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(−)-Deguelin

Item № 10010706
CAS № 522-17-8
Purity ≥98%
product image
                (CAS 522-17-8)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     5 mg $53.00 0.00
     10 mg $101.00 0.00
     25 mg $239.00 0.00
     50 mg $424.00 0.00

Pricing updated 2019-03-24. Prices are subject to change without notice.

Description
Synonyms
  • (−)-cis-Deguelin

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

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Technical Information
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
Synonyms
  • (−)-cis-Deguelin
Molecular Formula
C23H22O6
Formula Weight
394.4
Purity
≥98%
Formulation
A crystalline solid
λmax
238, 252, 270, 297 nm
SMILES
COC1=CC2=C(C=C1OC)OC[C@]3([H])[C@@]2([H])C(C(C=CC4=C5C=CC(C)(C)O4)=C5O3)=O
InChI Code
InChI=1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3/t19-,20+/m1/s1
InChI Key
ORDAZKGHSNRHTD-UXHICEINSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
Downloads & Resources
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Additional Information

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References & Product Citations
Product Description References

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 Proceedings of the National Academy of Sciences of the United States of America 95, 3380-3384 (1998).

2. Chun, K.H., Kosmeder, J.W., II, Sun, S., et al. Effects of deguelin on the phosphatidylinositol 3-kinase/Akt pathway and apoptosis in premalignant human bronchial epithelial cells Journal of the National Cancer Institute 95(4), 291-302 (2003).

3. Lee, H.Y., Oh, S.H., Woo, J.K., et al. Chemopreventive effects of deguelin, a novel Akt inhibitor, on tobacco-induced lung tumorigenesis Journal of the National Cancer Institute 97(22), 1695-1699 (2005).

4. Peng, X.H., Karna, P., O'Regan, R.M., et al. Down-regulation of inhibitor of apoptosis proteins by deguelin selectively induces apoptosis in breast cancer cells Molecular Pharmacology 71, 101-111 (2007).

5. Lee, H.Y., Suh, Y.A., Kosmeder, J.W., et al. Deguelin-induced inhibition of cyclooxygenase-2 expression in human bronchial epithelial cells Clinical Cancer Research 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 Chemical Research in Toxicology 17, 1540-1548 (2004).

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