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Copper(II) complexes with aromatic nitrogen-containing heterocycles as effective inhibitors of quorum sensing activity in Pseudomonas aeruginosa

Authorized Users Only
2016
Authors
Glišić, Biljana Đ.
Aleksić, Ivana
Comba, Peter
Wadepohl, Hubert
Ilić-Tomić, Tatjana
Nikodinović-Runić, Jasmina
Đuran, Miloš I.
Article (Published version)
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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.

Keywords:
gram-negative bacteria / crystal-structure / chromobacterium-violaceum / biological-activity / spectroscopic properties / biofilm formation / virulence / resistance / strategies / ligands
Source:
RSC Advances, 2016, 6, 89, 86695-86709
Publisher:
  • Royal Soc Chemistry, Cambridge
Funding / projects:
  • Synthesis of new metal complexes and investigation of their reactions with peptides (RS-172036)
  • Microbial diversity study and characterization of beneficial environmental microorganisms (RS-173048)

DOI: 10.1039/c6ra19902j

ISSN: 2046-2069

WoS: 000384322700119

Scopus: 2-s2.0-84987899360
[ Google Scholar ]
21
19
URI
https://cherry.chem.bg.ac.rs/handle/123456789/2317
Collections
  • Publikacije
Institution/Community
Inovacioni centar
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
UR  - Kon_3133
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",
url = "Kon_3133"
}
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
Kon_3133
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
Kon_3133 .
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 .,
Kon_3133 .

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