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(−)-Deguelin

Cayman Chemical Item Number 10010706

(−)-cis-Deguelin (CAS 522-17-8)

(-)-Deguelin (CAS 522-17-8)

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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.1 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.2,3,4 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.2,5 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.6

1 Fang, N., and 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).

2 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).

3 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).

4 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).

5 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).

6 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).

Synonyms
  • (-)-cis-Deguelin
Formal Name 13,​13aS-​dihydro-​9,​10-​dimethoxy-​3,​3-​dimethyl-​3H-​[1]benzopyrano[3,​4-​b]pyrano[2,​3-​h][1]benzopyran-​7(7aS)-​one
CAS Number 522-17-8
Molecular Formula C23H22O6
Formula Weight 394.1
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
COc1cc2c(OC[C@H]​3Oc4c(ccc5OC(C)​(C)​C=Cc45)​C(=O)​[C@@H]​23)​cc1OC

Background Reading

Fang, N., and 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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Size Price Quantity Subtotal
5 mg $53.00 $0.00
10 mg $101.00 $0.00
25 mg $239.00 $0.00
50 mg $424.00 $0.00
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