TY  - JOUR
AU  - Glišić, Biljana
AU  - Nikodinović-Runić, Jasmina
AU  - Ilić-Tomić, Tatjana
AU  - Wadepohl, Hubert
AU  - Veselinović, Aleksandar
AU  - Opsenica, Igor M.
AU  - Djuran, Milos I.
PY  - 2018
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1166
AB  - Mononuclear copper(II) complexes with 2,2':6',2 ''-terpyridine (terpy), [Cu(terpy)(ClO4)(2)(H2O)] (1) and [Cu(terpy())2](CF3SO3)(2)center dot 2H(2)O (2), were synthesized and structurally characterized by UV-Vis and IR spectroscopy, ESI mass spectrometry and single-crystal X-ray diffraction analysis. In vitro study of cytotoxicity of the complexes demonstrated good antiproliferative properties in the case of human non-small cell lung cancer (A549), as well as in lung fibroblast (MRC5) cell line. Copper(II) complexes with terpy showed significant ability to interact with the high molecular weight double stranded DNA, without induction of DNA damage. On the other side, they caused nicking of plasmid DNA without presence of co-oxidant, indicating moderate nucleolytic activity. Circular dichroism spectra confirmed intercalation of the complexes to double-stranded DNA. Molecular docking studies also indicated strong binding affinity of the complexes with DNA revealing that two forms of 1 (1a and 1b with and without coordinated perchlorate ion, respectively) and 2 bind to the major groove of DNA.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Polyhedron
T1  - Synthesis, cytotoxic activity and DNA-binding properties of copper(II) complexes with terpyridine
EP  - 322
SP  - 313
VL  - 139
DO  - 10.1016/j.poly.2017.11.008
ER  - 

@article{
author = "Glišić, Biljana and Nikodinović-Runić, Jasmina and Ilić-Tomić, Tatjana and Wadepohl, Hubert and Veselinović, Aleksandar and Opsenica, Igor M. and Djuran, Milos I.",
year = "2018",
abstract = "Mononuclear copper(II) complexes with 2,2':6',2 ''-terpyridine (terpy), [Cu(terpy)(ClO4)(2)(H2O)] (1) and [Cu(terpy())2](CF3SO3)(2)center dot 2H(2)O (2), were synthesized and structurally characterized by UV-Vis and IR spectroscopy, ESI mass spectrometry and single-crystal X-ray diffraction analysis. In vitro study of cytotoxicity of the complexes demonstrated good antiproliferative properties in the case of human non-small cell lung cancer (A549), as well as in lung fibroblast (MRC5) cell line. Copper(II) complexes with terpy showed significant ability to interact with the high molecular weight double stranded DNA, without induction of DNA damage. On the other side, they caused nicking of plasmid DNA without presence of co-oxidant, indicating moderate nucleolytic activity. Circular dichroism spectra confirmed intercalation of the complexes to double-stranded DNA. Molecular docking studies also indicated strong binding affinity of the complexes with DNA revealing that two forms of 1 (1a and 1b with and without coordinated perchlorate ion, respectively) and 2 bind to the major groove of DNA.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Polyhedron",
title = "Synthesis, cytotoxic activity and DNA-binding properties of copper(II) complexes with terpyridine",
pages = "322-313",
volume = "139",
doi = "10.1016/j.poly.2017.11.008"
}

Glišić, B., Nikodinović-Runić, J., Ilić-Tomić, T., Wadepohl, H., Veselinović, A., Opsenica, I. M.,& Djuran, M. I.. (2018). Synthesis, cytotoxic activity and DNA-binding properties of copper(II) complexes with terpyridine. in Polyhedron
Pergamon-Elsevier Science Ltd, Oxford., 139, 313-322.
https://doi.org/10.1016/j.poly.2017.11.008

Glišić B, Nikodinović-Runić J, Ilić-Tomić T, Wadepohl H, Veselinović A, Opsenica IM, Djuran MI. Synthesis, cytotoxic activity and DNA-binding properties of copper(II) complexes with terpyridine. in Polyhedron. 2018;139:313-322.
doi:10.1016/j.poly.2017.11.008 .

Glišić, Biljana, Nikodinović-Runić, Jasmina, Ilić-Tomić, Tatjana, Wadepohl, Hubert, Veselinović, Aleksandar, Opsenica, Igor M., Djuran, Milos I., "Synthesis, cytotoxic activity and DNA-binding properties of copper(II) complexes with terpyridine" in Polyhedron, 139 (2018):313-322,
https://doi.org/10.1016/j.poly.2017.11.008 . .

TY  - JOUR
AU  - Glišić, Biljana
AU  - Šenerović, Lidija
AU  - Comba, Peter
AU  - Wadepohl, Hubert
AU  - Veselinović, Aleksandar
AU  - Milivojević, Dušan
AU  - Djuran, Milos I.
AU  - Nikodinović-Runić, Jasmina
PY  - 2016
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/976
AB  - Five silver(I) complexes with aromatic nitrogen-containing heterocycles, phthalazine (phtz) and quinazoline (qz), were synthesized, characterized and analyzed by single-crystal X-ray diffraction analysis. Although different AgX salts reacted with phtz, only dinuclear silver(I) complexes of the general formula {[Ag(X-O)(phtz-N)](2)(mu-phtz-N,N')(2)} were formed, X = NO3- (1), CF3SO3- (2) and ClO4- (3). However, reactions of qz with an equimolar amount of AgCF3SO3 and AgBF4 resulted in the formation of polynuclear complexes, {[Ag(CF3SO3-O)(qz-N)](2)}(n) (4) and {[Ag(qz-N)][BF4]}(n) (5). Complexes 1-5 were evaluated by in vitro antimicrobial studies against a panel of microbial strains that lead to many skin and soft tissue, respiratory, wound and nosocomial infections. The obtained results indicate that all tested silver(I) complexes have good antibacterial activity with MIC (minimum inhibitory concentration) values in the range from 2.9 to 48.0 mu M against the investigated strains. Among the investigated strains, these complexes were particularly efficient against pathogenic Pseudomonas aeruginosa (MIC = 2.9-29 mu M) and had a marked ability to disrupt clinically relevant biofilms of strains with high inherent resistance to antibiotics. On the other hand, their activity against the fungus Candida albicans was moderate. In order to determine the therapeutic potential of silver(I) complexes 1-5, their antiproliferative effect on the human lung fibroblastic cell line MRC5, has been also evaluated. The binding of complexes 1-5 to the genomic DNA of P. aeruginosa was demonstrated by gel electrophoresis techniques and well supported by molecular docking into the DNA minor groove. All investigated complexes showed an improved cytotoxicity profile in comparison to the clinically used AgNO3.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - Silver(I) complexes with phthalazine and quinazoline as effective agents against pathogenic Pseudomonas aeruginosa strains
EP  - 128
SP  - 115
VL  - 155
DO  - 10.1016/j.jinorgbio.2015.11.026
ER  - 

@article{
author = "Glišić, Biljana and Šenerović, Lidija and Comba, Peter and Wadepohl, Hubert and Veselinović, Aleksandar and Milivojević, Dušan and Djuran, Milos I. and Nikodinović-Runić, Jasmina",
year = "2016",
abstract = "Five silver(I) complexes with aromatic nitrogen-containing heterocycles, phthalazine (phtz) and quinazoline (qz), were synthesized, characterized and analyzed by single-crystal X-ray diffraction analysis. Although different AgX salts reacted with phtz, only dinuclear silver(I) complexes of the general formula {[Ag(X-O)(phtz-N)](2)(mu-phtz-N,N')(2)} were formed, X = NO3- (1), CF3SO3- (2) and ClO4- (3). However, reactions of qz with an equimolar amount of AgCF3SO3 and AgBF4 resulted in the formation of polynuclear complexes, {[Ag(CF3SO3-O)(qz-N)](2)}(n) (4) and {[Ag(qz-N)][BF4]}(n) (5). Complexes 1-5 were evaluated by in vitro antimicrobial studies against a panel of microbial strains that lead to many skin and soft tissue, respiratory, wound and nosocomial infections. The obtained results indicate that all tested silver(I) complexes have good antibacterial activity with MIC (minimum inhibitory concentration) values in the range from 2.9 to 48.0 mu M against the investigated strains. Among the investigated strains, these complexes were particularly efficient against pathogenic Pseudomonas aeruginosa (MIC = 2.9-29 mu M) and had a marked ability to disrupt clinically relevant biofilms of strains with high inherent resistance to antibiotics. On the other hand, their activity against the fungus Candida albicans was moderate. In order to determine the therapeutic potential of silver(I) complexes 1-5, their antiproliferative effect on the human lung fibroblastic cell line MRC5, has been also evaluated. The binding of complexes 1-5 to the genomic DNA of P. aeruginosa was demonstrated by gel electrophoresis techniques and well supported by molecular docking into the DNA minor groove. All investigated complexes showed an improved cytotoxicity profile in comparison to the clinically used AgNO3.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "Silver(I) complexes with phthalazine and quinazoline as effective agents against pathogenic Pseudomonas aeruginosa strains",
pages = "128-115",
volume = "155",
doi = "10.1016/j.jinorgbio.2015.11.026"
}

Glišić, B., Šenerović, L., Comba, P., Wadepohl, H., Veselinović, A., Milivojević, D., Djuran, M. I.,& Nikodinović-Runić, J.. (2016). Silver(I) complexes with phthalazine and quinazoline as effective agents against pathogenic Pseudomonas aeruginosa strains. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 155, 115-128.
https://doi.org/10.1016/j.jinorgbio.2015.11.026

Glišić B, Šenerović L, Comba P, Wadepohl H, Veselinović A, Milivojević D, Djuran MI, Nikodinović-Runić J. Silver(I) complexes with phthalazine and quinazoline as effective agents against pathogenic Pseudomonas aeruginosa strains. in Journal of Inorganic Biochemistry. 2016;155:115-128.
doi:10.1016/j.jinorgbio.2015.11.026 .

Glišić, Biljana, Šenerović, Lidija, Comba, Peter, Wadepohl, Hubert, Veselinović, Aleksandar, Milivojević, Dušan, Djuran, Milos I., Nikodinović-Runić, Jasmina, "Silver(I) complexes with phthalazine and quinazoline as effective agents against pathogenic Pseudomonas aeruginosa strains" in Journal of Inorganic Biochemistry, 155 (2016):115-128,
https://doi.org/10.1016/j.jinorgbio.2015.11.026 . .

TY  - JOUR
AU  - Glišić, Biljana
AU  - Aleksić, Ivana
AU  - Comba, Peter
AU  - Wadepohl, Hubert
AU  - Ilić-Tomić, Tatjana
AU  - Nikodinović-Runić, Jasmina
AU  - Djuran, Milos I.
PY  - 2016
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/930
AB  - Five copper(II) complexes 1-5 with aromatic nitrogen-containing heterocycles, pyrimidine (pm, 1), pyrazine (pz, 2), quinazoline (qz, 3 and 4) and phthalazine (phtz, 5) have been synthesized and structurally characterized by spectroscopic and single-crystal X-ray diffraction techniques. The crystallographic results show that, dependent on the ligand structure, complexes 1-5 are of different nuclearity. The antimicrobial efficiency of complexes 1-5 has been evaluated against three clinically relevant microorganisms and none of the complexes showed significant growth inhibiting activity, with values of minimum inhibitory concentrations (MIC) in the mM range. Since in many bacteria, pathogenicity and virulence are regulated by intercellular communication processes, quorum sensing (QS), the effect of the copper(II) complexes on bacterial QS has also been examined. The results indicate that the investigated complexes inhibit violacein production in Chromobacterium violaceum CV026, suggesting an anti-QS activity. In order to differentiate, which of the QS pathways was affected by the copper(II) complexes, three biosensor strains were used: the PAO1 Delta rhlIpKD-rhlA and the PA14-R3 Delta lasIPrsaI lux strain to directly measure the levels of C4-HSL (N-butanoyl-homoserine lactone) and 3OC12-HSL (N-3-oxo-dodecanoyl- homoserine lactone), respectively, and PAO1 Delta pqsA mini-CTX luxPpqsA for the detection of AHQs (2-alkyl-4-quinolones). Complexes 1-5 were shown to be efficient inhibitors of biofilm formation of the human opportunistic pathogen Pseudomonas aeruginosa PAO1, with the qz-containing complex 3 being the most active. Finally, the most anti-QS-active complexes 1 and 3 showed synergistic activity against a multi-drug resistant clinical isolate of P. aeruginosa, when supplied in combination with the known antibiotics piperacillin and ceftazidime.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Copper(II) complexes with aromatic nitrogen-containing heterocycles as effective inhibitors of quorum sensing activity in Pseudomonas aeruginosa
EP  - 86709
IS  - 89
SP  - 86695
VL  - 6
DO  - 10.1039/c6ra19902j
ER  - 

@article{
author = "Glišić, Biljana and Aleksić, Ivana and Comba, Peter and Wadepohl, Hubert and Ilić-Tomić, Tatjana and Nikodinović-Runić, Jasmina and Djuran, Milos I.",
year = "2016",
abstract = "Five copper(II) complexes 1-5 with aromatic nitrogen-containing heterocycles, pyrimidine (pm, 1), pyrazine (pz, 2), quinazoline (qz, 3 and 4) and phthalazine (phtz, 5) have been synthesized and structurally characterized by spectroscopic and single-crystal X-ray diffraction techniques. The crystallographic results show that, dependent on the ligand structure, complexes 1-5 are of different nuclearity. The antimicrobial efficiency of complexes 1-5 has been evaluated against three clinically relevant microorganisms and none of the complexes showed significant growth inhibiting activity, with values of minimum inhibitory concentrations (MIC) in the mM range. Since in many bacteria, pathogenicity and virulence are regulated by intercellular communication processes, quorum sensing (QS), the effect of the copper(II) complexes on bacterial QS has also been examined. The results indicate that the investigated complexes inhibit violacein production in Chromobacterium violaceum CV026, suggesting an anti-QS activity. In order to differentiate, which of the QS pathways was affected by the copper(II) complexes, three biosensor strains were used: the PAO1 Delta rhlIpKD-rhlA and the PA14-R3 Delta lasIPrsaI lux strain to directly measure the levels of C4-HSL (N-butanoyl-homoserine lactone) and 3OC12-HSL (N-3-oxo-dodecanoyl- homoserine lactone), respectively, and PAO1 Delta pqsA mini-CTX luxPpqsA for the detection of AHQs (2-alkyl-4-quinolones). Complexes 1-5 were shown to be efficient inhibitors of biofilm formation of the human opportunistic pathogen Pseudomonas aeruginosa PAO1, with the qz-containing complex 3 being the most active. Finally, the most anti-QS-active complexes 1 and 3 showed synergistic activity against a multi-drug resistant clinical isolate of P. aeruginosa, when supplied in combination with the known antibiotics piperacillin and ceftazidime.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Copper(II) complexes with aromatic nitrogen-containing heterocycles as effective inhibitors of quorum sensing activity in Pseudomonas aeruginosa",
pages = "86709-86695",
number = "89",
volume = "6",
doi = "10.1039/c6ra19902j"
}

Glišić, B., Aleksić, I., Comba, P., Wadepohl, H., Ilić-Tomić, T., Nikodinović-Runić, J.,& Djuran, M. I.. (2016). Copper(II) complexes with aromatic nitrogen-containing heterocycles as effective inhibitors of quorum sensing activity in Pseudomonas aeruginosa. in RSC Advances
Royal Soc Chemistry, Cambridge., 6(89), 86695-86709.
https://doi.org/10.1039/c6ra19902j

Glišić B, Aleksić I, Comba P, Wadepohl H, Ilić-Tomić T, Nikodinović-Runić J, Djuran MI. Copper(II) complexes with aromatic nitrogen-containing heterocycles as effective inhibitors of quorum sensing activity in Pseudomonas aeruginosa. in RSC Advances. 2016;6(89):86695-86709.
doi:10.1039/c6ra19902j .

Glišić, Biljana, Aleksić, Ivana, Comba, Peter, Wadepohl, Hubert, Ilić-Tomić, Tatjana, Nikodinović-Runić, Jasmina, Djuran, Milos I., "Copper(II) complexes with aromatic nitrogen-containing heterocycles as effective inhibitors of quorum sensing activity in Pseudomonas aeruginosa" in RSC Advances, 6, no. 89 (2016):86695-86709,
https://doi.org/10.1039/c6ra19902j . .

TY  - JOUR
AU  - Savić, Nada D.
AU  - Glišić, Biljana
AU  - Wadepohl, Hubert
AU  - Pavić, Aleksandar
AU  - Šenerović, Lidija
AU  - Nikodinović-Runić, Jasmina
AU  - Djuran, Milos I.
PY  - 2016
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/983
AB  - New silver.I) complexes with quinazoline (qz) and phthalazine (phtz), [Ag(NO3)(qz)](n) (1) and {[Ag(CH3CN)](2)(mu-phtz)(2)}[BF4](2) (2), have been synthesized and structurally characterized by using different spectroscopic and single-crystal X-ray diffraction techniques. The obtained results revealed that the reaction of AgNO3 with qz at room temperature in a 2 : 1 molar ratio led to the formation of the polynuclear complex 1. However, the reaction of AgBF4 with phtz under the same experimental conditions resulted in the formation of the dinuclear complex 2. The solution behaviour and air/light stability of these silver.I) complexes have been investigated. The complexes 1 and 2, along with the silver.I) salts used for their synthesis, were evaluated by in vitro antimicrobial studies against a panel of microbial strains that lead to many skin and soft tissue, respiratory, wound, and nosocomial infections. The obtained results indicate that all tested silver(I) compounds have good antibacterial activity with MIC values in the range from 1.5 to 15.6 mu g mL(-1) against the investigated strains. On the other hand, their antifungal activity against Candida albicans was moderate. In order to determine the therapeutic potential of 1 and 2, their antiproliferative effect on the normal human lung fibroblast cell line MRC5, hemolytic effect on red blood cells and embryotoxicity on zebrafish (Danio rerio) have also been evaluated.
PB  - Royal Soc Chemistry, Cambridge
T2  - Medchemcomm
T1  - Silver(I) complexes with quinazoline and phthalazine: synthesis, structural characterization and evaluation of biological activities
EP  - 291
IS  - 2
SP  - 282
VL  - 7
DO  - 10.1039/c5md00494b
ER  - 

@article{
author = "Savić, Nada D. and Glišić, Biljana and Wadepohl, Hubert and Pavić, Aleksandar and Šenerović, Lidija and Nikodinović-Runić, Jasmina and Djuran, Milos I.",
year = "2016",
abstract = "New silver.I) complexes with quinazoline (qz) and phthalazine (phtz), [Ag(NO3)(qz)](n) (1) and {[Ag(CH3CN)](2)(mu-phtz)(2)}[BF4](2) (2), have been synthesized and structurally characterized by using different spectroscopic and single-crystal X-ray diffraction techniques. The obtained results revealed that the reaction of AgNO3 with qz at room temperature in a 2 : 1 molar ratio led to the formation of the polynuclear complex 1. However, the reaction of AgBF4 with phtz under the same experimental conditions resulted in the formation of the dinuclear complex 2. The solution behaviour and air/light stability of these silver.I) complexes have been investigated. The complexes 1 and 2, along with the silver.I) salts used for their synthesis, were evaluated by in vitro antimicrobial studies against a panel of microbial strains that lead to many skin and soft tissue, respiratory, wound, and nosocomial infections. The obtained results indicate that all tested silver(I) compounds have good antibacterial activity with MIC values in the range from 1.5 to 15.6 mu g mL(-1) against the investigated strains. On the other hand, their antifungal activity against Candida albicans was moderate. In order to determine the therapeutic potential of 1 and 2, their antiproliferative effect on the normal human lung fibroblast cell line MRC5, hemolytic effect on red blood cells and embryotoxicity on zebrafish (Danio rerio) have also been evaluated.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Medchemcomm",
title = "Silver(I) complexes with quinazoline and phthalazine: synthesis, structural characterization and evaluation of biological activities",
pages = "291-282",
number = "2",
volume = "7",
doi = "10.1039/c5md00494b"
}

Savić, N. D., Glišić, B., Wadepohl, H., Pavić, A., Šenerović, L., Nikodinović-Runić, J.,& Djuran, M. I.. (2016). Silver(I) complexes with quinazoline and phthalazine: synthesis, structural characterization and evaluation of biological activities. in Medchemcomm
Royal Soc Chemistry, Cambridge., 7(2), 282-291.
https://doi.org/10.1039/c5md00494b

Savić ND, Glišić B, Wadepohl H, Pavić A, Šenerović L, Nikodinović-Runić J, Djuran MI. Silver(I) complexes with quinazoline and phthalazine: synthesis, structural characterization and evaluation of biological activities. in Medchemcomm. 2016;7(2):282-291.
doi:10.1039/c5md00494b .

Savić, Nada D., Glišić, Biljana, Wadepohl, Hubert, Pavić, Aleksandar, Šenerović, Lidija, Nikodinović-Runić, Jasmina, Djuran, Milos I., "Silver(I) complexes with quinazoline and phthalazine: synthesis, structural characterization and evaluation of biological activities" in Medchemcomm, 7, no. 2 (2016):282-291,
https://doi.org/10.1039/c5md00494b . .