ABSTRACT
In this study, 2-hydroxy-5-methoxyacetophenone thiosemicarbazone (HMAT) and its novel N(4) substituted derivatives were synthesized and characterized by different techniques. The optical band gap of the compounds and the energy of HOMO were experimentally examined by UV-vis spectra and cyclic voltammetry measurements, respectively. Furthermore, the conformational spaces of the compounds were scanned with molecular mechanics method. The geometry optimization, HOMO and LUMO energies, the energy gap of the HOMO-LUMO, dipole moment of the compounds were theoretically calculated by the density functional theory B3LYP/6-311++G(d,p) level. The minimal electronic excitation energy and maximum wavelength calculations of the compounds were also performed by TD-DFT//B3LYP/6-311++G(d,p) level of theory. Theoretically calculated values were compared with the related experimental values. The combined results exhibit that all compounds have good electron-donor properties which affect anti-proliferative activity. The cytotoxic effects of the compounds were also evaluated against HeLa (cervical carcinoma), MCF-7 (breast carcinoma) and PC-3 (prostatic carcinoma) cell lines using the standard MTT assay. All tested compounds showed antiproliferative effect having IC50 values in different range. In comparison with that of HMAT, it was obtained that while ethyl group on 4(N)-substituted position decreased in potent anti-proliferative effect, the phenyl group on the position increased in anti-proliferative effect for the tested cancer cell line. Considering the molecular energy parameters, the cytotoxicity activities of the compounds were discussed.
Subject(s)
Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Thiosemicarbazones/chemistry , Thiosemicarbazones/pharmacology , Antineoplastic Agents/chemical synthesis , Cell Line, Tumor , Cell Proliferation/drug effects , Cell Survival/drug effects , Electrochemical Techniques , Electrons , Humans , Models, Molecular , Neoplasms/drug therapy , Spectrophotometry, Ultraviolet , Thiosemicarbazones/chemical synthesisABSTRACT
Methylsulfonylmethane (or dimethyl sulfone), a naturally produced and vitally important organosulfur compound in living organisms, was irradiated with gamma rays, and the produced radicals were investigated using electron paramagnetic resonance spectroscopy at different temperatures. The structure and behavior of the radical changed when the temperatures varied. The hyperfine splitting of the CH(3) group was small, and the (33)S splitting was relatively high between 80 and -50 °C. When the temperature was between -50 and -160 °C, the (33)S splitting became small and the CH(3) splitting was higher. However, the group kept rotating; therefore, only the isotropic splitting values were measured, and the g-values were anisotropic. When the temperature decreased below -180 °C, the CH(3) group stopped rotating, and the hydrogen splitting values became nonequivalent due to an inhomogeneous electron distribution. The observed structures can be explained by referring to both the experimental and theoretically calculated values reported.
Subject(s)
Dimethyl Sulfoxide/chemistry , Models, Molecular , Molecular Conformation , Sulfones/chemistry , Temperature , Electron Spin Resonance SpectroscopyABSTRACT
In the crystal structure of the title compound, C(20)H(20)OP(+)·Cl(-), the cations and anions are linked by inter-molecular C-Hâ¯Cl and O-Hâ¯Cl hydrogen bonds into chains running parallel to the b axis. In the cation, the hy-droxy-ethyl group is disordered over two orientations with site-occupancy factors of 0.554â (4) and 0.446â (4).
