Supplementary data for article: Senerovic, L.; Zivkovic, M. D.; Veselinovic, A.; Pavic, A.; Djuran, M. I.; Rajkovic, S.; Nikodinovic-Runic, J. Synthesis and Evaluation of Series of Diazine-Bridged Dinuclear Platinum(II) Complexes through in Vitro Toxicity and Molecular Modeling: Correlation between Structure and Activity of Pt(II) Complexes. Journal of Medicinal Chemistry 2015, 58 (3), 1442–1451. https://doi.org/10.1021/jm5017686

Supporting information for: [https://doi.org/10.1021/jm5017686]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/1659

Supplementary data for the article: Andrejević, T. P.; Nikolić, A. M.; Glišić, B. Đ.; Wadepohl, H.; Vojnovic, S.; Zlatović, M.; Petković, M.; Nikodinovic-Runic, J.; Opsenica, I. M.; Djuran, M. I. Synthesis, Structural Characterization and Antimicrobial Activity of Silver(I) Complexes with 1-Benzyl-1H-Tetrazoles. Polyhedron 2018, 154, 325–333. https://doi.org/10.1016/j.poly.2018.08.001

Supplementary data for: [https://doi.org/10.1016/j.poly.2018.08.001]Research data for this article: [https://www.ccdc.cam.ac.uk/structures/search?id=doi:10.5517/ccdc.csd.cc2046ft&sid=DataCite]Research data for this article: [https://www.ccdc.cam.ac.uk/structures/search?id=doi:10.5517/ccdc.csd.cc2046gv&sid=DataCite]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/2228]Related to accepted version: [http://cherry.chem.bg.ac.rs/handle/123456789/2991

Supplementary data for the article: Glišić, B. Đ.; Nikodinovic-Runic, J.; Ilic-Tomic, T.; Wadepohl, H.; Veselinović, A.; Opsenica, I. M.; Djuran, M. I. Synthesis, Cytotoxic Activity and DNA-Binding Properties of Copper(II) Complexes with Terpyridine. Polyhedron 2018, 139, 313–322. https://doi.org/10.1016/j.poly.2017.11.008

Supplementary material for: [https://doi.org/10.1016/j.poly.2017.11.008]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/2581

CCDC 2220150: Experimental Crystal Structure Determination. Crystallographic data 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"

TEZMIY: Space Group: P 21/n (14), Cell: a 11.0042(12)Å b 12.8657(8)Å c 12.5820(12)Å, α 90° β 115.436(13)° γ 90°Crystallographic data (CCDC 2220150) 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/D2RA07401JArticle: [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]Supplementary information: [https://cer.ihtm.bg.ac.rs/handle/123456789/5674

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"

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.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

CCDC 2220146: Experimental Crystal Structure Determination. Crystallographic data 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"

TEZLOD : New Structure undergoing enhancement Space Group: P 1 (2), Cell: a 7.7916(6)Å b 8.9848(6)Å c 11.9955(7)Å, α 104.394(6)° β 106.396(6)° γ 104.368(6)°Crystallographic data (CCDC 2220146) 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/D2RA07401JArticle: [https://cer.ihtm.bg.ac.rs/handle/123456789/5654]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]Supplementary information: [https://cer.ihtm.bg.ac.rs/handle/123456789/5674

Silver(I) complexes with voriconazole as promising anti-Candida agents

Recognizing that metal ions play an important role in modifying the pharmacological properties of known organic-based drugs, the present manuscript addresses the complexation of the antifungal agent voriconazole (vcz) with the biologically relevant silver(I) ion as a strategy for the development of new antimycotics. The synthesized silver(I) complexes with vcz were characterized by mass spectrometry, IR, UV–Vis and NMR spectroscopy and single-crystal X-ray diffraction analysis. The crystallographic results showed that complexes {[Ag(vcz)(H2O)]CH3SO3}n (1), {[Ag(vcz)2]BF4}n (2) and {[Ag(vcz)2]PF6}n (3) have polymeric structures in the solid state, in which silver(I) ions have a distorted tetrahedral geometry. On the other hand, DFT calculations revealed that the investigated silver(I) complexes 1–3 in DMSO exist as linear [Ag(vcz-N2)(vcz-N19)]+ (1a), [Ag(vcz-N2)(vcz-N4)]+ (2a) and [Ag(vcz-N4)2]+ (3a) species, respectively. The evaluated complexes showed an enhanced anti-Candida activity compared to the parent drug with minimal inhibitory concentration (MIC) values in the range of 0.02–1.05 μM. In comparison with vcz, the corresponding silver(I) complexes showed better activity in prevention hyphae and biofilm formation of C. albicans, indicating that they could be considered as promising agents against Candida that significantly inhibit its virulence. Also, these complexes are much better inhibitors of ergosterol synthesis in the cell membrane of C. albicans at the concentration of 0.5 × MIC. This is also confirmed by a molecular docking, which revealed that complexes 1a – 3a showed better inhibitory activity than vcz against the sterol 14α-demethylase enzyme cytochrome P450 (CYP51B), which plays a crucial role in the formation of ergosterol

CCDC 2220147: Experimental Crystal Structure Determination. Crystallographic data 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"

TEZLUJ : New Structure undergoing enhancement Space Group: P 1 (2), Cell: a 8.2856(3)Å b 12.1191(5)Å c 19.2393(6)Å, α 82.105(3)° β 86.220(3)° γ 77.071(3)°Crystallographic data (CCDC 2220147) 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/D2RA07401JArticle: [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 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]Supplementary information: [https://cer.ihtm.bg.ac.rs/handle/123456789/5674

In vitro antimicrobial activity and cytotoxicity of nickel(II) complexes with different diamine ligands

Three diamines, 1,3-propanediamine (1,3-pd), 2,2-dimethyl-1,3-propanediamine (2,2-diMe-1,3-pd) and (+/-)-1,3-pentanediamine (1,3-pnd), were used for the synthesis of nickel(II) complexes 1-3, respectively, of the general formula [Ni(L)(2)(H2O)(2)]Cl-2. The stoichiometries of the complexes were confirmed by elemental microanalysis, and their structures were elucidated by spectroscopic (UV-Vis and IR) and molar conductivity measurements. The complexes 1-3, along with NiCl2 center dot 6H(2)O and the diamine ligands, were evaluated against a panel of microbial strains that are associated with skin, wound, urinary tract and nosocomial infections. The obtained results revealed no significant activity of 1-3 against the investigated bacterial strains. On the other hand, they showed good antifungal activity against pathogenic Candida strains, with minimum inhibitory concentration (MIC) values in the range from 15.6 to 62.5 mu g mL(-1). The best anti-Candida activity was observed for complex 2 against C. parapsilosis, while the least susceptible to the effect of the complexes was C. krusei. The antiproliferative effect on normal human lung fibro-blast cell line MRC-5 was also evaluated in order to determine the therapeutic potential of nickel(II) complexes 1-3. These complexes showed lower negative effects on the viability of the MRC-5 cell line than the clinically used nystatin and comparable selectivity indexes to that of this antifungal drug

Supplementary data for article: Warzajtis, B.; Glišić, B. D.; Savić, N. D.; Pavic, A.; Vojnovic, S.; Veselinović, A.; Nikodinovic-Runic, J.; Rychlewska, U.; Djuran, M. I. Mononuclear Gold(Iii) Complexes with l-Histidine-Containing Dipeptides: Tuning the Structural and Biological Properties by Variation of the N-Terminal Amino Acid and Counter Anion. Dalton Transactions 2017, 46 (8), 2594–2608. https://doi.org/10.1039/c6dt04862e

Supplementary material for: [https://doi.org/10.1039/c6dt04862e]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/2429]Related to accepted version: [http://cherry.chem.bg.ac.rs/handle/123456789/3107