TY  - JOUR
AU  - Glišić, Biljana Đ.
AU  - Aleksić, Ivana
AU  - Comba, Peter
AU  - Wadepohl, Hubert
AU  - Ilić-Tomić, Tatjana
AU  - Nikodinović-Runić, Jasmina
AU  - Đuran, Miloš I.
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2317
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
VL  - 6
IS  - 89
SP  - 86695
EP  - 86709
DO  - 10.1039/c6ra19902j
ER  - 

@article{
author = "Glišić, Biljana Đ. and Aleksić, Ivana and Comba, Peter and Wadepohl, Hubert and Ilić-Tomić, Tatjana and Nikodinović-Runić, Jasmina and Đuran, Miloš 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",
volume = "6",
number = "89",
pages = "86695-86709",
doi = "10.1039/c6ra19902j"
}

Glišić, B. Đ., Aleksić, I., Comba, P., Wadepohl, H., Ilić-Tomić, T., Nikodinović-Runić, J.,& Đuran, 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 BĐ, Aleksić I, Comba P, Wadepohl H, Ilić-Tomić T, Nikodinović-Runić J, Đuran 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 Đ., Aleksić, Ivana, Comba, Peter, Wadepohl, Hubert, Ilić-Tomić, Tatjana, Nikodinović-Runić, Jasmina, Đuran, Miloš 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  - Glišić, Biljana Đ.
AU  - Šenerović, Lidija
AU  - Comba, Peter
AU  - Wadepohl, Hubert
AU  - Veselinović, Aleksandar
AU  - Milivojević, Dušan R.
AU  - Đuran, Miloš I.
AU  - Nikodinović-Runić, Jasmina
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1964
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. (C) 2015 Elsevier Inc. All rights reserved.
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
VL  - 155
SP  - 115
EP  - 128
DO  - 10.1016/j.jinorgbio.2015.11.026
ER  - 

@article{
author = "Glišić, Biljana Đ. and Šenerović, Lidija and Comba, Peter and Wadepohl, Hubert and Veselinović, Aleksandar and Milivojević, Dušan R. and Đuran, Miloš 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. (C) 2015 Elsevier Inc. All rights reserved.",
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",
volume = "155",
pages = "115-128",
doi = "10.1016/j.jinorgbio.2015.11.026"
}

Glišić, B. Đ., Šenerović, L., Comba, P., Wadepohl, H., Veselinović, A., Milivojević, D. R., Đuran, 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 BĐ, Šenerović L, Comba P, Wadepohl H, Veselinović A, Milivojević DR, Đuran 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 Đ., Šenerović, Lidija, Comba, Peter, Wadepohl, Hubert, Veselinović, Aleksandar, Milivojević, Dušan R., Đuran, Miloš 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 . .