Synthesis, Characterization, and Biological Evaluation of Novel Naringenin Derivatives as Anticancer Agents

2020 ◽  
Vol 16 (4) ◽  
pp. 442-448 ◽  
Author(s):  
Yogesh Murti ◽  
Pradeep Mishra
Keyword(s):  
Anticancer Activity ◽  
Anticancer Agents ◽  
Colorimetric Assay ◽  
Biological Evaluation ◽  
Proton Nuclear Magnetic Resonance ◽  
Sulforhodamine B ◽  
Ic50 Values ◽  
Grinding Technique ◽  
Ht 29 ◽  
Mcf 7

Background: In the present study, a series of substituted naringenin derivatives was synthesized by Claisen–Schmidt reaction using grinding technique. Methods: Synthesized compounds were characterized on the basis of Fourier-Transform Infrared Spectroscopy (FTIR), proton Nuclear Magnetic Resonance (1H NMR), Mass Spectroscopy (MS) and elemental analysis. These derivatives were screened for anticancer activity on breast (MCF-7) and colon (HT-29) cell lines using Sulforhodamine B (SRB) colorimetric assay. Results: Results displayed improved inhibitory concentration (IC50) values of naringenin derivatives. IC50 values of 3(4-chlorobenzylidene)-5,7-dihydroxy-2(4-hydroxyphenyl)chroman-4-one are 10.35 μM (MCF-7) & 12.03 μM (HT-29), which is most potent compound in the series. These finding confirms the suitability of 3-substituted naringenin in improving the anticancer effect. Conclusion: Due to the intense interest in the development of drugs capable of inhibiting cancerous cells, naringenin derivatives may represent important precursor molecules for the therapeutic armamentarium of colon and breast cancer. Further structural modification in these structures will be of interest and may result in compounds having a better anticancer activity.

Design, Synthesis and Biological Evaluation of Novel Urea and Thiourea Bearing thieno[3,2-d]-pyrimidines as PI3 Kinase Inhibitors

2018 ◽  
Vol 18 (6) ◽  
pp. 891-902 ◽  
Author(s):  
Srinu Bodige ◽  
Parameshwar Ravula ◽  
Kali Charan Gulipalli ◽  
Srinivas Endoori ◽  
J.N. Narendra Sharath Chandra ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Cell Lines ◽  
Inhibitory Activity ◽  
Intracellular Signaling ◽  
Research Work ◽  
Docking Studies ◽  
Biological Evaluation ◽  
Intracellular Enzyme ◽  
Ht 29 ◽  
Mcf 7

Background: Phosphatidylinositol-3-kinase α (PI3Kα) is a ubiquitous intracellular enzyme, mainly involved in intracellular signaling pathways, promotes cellular growth, proliferation, and differentiation. Therefore, inhibition of PI3K can be a hotspot in molecular targeted therapy for the treatment of cancer. Methods: The present research work involves molecular docking studies performed to screen derivatives of urea and thiourea bearing thieno [3,2-d]-pyrimidines against the active site of PI3K enzyme using MOE.2008.10. The designed structures (6a-f) and (7a-j) were synthesized by the facile synthetic methods and evaluated for their anticancer activity against HT-29 and MCF-7 cell lines and inhibitory activity against PI3Kα enzyme. Results: Among the tested compounds, 4-(4-(2-(3-(pyrimidin-2-yl)thioureido)ethyl)piperazin-1-yl)thieno[3,2- d]pyrimidine-6-carboxamide (7f) showed the highest anticancer activity against HT-29 and MCF-7 cell lines with IC50 values of 2.18 µM and 4.25 µM, respectively. Further, the same compound also exhibited potent PI3Kα inhibitory activity with IC50 value of 1.26 µM. Conclusion: Docking studies supported the initial pharmacophoric hypothesis and suggested a mode of interaction at the active binding site of PI3Kα, demonstrating that the target compounds were potential inhibitory agents for cancer therapy.

One-pot synthesis and biological evaluation of novel 3-(5-((aryl) methyl) isoxazol-3-yl)-4H-chromen-4-one derivatives as potent antibacterial and anticancer agents

2021 ◽  
Vol 25 (11) ◽  
pp. 80-85
Author(s):  
Rani Janapatla Uma ◽  
Babu H. Ramesh ◽  
M. Prashanthi
Keyword(s):  
Antibacterial Activity ◽  
Anticancer Activity ◽  
Cell Line ◽  
Anticancer Agents ◽  
Biological Evaluation ◽  
Bacterial Strains ◽  
Standard Drug ◽  
Cell Line Hela ◽  
Aryl Methyl ◽  
Mcf 7

In search of better antibacterial and anticancer agents, a series of novel 3-(5-((aryl) methyl) isoxazol-3-yl)-4Hchromen- 4-one derivatives was synthesized (4a-4l) by using 4-oxo-4H-chromene-3-carbaldehyde and alkyne via in situ generated nitrile oxide and evaluated for their antibacterial and anticancer activity in vitro. Antibacterial activity was evaluated against three G+ bacterial strains and anticancer activity against breast cancer cell line (MCF-7) and cervical carcinoma cell line (HeLa). Among all the tested compounds, 4j and 4g exhibited potent antibacterial activity against tested grampositive bacterial strains. 4g, 4i and 4j exhibited potent cytotoxic activity against MCF-7 with IC50 values nearer to the standard drug doxorubicin.

Synthesis and Biological Evaluation of New Quinoline-Based Thiazolyl Hydrazone Derivatives as Potent Antifungal and Anticancer Agents

2018 ◽  
Vol 15 (2) ◽  
pp. 193-202 ◽  
Author(s):  
Ali Erguc ◽  
Mehlika Dilek Altintop ◽  
Ozlem Atli ◽  
Belgin Sever ◽  
Gokalp Iscan ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Cell Lines ◽  
Mtt Assay ◽  
Anticancer Agents ◽  
Mouse Embryonic Fibroblast ◽  
Biological Evaluation ◽  
Diffusion Method ◽  
Breast Adenocarcinoma ◽  
Nih 3T3 ◽  
Mcf 7

Background: In medicinal chemistry, thiazoles have gained great importance in antifungal and anticancer drug design and development. Objectives: The aim of this study was to synthesize new quinoline-based thiazolyl hydrazone derivatives and evaluate their anticandidal and anticancer effects. Methods: New thiazolyl hydrazone derivatives were evaluated for their anticandidal effects using disc diffusion method. Ames MPF assay was carried out to determine the genotoxicity of the most effective antifungal derivative. MTT assay was also performed to assess the cytotoxic effects of the compounds on A549 human lung adenocarcinoma, HepG2 human hepatocellular carcinoma, MCF- 7 human breast adenocarcinoma and NIH/3T3 mouse embryonic fibroblast (healthy) cell lines. Methods: Results: 4-(4-Fluorophenyl)-2-(2-((quinolin-4-yl)methylene)hydrazinyl)thiazole (4) showed antifungal activity against Candida albicans and Candida krusei in the concentration of 1 mg/mL. In MTT and Ames MPF tests, it was determined that compound 4 did not show cytotoxic and genotoxic effects. MTT assay indicated that 4-(naphthalen-2-yl)-2-(2-((quinolin-4-yl)methylene) hydrazinyl)thiazole (10) showed more selective anticancer activity than cisplatin against A549 and MCF-7 cell lines. Besides, 4-(4-chlorophenyl)-2-(2-((quinolin-4-yl)methylene)hydrazinyl)thiazole (5) exhibited more selective anticancer activity than cisplatin against HepG2 cell line. Conclusion: Due to their high selectivity index, these compounds are considered as candidate compounds to participate in further research.

Design, Synthesis of novel coumarin conjugated acetamides as promising anticancer agents: An in-silico and in-vitro approach.

2020 ◽  
Vol 20 ◽  
Author(s):  
Mamatha S. V ◽  
S. L. Belagali ◽  
Mahesh Bhat ◽  
Vijay M. Kumbar
Keyword(s):  
Anticancer Activity ◽  
Cell Lines ◽  
Mtt Assay ◽  
Anticancer Agents ◽  
In Silico ◽  
Active Sites ◽  
Biological Activities ◽  
Biological Evaluation ◽  
Mcf 7

Background: Coumarin and benzophenone possess a vast sphere of biological activities whereas thiazoles display various pharmacological properties. Hence we focused on incorporation of coumarin and thiazole core to the benzophenone skeleton to enhance the bioactivity anticipating their interesting biological properties. Objective: The objective of the current work is synthesis and biological evaluation of a novel series of coumarin fused thiazole derivatives. Methods: A novel series of Coumarin conjugated thiazolyl acetamide hybrid derivatives were synthesized by multistep reaction sequence and were characterized by the FT-IR, LCMS and NMR spectral techniques. The newly synthesized compounds were screened for anticancer activity by in-silico and in-vitro methods. The cytotoxicity of the synthesized unique compounds had been executed for two different cancer cell lines MCF-7 (Breast cancer) and KB (Oral cancer) in comparison with standard paclitaxel by MTT assay. Results: The compound 7f is the potent motif with an acceptable range of IC 50 values for anticancer activity were 63.54 µg/ml and 55.67 µg/ml, against the MCF-7 and KB cell lines, respectively. Molecule docking model revealed that this compound formed three conventional hydrogen bonds with the active sites of the amino acids MET 769, ARG 817 and LYS 721. Conclusion: Compound 7f with two methyl groups on the phenoxy ring and one 4-position methoxy group on the benzoyl ring, showed a significant cytotoxic effect. An advantageous level of low toxicity against normal cell line (L292) by MTT assay was determined.

scholarly journals Synthesis and biological evaluation of 4-(1H-1,2,4-triazol-1-yl)benzoic acid hybrids as anticancer agents

RSC Advances ◽  
2019 ◽  
Vol 9 (33) ◽  
pp. 19065-19074 ◽  
Author(s):  
Hatem A. Abuelizz ◽  
Hanem M. Awad ◽  
Mohamed Marzouk ◽  
Fahd A. Nasr ◽  
Ali S. Alqahtani ◽  
...  
Keyword(s):  
Benzoic Acid ◽  
Anticancer Activity ◽  
Anticancer Agents ◽  
Biological Evaluation ◽  
Ms Analysis ◽  
Normal Human ◽  
Hct 116 ◽  
Synthesis And Biological Evaluation ◽  
Mcf 7

A series of 4-(1H-1,2,4-triazol-1-yl)benzoic acid hybrids (1–17) was successfully synthesized and their structures were established by NMR and MS analysis. Their anticancer activity against HCT-116, MCF-7 and normal human RPE-1 cells were examined.

scholarly journals Design, Synthesis, and Anticancer Activity Studies of Novel Quinoline-Chalcone Derivatives

Molecules ◽  
2021 ◽  
Vol 26 (16) ◽  
pp. 4899
Author(s):  
Yong-Feng Guan ◽  
Xiu-Juan Liu ◽  
Xin-Ying Yuan ◽  
Wen-Bo Liu ◽  
Yin-Ru Li ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Anticancer Agents ◽  
Ros Generation ◽  
Dependent Manner ◽  
Gastric Cancer Cells ◽  
Design Synthesis ◽  
Chalcone Derivatives ◽  
Ic50 Values ◽  
Hct 116 ◽  
Mcf 7

The chalcone and quinoline scaffolds are frequently utilized to design novel anticancer agents. As the continuation of our work on effective anticancer agents, we assumed that linking chalcone fragment to the quinoline scaffold through the principle of molecular hybridization strategy could produce novel compounds with potential anticancer activity. Therefore, quinoline-chalcone derivatives were designed and synthesized, and we explored their antiproliferative activity against MGC-803, HCT-116, and MCF-7 cells. Among these compounds, compound 12e exhibited a most excellent inhibitory potency against MGC-803, HCT-116, and MCF-7 cells with IC50 values of 1.38, 5.34, and 5.21 µM, respectively. The structure–activity relationship of quinoline-chalcone derivatives was preliminarily explored in this report. Further mechanism studies suggested that compound 12e inhibited MGC-803 cells in a dose-dependent manner and the cell colony formation activity of MGC-803 cells, arrested MGC-803 cells at the G2/M phase and significantly upregulated the levels of apoptosis-related proteins (Caspase3/9 and cleaved-PARP) in MGC-803 cells. In addition, compound 12e could significantly induce ROS generation, and was dependent on ROS production to exert inhibitory effects on gastric cancer cells. Taken together, all the results suggested that directly linking chalcone fragment to the quinoline scaffold could produce novel anticancer molecules, and compound 12e might be a valuable lead compound for the development of anticancer agents.

scholarly journals Synthesis and Biological Evaluation of Novel Triple-Modified Colchicine Derivatives as Potent Tubulin-Targeting Anticancer Agents

Cells ◽  
2018 ◽  
Vol 7 (11) ◽  
pp. 216 ◽  
Author(s):  
Urszula Majcher ◽  
Greta Klejborowska ◽  
Magdalena Kaik ◽  
Ewa Maj ◽  
Joanna Wietrzyk ◽  
...  
Keyword(s):  
Cell Lines ◽  
Anticancer Agents ◽  
Binding Free Energy ◽  
3D Structure ◽  
Human Tumor ◽  
Biological Evaluation ◽  
Energy Estimates ◽  
Colchicine Derivatives ◽  
Mcf 7

Specific modifications of colchicine followed by synthesis of its analogues have been tested in vitro with the objective of lowering colchicine toxicity. Our previous studies have clearly shown the anticancer potential of double-modified colchicine derivatives in C-7 and C-10 positions. Here, a series of novel triple-modified colchicine derivatives is reported. They have been obtained following a four-step strategy. In vitro cytotoxicity of these compounds has been evaluated against four human tumor cell lines (A549, MCF-7, LoVo, and LoVo/DX). Additionally, the mode of binding of the synthesized compounds was evaluated in silico using molecular docking to a 3D structure of β-tubulin based on crystallographic data from the Protein Data Bank and homology methodology. Binding free energy estimates, binding poses, and MlogP values of the compounds were obtained. All triple-modified colchicine derivatives were shown to be active at nanomolar concentrations against three of the investigated cancer cell lines (A549, MCF-7, LoVo). Four of them also showed higher potency against tumor cells over normal cells as confirmed by their high selectivity index values. A vast majority of the synthesized derivatives exhibited several times higher cytotoxicity than colchicine, doxorubicin, and cisplatin.

scholarly journals A Nitrocarbazole as a New Microtubule-Targeting Agent in Breast Cancer Treatment

2021 ◽  
Vol 11 (19) ◽  
pp. 9139
Author(s):  
Maria Stefania Sinicropi ◽  
Cinzia Tavani ◽  
Camillo Rosano ◽  
Jessica Ceramella ◽  
Domenico Iacopetta ◽  
...  
Keyword(s):  
Breast Cancer ◽  
Anticancer Activity ◽  
Breast Cancer Cell Lines ◽  
Cellular Functions ◽  
Anticancer Properties ◽  
Cycle Arrest ◽  
In Silico Studies ◽  
Ic50 Values ◽  
Mcf 7

Breast cancer is still considered a high-incidence disease, and numerous are the research efforts for the development of new useful and effective therapies. Among anticancer drugs, carbazole compounds are largely studied for their anticancer properties and their ability to interfere with specific targets, such as microtubule components. The latter are involved in vital cellular functions, and the perturbation of their dynamics leads to cell cycle arrest and subsequent apoptosis. In this context, we report the anticancer activity of a series of carbazole analogues 1–8. Among them, 2-nitrocarbazole 1 exhibited the best cytotoxic profile, showing good anticancer activity against two breast cancer cell lines, namely MCF-7 and MDA-MB-231, with IC50 values of 7 ± 1.0 and 11.6 ± 0.8 μM, respectively. Furthermore, compound 1 did not interfere with the growth of the normal cell line MCF-10A, contrarily to Ellipticine, a well-known carbazole derivative used as a reference molecule. Finally, in vitro immunofluorescence analysis and in silico studies allowed us to demonstrate the ability of compound 1 to interfere with tubulin organization, similarly to vinblastine: a feature that results in triggering MCF-7 cell death by apoptosis, as demonstrated using a TUNEL assay.

scholarly journals Cytotoxic Sterols from Philippine Mushrooms

2020 ◽  
Vol 32 (5) ◽  
pp. 1197-1202
Author(s):  
Consolacion Y. Ragasa ◽  
Glenn G. Oyong ◽  
Maria Carmen S. Tan ◽  
Mariquit M. De Los Reyes ◽  
Maria Ellenita G. De Castro
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Human Cancer ◽  
Dermal Fibroblast ◽  
Cancer Cell Lines ◽  
Cytotoxic Activities ◽  
Cell Viability Assay ◽  
Ic50 Values ◽  
Ht 29 ◽  
Mcf 7

Ergosterol peroxide (1) and ergosterol (2) were commonly isolated as the major compounds of Philippine mushrooms. Sterols 1 and 2 from the dichloromethane extract of Geastrum triplex and Termitomyces clypeatus, respectively, were evaluated for their cytotoxic activities against four human cancer cell lines, viz., breast cancer (MCF-7), colon cancer (HT-29), leukemia (THP-1), and small lung cell carcinoma (H69PR), and a human normal cell line, human dermal fibroblast-neonatal (HDFn), using the PrestoBlue® cell viability assay. Compounds 1 and 2 exhibited the strongest activities against HT-29 with IC50 values of 1.79 and 2.98 μg/mL, respectively, while Zeocin gave an IC50 of 4.89 μg/mL. These compounds also exhibited strong antiproliferative effects against MCF-7 with IC50 values of 4.13 for 1 and 4.20 μg/mL for compound 2, comparable to Zeocin with IC50 = 3.68 μg/mL. Only moderate cytotoxicity resulted when compounds 1 and 2 were tested against H69PR with IC50 values of 7.78 and 6.83 μg/mL, respectively, while Zeocin exhibited an IC50 of 9.81 μg/mL. Furthermore, compounds 1 and 2 showed no effects against THP-1 (IC50 > 100 μg/mL), while Zeocin showed an IC50 of 4.73 μg/mL. Although compounds 1 and 2 have been reported to exhibit different bioactivities in previous studies, the cancer cell lines tested and/or the polarities of the solvents for extraction varied. Therefore, comparisons of the cytotoxic activities of compounds 1 and 2 with earlier studies could not be made extensively.

Anticancer Activity of Some Bisbenzimidazoles

2011 ◽  
Vol 66 (9-10) ◽  
pp. 465-470 ◽  
Author(s):  
İlhan Işıkdağ ◽  
Yusuf Özkay ◽  
Zerrin İncesu ◽  
Gülşen Akalın
Keyword(s):  
Anticancer Activity ◽  
Cell Lines ◽  
Topoisomerase I ◽  
Carcinoma Cell ◽  
Dna Topoisomerase ◽  
Carcinoma Cell Lines ◽  
Activity Screening ◽  
Breast Carcinoma Cell Lines ◽  
Ht 29 ◽  
Mcf 7

The discovery of DNA topoisomerases has added a new dimension to the study of anticancer drugs. Bisbenzimidazole derivatives are important compounds known as DNA topoisomerase I inhibitors. In the present study, some symmetrical bisbenzimidazole derivatives were synthesized and investigated for their anticancer activity. Anticancer activity screening was applied on HT-29 (colon carcinoma) and MCF-7 (breast carcinoma) cell lines by investigation of cytotoxicity, analysis of DNA synthesis, and DNA fragmentation assays. One of the seven compounds tested showed signifi cant cytotoxicity in both cell lines and caused DNA degradation in the HT-29 cell line.

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