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Öğe Cytotoxic Properties of Peptide Substituted Novel Cyclotriphosphazene Compound(Wiley, 2019) Koran, Kenan; Tekin, Suat; Caliskan, Eray; Capan, Trfan; Sandal, Suleyman; Gorgulu, Ahmet Orhan[Abstract Not Available]Öğe (E)-1-(4-Hydroxyphenyl)-3-(substituted-phenyl) prop-2-en-1-ones: Synthesis, In Vitro Cytotoxic Activity and Molecular Docking Studies(Slovensko Kemijsko Drustvo, 2022) Sirka, Lutfiye; Dogan, Hacer; Bahar, Mehmet Refik; Caliskan, Eray; Tekin, Suat; Uslu, Harun; Koran, KenanA series of chalcone compounds (2-11) were designed and synthesized to determine their cytotoxic effects. The structures of 2-11 were fully characterized by their physical and spectral data. The in vitro cytotoxic effects of 2-11 were evaluated against human ovarian cancer (A2780), breast cancer (MCF-7) and prostate cancer (PC-3 and LNCaP) cell lines. The activity potentials of compounds were further evaluated through molecular docking studies with AutoDock4 and Vina softwares. All the compounds (except compound 5) showed significant cytotoxic effects at high doses in all cancer cell lines. Among all the compounds studied, one compound i.e. compound 2 demonstrated dose-dependent activity, particularly against A2780/LNCaP cancer cell lines. The most effective compounds 8, 9, 10 and 11 reduced the cell viability of A2780, MCF-7, PC-3 and LNCaP cells by 50-98%, while other compounds 2, 4 and 7 reduced the cell viability of A2780 cells by 70-90% at concentrations of 50 and 100 mu M.Öğe The first peptide derivatives of dioxybiphenyl-bridged spiro cyclotriphosphazenes: In vitro cytotoxicity activities and DNA damage studies(Academic Press Inc Elsevier Science, 2023) Koran, Kenan; Caliskan, Eray; Ozturk, Dilara Altay; Capan, Irfan; Tekin, Suat; Sandal, Suleyman; Gorgulu, Ahmet OrhanIn this study, we aimed to synthesize new peptide-substituted cyclotriphosphazenes from a series of tyrosine -based peptides and dioxyphenyl-substituted spirocyclotriphosphazenes, and to evaluate their in vitro cytotox-icity and genotoxicity activities. Genotoxicity studies were conducted to understand whether the cytotoxic compounds cause cell death through DNA damage. The structures of the novel series of phosphazenes were characterized by FT-IR, elemental analysis, MS, 1D (31P, 1H, and 13C-APT NMR), and 2D (HETCOR) NMR spectroscopic techniques. In vitro cytotoxic activities were carried out against human breast (MCF-7), ovarian (A2780), prostate (PC-3), colon (Caco-2) cancer cell lines and human normal epithelial cell line (MCF-10A) at different concentrations by using an MTT assay. The compounds showed considerable reductions in cell viability against all human cancer cell lines. Especially, the compounds exhibited notable effects in A2780 cell lines (p < 0.05). The IC50 values of the compounds in the A2780 cell line were calculated to be 1.914 mu M for TG, 20.21 mu M for TV, 20.45 mu M for TA, 4.643 mu M for TP, 5.615 mu M for BTG, 1.047 mu M for BTV, 27.02 mu M for BTA, 0.7734 mu M for BTP, 21.5 mu M for DTG, 1.65 mu M for DTV, 2.89 mu M for DTA and 4.599 mu M for DTP. DNA damage studies of the compounds were conducted by the comet assay method using tail length, tail density, olive tail moment, head length, and head density parameters, and the results showed that the cell death occurred through DNA damage mechanism. In a nutshell, these compounds show promising cytotoxic effects and can be considered powerful candidate molecules for pharmaceutical applications.Öğe Hexa-substituted cyclotriphosphazene derivatives containing hetero-ring chalcones: Synthesis, in vitro cytotoxic activity and their DNA damage determination(Academic Press Inc Elsevier Science, 2022) Beytur, Asiye; Tekin, Cigdem; Caliskan, Eray; Tekin, Suat; Koran, Kenan; Gorgulu, Ahmet Orhan; Sandal, SuleymanIn this study, hetero ring hexasubstituted cyclotriphosphazes were obtained in two steps and these compounds were investigated in terms of in vitro cytotoxicity and genotoxicity. The structural characterizations of the starting compounds 1-4 were defined by FT-IR, elemental analysis, and NMR (1H and 13C) spectroscopy techniques. In addition to these techniques, the 31P NMR spectroscopy technique was also used in the characterization of cyclotriphosphazenes (FSC 1-4). The changes in cell viability at 1, 5, 25, 50, and 100 mu M concentrations against human ovarian (A2780) and human prostate (PC-3 and LNCaP) cell lines for 24 h were determined by the MTT assay method. According to MTT assay results, the inhibitory concentration 50 (IC50/ LogIC50) value was calculated in Graphpad Prism 6 program. The comet assay was performed to determine whether the effects of compounds on cell viability were through DNA damage. In the comet assay experiments, the highest concentration of compounds (100 mu M) was applied to the cells for 24 h and tail length (TL), tail intensity (TI), olive tail moment (OTM) parameters were examined. The results showed that the compound 1-4 and FSC 1-4 compounds reduced the cell viability against all cancer cell lines (p < 0.05). At the same time, different concentrations of these compounds caused DNA damage in all three cell types (p < 0.05). The possible interactions and chemical mechanisms of the synthesized compounds were explained by computational methods with molecular docking. In addition, pharmacological properties of drug candidate molecules have been defined. Experimental and calculated data comply with each other. The study results showed that these compounds have cytotoxic effects against cancer cells and suggested that these effects have occurred through genotoxicity.Öğe In Vitro Cytotoxic and Genotoxic Properties of Hexa Substituted New Organophosphazene Compounds(Wiley, 2019) Dogan, Hacer; Bahar, Mehmet Refik; Caliskan, Eray; Koran, Kenan; Tekin, Suat; Sandal, Suleyman; Gorgulu, Ahmet Orhan[Abstract Not Available]Öğe Investigation of Cytotoxic and Genotoxic Properties of Hybrid Compounds Containing New Generation Amino Acid Structures(Wiley, 2023) Sekerci, Guldeniz; Yuksel, Furkan; Tekin, Suat; Caliskan, Eray; Biryan, Fatih; Koran, Kenan; Sandal, Suleyman[Abstract Not Available]Öğe Laparoscopic endometrioma resection increases peri-implantation endometrial HOXA-10 and HOXA-11 mRNA expression(Elsevier Science Inc, 2015) Celik, Onder; Unlu, Cihat; Otlu, Baris; Celik, Nilufer; Caliskan, ErayObjective: To determine whether laparoscopic endometrioma resection alters peri-implantation endometrial HOXA-10, HOXA-11, LIF, ITGB3 and ITGAV mRNA expression. Design: Case-control study. Setting: Medical school. Patient(s): Twenty infertile patients with uni-or bilateral endometrioma, five infertile patients having nonendometriotic benign ovarian cyst, and five fertile control subjects. Intervention(s): Mid-luteal-phase endometrial sampling was performed at the time of surgery. Second endometrial biopsies were obtained 3 months after laparoscopic endometrioma resection during the mid-luteal phase of the cycle. Main Outcome Measure(s): Endometrial HOXA-10, HOXA-11, LIF, ITGAV, and ITGB3 mRNA expressions were evaluated with the use of reverse-transcription polymerase chain reaction. Result(s): Significantly decreased endometrial ITGAV mRNA expression was noted in biopsies obtained from endometrioma and nonendometriotic cyst groups before surgery. Trends toward decreased endometrial HOXA-10, HOXA-11, LIF, and ITGB3 mRNA expressions were noted in the endometrioma and nonendometriotic cyst groups before surgery compared with the fertile subjects. However, the differences failed to show statistical significance. Compared with preoperative values, significantly increased HOXA-10 (12.1-fold change) and HOXA-11 (17.2-fold change) mRNA expressions were noted in endometrial biopsies obtained from subjects who were undergoing endometrioma surgery. Fold change in endometrial ITGAV mRNA after endometrioma surgery was found to be 30.1 and indicated a positive regulation. However, this fold increase was statistically insignificant. Expressions of these endometrial receptivity markers did not change significantly after surgical removal of nonendometriotic benign ovarian cysts. Conclusion(s): Laparoscopic endometrioma resection increases peri-implantation endometrial HOXA-10 and HOXA-11 mRNA expression, suggesting an improvement in endometrial receptivity. (C) 2015 by American Society for Reproductive Medicine.Öğe Synthesis and spectroscopic characterizations of hexakis[(1-(4 '-oxyphenyl)-3-(substituted-phenyl)prop-2-en-1-one)]cyclotriphosphazenes: their in vitro cytotoxic activity, theoretical analysis and molecular docking studies(Taylor & Francis Inc, 2022) Dogan, Hacer; Bahar, Mehmet Refik; Caliskan, Eray; Tekin, Suat; Uslu, Harun; Akman, Feride; Koran, KenanThe hexachlorocyclotriphosphaze compound (N3P3Cl6, HCCP) was reacted with excess (E)-(1-(4 '-oxyphenyl)-3-(substituted-phenyl)prop-2-en-1-ones (2-11) to produce hexakis[(1-(4-oxyphenyl)-3-(substituted-phenyl)prop-2-en-1-one)]cyclotriphosphazenes (CP 2-11). The structures of products (CP 2-11) were confirmed using elemental analysis, FT-IR, MS spectral analysis as well as P-31, H-1 and C-13-APT NMR techniques and their thermal properties determined by TGA and DSC techniques. The HOMO-LUMO energy gap and chemical reactivity identifiers were calculated and HOMO and LUMO images were viewed. According to the calculations, all the chemical potential values of CP 2-11 are negative and it shown that the molecules are stable. The in vitro cytotoxic of CP 2-11 investigated and their activity potentials were evaluated by molecular docking studies with Autodock Vina softwares. CP 2-11 compounds were found to demonstrate cytotoxic activity against human cancer cell lines (A2780, LNCaP and PC-3). The CP 2-11 compounds reduced the cell viability against all cancer cell lines in the range 36%-90% especially. The results showed that these compounds are powerful candidate molecules for pharmaceutical applications.Öğe Synthesis of New Amino Acid Conjugates Containing Cinnamic Acid Derivatives and Investigation of Their Cytotoxic and Genotoxic Properties(Wiley, 2023) Sandal, Suleyman; Tekin, Suat; Caliskan, Eray; Koran, Kenan; Gorgulu, Ahmet Orhan; Cetin, Ahmet[Abstract Not Available]Öğe Synthesis of New Cinnamoyl-Amino Acid Conjugates and in Vitro Cytotoxicity and Genotoxicity Studies(Wiley-V C H Verlag Gmbh, 2022) Caliskan, Eray; Ozturk, Dilara Altay; Koran, Kenan; Tekin, Suat; Sandal, Suleyman; Erkan, Sultan; Gorgulu, Ahmet OrhanAmino acid conjugates are described by the reaction of amino acids with bioactive organic groups such as vitamins, hormones, flavonoids, steroids, and sugars. In this study, 12 new conjugates were synthesized by reaction of cinnamic acid derivatives with various amino acids. Cytotoxic studies against four different human cancer cells (MCF7, PC-3, Caco-2, and A2780) were carried out by MTT assay method at five different concentrations. The structure-activity relationships based on the cell viability rates were evaluated. To compare the anticancer activities of the compounds using computational chemistry methods, they were docked against A2780 human ovarian cancer, Michigan Cancer Foundation-7 (MCF7), human prostate cancer (PC-3) and human colon epidermal adenocarcinoma (Caco-2) cell lines and compared with the standard 5-Fluorouracil. The results indicate that the efficacy of cinnamic acid derivatives increases with the presence of amino acids. Comet assay was conducted to understand whether the cell deaths occur through DNA damage mechanism and the results exhibit that the changes in the specified parameters were statistically significant (p<0.05). Our study demonstrated that the compounds cause cell death through the formation of DNA damage mechanism.Öğe Synthesis, docking studies, in vitro cytotoxicity evaluation and DNA damage mechanism of new tyrosine-based tripeptides(Wiley, 2023) Caliskan, Eray; Kaplan, Alpaslan; Sekerci, Guldeniz; Capan, Irfan; Tekin, Suat; Erkan, Sultan; Koran, KenanPeptides are one of the leading groups of compounds that have been the subject of a great deal of biological research and still continue to attract researchers' attention. In this study, a series of tripeptides based on tyrosine amino acids were synthesized by the triazine method. The cytotoxicity properties of all compounds against human cancer cell lines (MCF-7), ovarian (A2780), prostate (PC-3), and colon cancer cell lines (Caco-2) were determined by the 3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide assay method, and % cell viability and logIC50 values of the compounds were calculated. Significant decreases in cell viability were observed in all cells (p < 0.05). The comet assay method was used to understand that the compounds that showed a significant decrease in cell viability had this effect through DNA damage. Most of the compounds exhibited cytotoxicity by DNA damage mechanism. Besides, their interactions between investigated molecule groups with PDB ID: 3VHE, 3C0R, 2ZCL, and 2HQ6 target proteins corresponding to cancer cell lines, respectively, were investigated by docking studies. Finally, molecules with high biological activity against biological receptors were determined by ADME analysis.Öğe Synthesis, structural and thermal characterizations and in vitro cytotoxic activities of new cyclotriphosphazene derivatives(Taylor & Francis Ltd, 2017) Koran, Kenan; Tekin, Cigdem; Caliskan, Eray; Tekin, Suat; Sandal, Suleyman; Gorgulu, Ahmet OrhanWe investigated the cytotoxic effects of the newly synthesized cyclotriphosphazene derivatives on A2780 (ovarian), PC-3 and LNCaP (prostate) cancer cell lines. 4'-hydroxy-substituted-chalcone compounds (2-8) were reacted with diphenyl-cyclotriphosphazene (DPP) in the presence of acetone/K2CO3 in order to obtain novel cyclotriphosphazene compounds (DPP 2-8). The structures of DPP2-8 were characterized by MALDI-TOF mass spectrometry, FT-IR, elemental analysis, H-1, C-13-APT, and P-31 NMR measurements. The thermal properties of all phosphazene compounds have been studied after synthesis and characterization procedure. The cytotoxic effects of DPP 2-8 were examined primarily by applying the MTT method based on the measurement of mitochondrial activity. In this regard, several phosphazene compounds have shown high chemotherapeutic effect at low dose (p < 0.05). When the cytotoxic effects of DPP 2-8 at doses of 1, 5, 25, 50 and 100 mu M on A2780 cells were examined, it was observed that DPP-3, DPP-4, DPP-5 and DPP-7 were more effective than other derivatives suggested by their high Log IC50 values (p < 0.05). The compounds DPP 2-8 possess cytotoxic activity against PC-3 and LNCaP cells (especially compounds DPP-4 and DPP-5, p < 0.05).Öğe Tripeptide linked dispiro cyclotriphosphazene conjugates: Synthesis, molecular docking analysis of compounds binding within cancer cell line receptors and in vitro cytotoxic and genotoxic activities(Academic Press Inc Elsevier Science, 2024) Caliskan, Eray; Capan, Irfan; Tekin, Suat; Qaoud, Mohammed T.; Biryan, Fatih; Koran, Kenan; Sandal, SuleymanThe novel dioxybiphenyl bridged-cyclotriphosphazenes (DPP) bearing tripeptide were synthesized and investigated for their molecular docking analysis, visualizing their binding profiles within various cancer cell line receptors and in vitro cytotoxic and genotoxic properties. The dipeptide compound (Tyr- Phe) was treated with various amino acids to obtain the tripeptide compounds (Tyr- Phe- Gly, Tyr- Phe- Ala, Tyr- Phe- Val, Tyr- Phe- Phe, and Tyr- Phe- Leu). These synthesized tripeptides were subsequently treated with DPP to obtain novel phosphazene compounds bearing tripeptide structures. As a result, the synthesis of target molecules with phosphazene compound in the center and biphenyl and tripeptide groups in the side arms was obtained for the first time in this study. Examining the cytotoxic studies in vitro of our newly synthesized compounds demonstrated the anticancer properties against four selected human cancer cell lines, including breast (MCF-7), ovarian (A2780), prostate (PC-3), and colon (Caco-2) cancer cells. The Comet Assay analysis determined that the cell death mechanism of most of the compounds with cytotoxic activity stemmed from the DNA damage mechanism. Among the compounds, the DPP-Tyr- Phe- Phe compound seems to have the best anticancer activity against the subjected cell lines (Except for A2780) with IC 50 values equal to 20.18, 72.14, 12.21, and 5.17 mu M against breast, ovarian, prostate, and colon cancer cell lines, respectively. For this reason, the molecular docking analysis was conducted for the DTPP compound to visualize its binding geometry and profile within the target enzyme 's binding site associated with the specific cancer cell line. The analysis revealed that the DTPP derivative exhibited an optimal binding conformation and characteristics within the target enzyme 's binding site, aligning well with the experimental data. Based on the data, these compounds are believed to be strong candidate molecules for both pharmaceutical and clinical applications.
