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Butein (Synonyms: 2’,3,4,4’tetrahydroxy Chalcone)

Catalog No.GC10944

부테인은 PDE4에 대한 IC50이 10.4μM인 cAMP 특이적 PDE 억제제입니다. 부테인은 HepG2 세포에서 EGFR 및 p60c-src에 대해 16 및 65μM의 IC50을 갖는 특정 단백질 티로신 키나제 억제제입니다. 부테인은 FoxO3a를 표적으로 하여 AKT 및 ERK/p38 MAPK 경로를 통해 HeLa 세포를 Cisplatin에 민감하게 합니다. 부테인은 SIRT1 활성화제(STAC)입니다.

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Butein Chemical Structure

Cas No.: 487-52-5

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10mM (in 1mL DMSO)
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5mg
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25mg
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100mg
US$680.00
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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Background

Butein, a chalconoid has anti-oxidant effect, which has various pharmacological effects.
Reactive oxygen species (ROS), produced intracellularly through multiple mechanisms and depending on the cell and tissue types, mainly ROS NADPH oxidase (NOX) complexes in cell membranes, mitochondria, peroxisomes, and endoplasmic reticulum, via dental adhesive bleaching agents and pulpal disease, can cause oxidative stress. [1] ROS are formed as a natural product of the normal metabolism of oxygen and have important roles in cell signaling and homeostasis. However, during times of environmental stress, ROS levels can increase dramatically.[2] H2O2-induced cytotoxicity and production of ROS were blocked in the presence of butein, and these effects were dose dependent.Due to the dual role of ROS, both prooxidant and antioxidant-based anticancer agents have been developed.
Butein can induce the apoptosis in B16 melanoma cells and human promyelocytic leukemia cells, inhibit diabetes complications, and inhibit enzymes such as protein kinases and glutathione reductase. [3,4,5,6] Recently, Butein was isolated from R. verniciflua which suppress cellular damage from oxidation caused by H2O2 in HDP cells, through JNK–Nrf2/ARE-dependent HO-1 expression.[7] In addition, Butein attenuated VEGF and MMP-9 activities via the suppression of NF-kB activity by flow cytometric analysis and RT-PCR in vitro. Furthermore, Butein repressed the expression of VEGF and MMP-9 induced by treatment with tumor necrosis factor-ɑ and phorbol-12-myristate-13-acetate mainly through Electrophoretic mobility shift assay (EMSA) and Enzyme-linked immunosorbent assay (ELISA), resulting in an inhibition of cell growth, invasion and angiogenesis of prostate cancer .[8] Thus, Butein may be a promising therapeutic agent for the treatment of various dental diseases.
References:
1.Han D, Williams E, Cadenas E."Mitochondrial respiratory chain-dependent generation of superoxide anion and its release into the intermembrane space". Biochem. J. 2010, 353 (2): 411-6.
2.Devasagayam, TPA; Tilak JC; Boloor KK; Sane Ketaki S; Ghaskadbi Saroj S; Lele RD. "Free Radicals and Antioxidants in Human Health: Current Status and Future Prospects". Journal of Association of Physicians of India (JAPI), 2004, 52: 796.
3.S. Sogawa, Y. Nero, H. Ueda, T. Miki. Protective effects of hydroxychalcones on free radical-induced cell damage. Biol. Pharm. Bull., 1994, 251-256.
4.J.C. Lee, K.T. Lim, Y.S. Jang. Identification of Rhus verniciflua Stokes compounds that exhibit free radical scavenging and anti-apoptotic properties. Biochim. Biophys. Acta, 2002, 181-191.
5.S.M. Yu, Z.J. Cheng, S.C. Kuo. Endothelium-dependent relaxation of rat aorta by butein, a novel cyclic AMP-specific phosphodiesterase inhibitor. Eur. J. Pharmacol., 1995, 69-77.
6.K. Iwashita, M. Kobori, K. Yamaki, T. Tsushida. Flavonoids inhibit cell growth and induce apoptosis in B16 melanoma 4A5 cells. Biosci. Biotechnol. Biochem., 2000, 1813-1820.
7.Dong-Sung Lee.et al. Butein protects human dental pulp cells from hydrogen peroxide-induced oxidative toxicity via Nrf2 pathway-dependent heme oxygenase-1 expressions.Toxicology in Vitro, 2013, 874-881.
8.Dong-Oh Moona.et al. Butein suppresses the expression of nuclear factor-kappa B-mediated matrix metalloproteinase-9 and vascular endothelial growth factor in prostate cancer cells. Toxicology in Vitro, 2010,24(7) ,1927-1934.

Chemical Properties

Cas No. 487-52-5 SDF
Synonyms 2’,3,4,4’tetrahydroxy Chalcone
Chemical Name (E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one
Canonical SMILES C1=CC(=C(C=C1C=CC(=O)C2=C(C=C(C=C2)O)O)O)O
Formula C15H12O5 M.Wt 272.25
Solubility ≥ 13.6mg/mL in DMSO Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 3.6731 mL 18.3655 mL 36.7309 mL
5 mM 0.7346 mL 3.6731 mL 7.3462 mL
10 mM 0.3673 mL 1.8365 mL 3.6731 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 16 reference(s) in Google Scholar.)

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