Browsing by Author "Cakmak, Resit"

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Molecular Hybrid Design, Synthesis, in Vitro Cytotoxicity, in Silico Adme and Molecular Docking Studies of New Benzoate Ester-Linked Arylsulfonyl Hydrazones
(Mdpi, 2024) Ergan, Erdem; Cakmak, Resit; Basaran, Eyup; Mali, Suraj N.; Akkoc, Senem; Annadurai, Sivakumar
In this paper, we present the synthesis and characterization of two known sulfonyl hydrazides (1 and 2) and their new sulfonyl hydrazone derivatives (9-20), as well as in vitro and in silico investigations of their cytotoxic properties against human lung (A549) and human breast (MCF-7) cancer cell lines. The target compounds (9-20) obtained in high yields were synthesized for the first time by a multi-step reaction, and their structures were confirmed by elemental analysis and various spectral techniques, including FT-IR, 1H-, and 13C-NMR. The antiproliferative profiles of these compounds (1, 2, and 9-20) in this study were determined at concentrations of 200, 100, 50, and 25 mu M against selected cancer cell lines for 72 h using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) method. Except for compounds 1 and 2, other compounds (9-20) demonstrated cytotoxic activity at concentrations lower than 200 mu M. The newly synthesized compounds (9-20) demonstrated antiproliferative activities at a micromolar level, with IC50 values in the range of 29.59-176.70 mu M for the A549 cell line and 27.70-170.30 mu M for the MCF-7 cell line. Among these compounds, compound 15 (IC50 = 29.59 mu M against A549 cell line and IC50 = 27.70 mu M against MCF-7 cell line) showed the highest cytotoxic activity against these two cancer cell lines compared to the reference drug cisplatin (IC50 = 22.42 mu M against A549 cell line and IC50 = 18.01 mu M against MCF-7 cell line). From docking simulations, to establish a plausible binding mode of compounds, we noticed that compound 15 demonstrated the highest affinity (-6.8508 kcal/mol) for estrogen receptor-beta (ERbeta) compared to others, suggesting promising ERbeta binding potential. Most compounds followed Lipinski's rule of five, with acceptable logP values. Additionally, all had mixed gastrointestinal absorption and limited blood-brain barrier permeability. Overall, our study proposed new sulfonyl hydrazones as a potential class of anticancer agents.
Silica Gel-Immobilized 5-Aminoisophthalohydrazide: a Novel Sorbent for Solid Phase Extraction of Cu, Zn and Pb From Natural Water Samples
(Wiley, 2020) Aydin, Funda; Cakmak, Resit; Levent, Abdulkadir; Soylak, Mustafa
A novel silica sorbent, silica gel-immobilized 5-aminoisophthalohydrazide (SiO2-APH), was prepared by the condensation of 3-chloropropyl-functionalized silica gel with 5-aminoisophthalohydrazide (APH) derived from dimethyl 5-aminoisophthalate as a starting material and used for separation and preconcentration of Cu, Zn, and Pb metals in water samples using Flame Atomic Absorption Spectrometry (FAAS). The characterization of the new sorbent was carried out by Elemental Analysis, Thermogravimetric Analysis (TGA) and Fourier Transform Infrared Spectroscopy (FTIR). Important analytical parameters including as pH, amount of sorbent, type and amount of eluting solvent, sample volume, vortex and ultrasonic bath time, matrix ions that effect the developed SiO2-APH-solid phase extraction (SPE) method were investigated and optimum parameters were detected. Recoveries of examined metals were obtained as 98% for Cu and Pb and 101% for Zn. The relative standard deviation (RSD, n = 8) of Cu, Zn and Pb metals were 3.2, 2.8 and 1.6%, respectively. Limit of detections (LODs) (n = 10) were found as 2.7 mu g L-1 for Cu, 7.4 mu g L-1 for Zn and 3.5 mu g L-1 for Pb mu g L-1. The accuracy of the new method was assessed by analyzing of TMDA-51.4 and TMDA-70.2 certified reference materials. The results obtained for metals were in a good agreement with certified values. Addition/recovery test was applied to the real well, river, dam and stream water samples to check the accuracy of the method. The results showed that the developed SiO2-APH-SPE method can be effectively used as an alternative method for determination of Cu, Zn, and Pb metals in water samples.