Synthesis, characterization, in vitro antiproliferative and cytotoxicity effects of a new class of 2-((1R,2S)-2-((E)-4-substitutedstyryl)  cyclooctyl)benzo[d]thiazole derivatives

Uremis, Muhammad Mehdi; Yağlıoğlu, Ayşe Şahin; Budak, Yakup; Ceylan, Mustafa

doi:10.25135/acg.oc.18.17.02.009

Cited by 7 publications

(4 citation statements)

References 32 publications

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“…Therefore, the utilization of compounds that induce apoptosis is crucial in cancer treatment (Ceylan et al, 2020;Pfeffer & Singh, 2018;Uremis et al, 2017a;2017b). Although limited studies have demonstrated that CuD, CuI, and CuE induce apoptosis in HCC through apoptotic proteins, they have been reported to induce apoptosis in various cancer types.…”

Section: Discussionmentioning

confidence: 99%

“…In the process of cancer formation, damaged cells promote prolonged cell survival by genetic mutations, the release of apoptosis inhibitor proteins, and the expression of antiapoptotic proteins from the Bcl‐2 family, thereby increasing the continuity of the cell cycle. Therefore, the utilization of compounds that induce apoptosis is crucial in cancer treatment (Ceylan et al, 2020; Pfeffer & Singh, 2018; Uremis et al, 2017a; 2017b). Although limited studies have demonstrated that CuD, CuI, and CuE induce apoptosis in HCC through apoptotic proteins, they have been reported to induce apoptosis in various cancer types.…”

Section: Discussionmentioning

confidence: 99%

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Investigation of apoptotic effects of Cucurbitacin D, I, and E mediated by Bax/Bcl‐xL, caspase‐3/9, and oxidative stress modulators in HepG2 cell line

Üremiş,

Türköz,

Üremiş

2024

Drug Development Research

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Cucurbitacins, natural compounds highly abundant in the Cucurbitaceae plant family, are characterized by their anticancer, anti‐inflammatory, and hepatoprotective properties. These compounds have potential as therapeutic agents in the treatment of liver cancer. This study investigated the association of cucurbitacin D, I, and E (CuD, CuI, and CuE) with the caspase cascade, Bcl‐2 family, and oxidative stress modulators in the HepG2 cell line. We evaluated the antiproliferative effects of CuD, CuI, and CuE using the MTT assay. We analyzed Annexin V/PI double staining, cell cycle, mitochondrial membrane potential, and wound healing assays at different doses of the three compounds. To examine the modulation of the caspase cascade, we determined the protein and gene expression levels of Bax, Bcl‐xL, caspase‐3, and caspase‐9. We evaluated the total antioxidant status (TAS), total oxidant status (TOS), superoxide dismutase (SOD), glutathione (GSH), Total, and Native Thiol levels to measure cellular redox status. CuD, CuI, and CuE suppressed the proliferation of HepG2 cells in a dose‐dependent manner. The cucurbitacins induced apoptosis by increasing caspase‐3, caspase‐9, and Bax activity, inhibiting Bcl‐xL activation, causing loss of ΔΨm, and suppressing cell migration. Furthermore, cucurbitacins modulated oxidative stress by increasing TOS levels and decreasing SOD, GSH, TAS, and total and native Thiol levels. Our findings suggest that CuD, CuI, and CuE exert apoptotic effects on the hepatocellular carcinoma cell line by regulating Bax/Bcl‐xL, caspase‐3/9 signaling, and causing intracellular ROS increase in HepG2 cells.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Investigation of apoptotic effects of Cucurbitacin D, I, and E mediated by Bax/Bcl‐xL, caspase‐3/9, and oxidative stress modulators in HepG2 cell line

Üremiş,

Türköz,

Üremiş

2024

Drug Development Research

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“…Recently, we reported the in vitro cytotoxic evaluation of some cis‐ substituted 1,3‐benzothiazole derivatives against HeLa (Human Cervical Carcinoma Cells) and C6 (Rat Brain Tumor) cancer cells. Compounds showed high activity with IC 50 values ranging from IC 50 ≤5 μ m to IC 50 =9.53 μ m compared to 5‐FU (IC 50 ≤5 μ m ).…”

Section: Introductionmentioning

confidence: 99%

Antiproliferative Evaluation of Some 2‐[2‐(2‐Phenylethenyl)‐cyclopent‐3‐en‐1‐yl]‐1,3‐benzothiazoles: DFT and Molecular Docking Study

Ceylan

Erkan

Yağlıoğlu

et al. 2020

Chemistry & Biodiversity

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The 2-[2-(2-phenylethenyl)cyclopent-3-en-1-yl]-1,3-benzothiazoles were synthesized from the reactions of 7benzylidenebicyclo[3.2.0]hept-2-en-6-ones with 2-aminobenzenethiol. The antiproliferative activities of 2-[2-(2phenylethenyl)cyclopent-3-en-1-yl]-1,3-benzothiazoles were determined against C6 (rat brain tumor) and HeLa (human cervical carcinoma cells) cell lines using BrdU cell proliferation ELISA assay. Cisplatin and 5-fluorouracil (5-FU) were used as standards. The most active compound was 2-{(1S,2S)-2-[(E)-2-(4-methylphenyl)ethenyl] cyclopent-3-en-1-yl}-1,3-benzothiazole against C6 cell lines with IC 50 = 5.89 μM value (cisplatin, IC 50 = 14.46 μM and 5-FU, IC 50 = 76.74 μM). Furthermore, the most active compound was 2-{(1S,2S)-2-[(E)-2-(2-methoxyphenyl) ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole against HeLa cell lines with IC 50 = 3.98 μM (cisplatin, IC 50 = 37.95 μM and 5-FU, IC 50 = 46.32 μM). Additionally, computational studies of related molecules were performed by using B3LYP/6-31G + (d,p) level in the gas phase. Experimental IR and NMR data were compared with the calculated results and were found to be compatible with each other. Molecular electrostatic potential (MEP) maps of the most active 2-{(1S,2S)-2-[(E)-2-(2methoxyphenyl)ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole against HeLa and the most active 2-{(1S,2S)-2-[(E)-2-(4-methylphenyl)ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole against C6 were investigated, aiming to determine the region that the molecule is biologically active. Biological activities of mentioned molecules were investigated with molecular docking analyses. The appropriate target protein (PDB codes: 1 M17 for the HeLa cells and 1JQH for the C6 cells) was used for 2-{(1S,2S)-2-[(E)-2-(2-methoxyphenyl)ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole and 2-{(1S,2S)-2-[(E)-2-(4-methylphenyl)ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole molecules exhibiting the highest biological activity against HeLa and C6 cells in the docking studies. As a result, it was determined that these molecules are the best candidates for the anticancer drug. Figure 5. Interaction of molecule 5c (pink balls) with protein 1M17 and that of molecule 5e (red balls) with protein 1JQH.1 H-NMR (400 MHz, CDCl 3 ): 8.02 (d, J = 8.2, 1H), 7.87 (d, J = 7.8, 1H), 7.48 (ddd, J = 8.3, 7.2, 1.3, 2H), 7.43-7.31 (m, 4H), 7.06 -6.97 (m, 2H), 6.46 (d, J = 15.8, 1H), 6.22 (dd, J = 15.8, 8.0, 1H), 5.98 -5.92 (m, 1H), 5.82 -5.76 (m, 1H), 3.99 -3.87 (m, 1H), 3.77 (dt, J = 8.8, 7.3, 1H), 3.16 -3.03 (m, 1H), 3.00 -2.89 (m, 1H). 13 C-NMR (101 MHz,

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“…10 µL suspended cell was mixed with 10 µL trypan blue, then 10 µL of this mixture was pipetted to Thoma cell counting chamber to determine the cell concentration. The cell stock suspension was prepared into the 15 mL of falcon tube, then pippeted into the cell plates (5 ×10 3 cells/well) [35,36].…”

Section: Cell Cultures Preparationmentioning

confidence: 99%

Inhibition of Various Cancer Cells Proliferation of Bornyl Acetate and Essential Oil from Inula graveolens (Linnaeus) Desf.

Karan¹,

Yildiz²,

Aydın³

et al. 2018

Rec.Nat.Prod.

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Inula species are medicinal and aromatic plants used for folk medicine extensively. In this work, hydrodistilled essential oil of Inula graveolens (Linnaeus) Desf. analyzed by GC-MS which revealed that bornyl acetate was the major product (69.15%). Camphene was the second major compound (11.11%). Antiproliferative activity of the essential oil and bornyl acetate was investigated on HeLa (human cervix carcinoma), HT29 (human colon carcinoma), A549 (human lung carcinoma), MCF7 (human breast adenocarcinoma) cancer cells and FL (human amnion cells) normal cells. The cytotoxicity was executed by a Lactate Dehydrogenase (LDH) Cytotoxicity Detection Kit. Essential oil and bornyl acetate displayed the outstanding activities on HeLa (IC 50 , 64.1, 72.0 µg/mL), HT29 (IC 50 , 24.6, 60.5 µg/mL), A549 (IC 50 , 28.3,44.1 µg/mL), MCF-7 (IC 50 , 66.5, 85.6 µg/mL), and FL (IC 50 , 42.1, 50.6 µg/mL) cell lines respectively.

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Synthesis, characterization, in vitro antiproliferative and cytotoxicity effects of a new class of 2-((1R,2S)-2-((E)-4-substitutedstyryl) cyclooctyl)benzo[d]thiazole derivatives

Cited by 7 publications

References 32 publications

Investigation of apoptotic effects of Cucurbitacin D, I, and E mediated by Bax/Bcl‐xL, caspase‐3/9, and oxidative stress modulators in HepG2 cell line

Investigation of apoptotic effects of Cucurbitacin D, I, and E mediated by Bax/Bcl‐xL, caspase‐3/9, and oxidative stress modulators in HepG2 cell line

Antiproliferative Evaluation of Some 2‐[2‐(2‐Phenylethenyl)‐cyclopent‐3‐en‐1‐yl]‐1,3‐benzothiazoles: DFT and Molecular Docking Study

Inhibition of Various Cancer Cells Proliferation of Bornyl Acetate and Essential Oil from Inula graveolens (Linnaeus) Desf.

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