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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
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, [CuCl(2)(py-2pz)](2) (1), [Cu(CF(3)SO(3))(H(2)O)(py-2pz)(2)]CF(3)SO(3)·2H(2)O (2), [Ag(py-2pz)(2)]PF(6) (3) and {[Ag(NO(3))(py-2pz)]·0.5H(2)O}(n) (4). The c...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9890663/ https://www.ncbi.nlm.nih.gov/pubmed/36744286 http://dx.doi.org/10.1039/d2ra07401j |
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author | Andrejević, Tina P. Aleksic, Ivana Kljun, Jakob Počkaj, Marta Zlatar, Matija Vojnovic, Sandra Nikodinovic-Runic, Jasmina Turel, Iztok Djuran, Miloš I. Glišić, Biljana Đ. |
author_facet | Andrejević, Tina P. Aleksic, Ivana Kljun, Jakob Počkaj, Marta Zlatar, Matija Vojnovic, Sandra Nikodinovic-Runic, Jasmina Turel, Iztok Djuran, Miloš I. Glišić, Biljana Đ. |
author_sort | Andrejević, Tina P. |
collection | PubMed |
description | 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, [CuCl(2)(py-2pz)](2) (1), [Cu(CF(3)SO(3))(H(2)O)(py-2pz)(2)]CF(3)SO(3)·2H(2)O (2), [Ag(py-2pz)(2)]PF(6) (3) and {[Ag(NO(3))(py-2pz)]·0.5H(2)O}(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. |
format | Online Article Text |
id | pubmed-9890663 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-98906632023-02-03 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 Andrejević, Tina P. Aleksic, Ivana Kljun, Jakob Počkaj, Marta Zlatar, Matija Vojnovic, Sandra Nikodinovic-Runic, Jasmina Turel, Iztok Djuran, Miloš I. Glišić, Biljana Đ. RSC Adv Chemistry 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, [CuCl(2)(py-2pz)](2) (1), [Cu(CF(3)SO(3))(H(2)O)(py-2pz)(2)]CF(3)SO(3)·2H(2)O (2), [Ag(py-2pz)(2)]PF(6) (3) and {[Ag(NO(3))(py-2pz)]·0.5H(2)O}(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. The Royal Society of Chemistry 2023-02-01 /pmc/articles/PMC9890663/ /pubmed/36744286 http://dx.doi.org/10.1039/d2ra07401j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Andrejević, Tina P. Aleksic, Ivana Kljun, Jakob Počkaj, Marta Zlatar, Matija Vojnovic, Sandra Nikodinovic-Runic, Jasmina Turel, Iztok Djuran, Miloš I. Glišić, Biljana Đ. 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 |
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 |
title_full | 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 |
title_fullStr | 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 |
title_full_unstemmed | 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 |
title_short | 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 |
title_sort | 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 |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9890663/ https://www.ncbi.nlm.nih.gov/pubmed/36744286 http://dx.doi.org/10.1039/d2ra07401j |
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