Butein

NF-κB Pathway Inhibitor; Stabilizes IκB

Butein

NF-κB Pathway Inhibitor; Stabilizes IκB

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NF-κB Pathway Inhibitor; Stabilizes IκB
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Overview

Butein is a plant polyphenol, tetrahydroxychalcone that inhibits nuclear factor (NF)-κB (Yang et al; Pandey et al. 2007). Butein has been shown to prevent phosphorylation and degradation of TNF-dependent IκBα, an inhibitory subunit of NF-κB (IC₅₀ = 38 μM; Orlikova et al.). Butein also inhibits 5-lipoxygenase (IC₅₀ = 0.01 μM; Sogawa et al.), the enoyl-acyl-carrier protein reductase of Plasmodium falciparum (Ki = 2.97 μM; Sharma et al.), angiotensin-converting enzyme (IC₅₀ = 0.73 mM; Bonesi et al.), and SRC kinase (Pandey et al. 2009).

METABOLISM
· Inhibits iron-induced lipid peroxidation in rat brain homogenate in a concentration-dependent manner (Cheng et al.).

CANCER RESEARCH
· Inhibits TNF-α-induced invasion of human lung adenocarcinoma H1299 cells (Pandey et al. 2007; Gupta et al.).
· Inhibits growth in human hepatoma cancer cell lines HepG2 and Hep3B, by inducing G2/M phase arrest (Moon et al.; Gupta et al.).
· Inhibits testosterone-induced proliferation in breast cancer cells (Wang et al.)

IMMUNOLOGY
· Exhibits anti-inflammatory properties in a mouse macrophage cell line by inhibiting LPS-induced expression of iNOS (Lee et al.).
Alternative Names
2',3,4,4'-Tetrahydroxychalcone
Cell Type
Cancer Cells and Cell Lines, Macrophages
Species
Human, Mouse, Non-Human Primate, Other, Rat
Area of Interest
Cancer, Immunology, Metabolism
CAS Number
487-52-5
Chemical Formula
C₁₅H₁₂O₅
Molecular Weight
272.3 g/mol
Purity
≥ 95%
Pathway
NF-κB
Target
IκB

Protocols and Documentation

Find supporting information and directions for use in the Product Information Sheet or explore additional protocols below.

Document Type
Product Name
Catalog #
Lot #
Language
Product Name
Butein
Catalog #
73464
Lot #
All
Language
English
Document Type
Safety Data Sheet
Product Name
Butein
Catalog #
73464
Lot #
All
Language
English

Resources and Publications

Publications (12)

Natural chalcones as dual inhibitors of HDACs and NF-κB. Orlikova B et al. Oncology reports 2012 SEP

Abstract

Histone deacetylase enzymes (HDACs) are emerging as a promising biological target for cancer and inflammation. Using a fluorescence assay, we tested the in vitro HDAC inhibitory activity of twenty-one natural chalcones, a widespread group of natural products with well-known anti-inflammatory and antitumor effects. Since HDACs regulate the expression of the transcription factor NF-κB, we also evaluated the inhibitory potential of the compounds on NF-κB activation. Only four chalcones, isoliquiritigenin (no. 10), butein (no. 12), homobutein (no. 15) and the glycoside marein (no. 21) showed HDAC inhibitory activity with IC50 values of 60-190 µM, whereas a number of compounds inhibited TNFα-induced NF-κB activation with IC50 values in the range of 8-41 µM. Interestingly, three chalcones (nos. 10, 12 and 15) inhibited both TNFα-induced NF-κB activity and total HDAC activity of classes I, II and IV. Molecular modeling and docking studies were performed to shed light into dual activity and to draw structure-activity relationships among chalcones (nos. 1-21). To the best of our knowledge this is the first study that provides evidence for HDACs as potential drug targets for natural chalcones. The dual inhibitory potential of the selected chalcones on NF-κB and HDACs was investigated for the first time. This study demonstrates that chalcones can serve as lead compounds in the development of dual inhibitors against both targets in the treatment of inflammation and cancer.
Regulation of survival, proliferation, invasion, angiogenesis, and metastasis of tumor cells through modulation of inflammatory pathways by nutraceuticals. Gupta SC et al. Cancer metastasis reviews 2010 SEP

Abstract

Almost 25 centuries ago, Hippocrates, the father of medicine, proclaimed Let food be thy medicine and medicine be thy food." Exploring the association between diet and health continues today. For example�
The synthesis and angiotensin converting enzyme (ACE) inhibitory activity of chalcones and their pyrazole derivatives. Bonesi M et al. Bioorganic & medicinal chemistry letters 2010 MAR

Abstract

A series of chalcones (1-9) and pyrazoles (10-18) was prepared to investigate their potential activity as Angiotensin I-Converting Enzyme (ACE) inhibitors. Their structures were verified by elemental analysis, UV, IR, MS, (1)H NMR, (13)C NMR, and 2D NMR experiments. Among tested compounds, chalcone 7 exerted the highest activity with an IC(50) value of 0.219 mM, while the most potent pyrazole was 15 (IC(50) value of 0.213 mM).