scholarly journals Biological Evaluation of 3-Benzylidenechromanones and Their Spiropyrazolines-Based Analogues

Molecules ◽  
2020 ◽  
Vol 25 (7) ◽  
pp. 1613 ◽  
Author(s):  
Angelika A. Adamus-Grabicka ◽  
Magdalena Markowicz-Piasecka ◽  
Marcin Cieślak ◽  
Karolina Królewska-Golińska ◽  
Paweł Hikisz ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Cell Lines ◽  
Cancer Cell ◽  
Anticancer Agents ◽  
Dna Cleavage ◽  
Cancer Cell Lines ◽  
Inhibitory Effect ◽  
Biological Evaluation ◽  
Proliferative Potential ◽  
Monoclinic System

A series of 3-benzylidenechrmanones 1, 3, 5, 7, 9 and their spiropyrazoline analogues 2, 4, 6, 8, 10 were synthesized. X-ray analysis confirms that compounds 2 and 8 crystallize in a monoclinic system in P21/n space groups with one and three molecules in each asymmetric unit. The crystal lattice of the analyzed compounds is enhanced by hydrogen bonds. The primary aim of the study was to evaluate the anti-proliferative potential of 3-benzylidenechromanones and their spiropyrazoline analogues towards four cancer cell lines. Our results indicate that parent compounds 1 and 9 with a phenyl ring at C2 have lower cytotoxic activity against cancer cell lines than their spiropyrazolines analogues. Analysis of IC50 values showed that the compounds 3 and 7 exhibited higher cytotoxic activity against cancer cells, being more active than the reference compound (4-chromanone or quercetin). The results of this study indicate that the incorporation of a pyrazoline ring into the 3-arylideneflavanone results in an improvement of the compounds’ activity and therefore it may be of use in the search of new anticancer agents. Further analysis allowed us to demonstrate the compounds to have a strong inhibitory effect on the cell cycle. For instance, compounds 2, 10 induced 60% of HL-60 cells to be arrested in G2/M phase. Using a DNA-cleavage protection assay we also demonstrated that tested compounds interact with DNA. All compounds at the concentrations corresponding to cytotoxic properties are not toxic towards red blood cells, and do not contribute to hemolysis of RBCs.

scholarly journals Design, Synthesis, Biological Evaluation and Silico Prediction of Novel Sinomenine Derivatives

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3466
Author(s):  
Shoujie Li ◽  
Mingjie Gao ◽  
Xin Nian ◽  
Liyu Zhang ◽  
Jinjie Li ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Cytotoxic Activity ◽  
Cell Lines ◽  
Cancer Cell ◽  
Anticancer Agents ◽  
Biological Activities ◽  
Cancer Cell Lines ◽  
Biological Evaluation ◽  
Design Synthesis ◽  
Nucleus Structure

Sinomenine is a morphinan alkaloid with a variety of biological activities. Its derivatives have shown significant cytotoxic activity against different cancer cell lines in many studies. In this study, two series of sinomenine derivatives were designed and synthesized by modifying the active positions C1 and C4 on the A ring of sinomenine. Twenty-three compounds were synthesized and characterized by spectroscopy (IR, 1H-NMR, 13C-NMR, and HRMS). They were further evaluated for their cytotoxic activity against five cancer cell lines, MCF-7, Hela, HepG2, SW480 and A549, and a normal cell line, Hek293, using MTT and CCK8 methods. The chlorine-containing compounds exhibited significant cytotoxic activity compared to the nucleus structure of sinomenine. Furthermore, we searched for cancer-related core targets and verified their interaction with derivatives through molecular docking. The chlorine-containing compounds 5g, 5i, 5j, 6a, 6d, 6e, and 6g exhibited the best against four core targets AKT1, EGFR, HARS and KARS. The molecular docking results were consistent with the cytotoxic results. Overall, results indicate that chlorine-containing derivatives might be a promising lead for the development of new anticancer agents.

scholarly journals Synthesis and Cytotoxic Analysis of Novel Myrtenyl Grafted Pseudo-Peptides Revealed Potential Candidates for Anticancer Therapy

Molecules ◽  
2020 ◽  
Vol 25 (8) ◽  
pp. 1911 ◽  
Author(s):  
Odette Concepción ◽  
Julio Belmar ◽  
Alexander F. de la Torre ◽  
Francisco M. Muñiz ◽  
Mariano W. Pertino ◽  
...  
Keyword(s):  
T Cells ◽  
Cytotoxic Activity ◽  
Cell Lines ◽  
Cancer Cell ◽  
Anticancer Agents ◽  
Cd4 T Cells ◽  
Dermal Fibroblast ◽  
Colon Adenocarcinoma ◽  
Cancer Cell Lines ◽  
Biological Properties

Myrtenal is a natural monoterpene isolated from essential oils of several plants and their derivates have shown to have several biological properties including cytotoxicity. The cytotoxic activity of these derivates are being investigated for their antitumor effect leading to the development of potential anticancer agents. In this study, novels Myrtenyl grafted pseudo-peptides were designed, synthesized and functionally characterized as possible therapeutic agents for cancer treatment. Thirteen novel Myrtenyl grafted pseudo-peptides were prepared in high atom economy and efficiency by a classic Ugi-4CR and sequential post-modification. Their structures were confirmed by NMR, and ESI-MS, and its cytotoxic activity was evaluated in three cancer cell lines and primary CD4+ T cells at different proliferative cycles. Our results revealed that some of these compounds showed significant cytotoxicity against human gastric, breast and colon adenocarcinoma cells lines, but not against human dermal fibroblast cell line. Moreover, from the thirteen novel myrtenyl synthesized the compound (1R,5S)-N-{[1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl]methyl}-N-[2-(cyclohexylamino)-2–oxoethyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxamide (3b) proved to be the best candidate in terms of acceptable EC50, and Emax values in cancer cell lines and at inducing cytotoxicity in CD4+ T cells undergoing active proliferation, without affecting non-proliferating T cells. Overall, the synthesis and characterization of our Myrtenyl derivates revealed novel potential anticancer candidates with selective cytotoxic activity.

Terpyridine Copper(II) Complexes as Potential Anticancer Agents by Inhibiting Cell Proliferation, Blocking Cell Cycle and Inducing Apoptosis in BEL-7402 Cells

2022 ◽  
Author(s):  
Yunqiong Gu ◽  
Yu-Jun Zhong ◽  
Mei-Qi Hu ◽  
Huan-Qing Li ◽  
Kun Yang ◽  
...  
Keyword(s):  
Cell Cycle ◽  
Cell Proliferation ◽  
Cytotoxic Activity ◽  
Cell Lines ◽  
Cancer Cell ◽  
Anticancer Agents ◽  
Cancer Cell Lines

Four mononuclear terpyridine complexes [Cu(H-La)Cl2]·CH3OH (1), [Cu(H-La)Cl]ClO4 (2), [Cu(H-Lb)Cl2]·CH3OH (3), and [Cu(H-Lb)(CH3OH)(DMSO)](ClO4)2 (4) were prepared and fully characterized. Complexes 14 exhibited higher cytotoxic activity against several tested cancer cell lines...

scholarly journals Cytotoxicity to Five Cancer Cell Lines of the Respiratory Tract System and Anti-inflammatory Activity of Thai Traditional Remedy

2019 ◽  
Vol 14 (5) ◽  
pp. 1934578X1984581
Author(s):  
Thana Juckmeta ◽  
Weerachai Pipatrattanaseree ◽  
Wuttichai Jaidee ◽  
Bhanuz Dechayont ◽  
Jitpisute Chunthorng-Orn ◽  
...  
Keyword(s):  
Respiratory Tract ◽  
Cytotoxic Activity ◽  
Cell Lines ◽  
Cancer Cell ◽  
Cancer Cell Lines ◽  
Inhibitory Effect ◽  
Inflammatory Activity ◽  
Traditional Remedy ◽  
Anti Inflammatory ◽  
Minor Compounds

A Thai traditional remedy called Benchalokawichian (BLW) consists of 5 plant species, Ficus racemosa, Capparis micracantha, Clerodendrum petasites, Harrisonia perforata, and Tiliacora triandra. It has long been used in Thai traditional medicine to reduce fever in respiratory tract infection, but there is no report on either cytotoxicity against cancer cell lines of the respiratory tract system or anti-inflammatory effect. Thus, the objectives of this research were to investigate the cytotoxic activity of the ethanolic and water extracts of BLW, its single plant ingredients and its isolated compounds against 5 cancer cell lines of the respiratory tract, by SRB assay. Anti-inflammatory activity of all extracts and compounds was also tested by using lipopolysaccharide-induced nitric oxide (NO) in RAW 264.7 cells. The main compounds were isolated by high-performance liquid chromatography and compared with BLW and plant ingredients. A major compound of BLW and H. perforata ethanolic extracts is perforatic acid, which inhibited the growth of 2 lung cancer cell lines, A549 and H226, with IC50 values of 6.7 and 13.2 µg/mL. The ethanolic extract of BLW and T. triandra showed cytotoxic activity against all cancer cell lines with IC50 values in the range of 10.1 to 45.2 µg/mL. In contrast, all EtOH extracts showed moderate anti-inflammatory activity, but the water extract had no inhibitory effect on either activity. Pectolinarigenin and O-methyllaloptaeroxyrin, 2 minor compounds, exhibited NO inhibitory effect with IC50 values of 7.1 and 7.9 µg/mL, respectively, whereas perforatic acid was inactive (>50 µg/mL). Moreover, pectolinarigenin showed high cytotoxic activity against all cancer cell lines of the respiratory system with IC50 values in the range of 1.9 to 9.1 µg/mL. As a result, these 2 minor compounds can be used as markers for quality control of BLW for anti-inflammatory activity. Perforatic acid and pectolinarigenin are of interest for further study on their cytotoxic mechanism. Remarkably, T. triandra, one of the plant components of BLW, is possibly the source of the active cytotoxic compounds.

Synthesis and Biological Evaluation of matrine derivatives as a Novel Family of Potential Anticancer Agents

2019 ◽  
Vol 15 ◽  
Author(s):  
Jing Wang ◽  
Hang Liu ◽  
Xiao-Bin Zhuo ◽  
Guang-Ming Ye ◽  
Qing-Jie Zhao
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Anticancer Agents ◽  
Human Cancer ◽  
Biological Activities ◽  
Parent Compound ◽  
Human Tumor ◽  
Cancer Cell Lines ◽  
Biological Evaluation ◽  
Novel Scaffold

Background: ‘FufangKushen injection’ was a Chinese Traditional anticancer drug, which has been widely used to treat cancer in combination with other anticancer drugs. Objective: Our goal is to synthesize a series of novel 13-dithiocarbamates matrine derivatives using matrine (1) as the lead compounnd, and evaluate biological activities of obtained compounds. Method: The in vitro cytotoxicity of the target compounds against three human cancer cell lines (Hep3B, LM3 and BeL-7404) was evaluated. To investigate the mechanism of biological activity, Cell cycle analysis were performed. Result: The results revealed that compound 6o and 6v displayed the most significant anticancer activity against three cancer cell lines with IC50 values in range of 3.42–8.05 μM, which showed better activity than the parent compound (Matrine). SAR analysis indicated that introduction of a substituted amino dithiocarbamate might significantly enhance the antiproliferative activity. Conclusion: During the newly synthesized compounds, matrine analogue 6v exhibited a potent effect against three human tumor cell lines. The mode of action of 6v was to inhibit the G0/G1 phase arrest. Therefore, compound 6v has been selected as a novel-scaffold lead for further structural optimizations or as a chemical probe for exploring anticancer pathways of this kinds of compounds.

Synthesis of imidazo[2,1-b][1,3,4]thiadiazole–chalcones as apoptosis inducing anticancer agents

MedChemComm ◽  
2014 ◽  
Vol 5 (11) ◽  
pp. 1718-1723 ◽  
Author(s):  
Ahmed Kamal ◽  
Vangala Santhosh Reddy ◽  
Karnewar Santosh ◽  
G. Bharath Kumar ◽  
Anver Basha Shaik ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Anticancer Activity ◽  
Cell Lines ◽  
Cancer Cell ◽  
Anticancer Agents ◽  
Human Cancer ◽  
Cancer Cell Lines ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines

A library of imidazothiadiazole–chalcone conjugates were synthesised and investigated for their cytotoxic activity against various human cancer cell lines. Some of the tested compounds like 7a, 7b, 11a and 11b exhibited promising anticancer activity.

scholarly journals Isolation and Cytotoxic Activity of Phyllocladanes from the Roots of Acacia schaffneri (Leguminosae)

Molecules ◽  
2020 ◽  
Vol 25 (17) ◽  
pp. 3944
Author(s):  
José de Jesús Manríquez-Torres ◽  
Marco Antonio Hernández-Lepe ◽  
José Román Chávez-Méndez ◽  
Susana González-Reyes ◽  
Idanya Rubí Serafín-Higuera ◽  
...  
Keyword(s):  
Cell Cycle ◽  
Cytotoxic Activity ◽  
Cell Lines ◽  
Cancer Cell ◽  
Anticancer Agents ◽  
Spectroscopic Properties ◽  
Cancer Cell Lines ◽  
Moderate Activity ◽  
Cycle Arrest ◽  
Ic50 Values

In research on natural molecules with cytotoxic activity that can be used for the development of new anticancer agents, the cytotoxic activity of hexane, chloroform, and methanol extracts from the roots of Acacia schaffneri against colon, lung, and skin cancer cell lines was explored. The hexane extract showed the best activity with an average IC50 of 10.6 µg mL−1. From this extract, three diterpenoids, phyllocladan-16α,19-diol (1), phyllocladan-16α-ol (2), and phylloclad-16-en-3-ol (3), were isolated and characterized by their physical and spectroscopic properties. Diterpenoids 1 and 2 were tested against the same cancer cell lines, as well as their healthy counterparts, CCD841 CoN, MRC5, and VH10, respectively. Compound 1 showed moderate activity (IC50 values between 24 and 70 μg mL−1), although it showed a selective effect against cancer cell lines. Compound 2 was practically inactive. The cytotoxicity mechanism of 1 was analyzed by cell cycle, indicating that the compound induces G0/G1 cell cycle arrest. This effect might be generated by DNA alkylation damage. In addition, compound 1 decreased migration of HT29 cells.

Synthesis and biological evaluation of bivalent β-carbolines as potential anticancer agents

MedChemComm ◽  
2016 ◽  
Vol 7 (4) ◽  
pp. 636-645 ◽  
Author(s):  
Hongtao Du ◽  
Hongling Gu ◽  
Na Li ◽  
Junru Wang
Keyword(s):  
Cell Cycle ◽  
Cell Lines ◽  
Cancer Cell ◽  
Anticancer Agents ◽  
Cancer Cell Lines ◽  
Biological Evaluation ◽  
Apoptosis Induction ◽  
Synthesis And Biological Evaluation

A series of novel bivalent β-carbolines were synthesized and evaluated for their anti-proliferative activities on a panel of cancer cell lines, apoptosis induction and cell cycle effects.

scholarly journals Design, Synthesis, and Biological Evaluation of Novel N-Acylhydrazone Bond Linked Heterobivalent β-Carbolines as Potential Anticancer Agents

Molecules ◽  
2019 ◽  
Vol 24 (16) ◽  
pp. 2950 ◽  
Author(s):  
Chen ◽  
Guo ◽  
Ma ◽  
Chen ◽  
Fan ◽  
...  
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Anticancer Agents ◽  
Chorioallantoic Membrane ◽  
Cancer Cell Lines ◽  
Biological Evaluation ◽  
In Vivo Model ◽  
Ic50 Values

Utilizing a pharmacophore hybridization approach, we have designed and synthesized a novel series of 28 new heterobivalent β-carbolines. The in vitro cytotoxic potential of each compound was evaluated against the five cancer cell lines (LLC, BGC-823, CT-26, Bel-7402, and MCF-7) of different origin—murine and human, with the aim of determining the potency and selectivity of the compounds. Compound 8z showed antitumor activities with half-maximal inhibitory concentration (IC50) values of 9.9 ± 0.9, 8.6 ± 1.4, 6.2 ± 2.5, 9.9 ± 0.5, and 5.7 ± 1.2 µM against the tested five cancer cell lines. Moreover, the effect of compound 8z on the angiogenesis process was investigated using a chicken chorioallantoic membrane (CAM) in vivo model. At a concentration of 5 μM, compound 8z showed a positive effect on angiogenesis. The results of this study contribute to the further elucidation of the biological regulatory role of heterobivalent β-carbolines and provide helpful information on the development of vascular targeting antitumor drugs.

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