| Identification | Back Directory | [Name]
(E)-2-(2-Chlorostyryl)-3,5,6-trimethylpyrazine | [CAS]
1000672-89-8 | [Synonyms]
(E)-2-(2-Chlorostyryl)-3,5,6-trimethylpyrazine
Pyrazine, 2-[(1E)-2-(2-chlorophenyl)ethenyl]-3,5,6-trimethyl- | [Molecular Formula]
C15H15ClN2 | [MOL File]
1000672-89-8.mol | [Molecular Weight]
258.75 |
| Chemical Properties | Back Directory | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 20 mg/ml; DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml; DMSO: 2 mg/ml; Ethanol: 2 mg/ml | [form ]
A crystalline solid |
| Hazard Information | Back Directory | [Description]
(E)-2-(2-Chlorostyryl)-3,5,6-trimethylpyrazine (CSTMP) is a stilbene derivative with antioxidant and anticancer activities.1,2,3 It stimulates proliferation of hydrogen peroxide-damaged ECV-304 cells (EC50 = 24.9 nM).1 CSTMP reduces hydrogen peroxide-induced release of lactate dehydrogenase (LDH) in and increases viability of human umbilical vein endothelial cells (HUVECs) in a concentration-dependent manner via inhibition of apoptosis.2 It reverses hydrogen peroxide-induced release of malondialdehyde (MDA) and decreases in superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px) activities as well as increases constitutive nitric oxide synthase (cNOS) activity and nitric oxide (NO) production in HUVECs. CSTMP also induces cell death of A549 non-small cell lung cancer (NSCLC) cells in an IRE1α-dependent manner through induction of IRE1α-TRAF2-ASK1 complex-mediated endoplasmic reticulum (ER) stress and mitochondrial apoptosis.3 | [References]
1. Deng, L., Guo, X., Zhai, L., et al. Ligustrazine derivatives. Part 4: Design, synthesis, and biological evaluation of novel ligustrazine-based stilbene derivatives as potential cardiovascular agents Chem. Biol. Drug Des. 79(5),731-739(2012).
2. Zhai, L., Zhang, P., Sun, R.-Y., et al. Cytoprotective effects of CSTMP, a novel stilbene derivative, against H2O2-induced oxidative stress in human endothelial cells Pharmacol. Rep. 63(6),1469-1480(2011).
3. Zhang, J., Liang, Y., Lin, Y., et al. IRE1α-TRAF2-ASK1 pathway is involved in CSTMP-induced apoptosis and ER stress in human non-small cell lung cancer A549 cells Biomed. Pharmacother. 82,281-289(2016). |
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