Scopus İndeksli Yayınlar Koleksiyonu / Scopus Indexed Publications Collection
Permanent URI for this collectionhttps://hdl.handle.net/11147/7148
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Article Design, Synthesis, and Evaluation of Anticancer Activities of 1,2-Diborolane Derivatives for Hepatocellular Carcinoma: an in Vitro and in Silico Study(Elsevier, 2026) Sahin, Yuksel; Antika, Gizem; Aktan, Cagdas; Metin, Kubilay; Ozgener, HuseyinHepatocellular carcinoma (HCC) is the most prevalent form of primary liver cancer and remains a major global health challenge due to limited treatment options and poor prognosis. Boron-containing compounds have garnered attention for their diverse biological activities, including pro-apoptotic effects in various types of cancer. In this study, we synthesized a panel of novel 1,2-N-substituted-1,2-diborolane derivatives and evaluated their antiproliferative, antimigratory, and apoptotic effects on hepatocellular carcinoma cell lines, HepG2 and Hep3B. Spectroscopic analyses confirmed the structural integrity of the synthesized compounds, revealing characteristic 1H-, 11B-, and 13C-NMR shifts consistent with boron-oxygen and boron-nitrogen bonding patterns. The derivatives, particularly compounds 2, 3, and 6, demonstrated potent and selective cytotoxicity toward HCC cells, with compound 3 exhibiting the lowest IC50 value (6.75 mu M) in HepG2 cells. Their time-dependent anti-proliferative effects were further supported by colony formation assays demonstrating long-term growth suppression, while wound healing assays revealed marked inhibition of HepG2 cell migration, indicating the compound's anti-metastatic potential. Our results demonstrate that the compound significantly induces apoptosis, modulates the expression of key apoptotic genes (Bax, Bcl-2, and caspase-3). In silico molecular docking further confirmed strong binding affinity to the anti-apoptotic Bcl-2 protein, supporting the proposed mechanism of action. These findings highlight the compound as a promising candidate for further preclinical evaluation in liver cancer therapy.Article Citation - WoS: 3Citation - Scopus: 3Synthesis and Antifungal and Antibacterial Bioactivities of Diborolanes Containing Arylamines(Elsevier, 2023) Aygün, Muhittin; Sevinçek, Resul; Özgener, Hüseyin; Bıyık, Hacı Halil; Metin, Kubilay; Şahin, Yüksel; Poyrazoğlu Çoban, Esra; Gürbüz, BurçinA good yield of 1,2-diarylamino-1,2-diborolanes 2 was obtained from the reaction of 1,2-dichloro-1,2-diborolane 1 and ArNHLi (an anilide). The structures of these new derivatives were characterized by nuclear magnetic resonance spectroscopy. The molecular structures of 2a and 2b were also determined using single-crystal X-ray diffraction. Antimicrobial activities of synthesized compounds against some Gram-positive and -negative bacteria and yeasts were determined. Some compounds were found to have strong antibacterial and antifungal properties, especially against the bacterium, S. pneumonia, which is the causative agent of pneumonia, and the fungus, C. albicans, which is the causative agent of candidiasis. The compounds 2a and 3 had a powerful effect (compound 2a and 3 = 1 μgmL−1) against S. pneumoniae ATCC 27336 bacteria. In addition, compounds 2a, 3 and 2f were observed to have strong effects (compound 2a, 3, 2f = 2 μgmL−1) against C. albicans ATCC 10231 and C. utilis ATCC 9950. The results obtained were found to be more effective than the MIC values (128–64 μgmL−1) of Streptomycin and Flukanozol drugs used for bacteria and yeasts. The results of our study show that the synthesized substances can be used for new drug applications that are being developed against infectious diseases in the pharmaceutical industry. © 2023 Elsevier B.V.Article Citation - WoS: 4Citation - Scopus: 5Cytotoxic and Apoptotic Effects of 1,2-Diborolanes With Strong Donor Substitutes on Human Cancer Cells(Elsevier, 2021) Şahin, Yüksel; Aslantürk, Özlem Sultan; Çelik, Tülay; Sevinçek, Resul; Aygün, Muhittin; Metin, Kubilay; Fırıncı, Erkan; Özgener, HüseyinIn recent years, boron compounds have become more common as chemotherapy agents against certain types of cancers. Along with the development of boron-based therapeutic agents have come investigations into the various cancers and biochemical and molecular mechanisms affected by boron compounds and the relationships between boron compounds and chemical protection against cancer. In this preliminary study, the effects of new 1,2-N-substituted-1,2-diborolane derivatives on types of breast and liver cancers were examined for the first time. Four were found to significantly affect the cell viabilities and mitochondrial membrane potential changes in MCF-7, HepG2 and Hep3B cancer cells. Each was prepared in n-hexane at various concentrations (5, 10, 25, 50, 75 and 100 µg/mL). Human peripheral blood lymphocytes were used as control cells. Compounds 1, 2, 3a, and 3b 1,2-diborolane derivatives selectively killed cancer cells, but compound 1 was cytotoxic in a concentration-dependent manner on HepG2 and Hep3B and only at concentrations of at least 75 µg/mL on MCF-7 cells. Compound 3a exhibited cytotoxic effect on lymphocytes at 75 and 100 µgmL-1 concentrations, but compounds 1, 2 and 3b, 3c and 3d have not possessed significant cytotoxic effect on lymphocytes. Compounds 3c and 3d have not possessed significant cytotoxic effects. Mitochondrial membrane potential assay results supported these findings. Our results reveal that 1,2-diborolane derivates have high cytotoxic and apoptotic activities on human hepatocarcinoma cells and are therefore potential candidates in the development of new drugs against liver cancer.Article Citation - WoS: 8Citation - Scopus: 91,2-Diborolanes With Strong Donor Substituents: Synthesis and High Antimicrobial Activity(Academic Press, 2021) Şahin, Yüksel; Poyrazoğlu Çoban, Esin; Sevinçek, Resul; Bıyık, Halil H.; Özgener, Hüseyin; Aygün, Muhittin1,2-diborolanes with strong and without strong donor substituents have been described, and are also referred to as 1,2-diboracyclopentane. The 1,2-diaryl/alkyl-amino-1,2-diboracyclopentanes 2, 3, and 4 were obtained in good yield after the reaction of 1,2-dichloro-1,2-diboracyclopentane 1 with ArNHLi and Me3Si-NR2. The structures of these new derivatives were characterized by nuclear magnetic resonance spectroscopy. The molecular structures of 2b, 2c, 2e, 4, and 5f were also determined by single-crystal X-ray diffraction. The newly synthesized 1,2-borolanes are stable in air and showed particularly high activity against some Gram-positive bacteria. © 2020 Elsevier Inc.Article Citation - WoS: 5Citation - Scopus: 5Synthesis and Structures of 1,3,2,4,5-Diazatriborolidines(Elsevier, 2019) Fırıncı, Erkan; Sevinçek, Resul; Bursalı, Banu; Özgener, Hüseyin; Burgaz, Osman; Şen, Ceren; Şahin, YükselThe derivatives of diazatriborolidine are a class of 5-membered heterocyclic compounds containing a ring with two nitrogen atoms and three boron atoms. The 1,3,2,4,5-diazatriborolidine derivatives were synthesized from 1,2-bis(N-lithium-arylamino) diborane(4) and dichloro-dimethylaminoborane with high yield. The structures of these new derivatives were determined using nuclear magnetic resonance (NMR) spectroscopy. The molecular structures of 3a, 3b, 3d, 4b and 4c were determined using single-crystal X-ray diffraction. Their structural features were discussed and compared with similar diazatriborolidines. In addition, the enthalpy of formation of B and N atoms containing five membered heterocycles were calculated theoretically for the first time. Also, an easy and efficient synthesis route has been reported for preparation of 1,3,2,4,5-diazatriborolidine derivatives.Article Citation - WoS: 11Citation - Scopus: 9Biophysical Evaluation of Physiological Effects of Gilthead Sea Bream (sparus Aurata) Farming Using Ftir Spectroscopy(Elsevier Ltd., 2014) Ceylan, Çağatay; Tanrıkul, Tansel; Özgener, HüseyinSparus aurata is one of the two most important cultured fish species in the Mediterranean region. The present work investigates the effects of culturing in S. aurata liver tissue at the molecular level using Fourier Transform Infrared (FTIR) spectroscopy. FTIR spectroscopy revealed dramatic differences between the wild and aquacultured fish liver cells, which mainly indicated that the level of glycogen increased in the aquacultured samples and the protein/lipid ratio decreased by 42.29% indicating that triglycerides and cholesterol esters increased and the protein content decreased in the aquacultured samples. The 15.99% increase in the level of unsaturation indicated elevated lipid peroxidation. Structural/organisational changes in the nucleic acids along with increased transcriptional status of the liver tissue cells were observed in the cultured fish tissue. All these results indicated that culturing induces significant changes in fish physiology. In addition FTIR spectroscopy is a promising method to monitor the physiological changes in fish physiology.Article Citation - WoS: 12Citation - Scopus: 12Modification of Metal/Semiconductor Junctions by Self-Assembled Monolayer Organic Films(Elsevier Ltd., 2009) Yakuphanoğlu, Fahrettin; Okur, Salih; Özgener, HüseyinTwo new metal/molecule/semiconductor contacts, Au/n-Si/TDA/Au and Au/p-Si/ODM/Au, were fabricated to understand effect of organic compounds, tridecylamine and octadecylmercaptan self-assembled monolayer (SAM) films, on electrical charge transport properties of the metal/semiconductor junctions. The morphology of the organic monolayers deposited on Si substrates was investigated by atomic force microscopy. The molecular coverage of ODM deposited on p-Si is poorer than that of TDA on n-Si substrate. The ideality factors of the p-Si/ODM and n-Si/TDA diodes were found to be 1.66 and 1.48, respectively. The electrical results show that the tridecylamine monolayer passivated junction has a lower ideality factor. The ideality factor indicates clear dependence on two different type functional groups R-SH (Thiol) and R-NH2 (Amin) groups and it increases with different functional groups of organic molecule. The barrier height φb value of the n-Si/TDA diode is smaller than that of p-Si/ODM diode, as a result of chain length of the SAM organic molecules. The interface state density Dit values of the diodes were determined using conductance technique. The n-Si/TDA diode has the smaller interface state density according to p-Si/ODM diode. We have evaluated that the organic molecules control the electronic parameters of metal/semiconductor diodes and thus, organic modification helps to get one step closer towards to new organic assisted silicon based microelectronic devices.