3-Hydrazinoindolin-2-one derivatives: Chemical classification and investigation of their targets as anticancer agents

Ibrahim, Hany S.; Abou‐Seri, Sahar M.; Abdel‐Aziz, Hatem A.

doi:10.1016/j.ejmech.2016.06.034

Cited by 27 publications

(13 citation statements)

References 79 publications

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“…Some derivatives have attracted much attentions because they are regarded as new anticancer agents [4][5][6][7]. Recently, our group synthesized two platinum(II) complexes with methyl hydrazinecarbodithioate derivatives of indolin-2-one, which can non-covalently bind to DNA with high affinity and exhibit cytotoxicity against cancer cells by inducing apoptosis [8].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C₁₀H₈FN₃OS₂

Qin

Cao

2017

Zeitschrift Für Kristallographie - New Crystal Structures

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C 10 H 8 FN 3 OS 2 , monoclinic, P2 1 /c (no. 14), a = 6.2909(2) Å, CCDC no.: 1557525The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. Source of materialThe title compound was obtained via condensation of 5-fluoroindoline-2,3-dione (0.3 g, 2 mmol) with methyl hydrazinecarbodithioate (0.2 g, 2 mmol) in 8 mL methanol at room temperature for 12 h. The mixture was isolated by column chromatography on silica gel with dichloromethane/methanol = 98:2 (v/v) as eluent to give the title compound methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate (yield 65%; m.p.

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Section: Discussionmentioning

confidence: 99%

Crystal structure of methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C₁₀H₈FN₃OS₂

Qin

Cao

2017

Zeitschrift Für Kristallographie - New Crystal Structures

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“…For example, studies have shown that certain isatin derivatives can significantly inhibit endothelial growth factor receptor (EGFR) activity, 6 migration and angiogenesis, 7 as well as vascular endothelial growth factor receptor (VEGFR), platelet-derived growth factor receptor (PDGFR) and Kit receptor families. 8 Additionally, some of these derivatives, such as sunitinib, have been developed as antitumor drugs. Furthermore, synthetic indolediones suppress the activity of protein tyrosine kinases (PTKs) related to growth factor receptors and cell proliferation.…”

Section: Introductionmentioning

confidence: 99%

<p>The Acetone Indigo Red Dehydrating Agent IF203 Induces HepG2 Cell Death Through Cell Cycle Arrest, Autophagy and Apoptosis</p>

Shang¹,

Wang²,

Li³

et al. 2020

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Background: Isatin derivatives have extensive biological activities, such as antitumor. IF203, a novel isatin derivative, has not previously been reported to have antitumor activity. Methods: Acid phosphatase assays (APAs) and Ki-67 immunohistochemistry were used to detect the proliferation of HepG2 cells. Transmission electron microscope (TEM) was applied to detect ultrastructural changes. Flow cytometry (FCM) was used to detect cell cycle, apoptosis, reactive oxygen species (ROS) and mitochondrial membrane potential (MMP) of HepG2 cells in vitro. TUNEL, MMP and ROS immunofluorescence assays were applied to assess apoptosis, MMP, and ROS of HepG2 cells in vivo. Western Blotting was applied to assess the levels of apoptosis-and autophagy-related proteins. Results: In this study, in vivo and in vitro experiments showed that IF203 possesses antitumor activity. The results of APAs and Ki-67 immunohistochemistry demonstrated that IF203 could inhibit the proliferation of HepG2 cells. Cell cycle assays, downregulation of Cyclin B1 and Cdc2, and upregulation of P53 suggested that IF203 could lead to G2/M cell cycle arrest. In addition, ultrastructural changes, apoptosis assays, TUNEL immunofluorescence results, upregulated expression of Bax, and downregulated expression of Bcl-2 suggest that IF203 can induce apoptosis in HepG2 cells. After IF203 treatment, intracellular ROS levels increased, MMP decreased, JC-1 green fluorescence was enhanced, and the levels of Caspase-9, Caspase-3 and Cytochrome C expression were upregulated, suggesting that IF203 could induce apoptosis of HepG2 cells through the mitochondrial apoptosis pathway. Moreover, characteristic apoptotic ultrastructural changes were accompanied by the appearance of many autophagy bubbles and upregulation of Atg5, Atg12, ULK1, Beclin-1 and LC3-II proteins, suggesting that IF203 could induce autophagy in HepG2 cells. Conclusion: This study showed that IF203 leads to the death of HepG2 cells through cell cycle arrest, apoptotic induction, and autophagy promotion.

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“…Indolin-2-one derivatives exhibit promising antitumor activity by targeting different biomacromolecules [5,6], of which 3-hydrazinoindolin-2-one derivatives have particularly attracted intensive attention [7,8]. In our previous work, methyl hydrazinecarbodithioate derivatives of 5-fluoro-1-(2-morpholinoethyl)indolin-2-one and 5-methoxy-1-(2-morpholinoethyl)indolin-2-one were used as ligands to achieve two new Pt(II) complexes, which exhibited cytotoxicity against cancer cells by inducing apoptosis [9].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of tert-butyl (Z)-4-(2-(5-methoxy-3-(2-((methylthio)carbonothioyl)hydrazono)-2-oxoindolin-1-yl)ethyl)piperazine-1-carboxylate, C₂₂H₃₁N₅O₄S₂

Qin

Cao

2017

Zeitschrift Für Kristallographie - New Crystal Structures

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CCDC no.: 1557526The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. Source of materialThe title compound was synthesized via a three-step synthetic protocol. The reaction of 5-methoxyindoline-2,3-dione (0.9 g, 5 mmol) with 1,2-dibromoethane (2.8 g,15 mmol) in 15 mL of N,N-dimethylformamide (DMF) in the presence of potassium carbonate (1.0 g, 7.2 mmol) at 40-50°C gave 1-(2-bromoethyl)indoline-2,3-dione [4]. Next, 1-(2-bromoethyl) indoline-2,3-dione (0.6 g, 2.0 mmol) was reacted with tertbutyl piperazine-1-carboxylate (1.1 g, 0.6 mmol) in DMF (5 mL) for 12 h at room temperature to yield 1-((4-(tertbutyloxycarbonyl)piperazin-1-yl)ethyl)-5-methoxyindolin-2,3-dione. Finally, condensation of 1-((4-(tert-butyloxycarbonyl) piperazin-1-yl)-5-methoxyindolin-2,3-dione (0.4 g, 1 mmol) with methyl hydrazinecarbodithioate (0.1 g, 1 mmol) in 5 mL methanol at room temperature for 12 h gave a solid, which was collected by filtration and dried in air. The crude product was purified by recrystallization from methanol (yield 60%; m.p. 421-423 K). Crystals of the title compound were obtained by slow evaporation of the mixed solvent dichloromethane and methanol (5:1, v/v). Experimental detailsH atoms were placed in calculated positions. The U iso values of the hydrogen atoms of methyl groups were set to 1.5U eq (C) and the U iso values of all other hydrogen atoms were set to 1.2U eq (C, N). DiscussionIndolin-2-one derivatives exhibit promising antitumor activity by targeting different biomacromolecules [5,6], of which 3-hydrazinoindolin-2-one derivatives have particularly attracted intensive attention [7,8]. In our previous work, methyl hydrazinecarbodithioate derivatives of 5-fluoro-1-(2-morpholinoethyl)indolin-2-one and 5-methoxy-1-(2-morpholinoethyl)indolin-2-one were used as ligands to achieve two new Pt(II) complexes, which exhibited cytotoxicity against cancer cells by inducing apoptosis [9]. As a continuous work, herein we report a new methyl hydrazinecarbodithioate derivative. X-ray single-crystal diffraction analysis revealed that the hydrazinecarbodithioate and

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3-Hydrazinoindolin-2-one derivatives: Chemical classification and investigation of their targets as anticancer agents

Cited by 27 publications

References 79 publications

Crystal structure of methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C₁₀H₈FN₃OS₂

Crystal structure of methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C₁₀H₈FN₃OS₂

<p>The Acetone Indigo Red Dehydrating Agent IF203 Induces HepG2 Cell Death Through Cell Cycle Arrest, Autophagy and Apoptosis</p>

Crystal structure of tert-butyl (Z)-4-(2-(5-methoxy-3-(2-((methylthio)carbonothioyl)hydrazono)-2-oxoindolin-1-yl)ethyl)piperazine-1-carboxylate, C₂₂H₃₁N₅O₄S₂

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3-Hydrazinoindolin-2-one derivatives: Chemical classification and investigation of their targets as anticancer agents

Cited by 27 publications

References 79 publications

Crystal structure of methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C10H8FN3OS2

Crystal structure of methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C10H8FN3OS2

<p>The Acetone Indigo Red Dehydrating Agent IF203 Induces HepG2 Cell Death Through Cell Cycle Arrest, Autophagy and Apoptosis</p>

Crystal structure of tert-butyl (Z)-4-(2-(5-methoxy-3-(2-((methylthio)carbonothioyl)hydrazono)-2-oxoindolin-1-yl)ethyl)piperazine-1-carboxylate, C22H31N5O4S2

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Crystal structure of methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C₁₀H₈FN₃OS₂

Crystal structure of methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C₁₀H₈FN₃OS₂

Crystal structure of tert-butyl (Z)-4-(2-(5-methoxy-3-(2-((methylthio)carbonothioyl)hydrazono)-2-oxoindolin-1-yl)ethyl)piperazine-1-carboxylate, C₂₂H₃₁N₅O₄S₂