Electronic Supplementary Information for: "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"
Autori
Andrejević, Tina P.Aleksić, Ivana
Kljun, Jakob
Počkaj, Marta
Zlatar, Matija
Vojnović, Sandra
Nikodinović-Runić, Jasmina
Turel, Iztok
Đuran, Miloš
Glišić, Biljana
Skup podataka (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
1H NMR spectrum of py-2pz S5 1H NMR spectrum of complex 3 S6 1H NMR spectrum of complex 4 S7 Fig. S1 UV-Vis spectra of copper(II) complexes 1 and 2 recorded in DMSO at room temperature. S8 Fig. S2 UV-Vis spectra of silver(I) complexes 3 and 4 in respect to the spectrum of uncoordinated py-2pz recorded in DMSO at room temperature. S9 Fig. S3 Time-dependant UV-Vis spectra of copper(II) complex 2 and silver(I) complex 3 recorded in DMSO/PBS (v/v 2 : 1 and 1 : 42.9 for 2 and 3, respectively) at room temperature. S10 Fig. S4 Cyclic voltammogram of py-2pz ligand at GC electrode in DMSO (c = 1 × 10-3 M) and 0.1 M TBAHP as a supporting electrolyte with a scan rate of 50 mV s-1 . S11 Fig. S5 Graphical representation of the spin density of the high-spin state of 1. Isosurfaces were drawn at 0.003 a.u. with α-spin depicted by blue surfaces. S12 Fig. S6 Inhibition of violacein and prodigiosin production in the presence of complexes 1 – 4 and py-2pz ligand tested on Chromobacterium violaceu...m CV026 and Serratia marcescens at 100 µg per disc concentration. DMSO was used as a control. S13 Scheme S1 Catechol oxidase (CAO) and phenoxazinone synthase (PHS) activity. S14 Table S1 C. albicans ATCC10231 biofilm inhibition (%) in the presence of silver(I) complexes 3 and 4 in range of subinhibitory concentrations. Table S2 Details of the crystal structure determination for copper(II) complexes 1 and 2 S16 Table S3 Details of the crystal structure determination for silver(I) complexes 3 and 4 S17 Cartesian coordinates of all DFT optimized structures S18.
Ključne reči:
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 / biomimeticIzvor:
RSC Advances, 2023Izdavač:
- Royal Society of Chemistry (RSC)
Finansiranje / projekti:
- Ministarstvo nauke, tehnološkog razvoja i inovacija Republike Srbije, institucionalno finansiranje - 200042 (Univerzitet u Beogradu, Institut za molekularnu genetiku i genetičko inženjerstvo) (RS-MESTD-inst-2020-200042)
- Ministarstvo nauke, tehnološkog razvoja i inovacija Republike Srbije, institucionalno finansiranje - 200122 (Univerzitet u Kragujevcu, Prirodno-matematički fakultet) (RS-MESTD-inst-2020-200122)
- Ministarstvo nauke, tehnološkog razvoja i inovacija Republike Srbije, institucionalno finansiranje - 200026 (Univerzitet u Beogradu, Institut za hemiju, tehnologiju i metalurgiju - IHTM) (RS-MESTD-inst-2020-200026)
- 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-ScienceFundRS-Ideje-7750288)
Napomena:
- Suplementary information for: 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: http://dx.doi.org/10.1039/D2RA07401J
- Article: https://cer.ihtm.bg.ac.rs/handle/123456789/5654
- 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
Povezane informacije:
- Povezani sadržaj
http://dx.doi.org/10.1039/D2RA07401J - Povezani sadržaj
https://cer.ihtm.bg.ac.rs/handle/123456789/5654 - Povezani sadržaj
https://cer.ihtm.bg.ac.rs/handle/123456789/5669 - Povezani sadržaj
https://cer.ihtm.bg.ac.rs/handle/123456789/5670 - Povezani sadržaj
https://cer.ihtm.bg.ac.rs/handle/123456789/5671 - Povezani sadržaj
https://cer.ihtm.bg.ac.rs/handle/123456789/5672 - Povezani sadržaj
https://cer.ihtm.bg.ac.rs/handle/123456789/5673
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Institucija/grupa
IHTMTY - DATA 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/123456789/5674 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. AB - 1H NMR spectrum of py-2pz S5 1H NMR spectrum of complex 3 S6 1H NMR spectrum of complex 4 S7 Fig. S1 UV-Vis spectra of copper(II) complexes 1 and 2 recorded in DMSO at room temperature. S8 Fig. S2 UV-Vis spectra of silver(I) complexes 3 and 4 in respect to the spectrum of uncoordinated py-2pz recorded in DMSO at room temperature. S9 Fig. S3 Time-dependant UV-Vis spectra of copper(II) complex 2 and silver(I) complex 3 recorded in DMSO/PBS (v/v 2 : 1 and 1 : 42.9 for 2 and 3, respectively) at room temperature. S10 Fig. S4 Cyclic voltammogram of py-2pz ligand at GC electrode in DMSO (c = 1 × 10-3 M) and 0.1 M TBAHP as a supporting electrolyte with a scan rate of 50 mV s-1 . S11 Fig. S5 Graphical representation of the spin density of the high-spin state of 1. Isosurfaces were drawn at 0.003 a.u. with α-spin depicted by blue surfaces. S12 Fig. S6 Inhibition of violacein and prodigiosin production in the presence of complexes 1 – 4 and py-2pz ligand tested on Chromobacterium violaceum CV026 and Serratia marcescens at 100 µg per disc concentration. DMSO was used as a control. S13 Scheme S1 Catechol oxidase (CAO) and phenoxazinone synthase (PHS) activity. S14 Table S1 C. albicans ATCC10231 biofilm inhibition (%) in the presence of silver(I) complexes 3 and 4 in range of subinhibitory concentrations. Table S2 Details of the crystal structure determination for copper(II) complexes 1 and 2 S16 Table S3 Details of the crystal structure determination for silver(I) complexes 3 and 4 S17 Cartesian coordinates of all DFT optimized structures S18. PB - Royal Society of Chemistry (RSC) T2 - RSC Advances T1 - Electronic Supplementary Information for: "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" DO - 10.1039/D2RA07401J ER -
@misc{ 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., 1H NMR spectrum of py-2pz S5 1H NMR spectrum of complex 3 S6 1H NMR spectrum of complex 4 S7 Fig. S1 UV-Vis spectra of copper(II) complexes 1 and 2 recorded in DMSO at room temperature. S8 Fig. S2 UV-Vis spectra of silver(I) complexes 3 and 4 in respect to the spectrum of uncoordinated py-2pz recorded in DMSO at room temperature. S9 Fig. S3 Time-dependant UV-Vis spectra of copper(II) complex 2 and silver(I) complex 3 recorded in DMSO/PBS (v/v 2 : 1 and 1 : 42.9 for 2 and 3, respectively) at room temperature. S10 Fig. S4 Cyclic voltammogram of py-2pz ligand at GC electrode in DMSO (c = 1 × 10-3 M) and 0.1 M TBAHP as a supporting electrolyte with a scan rate of 50 mV s-1 . S11 Fig. S5 Graphical representation of the spin density of the high-spin state of 1. Isosurfaces were drawn at 0.003 a.u. with α-spin depicted by blue surfaces. S12 Fig. S6 Inhibition of violacein and prodigiosin production in the presence of complexes 1 – 4 and py-2pz ligand tested on Chromobacterium violaceum CV026 and Serratia marcescens at 100 µg per disc concentration. DMSO was used as a control. S13 Scheme S1 Catechol oxidase (CAO) and phenoxazinone synthase (PHS) activity. S14 Table S1 C. albicans ATCC10231 biofilm inhibition (%) in the presence of silver(I) complexes 3 and 4 in range of subinhibitory concentrations. Table S2 Details of the crystal structure determination for copper(II) complexes 1 and 2 S16 Table S3 Details of the crystal structure determination for silver(I) complexes 3 and 4 S17 Cartesian coordinates of all DFT optimized structures S18.", publisher = "Royal Society of Chemistry (RSC)", journal = "RSC Advances", title = "Electronic Supplementary Information for: "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"", 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). Electronic Supplementary Information for: "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).. 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. Electronic Supplementary Information for: "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;. 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, "Electronic Supplementary Information for: "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), https://doi.org/10.1039/D2RA07401J . .