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(-)-Deguelin
Flavonoids
Reference 10010706
Data
CAS number522-17-8
Molecular FormulaC23H22O6
FormulationA crystalline solid
Purity>98%
Stability2 years
Storage-20°C
ShippingWET ICE
Correlated Keywordsrotenoids, flavonids, cancers, antiproliferative, chemoprevention, Parkinsons, diseases, Akt, PKB, PI3K, COX-2, COX2, apoptosis, PI3-K
Synonyms(-)-cis-Deguelin
Description
Rotenoids, deriving from the flavonoid family of compounds, act as chemopreventive agents that inhibit NADH:ubiquinone oxidoreductase activity and suppress phorbol ester-induced ornithine decarboxylase (ODC) activity. The rotenoid compound deguelin, originally isolated from the bark of M. sericea (Leguminosae) to be used as an insecticide and fish poison, has chemopreventive and chemosensitizing effects in models of skin, mammary, colon, and lung carcinogenesis. Deguelin inhibits cell growth (IC50 = <10-8 M), blocks PI3K/Akt activation, suppresses COX-2 expression, and induces apoptosis in premalignant and squamous human bronchial epithelial (HBE) cells without affecting normal HBE cells. At 6 mg/kg, deguelin induces Parkinson’s disease-like symptoms in rats after six days of subcutaneous infusion and therefore may also serve as a useful model for Parkinson’s disease research.
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Documentation
Fang, N., Casida, J.E. Anticancer action of cubé insecticide: Correlation for rotenoid constituents between inhibition of NADH: Ubiquinone oxidoreductase and induced ornithine decarboxylase activities. Proc Natl Acad Sci USA 95 3380-3384 (1998).
Chun, K., Kosmeder, J.W.I., Sun, S., et al. Effects of deguelin on the phosphatidylinositol 3-kinase/Akt pathway and apoptosis in premalignant human bronchial epithelial cells. J Natl Cancer Inst 95(4) 291-302 (2003).
Lee, H., Oh, S., Woo, J.K., et al. Chemopreventive effects of deguelin, a novel Akt inhibitor, on tobacco-induced lung tumorigenesis. J Natl Cancer Inst 97(22) 1695-1699 (2005).
Peng, X., Karna, P., O'Regan, R.M., et al. Down-regulation of inhibitor of apoptosis proteins by deguelin selectively induces apoptosis in breast cancer cells. Mol Pharmacol 71 101-111 (2007).
Lee, H., Suh, Y., Kosmeder, J.W., et al. Deguelin-induced inhibition of cyclooxygenase-2 expression in human bronchial epithelial cells. Clin Cancer Res 10 1074-1079 (2004).
Caboni, P., Sherer, T.B., Zhang, N., et al. Rotenone, deguelin, their metabolites, and the rat model of Parkinson’s disease. Chem Res Toxicol 17 1540-1548 (2004).
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