Design, synthesis, and biological evaluation of (2E)-(2-oxo-1, 2-dihydro-3 H -indol-3-ylidene)acetate derivatives as anti-proliferative agents through ROS-induced cell apoptosis

Song, Zhuang; Chen, Caiping; Li, Jun; Wen, Xiaoan; Sun, Hongbin; Yuan, Haoliang

doi:10.1016/j.ejmech.2016.09.005

Cited by 31 publications

(10 citation statements)

References 32 publications

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“…ROS has been reported to be involved in early stages of apoptosis in many cellular systems. To determine whether the apoptosis was induced by the title compounds, the intracellular ROS level in compound 4d -treated HeLa cells was also examined by using 2′,7′-dichlorodihydrofluorescein diacetate (DCFH-DA), which could be converted into a green fluorescent DCF by ROS oxidation 40 . HeLa cells were exposed to compound 4d at 0 ∼ 0.2 μM concentrations for 48 h and the intracellular fluorescence intensity was quantitatively analysed by flow cytometry.…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis, and anticancer evaluation of novel quinoline derivatives of ursolic acid with hydrazide, oxadiazole, and thiadiazole moieties as potent MEK inhibitors

Jin

Chen

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

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In this article, a series of novel quinoline derivatives of ursolic acid (UA) bearing hydrazide, oxadiazole, or thiadiazole moieties were designed, synthesised, and screened for their in vitro antiproliferative activities against three cancer cell lines (MDA-MB-231, HeLa, and SMMC-7721). A number of compounds showed significant activity against at least one cell line. Among them, compound 4d exhibited the most potent activity against three cancer cell lines with IC 50 values of 0.12 ± 0.01, 0.08 ± 0.01, and 0.34 ± 0.03 lM, respectively. In particular, compound 4d could induce the apoptosis of HeLa cells, arrest cell cycle at the G0/G1 phase, elevate intracellular reactive oxygen species level, and decrease mitochondrial membrane potential. In addition, compound 4d could significantly inhibit MEK1 kinase activity and impede Ras/Raf/ MEK/ERK transduction pathway. Therefore, compound 4d may be a potential anticancer agent and a promising lead worthy of further investigation.

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Section: Resultsmentioning

confidence: 99%

Design, synthesis, and anticancer evaluation of novel quinoline derivatives of ursolic acid with hydrazide, oxadiazole, and thiadiazole moieties as potent MEK inhibitors

Jin

Chen

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…1 H chemical shifts ( δ ) are always given in ppm relative to the solvent residual peak and 13 C chemical shifts are relative to the central peak of the solvent signal . 7‐Chloroisatin ( 2′‐Cl ) and 5‐butylisatin ( 2‐Bu ) were prepared as described previously while the other isatins were purchased.…”

Section: Methodsmentioning

confidence: 99%

Conversion of Isatins to Tryptanthrins, Heterocycles Endowed with a Myriad of Bioactivities

et al. 2019

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The numerous bioactivities exhibited by tryptanthrins led chemists to develop synthetic approaches towards this important scaffold. In particular, conversion of isatins into tryptanthrins has been the subject of several studies. In this context, by using iodine and potassium hydroxide at room temperature, we have discovered a simple way to convert isatin and seven of its 5‐substituted derivatives (Bu, F, Cl, Br, I, OMe and OCF3) into the corresponding tryptanthrins. Furthermore, a mechanism was proposed to explain this original reactivity. Finally, we evaluated the antibacterial, antifungal, antioxidant and cytotoxic properties of the synthesized tryptanthrins. The unprecedented inhibition of human 20S constitutive proteasome was finally evaluated.

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“…The results indicated that compound 273 (Figure ) has the best antiproliferative activity in vitro (Table ). In addition, they demonstrated that compound 273 could inhibit TrxR activity with a dose‐dependent manner, which contributed to its antiproliferative activity . Arner and co‐workers utilized recombinant rat TrxR1 in a single assay as a means to discover two novel inhibitors rottlerin (or named mallotoxin, 274 , Figure ) and protoporphyrin IX (PpIX, 275 , Figure ).…”

Section: Thioredoxin Reductase Inhibitorsmentioning

confidence: 99%

Small molecule inhibitors of mammalian thioredoxin reductase as potential anticancer agents: An update

Zhang

et al. 2018

Medicinal Research Reviews

135

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Mammalian thioredoxin reductase (TrxR) enzymes are homodimeric flavin proteins sharing a unique yet essential selenocysteine residue at their C-terminus. TrxRs, together with their endogenous substrate thioredoxins, play a crucial role in regulating diverse cellular redox events. A wealth of evidence from both clinic observations and bench studies supports that overactivation/dysfunction of TrxRs has a close link to the onset and development of various diseases, such as cancer and neurodegeneration. Thus, an increasing interest has been attracted to find small molecule modulators of TrxRs during the past years. Herein, we briefly discussed the relevance of targeting TrxRs inhibition for cancer treatment, and presented the small molecule inhibitors of mammalian TrxRs published in the nonpatent literatures from 2011 to 2016. The mechanisms of inhibition by different classes of molecules were summarized, and some inhibitors with promising anticancer activity were further discussed. We expect this work would be a comprehensive reference in the medicinal chemistry, and have a broad audience across multiple disciplines.

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Design, synthesis, and biological evaluation of (2E)-(2-oxo-1, 2-dihydro-3 H -indol-3-ylidene)acetate derivatives as anti-proliferative agents through ROS-induced cell apoptosis

Cited by 31 publications

References 32 publications

Design, synthesis, and anticancer evaluation of novel quinoline derivatives of ursolic acid with hydrazide, oxadiazole, and thiadiazole moieties as potent MEK inhibitors

Design, synthesis, and anticancer evaluation of novel quinoline derivatives of ursolic acid with hydrazide, oxadiazole, and thiadiazole moieties as potent MEK inhibitors

Conversion of Isatins to Tryptanthrins, Heterocycles Endowed with a Myriad of Bioactivities

Small molecule inhibitors of mammalian thioredoxin reductase as potential anticancer agents: An update

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