Master Degree / Yüksek Lisans Tezleri
Permanent URI for this collectionhttps://hdl.handle.net/11147/3008
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Master Thesis Investigation of Stilbene-Fused Chalcone and Flavanone Derivatives for Their Cytotoxic and Anti-Cancer Properties(Izmir Institute of Technology, 2012) Odacı, Burcu; Çağır, AliStilbene, chalcone and flavanones are three major classes of molecules, which can be found in plants as secondary metabolites. Derivatives of those may possess variety of biological activities. In this study it is aimed to synthesize a hybrid molecule which may show the biological activities of both flavanone and stilbene, or chalcone and stilbene simultaneously. For this purpose previously synthesized 11 simple chalcone, flavanone and stilbene derivatives and 31 stilbene-fused chalcones and stilbene-fused flavanones were tested for their cytotoxic activities in prostate cancer cell line (PC-3) and breast cancer cell line (MCF-7) by using MTT assay. Then aromatase inhibition properties of simple chalcones, flavanones, stilbenes, stilbene-fused chalcones and stilbene-fused flavanones were studied. Results of the study were evaluated in potential of the hybrid system to carry out more than one biological activity and mimicking performance of the simple ones. Results indicate that tested simple chalcone and flavanone derivatives are more cytotoxic than simple stilbenes in both cancer cell lines. On the contrary, simple stilbene structures were much more successful in aromatase inhibition assays. Cytotoxic activity profiles of stilbene-fused chalcones in cancer cells show that those molecules mostly mimic the simple chalcone structures. On the other hand, flavanones lost their cytotoxic activities when they were fused with stilbenes. In addition, aromatase inhibition assay showed that stilbene-fused chalcones again do mimic the simple chalcones but not simple stilbenes. In the same assays, stilbene-fused flavanones may mimic both simple flavanones and simple stilbenes by depending on the type and position of the substituent in terminal aromatic rings.Master Thesis Combinatorial Libraries of Stilbene Fused Chalcone and Flavanone Derivatives: Synthesis and Anti-Proliferative Properties(Izmir Institute of Technology, 2009) Akçok, İsmail; Çağır, AliFlavonoids and stilbenes have attracted great attention as potential pharmaceuticals. Up to date more than 5000 natural flavonoid derivatives have been isolated from natural resources. Flavonoids are most commonly known for their antioxidant activity. Additionally they might show various biological activities such as antibacterial, antiviral, anti-fungal, topoisomerase I and telomerase inhibitors, antiangiogenesis etc. Stilbenes are another class of compounds, which are also isolated from natural sources having anti-cancer, anti-inflammatory, blood sugar lowering and beneficial cardiovascular activities.In this study, synthesis of stilbene fused chalcone and stilbene fused flavanone systems were aimed. By means of that, it might be possible to produce a compound which can be used for at least two different biological activity or they might show a single activity with a great enhancement.For this purpose, a series of chalcone, flavanone, stilbene, stilbene fused chalcone, and stilbene fused flavanone derivatives were synthesized. Synthesis of stilbene fused chalcones and stilbene fused flavanones were accomplished by two different pathways. Two small combinatorial libraries of stilbene fused chalcones and stilbene fused flavanones have been built starting from four different acetophenones and four different styrenes. Preliminary anti-tumor activities of selected examples against human mammary adenocarcinoma cells (MCF-7) and human prostate cancer cell lines (PC3) were also evaluated.Master Thesis Synthesis and Aromatase Inhibition Properties of New Boronic Acid Chalcone Derivatives(Izmir Institute of Technology, 2011) Taç, Doğan; Çağır, AliChalcones (1,3-diaryl-2-propen-1-ones) are one of the best known naturally occurring biological active compounds belonging to flavonoid family. They possess wide range of biological properties such as; anti-cancer, anti-bacterial, antiinflammatory, anti-angiogenic. In addition, chalcone boronic acid derivatives have been tested for their anti-cancer properties and saccharide sensors abilities in few of the recent studies. In those studies, it is speculated that boronic acid chalcone derivatives are selectively cytotoxic against cancer cells rather than healthy cells. In the present study, synthesis of simple chalcones, derivatized by two boronic acids, and 2-naphthyl chalcones having a single boronic acid are reported first time in literature. For this purpose different commercially available acetylphenyl boronic acid and formylphenyl boronic acid derivatives are reacted in alkaline methanol to yield diboronic acid chalcone compounds. Similarly condensation reaction of 2-naphthaldehyde with different acetylphenyl boronic acids yielded the monoboronic acids derivatized 2-naphthyl chalcones. Synthesized diboronic acid chalcone derivatives and 2-naphthyl calcone boronic acid derivatives were tested for their anti-cancer properties against human mammary adenocarcinoma cancer cell lines (MCF-7), and human prostate cancer cell lines (PC3). Their aromatase inhibition potentials were also reported first time in here. In addition, their binding capabilities upon D-fructose, Dgalactose and D-glucose of these compounds in physiologic pH were also examined.