylococcus aureus) and two fungal strains (Candida albicans and Candida parapsilosis), while their cytotoxicity was tested on the normal human lung fibroblast cell line (MRC-5) and the model organism Caenorhabditis elegans. Complex 1 showed moderate activity against both Candida strains. However, this complex was twofold more cytotoxic compared to complex 2. The complexes tested had no effect on the survival rate of C. elegans. Complex 2 showed the ability to inhibit filamentation of C. albicans, while complex 1 was more effective than complex 2 in inhibiting biofilm formation. The interactions of complexes 1 and 2 with calf thymus DNA (ct-DNA) and bovine serum albumin (BSA) were studied to evaluate their binding affinity toward these biomolecules.
PB  - MDPI, Basel
T2  - Inorganics
T1  - Zinc(II) Complexes with Dimethyl 2,2 '-Bipyridine-4,5-dicarboxylate: Structure, Antimicrobial Activity and DNA/BSA Binding Study
IS  - 6
VL  - 10
DO  - 10.3390/inorganics10060071
ER  - 
@article{
author = "Andrejević, Tina P. and Aleksić, Ivana and Kljun, Jakob and Pantović, Bojana, V and Milivojević, Dušan and Vojnović, Sandra and Turel, Iztok and Djuran, Milos and Glišić, Biljana",
year = "2022",
abstract = "Two zinc(II) complexes with dimethyl 2,2 '-bipyridine-4,5-dicarboxylate (py-2py) of the general formula [Zn(py-2py)X-2], X = Cl- (1) and Br- (2) were synthesized and characterized by NMR, IR and UV-Vis spectroscopy and single-crystal X-ray diffraction analysis. Complexes 1 and 2 are isostructural and adopt a slightly distorted tetrahedral geometry with values of tetrahedral indices tau(4) and tau'(4) in the range of 0.80-0.85. The complexes were evaluated for their in vitro antimicrobial activity against two bacterial (Pseudomonas aeruginosa and Staphylococcus aureus) and two fungal strains (Candida albicans and Candida parapsilosis), while their cytotoxicity was tested on the normal human lung fibroblast cell line (MRC-5) and the model organism Caenorhabditis elegans. Complex 1 showed moderate activity against both Candida strains. However, this complex was twofold more cytotoxic compared to complex 2. The complexes tested had no effect on the survival rate of C. elegans. Complex 2 showed the ability to inhibit filamentation of C. albicans, while complex 1 was more effective than complex 2 in inhibiting biofilm formation. The interactions of complexes 1 and 2 with calf thymus DNA (ct-DNA) and bovine serum albumin (BSA) were studied to evaluate their binding affinity toward these biomolecules.",
publisher = "MDPI, Basel",
journal = "Inorganics",
title = "Zinc(II) Complexes with Dimethyl 2,2 '-Bipyridine-4,5-dicarboxylate: Structure, Antimicrobial Activity and DNA/BSA Binding Study",
number = "6",
volume = "10",
doi = "10.3390/inorganics10060071"
}
Andrejević, T. P., Aleksić, I., Kljun, J., Pantović, B. V., Milivojević, D., Vojnović, S., Turel, I., Djuran, M.,& Glišić, B.. (2022). Zinc(II) Complexes with Dimethyl 2,2 '-Bipyridine-4,5-dicarboxylate: Structure, Antimicrobial Activity and DNA/BSA Binding Study. in Inorganics
MDPI, Basel., 10(6).
https://doi.org/10.3390/inorganics10060071
Andrejević TP, Aleksić I, Kljun J, Pantović BV, Milivojević D, Vojnović S, Turel I, Djuran M, Glišić B. Zinc(II) Complexes with Dimethyl 2,2 '-Bipyridine-4,5-dicarboxylate: Structure, Antimicrobial Activity and DNA/BSA Binding Study. in Inorganics. 2022;10(6).
doi:10.3390/inorganics10060071 .
Andrejević, Tina P., Aleksić, Ivana, Kljun, Jakob, Pantović, Bojana, V, Milivojević, Dušan, Vojnović, Sandra, Turel, Iztok, Djuran, Milos, Glišić, Biljana, "Zinc(II) Complexes with Dimethyl 2,2 '-Bipyridine-4,5-dicarboxylate: Structure, Antimicrobial Activity and DNA/BSA Binding Study" in Inorganics, 10, no. 6 (2022),
https://doi.org/10.3390/inorganics10060071 . .
10
5
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Clinically used antifungal azoles as ligands for gold(III) complexes: the influence of the Au(III) ion on the antimicrobial activity of the complex

Stevanović, Nevena Lj.; Kljun, Jakob; Aleksić, Ivana; Škaro Bogojević, Sanja; Milivojević, Dušan; Veselinović, Aleksandar; Turel, Iztok; Djuran, Milos; Nikodinović-Runić, Jasmina; Glišić, Biljana

(Royal Soc Chemistry, Cambridge, 2022)

TY  - JOUR
AU  - Stevanović, Nevena Lj.
AU  - Kljun, Jakob
AU  - Aleksić, Ivana
AU  - Škaro Bogojević, Sanja
AU  - Milivojević, Dušan
AU  - Veselinović, Aleksandar
AU  - Turel, Iztok
AU  - Djuran, Milos
AU  - Nikodinović-Runić, Jasmina
AU  - Glišić, Biljana
PY  - 2022
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1568
AB  - In a search for novel antimicrobial metal-based therapeutic agents, mononuclear gold(III) complexes 1-7 of the general formula [AuCl3(azole)], where azole stands for imidazole (im, 1), 1-isopropylimidazole (ipim, 2), 1-phenylimidazole (phim, 3), clotrimazole (ctz, 4), econazole (ecz, 5), tioconazole (tcz, 6) and voriconazole (vcz, 7) were synthesized, characterized and biologically evaluated. In all complexes, the corresponding azole ligand is monodentately coordinated to the Au(III) via the imidazole or triazole nitrogen atom, while the remaining coordination sites are occupied by chloride anions leading to the square-planar arrangement. In vitro antimicrobial assays showed that the complexation of inactive azoles, imidazole, 1-isopropylimidazole and 1-phenylimidazole, to the Au(III) ion led to complexes 1-3, respectively, with moderate activity against the investigated strains and low cytotoxicity on the human normal lung fibroblast cell line (MRC-5). Moreover, gold(III) complexes 4-7 with clinically used antifungal agents clotrimazole, econazole, tioconazole and voriconazole, respectively, have, in most cases, enhanced antimicrobial effectiveness relative to the corresponding azoles, with the best improvement achieved after complexation of tioconazole (6) and voriconazole (7). The complexes 4-7 and the corresponding antifungal azoles inhibited the growth of dermatophyte Microsporum canis at 50 and 25 mu g mL(-1). Gold(III) complexes 1-3 significantly reduced the amount of ergosterol in the cell membrane of Candida albicans at the subinhibitory concentration of 0.5 x MIC (minimal inhibitory concentration), while the corresponding imidazole ligands did not significantly affect the ergosterol content, indicating that the mechanism of action of the gold(III)-azole complexes is associated with inhibition of ergosterol biosynthesis. Finally, complexes 5 and 6 significantly reduced the production of pyocyanin, a virulence factor in Pseudomonas aeruginosa controlled by quorum sensing, and increased cell survival after exposure to this bacterium. These findings could be of importance for the development of novel gold(III)-based antivirulence therapeutic agents that attenuate virulence without pronounced effect on the growth of the pathogens, offering a lower risk for resistance development.
PB  - Royal Soc Chemistry, Cambridge
T2  - Dalton Transactions
T1  - Clinically used antifungal azoles as ligands for gold(III) complexes: the influence of the Au(III) ion on the antimicrobial activity of the complex
EP  - 5334
IS  - 13
SP  - 5322
VL  - 51
DO  - 10.1039/d2dt00411a
ER  - 
@article{
author = "Stevanović, Nevena Lj. and Kljun, Jakob and Aleksić, Ivana and Škaro Bogojević, Sanja and Milivojević, Dušan and Veselinović, Aleksandar and Turel, Iztok and Djuran, Milos and Nikodinović-Runić, Jasmina and Glišić, Biljana",
year = "2022",
abstract = "In a search for novel antimicrobial metal-based therapeutic agents, mononuclear gold(III) complexes 1-7 of the general formula [AuCl3(azole)], where azole stands for imidazole (im, 1), 1-isopropylimidazole (ipim, 2), 1-phenylimidazole (phim, 3), clotrimazole (ctz, 4), econazole (ecz, 5), tioconazole (tcz, 6) and voriconazole (vcz, 7) were synthesized, characterized and biologically evaluated. In all complexes, the corresponding azole ligand is monodentately coordinated to the Au(III) via the imidazole or triazole nitrogen atom, while the remaining coordination sites are occupied by chloride anions leading to the square-planar arrangement. In vitro antimicrobial assays showed that the complexation of inactive azoles, imidazole, 1-isopropylimidazole and 1-phenylimidazole, to the Au(III) ion led to complexes 1-3, respectively, with moderate activity against the investigated strains and low cytotoxicity on the human normal lung fibroblast cell line (MRC-5). Moreover, gold(III) complexes 4-7 with clinically used antifungal agents clotrimazole, econazole, tioconazole and voriconazole, respectively, have, in most cases, enhanced antimicrobial effectiveness relative to the corresponding azoles, with the best improvement achieved after complexation of tioconazole (6) and voriconazole (7). The complexes 4-7 and the corresponding antifungal azoles inhibited the growth of dermatophyte Microsporum canis at 50 and 25 mu g mL(-1). Gold(III) complexes 1-3 significantly reduced the amount of ergosterol in the cell membrane of Candida albicans at the subinhibitory concentration of 0.5 x MIC (minimal inhibitory concentration), while the corresponding imidazole ligands did not significantly affect the ergosterol content, indicating that the mechanism of action of the gold(III)-azole complexes is associated with inhibition of ergosterol biosynthesis. Finally, complexes 5 and 6 significantly reduced the production of pyocyanin, a virulence factor in Pseudomonas aeruginosa controlled by quorum sensing, and increased cell survival after exposure to this bacterium. These findings could be of importance for the development of novel gold(III)-based antivirulence therapeutic agents that attenuate virulence without pronounced effect on the growth of the pathogens, offering a lower risk for resistance development.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Dalton Transactions",
title = "Clinically used antifungal azoles as ligands for gold(III) complexes: the influence of the Au(III) ion on the antimicrobial activity of the complex",
pages = "5334-5322",
number = "13",
volume = "51",
doi = "10.1039/d2dt00411a"
}
Stevanović, N. Lj., Kljun, J., Aleksić, I., Škaro Bogojević, S., Milivojević, D., Veselinović, A., Turel, I., Djuran, M., Nikodinović-Runić, J.,& Glišić, B.. (2022). Clinically used antifungal azoles as ligands for gold(III) complexes: the influence of the Au(III) ion on the antimicrobial activity of the complex. in Dalton Transactions
Royal Soc Chemistry, Cambridge., 51(13), 5322-5334.
https://doi.org/10.1039/d2dt00411a
Stevanović NL, Kljun J, Aleksić I, Škaro Bogojević S, Milivojević D, Veselinović A, Turel I, Djuran M, Nikodinović-Runić J, Glišić B. Clinically used antifungal azoles as ligands for gold(III) complexes: the influence of the Au(III) ion on the antimicrobial activity of the complex. in Dalton Transactions. 2022;51(13):5322-5334.
doi:10.1039/d2dt00411a .
Stevanović, Nevena Lj., Kljun, Jakob, Aleksić, Ivana, Škaro Bogojević, Sanja, Milivojević, Dušan, Veselinović, Aleksandar, Turel, Iztok, Djuran, Milos, Nikodinović-Runić, Jasmina, Glišić, Biljana, "Clinically used antifungal azoles as ligands for gold(III) complexes: the influence of the Au(III) ion on the antimicrobial activity of the complex" in Dalton Transactions, 51, no. 13 (2022):5322-5334,
https://doi.org/10.1039/d2dt00411a . .
5
12
12

Copper(II) and Zinc(II) Complexes with the Clinically Used Fluconazole: Comparison of Antifungal Activity and Therapeutic Potential

Stevanović, Nevena Lj.; Aleksić, Ivana; Kljun, Jakob; Škaro Bogojević, Sanja; Veselinović, Aleksandar; Nikodinović-Runić, Jasmina; Turel, Iztok; Djuran, Milos ; Glišić, Biljana

(MDPI, Basel, 2021)

TY  - JOUR
AU  - Stevanović, Nevena Lj.
AU  - Aleksić, Ivana
AU  - Kljun, Jakob
AU  - Škaro Bogojević, Sanja
AU  - Veselinović, Aleksandar
AU  - Nikodinović-Runić, Jasmina
AU  - Turel, Iztok
AU  - Djuran, Milos 
AU  - Glišić, Biljana
PY  - 2021
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1484
AB  - Copper(II) and zinc(II) complexes with clinically used antifungal drug fluconazole (fcz), {[CuCl2(fcz)(2)](.)5H(2)O}(n), 1, and {[ZnCl2(fcz)(2)]Greek ano teleia2C(2)H(5)OH}(n), 2, were prepared and characterized by spectroscopic and crystallographic methods. The polymeric structure of the complexes comprises four fluconazole molecules monodentately coordinated via the triazole nitrogen and two chlorido ligands. With respect to fluconazole, complex 2 showed significantly higher antifungal activity against Candida krusei and Candida parapsilosis. All tested compounds reduced the total amount of ergosterol at subinhibitory concentrations, indicating that the mode of activity of fluconazole was retained within the complexes, which was corroborated via molecular docking with cytochrome P450 sterol 14 alpha-demethylase (CYP51) as a target. Electrostatic, steric and internal energy interactions between the complexes and enzyme showed that 2 has higher binding potency to this target. Both complexes showed strong inhibition of C. albicans filamentation and biofilm formation at subinhibitory concentrations, with 2 being able to reduce the adherence of C. albicans to A549 cells in vitro. Complex 2 was able to reduce pyocyanin production in Pseudomonas aeruginosa between 10% and 25% and to inhibit its biofilm formation by 20% in comparison to the untreated control. These results suggest that complex 2 may be further examined in the mixed Candida-P. aeruginosa infections.
PB  - MDPI, Basel
T2  - Pharmaceuticals
T1  - Copper(II) and Zinc(II) Complexes with the Clinically Used Fluconazole: Comparison of Antifungal Activity and Therapeutic Potential
IS  - 1
VL  - 14
DO  - 10.3390/ph14010024
ER  - 
@article{
author = "Stevanović, Nevena Lj. and Aleksić, Ivana and Kljun, Jakob and Škaro Bogojević, Sanja and Veselinović, Aleksandar and Nikodinović-Runić, Jasmina and Turel, Iztok and Djuran, Milos  and Glišić, Biljana",
year = "2021",
abstract = "Copper(II) and zinc(II) complexes with clinically used antifungal drug fluconazole (fcz), {[CuCl2(fcz)(2)](.)5H(2)O}(n), 1, and {[ZnCl2(fcz)(2)]Greek ano teleia2C(2)H(5)OH}(n), 2, were prepared and characterized by spectroscopic and crystallographic methods. The polymeric structure of the complexes comprises four fluconazole molecules monodentately coordinated via the triazole nitrogen and two chlorido ligands. With respect to fluconazole, complex 2 showed significantly higher antifungal activity against Candida krusei and Candida parapsilosis. All tested compounds reduced the total amount of ergosterol at subinhibitory concentrations, indicating that the mode of activity of fluconazole was retained within the complexes, which was corroborated via molecular docking with cytochrome P450 sterol 14 alpha-demethylase (CYP51) as a target. Electrostatic, steric and internal energy interactions between the complexes and enzyme showed that 2 has higher binding potency to this target. Both complexes showed strong inhibition of C. albicans filamentation and biofilm formation at subinhibitory concentrations, with 2 being able to reduce the adherence of C. albicans to A549 cells in vitro. Complex 2 was able to reduce pyocyanin production in Pseudomonas aeruginosa between 10% and 25% and to inhibit its biofilm formation by 20% in comparison to the untreated control. These results suggest that complex 2 may be further examined in the mixed Candida-P. aeruginosa infections.",
publisher = "MDPI, Basel",
journal = "Pharmaceuticals",
title = "Copper(II) and Zinc(II) Complexes with the Clinically Used Fluconazole: Comparison of Antifungal Activity and Therapeutic Potential",
number = "1",
volume = "14",
doi = "10.3390/ph14010024"
}
Stevanović, N. Lj., Aleksić, I., Kljun, J., Škaro Bogojević, S., Veselinović, A., Nikodinović-Runić, J., Turel, I., Djuran, M.,& Glišić, B.. (2021). Copper(II) and Zinc(II) Complexes with the Clinically Used Fluconazole: Comparison of Antifungal Activity and Therapeutic Potential. in Pharmaceuticals
MDPI, Basel., 14(1).
https://doi.org/10.3390/ph14010024
Stevanović NL, Aleksić I, Kljun J, Škaro Bogojević S, Veselinović A, Nikodinović-Runić J, Turel I, Djuran M, Glišić B. Copper(II) and Zinc(II) Complexes with the Clinically Used Fluconazole: Comparison of Antifungal Activity and Therapeutic Potential. in Pharmaceuticals. 2021;14(1).
doi:10.3390/ph14010024 .
Stevanović, Nevena Lj., Aleksić, Ivana, Kljun, Jakob, Škaro Bogojević, Sanja, Veselinović, Aleksandar, Nikodinović-Runić, Jasmina, Turel, Iztok, Djuran, Milos , Glišić, Biljana, "Copper(II) and Zinc(II) Complexes with the Clinically Used Fluconazole: Comparison of Antifungal Activity and Therapeutic Potential" in Pharmaceuticals, 14, no. 1 (2021),
https://doi.org/10.3390/ph14010024 . .
10
26
21

Tailoring copper(II) complexes with pyridine-4,5-dicarboxylate esters for anti-Candida activity

Andrejević, Tina P.; Aleksić, Ivana; Pockaj, Marta; Kljun, Jakob; Milivojević, Dušan; Stevanović, Nevena Lj.; Nikodinović-Runić, Jasmina; Turel, Iztok; Djuran, Milos; Glišić, Biljana

(Royal Soc Chemistry, Cambridge, 2021)

TY  - JOUR
AU  - Andrejević, Tina P.
AU  - Aleksić, Ivana
AU  - Pockaj, Marta
AU  - Kljun, Jakob
AU  - Milivojević, Dušan
AU  - Stevanović, Nevena Lj.
AU  - Nikodinović-Runić, Jasmina
AU  - Turel, Iztok
AU  - Djuran, Milos
AU  - Glišić, Biljana
PY  - 2021
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1492
AB  - Five novel copper(ii) complexes with pyridine-4,5-dicarboxylate esters as ligands, [Cu(NO3)(py-2tz)(H2O)(3)]NO3 (1), [Cu(NO3)(2)(py-2metz)(H2O)] (2), [Cu(NO3)(2)(py-2py)(H2O)]center dot H2O (3), [CuCl2(py-2tz)](2) (4) and [CuCl2(py-2metz)](n) (5) (py-2tz is dimethyl 2-(thiazol-2-yl)pyridine-4,5-dicarboxylate, py-2metz is dimethyl 2-(4-methylthiazol-2-yl)pyridine-4,5-dicarboxylate and py-2py is dimethyl 2,2 '-bipyridine-4,5-dicarboxylate), were synthesized and structurally characterized by different spectroscopic and electrochemical methods. The structure of these complexes was determined by single-crystal X-ray diffraction analysis, confirming the bidentate coordination mode of the corresponding pyridine-4,5-dicarboxylate ester to the Cu(ii) ion through the nitrogen atoms. The antimicrobial potential of copper(ii) complexes 1-5 was assessed against two bacterial and two Candida species. These complexes showed better growth inhibiting activity against Candida spp. with respect to the tested bacterial species, also being moderately toxic towards normal human lung fibroblast cells (MRC-5). Complexes 1 and 4 showed the greatest ability to inhibit the filamentation of C. albicans, which is an important process during fungal infection, and these two complexes efficiently inhibited the biofilm formation of C. albicans at subinhibitory concentrations. Complex 4 also successfully prevented the adhesion of C. albicans in an in vitro epithelial cell model. The mechanism of the antifungal activity of copper(ii) complexes 1-5 was studied through their interaction with ct-DNA, as one of the possible target biomolecules, by fluorescence spectroscopy and gel electrophoresis. Finally, the ability of these complexes to bind to bovine serum albumin (BSA) was studied by fluorescence emission spectroscopy.
PB  - Royal Soc Chemistry, Cambridge
T2  - Dalton Transactions
T1  - Tailoring copper(II) complexes with pyridine-4,5-dicarboxylate esters for anti-Candida activity
EP  - 2638
IS  - 7
SP  - 2627
VL  - 50
DO  - 10.1039/d0dt04061d
ER  - 
@article{
author = "Andrejević, Tina P. and Aleksić, Ivana and Pockaj, Marta and Kljun, Jakob and Milivojević, Dušan and Stevanović, Nevena Lj. and Nikodinović-Runić, Jasmina and Turel, Iztok and Djuran, Milos and Glišić, Biljana",
year = "2021",
abstract = "Five novel copper(ii) complexes with pyridine-4,5-dicarboxylate esters as ligands, [Cu(NO3)(py-2tz)(H2O)(3)]NO3 (1), [Cu(NO3)(2)(py-2metz)(H2O)] (2), [Cu(NO3)(2)(py-2py)(H2O)]center dot H2O (3), [CuCl2(py-2tz)](2) (4) and [CuCl2(py-2metz)](n) (5) (py-2tz is dimethyl 2-(thiazol-2-yl)pyridine-4,5-dicarboxylate, py-2metz is dimethyl 2-(4-methylthiazol-2-yl)pyridine-4,5-dicarboxylate and py-2py is dimethyl 2,2 '-bipyridine-4,5-dicarboxylate), were synthesized and structurally characterized by different spectroscopic and electrochemical methods. The structure of these complexes was determined by single-crystal X-ray diffraction analysis, confirming the bidentate coordination mode of the corresponding pyridine-4,5-dicarboxylate ester to the Cu(ii) ion through the nitrogen atoms. The antimicrobial potential of copper(ii) complexes 1-5 was assessed against two bacterial and two Candida species. These complexes showed better growth inhibiting activity against Candida spp. with respect to the tested bacterial species, also being moderately toxic towards normal human lung fibroblast cells (MRC-5). Complexes 1 and 4 showed the greatest ability to inhibit the filamentation of C. albicans, which is an important process during fungal infection, and these two complexes efficiently inhibited the biofilm formation of C. albicans at subinhibitory concentrations. Complex 4 also successfully prevented the adhesion of C. albicans in an in vitro epithelial cell model. The mechanism of the antifungal activity of copper(ii) complexes 1-5 was studied through their interaction with ct-DNA, as one of the possible target biomolecules, by fluorescence spectroscopy and gel electrophoresis. Finally, the ability of these complexes to bind to bovine serum albumin (BSA) was studied by fluorescence emission spectroscopy.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Dalton Transactions",
title = "Tailoring copper(II) complexes with pyridine-4,5-dicarboxylate esters for anti-Candida activity",
pages = "2638-2627",
number = "7",
volume = "50",
doi = "10.1039/d0dt04061d"
}
Andrejević, T. P., Aleksić, I., Pockaj, M., Kljun, J., Milivojević, D., Stevanović, N. Lj., Nikodinović-Runić, J., Turel, I., Djuran, M.,& Glišić, B.. (2021). Tailoring copper(II) complexes with pyridine-4,5-dicarboxylate esters for anti-Candida activity. in Dalton Transactions
Royal Soc Chemistry, Cambridge., 50(7), 2627-2638.
https://doi.org/10.1039/d0dt04061d
Andrejević TP, Aleksić I, Pockaj M, Kljun J, Milivojević D, Stevanović NL, Nikodinović-Runić J, Turel I, Djuran M, Glišić B. Tailoring copper(II) complexes with pyridine-4,5-dicarboxylate esters for anti-Candida activity. in Dalton Transactions. 2021;50(7):2627-2638.
doi:10.1039/d0dt04061d .
Andrejević, Tina P., Aleksić, Ivana, Pockaj, Marta, Kljun, Jakob, Milivojević, Dušan, Stevanović, Nevena Lj., Nikodinović-Runić, Jasmina, Turel, Iztok, Djuran, Milos, Glišić, Biljana, "Tailoring copper(II) complexes with pyridine-4,5-dicarboxylate esters for anti-Candida activity" in Dalton Transactions, 50, no. 7 (2021):2627-2638,
https://doi.org/10.1039/d0dt04061d . .
12
10
9

Structural Characterization, Antimicrobial Activity and BSA/DNA Binding Affinity of New Silver(I) Complexes with Thianthrene and 1,8-Naphthyridine

Ašanin, Darko P.; Škaro Bogojević, Sanja; Perdih, Franc; Andrejević, Tina P.; Milivojević, Dušan; Aleksić, Ivana; Nikodinović-Runić, Jasmina; Glišić, Biljana; Turel, Iztok; Djuran, Milos

(Basel : MDPI, 2021)

TY  - JOUR
AU  - Ašanin, Darko P.
AU  - Škaro Bogojević, Sanja
AU  - Perdih, Franc
AU  - Andrejević, Tina P.
AU  - Milivojević, Dušan
AU  - Aleksić, Ivana
AU  - Nikodinović-Runić, Jasmina
AU  - Glišić, Biljana
AU  - Turel, Iztok
AU  - Djuran, Milos
PY  - 2021
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1420
AB  - Three new silver(I) complexes [Ag(NO3)(tia)(H2O)](n) (Ag1), [Ag(CF3SO3)(1,8-naph)](n) (Ag2) and [Ag-2(1,8-naph)(2)(H2O)(1.2)](PF6)(2) (Ag3), where tia is thianthrene and 1,8-naph is 1,8-naphthyridine, were synthesized and structurally characterized by different spectroscopic and electrochemical methods and their crystal structures were determined by single-crystal X-ray diffraction analysis. Their antimicrobial potential was evaluated against four bacterial and three Candida species, and the obtained results revealed that these complexes showed significant activity toward the Gram-positive Staphylococcus aureus, Gram-negative Pseudomonas aeruginosa and the investigated Candida species with minimal inhibitory concentration (MIC) values in the range 1.56-7.81 mu g/mL. On the other hand, tia and 1,8-naph ligands were not active against the investigated strains, suggesting that their complexation with Ag(I) ion results in the formation of antimicrobial compounds. Moreover, low toxicity of the complexes was detected by in vivo model Caenorhabditis elegans. The interaction of the complexes with calf thymus DNA (ct-DNA) and bovine serum albumin (BSA) was studied to evaluate their binding affinity towards these biomolecules for possible insights into the mode of antimicrobial activity. The binding affinity of Ag1-3 to BSA was higher than that for DNA, indicating that proteins could be more favorable binding sites for these complexes in comparison to the nucleic acids.
PB  - Basel : MDPI
T2  - Molecules
T1  - Structural Characterization, Antimicrobial Activity and BSA/DNA Binding Affinity of New Silver(I) Complexes with Thianthrene and 1,8-Naphthyridine
IS  - 7
VL  - 26
DO  - 10.3390/molecules26071871
ER  - 
@article{
author = "Ašanin, Darko P. and Škaro Bogojević, Sanja and Perdih, Franc and Andrejević, Tina P. and Milivojević, Dušan and Aleksić, Ivana and Nikodinović-Runić, Jasmina and Glišić, Biljana and Turel, Iztok and Djuran, Milos",
year = "2021",
abstract = "Three new silver(I) complexes [Ag(NO3)(tia)(H2O)](n) (Ag1), [Ag(CF3SO3)(1,8-naph)](n) (Ag2) and [Ag-2(1,8-naph)(2)(H2O)(1.2)](PF6)(2) (Ag3), where tia is thianthrene and 1,8-naph is 1,8-naphthyridine, were synthesized and structurally characterized by different spectroscopic and electrochemical methods and their crystal structures were determined by single-crystal X-ray diffraction analysis. Their antimicrobial potential was evaluated against four bacterial and three Candida species, and the obtained results revealed that these complexes showed significant activity toward the Gram-positive Staphylococcus aureus, Gram-negative Pseudomonas aeruginosa and the investigated Candida species with minimal inhibitory concentration (MIC) values in the range 1.56-7.81 mu g/mL. On the other hand, tia and 1,8-naph ligands were not active against the investigated strains, suggesting that their complexation with Ag(I) ion results in the formation of antimicrobial compounds. Moreover, low toxicity of the complexes was detected by in vivo model Caenorhabditis elegans. The interaction of the complexes with calf thymus DNA (ct-DNA) and bovine serum albumin (BSA) was studied to evaluate their binding affinity towards these biomolecules for possible insights into the mode of antimicrobial activity. The binding affinity of Ag1-3 to BSA was higher than that for DNA, indicating that proteins could be more favorable binding sites for these complexes in comparison to the nucleic acids.",
publisher = "Basel : MDPI",
journal = "Molecules",
title = "Structural Characterization, Antimicrobial Activity and BSA/DNA Binding Affinity of New Silver(I) Complexes with Thianthrene and 1,8-Naphthyridine",
number = "7",
volume = "26",
doi = "10.3390/molecules26071871"
}
Ašanin, D. P., Škaro Bogojević, S., Perdih, F., Andrejević, T. P., Milivojević, D., Aleksić, I., Nikodinović-Runić, J., Glišić, B., Turel, I.,& Djuran, M.. (2021). Structural Characterization, Antimicrobial Activity and BSA/DNA Binding Affinity of New Silver(I) Complexes with Thianthrene and 1,8-Naphthyridine. in Molecules
Basel : MDPI., 26(7).
https://doi.org/10.3390/molecules26071871
Ašanin DP, Škaro Bogojević S, Perdih F, Andrejević TP, Milivojević D, Aleksić I, Nikodinović-Runić J, Glišić B, Turel I, Djuran M. Structural Characterization, Antimicrobial Activity and BSA/DNA Binding Affinity of New Silver(I) Complexes with Thianthrene and 1,8-Naphthyridine. in Molecules. 2021;26(7).
doi:10.3390/molecules26071871 .
Ašanin, Darko P., Škaro Bogojević, Sanja, Perdih, Franc, Andrejević, Tina P., Milivojević, Dušan, Aleksić, Ivana, Nikodinović-Runić, Jasmina, Glišić, Biljana, Turel, Iztok, Djuran, Milos, "Structural Characterization, Antimicrobial Activity and BSA/DNA Binding Affinity of New Silver(I) Complexes with Thianthrene and 1,8-Naphthyridine" in Molecules, 26, no. 7 (2021),
https://doi.org/10.3390/molecules26071871 . .
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Silver(I) complexes with different pyridine-4,5-dicarboxylate ligands as efficient agents for the control of cow mastitis associated pathogens

Andrejević, Tina P.; Milivojević, Dušan; Glišić, Biljana; Kljun, Jakob; Stevanović, Nevena Lj.; Vojnović, Sandra; Medić, Strahinja; Nikodinović-Runić, Jasmina; Turel, Iztok; Djuran, Milos

(Royal Soc Chemistry, Cambridge, 2020)

TY  - JOUR
AU  - Andrejević, Tina P.
AU  - Milivojević, Dušan
AU  - Glišić, Biljana
AU  - Kljun, Jakob
AU  - Stevanović, Nevena Lj.
AU  - Vojnović, Sandra
AU  - Medić, Strahinja
AU  - Nikodinović-Runić, Jasmina
AU  - Turel, Iztok
AU  - Djuran, Milos 
PY  - 2020
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1333
AB  - Infections of the cow udder leading to mastitis and lower milk quality are one of the biggest problems in the dairy industry worldwide. Unfortunately, therapeutic options for the treatment of cow mastitis are limited as a consequence of the development of pathogens that are resistant to conventionally used antibiotics. In the search for agents that will be active against cow mastitis associated pathogens, in the present study, five new silver(I) complexes with different chelating pyridine-4,5-dicarboxylate types of ligands, [Ag(NO3)(py-2py)](n) (1), [Ag(NO3)(py-2metz)](n) (2), [Ag(CH3CN)(py-2py)]BF4 (3), [Ag(py-2tz)(2)]BF4 (4) and [Ag(py-2metz)(2)]BF4 (5), py-2py is dimethyl 2,2'-bipyridine-4,5-dicarboxylate, py-2metz is dimethyl 2-(4-methylthiazol-2-yl)pyridine-4,5-dicarboxylate and py-2tz is dimethyl 2-(thiazol-2-yl)pyridine-4,5-dicarboxylate, were synthesized, structurally characterized and assessed for in vitro antimicrobial activity using both standard bioassay and clinical isolates from a contaminated milk sample obtained from a cow with mastitis. These complexes showed remarkable activity against the standard panel of microorganisms and a selection of clinical isolates from the milk of the cow diagnosed with mastitis. With the aim of determining the therapeutic potential of silver(I) complexes, their toxicity in vivo against the model organism, Caenorhabditis elegans (C. elegans), was investigated. The complexes that had the best therapeutic profile, 2 and 5, induced bacterial membrane depolarization and the production of reactive oxygen species (ROS) in Candida albicans cells and inhibited the hyphae as well as the biofilm formation. Taken together, the presented data suggest that the silver(I) complexes with pyridine ligands could be considered for the treatment of microbial pathogens, which are causative agents of cow mastitis.
PB  - Royal Soc Chemistry, Cambridge
T2  - Dalton Transactions
T1  - Silver(I) complexes with different pyridine-4,5-dicarboxylate ligands as efficient agents for the control of cow mastitis associated pathogens
EP  - 6096
IS  - 18
SP  - 6084
VL  - 49
DO  - 10.1039/d0dt00518e
ER  - 
@article{
author = "Andrejević, Tina P. and Milivojević, Dušan and Glišić, Biljana and Kljun, Jakob and Stevanović, Nevena Lj. and Vojnović, Sandra and Medić, Strahinja and Nikodinović-Runić, Jasmina and Turel, Iztok and Djuran, Milos ",
year = "2020",
abstract = "Infections of the cow udder leading to mastitis and lower milk quality are one of the biggest problems in the dairy industry worldwide. Unfortunately, therapeutic options for the treatment of cow mastitis are limited as a consequence of the development of pathogens that are resistant to conventionally used antibiotics. In the search for agents that will be active against cow mastitis associated pathogens, in the present study, five new silver(I) complexes with different chelating pyridine-4,5-dicarboxylate types of ligands, [Ag(NO3)(py-2py)](n) (1), [Ag(NO3)(py-2metz)](n) (2), [Ag(CH3CN)(py-2py)]BF4 (3), [Ag(py-2tz)(2)]BF4 (4) and [Ag(py-2metz)(2)]BF4 (5), py-2py is dimethyl 2,2'-bipyridine-4,5-dicarboxylate, py-2metz is dimethyl 2-(4-methylthiazol-2-yl)pyridine-4,5-dicarboxylate and py-2tz is dimethyl 2-(thiazol-2-yl)pyridine-4,5-dicarboxylate, were synthesized, structurally characterized and assessed for in vitro antimicrobial activity using both standard bioassay and clinical isolates from a contaminated milk sample obtained from a cow with mastitis. These complexes showed remarkable activity against the standard panel of microorganisms and a selection of clinical isolates from the milk of the cow diagnosed with mastitis. With the aim of determining the therapeutic potential of silver(I) complexes, their toxicity in vivo against the model organism, Caenorhabditis elegans (C. elegans), was investigated. The complexes that had the best therapeutic profile, 2 and 5, induced bacterial membrane depolarization and the production of reactive oxygen species (ROS) in Candida albicans cells and inhibited the hyphae as well as the biofilm formation. Taken together, the presented data suggest that the silver(I) complexes with pyridine ligands could be considered for the treatment of microbial pathogens, which are causative agents of cow mastitis.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Dalton Transactions",
title = "Silver(I) complexes with different pyridine-4,5-dicarboxylate ligands as efficient agents for the control of cow mastitis associated pathogens",
pages = "6096-6084",
number = "18",
volume = "49",
doi = "10.1039/d0dt00518e"
}
Andrejević, T. P., Milivojević, D., Glišić, B., Kljun, J., Stevanović, N. Lj., Vojnović, S., Medić, S., Nikodinović-Runić, J., Turel, I.,& Djuran, M.. (2020). Silver(I) complexes with different pyridine-4,5-dicarboxylate ligands as efficient agents for the control of cow mastitis associated pathogens. in Dalton Transactions
Royal Soc Chemistry, Cambridge., 49(18), 6084-6096.
https://doi.org/10.1039/d0dt00518e
Andrejević TP, Milivojević D, Glišić B, Kljun J, Stevanović NL, Vojnović S, Medić S, Nikodinović-Runić J, Turel I, Djuran M. Silver(I) complexes with different pyridine-4,5-dicarboxylate ligands as efficient agents for the control of cow mastitis associated pathogens. in Dalton Transactions. 2020;49(18):6084-6096.
doi:10.1039/d0dt00518e .
Andrejević, Tina P., Milivojević, Dušan, Glišić, Biljana, Kljun, Jakob, Stevanović, Nevena Lj., Vojnović, Sandra, Medić, Strahinja, Nikodinović-Runić, Jasmina, Turel, Iztok, Djuran, Milos , "Silver(I) complexes with different pyridine-4,5-dicarboxylate ligands as efficient agents for the control of cow mastitis associated pathogens" in Dalton Transactions, 49, no. 18 (2020):6084-6096,
https://doi.org/10.1039/d0dt00518e . .
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