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Tricarbonylrhenium(I) complexes with the N-methylpyridine-2-carbothioamide ligand – Synthesis, characterization and cytotoxicity studies
- Source :
- Journal of Organometallic Chemistry. 866:59-71
- Publication Year :
- 2018
- Publisher :
- Elsevier BV, 2018.
-
Abstract
- A new series of tricarbonyl complexes of rhenium(I) in the ‘2 + 1’ system with the bidentate ligand N-methylpyridine-2-carbothioamide (NC5H4-CS-NH-CH3, LH(Me)NS) and a monodentate ligand, being either an anion (Cl, Br, I or SCN) or a neutral molecule (3,5-dimethylpyrazole (Hdmpz) or imidazole (Him)), was synthesized. The use of mixed ligands leads to the formation of neutral or cationic (in the form of PF6− salts) tricarbonylrhenium(I) complexes: [Re(CO)3(LH(Me)NS)X] (X = Cl, Br, I, NCS) (complexes 1–4) and [Re(CO)3(LH(Me)NS)Y]+ (Y = Hdmpz, Him) (5 and 6), respectively. In case of the [Re(CO)3(LH(Me)NS)NCS] complex two polymorphic forms (4a and 4b) have been distinguished. Crystal structure of all complexes was determined by single-crystal X-ray diffraction method and the results were compared with the molecular structures obtained from DFT calculations. The compounds were characterized by FT-IR, NMR, UV-Vis and HPLC techniques. IR and UV-Vis spectra were also simulated by DFT and TD-DFT methods. Cytotoxicity of the complexes was estimated using human ovarian cancer cell line (A2780), its cisplatin resistant cell line (A2780cis) and non-cancerous human embryonic kidney cells (Hek-293). The toxicity of newly synthesized complexes was comparable to cisplatin when tested against both cancerous cell lines (IC50 = 2–49 μM), but lower than cisplatin towards non-cancerous cells (IC50 = 6–63 μM). Among them, the complexes with chloride and iodide anions exhibit remarkable cytotoxicities.
- Subjects :
- chemistry.chemical_classification
Denticity
010405 organic chemistry
Ligand
Organic Chemistry
Iodide
Cationic polymerization
chemistry.chemical_element
Crystal structure
Rhenium
010402 general chemistry
01 natural sciences
Biochemistry
Medicinal chemistry
0104 chemical sciences
Inorganic Chemistry
chemistry.chemical_compound
chemistry
Materials Chemistry
Imidazole
Physical and Theoretical Chemistry
Cytotoxicity
Subjects
Details
- ISSN :
- 0022328X
- Volume :
- 866
- Database :
- OpenAIRE
- Journal :
- Journal of Organometallic Chemistry
- Accession number :
- edsair.doi...........6d5078f1d8237eea5473d7d1d5034ff2