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Synthesis, Spectroscopy, Light Stability, Single-Crystal Analysis, and In Vitro Cytotoxic Activity on HepG2 Liver Cancer of Two Novel Silver(I) Complexes of Miconazole.

ABSTRACT: Two novel silver(I) complexes of the biologically active ligand miconazole in the form of Ag(MCZ)2X (MCZ = 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole]; X = NO3- (1), ClO4- (2)) were synthesized and fully characterized. The complexes were obtained by reactions of Ag(I) salts with miconazole (MCZ). Silver(I) complexes were characterized by elemental analysis, 1H-NMR and infrared (IR) spectroscopy, electrospray ionization (ESI)-MS spectrometry, and X-ray-crystallography. This work also presents a cytotoxicity study of the silver(I) complexes of miconazole and appropriate silver(I) salts using Balb/c 3T3 and HepG2 cell lines. The cytotoxicity of the compounds was assessed based on four biochemical endpoints: lysosomal activity (neutral red uptake (NRU) assay), mitochondrial activity (3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide (MTT) assay), total protein content (TPC assay), and cellular membrane integrity (lactate dehydrogenase (LDH) assay). The cancer HepG2 cells were more sensitive to the complexes tested, and the most affected endpoint was cellular membrane damage compared to Balb/c 3T3 fibroblasts. Moreover, study complexes inhibited the growth of cancer cells at submicromolecular concentrations (0.26-0.47 ?M) lower than that required for the anticancer agent, cisplatin, in MTT, NRU, and TPC assays. Both complexes were characterized by higher toxicity to human cancer cells (HepG2) than silver(I) salts and the free ligand. Combination of Ag(I) salts with miconazole is associated with the marked improvement of cytotoxic activities that can be considered as the significant point in the construction of a new generation of antineoplastic agents.

SUBMITTER: Stryjska K

PROVIDER: S-EPMC7279231 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Synthesis, Spectroscopy, Light Stability, Single-Crystal Analysis, and In Vitro Cytotoxic Activity on HepG2 Liver Cancer of Two Novel Silver(I) Complexes of Miconazole.

Stryjska Karolina K Radko Lidia L Chęcińska Lilianna L Kusz Joachim J Posyniak Andrzej A Ochocki Justyn J

International journal of molecular sciences 20200521 10

Two novel silver(I) complexes of the biologically active ligand miconazole in the form of Ag(MCZ)2X (MCZ = 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole]; X = NO3- (1), ClO4- (2)) were synthesized and fully characterized. The complexes were obtained by reactions of Ag(I) salts with miconazole (MCZ). Silver(I) complexes were characterized by elemental analysis, 1H-NMR and infrared (IR) ...[more]

PMID: 32455548

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Project description:We report the preparation and crystal structures of bis(diallydithiocarbamato)zinc(II) and silver(I) complexes. The compounds were used as single-source precursors to prepare zinc sulfide and silver sulfide nanophotocatalysts. The molecular structure of bis(diallydithiocarbamato)zinc(II) consists of a dimeric complex in which each zinc(II) ion asymmetrically coordinates with two diallydithiocarbamato anions in a bidentate chelating mode, and the centrosymmetrically related molecule is bridged through the S-atom that is chelated to the adjacent zinc(II) ion to form a distorted trigonal bipyramidal geometry around the zinc(II) ions. The molecular structure of bis(diallydithiocarbamato)silver(I) formed a cluster complex consisting of a trimetric Ag3S3 molecule in which the diallydithiocarbamato ligand is coordinated to all the Ag(I) ions. The complexes were thermolyzed in dodecylamine, hexadecylamine, and octadecylamine (ODA) to prepare zinc sulfide and silver sulfide nanoparticles. The powder X-ray diffraction patterns of the zinc sulfide nanoparticles correspond to the hexagonal wurtzite while silver sulfide is in the acanthite crystalline phase. The high-resolution transmission electron microscopy images show that quantum dot zinc sulfide nanoparticles are obtained with particle sizes ranging between 1.98 and 5.49 nm, whereas slightly bigger silver sulfide nanoparticles are obtained with particle sizes of 2.70-13.69 nm. The surface morphologies of the ZnS and AgS nanoparticles capped with the same capping agent are very similar. Optical studies revealed that the absorption band edges of the as-prepared zinc sulfide and silver sulfide nanoparticles were blue-shifted with respect to their bulk materials with some surface defects. The zinc sulfide and silver sulfide nanoparticles were used as nanophotocatalysts for the degradation of bromothymol blue (BTB) and bromophenol blue (BPB). ODA-capped zinc sulfide is the most efficient photocatalyst and degraded 87% of BTB and 91% of BPB.

Dataset Information

Synthesis, Spectroscopy, Light Stability, Single-Crystal Analysis, and In Vitro Cytotoxic Activity on HepG2 Liver Cancer of Two Novel Silver(I) Complexes of Miconazole.

Publications

Synthesis, Spectroscopy, Light Stability, Single-Crystal Analysis, and In Vitro Cytotoxic Activity on HepG2 Liver Cancer of Two Novel Silver(I) Complexes of Miconazole.

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