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Öğe 2-Morpholinoethyl-substituted N-heterocyclic carbene (NHC) precursors and their silver(I)NHC complexes: synthesis, crystal structure and in vitro anticancer properties(Springer, 2018) Aktas, Aydin; Kelestemur, Unzile; Gok, Yetkin; Balcioglu, Sevgi; Ates, Burhan; Aygun, MuhittinIn this study, a series of unsymmetrically 2-morpholinoethyl-substituted benzimidazolium salts and their Ag(I)NHC complexes were synthesized. The 1,3-dialkylbenzimidazolium salts (1a-d) were synthesized in dimethylformamide at 80 A degrees C temperature from the N-(2-morpholinoethyl)benzimidazole and alkyl halides. The Ag(I)NHC complexes (2a-d) were synthesized in dichloromethane at room temperature from the benzimidazolium salts and Ag2O. All compounds were characterized by spectroscopic techniques (NMR and FT-IR) and elemental analyses. Also, the salt 1c and complex 2c were characterized by single-crystal X-ray crystallography. Anticancer activities of 2-morpholinoethyl-substituted benzimidazolium salts and Ag(I)NHC complexes were investigated against the MCF-7 breast cancer cell line, and the IC30 and IC50 values of these compounds were found to be in the range of 241-490 and 6-14 A mu M, respectively.Öğe 4-Vinylbenzyl and 2-morpholinoethyl substituted ruthenium (II) complexes: Design, synthesis, and biological evaluation(Elsevier, 2020) Sari, Yakup; Gurses, Canbolat; Celepci, Duygu Barut; Kelestemur, Unzile; Aktas, Aydin; Yuksel, Sengul; Ates, BurhanRecently, the medical applications of organoruthenium complexes have attention attracted to organometallic chemists and biochemists. In this study, 4-vinylbenzyl and 2-morpholinoethyl substituted (NHC) Ru(II)(eta(6)-p-cymene) complexes were synthesized and in vitro DNA binding, cell cytotoxicity (anticancer activity) and genotoxicity properties were determined in order to understand the biological activities. These complexes have been prepared from the 4-vinylbenzyl and 2-morpholinoethyl substituted Ag(I) NHC complexes via transmetallation method. The characterization of the new (NHC)Ru(II)(eta(6)-p-cymene) complexes was performed by using H-1 NMR, C-13 NMR, FTIR spectroscopy and elemental analysis techniques. Also, molecular structure of complex 1b was obtained with single-crystal X-ray diffraction method. IC50 value of 1b against MCF-7 cell line was determined as 3.61 mu M and for 1b, an oxidation effect was observed in the concentrations higher than 50 mu g/mL. Comet assay unlike sister chromatid exchange (SCE) analysis data showed correlated results with cytotoxicity as well as DNA binding properties of the complexes. (C) 2019 Elsevier B.V. All rights reserved.Öğe Aliphatic Polyurethane Films Based on Hexamethylene Diisocyanate and Saccharides for Biocompatible Transparent Coating on Optic Medical Devices(Wiley-V C H Verlag Gmbh, 2022) Gurses, Canbolat; Karaaslan-Tunc, Merve Goksin; Kelestemur, Unzile; Balcioglu, Sevgi; Gulgen, Selam; Koytepe, Suleyman; Ates, BurhanPolyurethanes are widely used in daily life, from the textile industry to medical applications. In this study, a biocompatible and transparent coating from polyethylene glycol-based polyurethanes including different type of saccharide (xylose as monosaccharide, sucrose as disaccharide, or starch as polysaccharide) is prepared. Prepared optically transparent polyurethanes are characterized with different instrumental analysis techniques and contact-angle measurements. Thermogravimetric analysis data allow understanding that the synthesized saccharide based polyurethanes are resistant to high temperatures, which means that medical devices can be easily coated with one of the saccharide-based polymers during the manufacturing process. The study results also show that synthesized polyurethane samples having a different kind of saccharides present high biocompatibility and transparency properties via In vitro cytotoxicity analysis and optic transparency tests. For xylose, sucrose, or starch containing polyurethanes, the tranmittance values are 97.72%, 85.20%, and 89.23%, respectively. In addition, scanning electron microscope images show that the samples also have smooth surfaces which can be used for proper coating of medical devices. Consequently, this manuscript addresses synthesis and characterization of the optically transparent polyurethanes based on specific saccharides for biocompatible and transparent surfaces especially in optic medical devices such as colonoscopy applications and laparoscopic detection probes.Öğe Biomimetic approach to tunable adhesion of polyurethane adhesives through Fe3+ crosslinking and hydrophobic tween units with balance of adhesion/cohesion forces(Elsevier Sci Ltd, 2019) Ates, Burhan; Koytepe, Suleyman; Balcioglu, Sevgi; Karaaslan, Merve Goksin; Kelestemur, Unzile; Gulgen, Selam; Ozhan, OnuralBiocompatible adhesives have some limitations such as weak adhesion and low flexibility. To overcome these limitations, we described multiple strategies to provide strong adhesion and high flexibility through Tweens, chlorogenic acid (CLA) and polyethylene glycol (PEG) by reducing excessive interaction between tissue and the adhesive. We synthesized polyurethane-based adhesives using aliphatic 4,4'-methylenebis(cyclohexyl isocyanate) (HMDI), PEG, CLA and Tween units. Hydrophobic side chains in polymer resulted in lower Tg (- 36.95-30.36 degrees C) which indicated more flexibility. The highest adhesion strengths were found as almost 346 kPa for bare polyurethane and 492 kPa for chelated polymer (PU-T40-CLA-15% (5% Tween 40, 15% chlorogenic acid and 80% PEG 200 containing polymer)) with FeCl3. The addition of Tween units provided more stable structure to polymers which proved with in vitro erosion studies. Relatively low erosion values were seen as 5.7, 5.6 and 8.2% in PU-T40-CLA-5% (15% Tween 40, 5% chlorogenic acid and 80% PEG 200 containing polymer), PU-T40-CLA-10% (10% Tween 40, 10% chlorogenic acid and 80% PEG 200 containing polymer), and PU-T40-CLA-15% (5% Tween 40, 15% chlorogenic acid and 80% PEG 200 containing polymer), respectively. In vitro biocompatibility results showed high cell viability in PU-T40-15% as more than 100%. Overall, our findings indicated that these material designs (PU-T-CLAs) provided to overcome the significant challenges of tissue adhesives by improving the flexible character and adhesive strength of the adhesives.Öğe Cytotoxicity, Radical Scavenging, Antioxidant Properties and Chemical Composition of the Essential Oil of Satureja cilicica P.H. Davis from Turkey(Marmara Univ, Fac Pharmacy, 2017) Arabaci, Turan; Uzay, Gizem; Kelestemur, Unzile; Karaaslan, Merve Goksin; Balcioglu, Sevgi; Ates, BurhanSatureja cilicica P. H. Davis is an endemic species of Lamiaceae, distributed in Turkey. In this study, the essential oil of S. cilicica was obtained by hydrodistillation from the aerial parts. The essential oil was analyzed by GC/MS and the main constituents are identified. Radical scavenging capacities of oil obtained from S. cilicica were determined by using DPPH and ABTS radical scavenging assays. In addition, ferric-reducing power of the essential oil was detected. Cytotoxic activity of the essential oil was determined by MTT assay after 24 h treatment of MCF-7. The major components of the essential oil are p-cymene (17.68%), carvacrol (14.02%), gamma-terpinene (11.23 %) and thymol (8.76%). Radical scavenging capacities of the essential oil were measured as 3.28 +/- 0.02 and 238.15 +/- 3.59 mg Trolox equivalent per milliliter of oil in term of DPPH and ABTS radical scavenging, respectively. Ferric-reducing power of essential oil was found 39.76 +/- 3.66 mg Trolox equivalent per milliliter of essential oil. Growth inhibition effect of essential oil against MCF-7 cancer cell is established. According to the results, essential oil of S. cilicica exhibit low cytotoxic activity, with IC50 values, with IC50 value of 268 mu g/mL. The findings of the analyzed species are compared with the results of previous studies.Öğe Level of residual monomer released from orthodontic acrylic materials(E H Angle Education Research Foundation, Inc, 2014) Ica, R. Betul; Ozturk, Firat; Ates, Burhan; Malkoc, Meral Arslan; Kelestemur, UnzileObjective: To quantify, with high-pressure liquid chromatography (HPLC), the amount of residual monomer leached from different orthodontic acrylic materials prepared with two different manipulation methods. Materials and Methods: Eighty cylindrical specimens (5 x 25 mm) were divided into eight groups (n = 10). The specimens were prepared with four acrylic materials Orthocryl Neon Blue (Dentaurum), Orthocryl EQ (Dentaurum), Orthoplast (Vertex), and 0-80 (Imicryl) and with two different manipulation methods: doughing and spray-on. HPLC measurements were made at intervals of 2 hours, 6 hours, 1 day, 1 week, and 3 months. One-way analysis of variance (ANOVA) and Tukey's honestly significant difference multiple-comparison test were used to assess the amount of monomer eluted from the various groups. To assess the differences within each group over the various periods, repeated-measures ANOVA and paired t-tests were used. Results: Statistically significant differences were found within the groups in the amount of residual monomer in the specimens at different time intervals (P < .001). HPLC showed statistically significant differences among the groups (P < .05) in the amount of eluted monomer. Evaluation of the manipulation techniques showed that the monomer release rate was higher in the specimens prepared with the doughing method. When the four acrylic materials were compared, the specimens made from Orthoplast (Vertex) showed the highest rate of monomer release with both manipulation techniques. Conclusion: The spray-on method can be recommended to clinicians for the preparation of orthodontic appliances.Öğe Silver and ruthenium complexes with anthracene functionalized N-heterocyclic carbene ligands: catalytic and cytotoxicity properties(Springer, 2024) Karatas, Mert Olgun; Kelestemur, Unzile; Mumcu, Akin; Ozdemir, Namik; Erdogan, Ali; Kucukbay, HasanIn this study, we have synthesized two Ag (2a and 2b) and two Ru (3a and 3b) complexes with anthracene substituted N-heterocyclic carbene (NHC) ligands. Ag-NHC complexes have been synthesized by the interaction of corresponding benzimidazolium chloride and Ag2O. Ru-NHC complexes have been synthesized by the transmetalation reaction between corresponding Ag-NHC and [RuCl2(p-cymene)]2 dimer. The synthesized complexes have been characterized by elemental analysis, NMR (1H and 13C NMR), and mass (high resolution mass spectroscopy, HRMS) spectroscopic techniques. In order to assess the catalytic potential of the Ru-NHC complexes, we have conducted experiments involving the hydrosilylation of terminal alkynes. Both complexes have exhibited a moderate level of catalytic activity, achieving conversions ranging from 70 to 90%, along with a substantial beta-(Z) selectivity within the range of 80-90%. Furthermore, we have also subjected the benzimidazolium chlorides (1a and 1b), Ag-NHCs and Ru-NHCs to cytotoxicity testing using human breast cancer cells (MCF-7) and human colorectal cancer cells (Caco-2). The results of these assays have demonstrated that all compounds strongly inhibit the proliferation of both cell lines.Öğe Synthesis, reaction, and evaluation of the anticancer activity of 6,7,8,9-tetrahydro-5H-cyclohepta[4,5]selenopheno[2,3-d]pyrimidine derivatives(Tubitak Scientific & Technological Research Council Turkey, 2016) Doganay, Kadir; Kelestemur, Unzile; Balcioglu, Sevgi; Ates, Burhan; Altundas, AliyeThe cyclocondensation of 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]selenophene-3-carbonitrile (1) with formic acid and formamide gave the selenophenopyrimidine 15 and selenophenopyrimidone 6 derivatives. The reaction of 6 with phosphorus oxychloride produced 4-chloro-6,7,8,9-tetrahydro-5H-cyclohepta[4,5] seleno[2,3-d]pyrimidine (12), the key compound for our nucleophilic substitution reactions. The hydrazinoselenophenopyrimidine 19 obtained from the reaction of 12 with hydrazine hydrate was converted to its tetrazoloselenophenopyrimidine 21 and triazoloselenophenopyrimidine 26 derivatives. Moreover, the chloropyrimidine derivative was reacted with pyrrolidine and morpholine to afford 4-(1-pyrrolidinyl)-6,7,8,9-tetrahydro-5H-cylohepta[4,5]selenopheno [2, 3-d]pyrimidine (27) and 4- (6,7,8,9-tetrahydro-5H-cyclohept a [4,5]selenopheno [2,3-d]pirimidin-4-yl)morpholine (28). Anticancer activities of the synthesized compounds were investigated against the MCF-7 breast cancer cell line and the IC50 values of these compounds were in the range of 70.86-250.06 mu M.
