Next Article in Journal
FAK Family Kinases in Vascular Diseases
Previous Article in Journal
Three-Dimensional Printed Porous Titanium Screw with Bioactive Surface Modification for Bone–Tendon Healing: A Rabbit Animal Model
Open AccessArticle

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

1
Department of Bioinorganic Chemistry, Chair of Medicinal Chemistry, Medical University of Lodz, Muszyńskiego 1, 90-151 Łódź, Poland
2
Department of Pharmacology and Toxicology, National Veterinary Research Institute, Al. Partyzantów 57, 24-100 Puławy, Poland
3
Faculty of Chemistry, University of Lodz, Pomorska 163/165, 90-236 Łódź, Poland
4
Institute of Physics, University of Silesia, 75 Pułku Piechoty 1, 41-500 Chorzów, Poland
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2020, 21(10), 3629; https://doi.org/10.3390/ijms21103629
Received: 23 April 2020 / Revised: 13 May 2020 / Accepted: 17 May 2020 / Published: 21 May 2020
(This article belongs to the Section Molecular Toxicology)
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 μM) 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. View Full-Text
Keywords: silver(I) complex; cytotoxicity; NMR spectroscopy; IR spectroscopy; X-ray crystallography; Balb/c 3T3 cell line; HepG2 cell line silver(I) complex; cytotoxicity; NMR spectroscopy; IR spectroscopy; X-ray crystallography; Balb/c 3T3 cell line; HepG2 cell line
Show Figures

Graphical abstract

MDPI and ACS Style

Stryjska, K.; Radko, L.; Chęcińska, L.; Kusz, J.; Posyniak, A.; Ochocki, J. Synthesis, Spectroscopy, Light Stability, Single-Crystal Analysis, and In Vitro Cytotoxic Activity on HepG2 Liver Cancer of Two Novel Silver(I) Complexes of Miconazole. Int. J. Mol. Sci. 2020, 21, 3629.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Search more from Scilit
 
Search
Back to TopTop