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
Authors
Andrejević, Tina P.
Aleksić, Ivana

Kljun, Jakob

Počkaj, Marta

Zlatar, Matija

Vojnović, Sandra

Nikodinović-Runić, Jasmina

Turel, Iztok

Đuran, Miloš

Glišić, Biljana

Article (Published version)
Metadata
Show full item recordAbstract
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. alb...icans 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.
Keywords:
X-ray diffraction / copper(II) / silver(I) / complexes / chelate ligand / characterization / DFT / antimicrobial potential / antifungal properties / binding affinity / catalysis / Catechol oxidase / o-aminophenol / calf thymus DNA / bovine serum albumin / bioinorganic chemistry / coordination chemistry / biomimeticSource:
RSC Advances, 2023, 13, 7, 4376-4393Publisher:
- Royal Society of Chemistry (RSC)
Funding / projects:
- Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200042 (University of Belgrade, Institute of Molecular Genetics and Genetic Engineering) (RS-200042)
- Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200122 (University of Kragujevac, Faculty of Science) (RS-200122)
- Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200026 (University of Belgrade, Institute of Chemistry, Technology and Metallurgy - IChTM) (RS-200026)
- Slovenian Research Agency (grant P1-0175)
- Serbian Academy of Sciences and Arts (project No. F128)
- TMMagCat - Tailoring Molecular Magnets and Catalysts Based on Transition Metal Complexes (RS-7750288)
Note:
- Supplementary information: https://cer.ihtm.bg.ac.rs/handle/123456789/5674
- Related crystallographic data (CCDC 2220146): https://cer.ihtm.bg.ac.rs/handle/123456789/5669
- Related crystallographic data (CCDC 2220147): https://cer.ihtm.bg.ac.rs/handle/123456789/5670
- Related crystallographic data (CCDC 2220148): https://cer.ihtm.bg.ac.rs/handle/123456789/5671
- Related crystallographic data (CCDC 2220149): https://cer.ihtm.bg.ac.rs/handle/123456789/5672
- Related crystallographic data (CCDC 2220150): https://cer.ihtm.bg.ac.rs/handle/123456789/5673
Related info:
- Referenced by
https://cer.ihtm.bg.ac.rs/handle/123456789/5674 - Referenced by
https://cer.ihtm.bg.ac.rs/handle/123456789/5669 - Referenced by
https://cer.ihtm.bg.ac.rs/handle/123456789/5670 - Referenced by
https://cer.ihtm.bg.ac.rs/handle/123456789/5671 - Referenced by
https://cer.ihtm.bg.ac.rs/handle/123456789/5672 - Referenced by
https://cer.ihtm.bg.ac.rs/handle/123456789/5673
DOI: 10.1039/D2RA07401J
ISSN: 2046-2069
PubMed: 36744286
WoS: 000924413400001
Scopus: 2-s2.0-85147703206
Institution/Community
IHTMTY - 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 . .