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Butein

Catalog No. T6427 CAS 487-52-5

Synonyms: 2’,3,4,4’-tetrahydroxy Chalcone

Butein (2’,3,4,4’-tetrahydroxy Chalcone), a plant polyphenol, is isolated from Rhus verniciflua. It can inhibit the activation of protein tyrosine kinase, NF-κB and STAT3, and also can inhibit EGFR.

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Butein, CAS 487-52-5

Pack Size	Availability	Price/USD
1 mg	In stock	$ 36.00
2 mg	In stock	$ 51.00
5 mg	In stock	$ 80.00
10 mg	In stock	$ 108.00
25 mg	In stock	$ 225.00
50 mg	In stock	$ 363.00
100 mg	In stock	$ 578.00
1 mL * 10 mM (in DMSO)	In stock	$ 79.00

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Purity: 100%

Purity: 99.85%

Purity: 98.76%

Biological Description

Chemical Properties

Storage & Solubility Information

Description	Butein (2’,3,4,4’-tetrahydroxy Chalcone), a plant polyphenol, is isolated from Rhus verniciflua. It can inhibit the activation of protein tyrosine kinase, NF-κB and STAT3, and also can inhibit EGFR.
Targets&IC50	p60c-src:65 μM, EGF:65 μM
In vitro	Butein inhibits the epidermal growth factor (EGF)-stimulated auto-phosphotyrosine level of EGF receptor in HepG2 cells, and also inhibits tyrosine-specific protein kinase activities of EGF receptor and p60c-src with IC50 of 65 μM in vitro. The inhibition is competitive to ATP and non-competitive to the phosphate acceptor, poly (Glu, Ala, Tyr) 6:3:1 for EGF receptor tyrosine kinase. In contrast, Butein non-significantly inhibits the activities of serine- and threonine-specific protein kinases such as PKC or PKA. [1] Butein inhibits Nuclear Factor(NF)-κB and NF-κB-regulated gene expression through direct inhibition of IκBα Kinase β on Cysteine 179 Residue. [2] Butein (10 μM) inhibits over 90% iNOS and COX-2 expression, as well as nitrite and TNF-α production in LPS-stimulated RAW 264.7 cells. Butein (10 μM) inhibits LPS-induced DNA binding activity of NF-κB, which is mediated through inhibition of the degradation of inhibitory factor-κB and phosphorylation of Erk1/2 MAP kinase, as well as increases binding of the osteopontin a vb3 integrin receptor. [3] Butein (20 μM) treatment induces morphologic changes of bladder cancer cells BLS(M) from elongated morphology to rounded epithelial-like cells, accompanied by downregulation of vimentin, and gaining of E-cadherin compared to untreated control cells, indicating the reversal of mesenchymal-like phenotype. Butein (20 μM) suppresses motility and invasion capacity of BLS(M) cells, and reverts EMT-like phenotype induced by TNF-α, through the ERK1/2 and NF-κB signaling pathways. [4]
In vivo	Butein at 2 mg/kg induces significant inhibition of hepatocellular tumor growth compared with the corn oil-treated controls. At necropsy on day 22 after initial treatment, there is more than 2-fold decrease in tumor growth in the Butein-treated group (mean relativetumor burden, 3.90) compared with the control group (8.46), associated with reduced constitutive p-STAT3 (9% vs 81% of vehicle group), Bcl-2 levels (26% vs 96% of vehicle group), and increased caspase-3 level (98% vs 21% of vehicle group) in HCC tumor tissues. [5] Butein shows antifibrogenic activity. Butein (25 mg/kg/day) reduces serum AST and ALT activation to 35% and 69%, respectively, of control CCl4-induced rat levels. Butein (25 mg/kg/day) reduces liver hydroxyproline contents and TBAR4 concentration to 54% and 54%, respectively. α1(I) collagen and TIMP-1 expression in Butein-treated rats is 28% and 20.3% compared with the values for the respective CCl4-treated control. [7]
Cell Research	The cells (5× 103/mL) are incubated in triplicate in a 96-well plate in the presence or absence of indicated concentration of Butein in a final volume of 0.2 mL for different time intervals at 37 ℃. Thereafter, 20 μL MTT solution (5 mg/mL in PBS) is added to each well. After a 2-hour incubation at 37 ℃, 0.1 mL lysis buffer (20% SDS, 50% dimethylformamide) is added, incubation is continued overnight at 37 ℃, and then the optical density at 570 nm is measured by plate reader. (Only for Reference)
Source	Natural Products > Moraceae > Broussonetia

Synonyms	2’,3,4,4’-tetrahydroxy Chalcone
Molecular Weight	272.25
Formula	C15H12O5
CAS No.	487-52-5

Storage

Powder: -20°C for 3 years | In solvent: -80°C for 1 year

Solubility Information

DMSO: 51 mg/mL (187.3 mM)

Ethanol: 51 mg/mL (187.3 mM)

H2O: < 1 mg/mL (insoluble or slightly soluble)

References and Literature

1. Yang EB, et al. Biochem Biophys Res Commun, 1998, 17, 245(2), 435-438. 2. Pandey MK, et al. J Biol Chem, 2007, 282(24), 17340-17350. 3. Lee SH, et al. Biochem Biophys Res Commun, 2004 , 323(1), 125-132. 4. Zhang L, et al. FEBS Lett, 2008, 582(13), 1821-1828. 5. Rajendran P, et al. Clin Cancer Res, 2011, 17(6), 1425-1439. 6. Zhang L, et al. Butein sensitizes HeLa cells to cisplatin through the AKT and ERK/p38 MAPK pathways by targeting FoxO3a.Int J Mol Med. 2015 Oct;36(4):957-66.

Citations

1. Zhao L, Zhang W, Luan F, et al.Butein suppresses PD-L1 expression via downregulating STAT1 in non-small cell lung cancer.Biomedicine & Pharmacotherapy.2023, 157: 114030.

Related compound libraries

This product is contained In the following compound libraries：

Inhibitor Library Tyrosine Kinase Inhibitor Library Anti-Neurodegenerative Disease Compound Library Kinase Inhibitor Library Anti-Cancer Compound Library Target-Focused Phenotypic Screening Library Natural Product Library Anti-Breast Cancer Compound Library Covalent Inhibitor Library Bioactive Compound Library

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Keywords

Butein 487-52-5 Angiogenesis Apoptosis Autophagy JAK/STAT signaling Metabolism Others Tyrosine Kinase/Adaptors EGFR PDE PDE4 Epidermal growth factor receptor Inhibitor MAPK 2’,3,4,4’-tetrahydroxy Chalcone ErbB-1 FoxO3a inhibit cell SIRT1 Phosphodiesterase (PDE) ERK PKB AKT HeLa HER1 p38 HepG2 inhibitor

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