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239804

Sigma-Aldrich

Cyclopamine-KAAD

Cyclopamine- KAAD, CAS 306387-90-6, is a cell-permeable potent analog of Cyclopamine (Cat. No. 239803) that specifically inhibits Hedgehog (Hh) signaling with similar or lower toxicity (IC₅₀ = 20 nM).

Synonym(s):

Cyclopamine-KAAD, 3- Keto-N-( aminoethyl- aminocaproyl- dihydrocinnamoyl)cyclopamine, KAAD-Cyclopamine, Shh Signaling Antagonist II, 3-Keto-N-(aminoethyl-aminocaproyl-dihydrocinnamoyl)cyclopamine, KAAD-Cyclopamine, Shh Signaling Antagonist II

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About This Item

Empirical Formula (Hill Notation):
C44H63N3O4
Molecular Weight:
697.99
UNSPSC Code:
12352116

Quality Level

100

assay

≥70% (sum of two isomers, HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

pale yellow

solubility

ethanol: 1 mg/mL
methanol: 1 mg/mL
DMSO: 5 mg/mL

shipped in

wet ice

storage temp.

−20°C

General description

A cell-permeable potent analog of Cyclopamine (Cat. No. 239803) that specifically inhibits Hedgehog (Hh) signaling with similar or lower toxicity (IC50 = 20 nM in Shh-LIGHT2 assay; 50 nM in p2Ptch-/-cells; 500 nM in SmoA1-LIGHT cells). Binds to SmoA1 and promotes its exit from the endoplasmic reticulum. Suppresses both ShhNp-induced pathway activity and SmoA1-induced reporter activity. Reported to cause regression of murine tumor allografts in vivo and induce rapid cell death in human medulloblastoma. Shown to sensitize human glioma cells to TRAIL-induced apoptosis.
A potent, cell-permeable analog of Cyclopamine (Cat. No. 239803) that specifically inhibits the Hedgehog (Hh) signaling with similar or lower toxicity (IC50 = 20 nM in Shh-LIGHT2 assay; 50 nM in p2Ptch-/-cells; 500 nM in SmoA1-LIGHT cells). Binds to SmoA1 and promotes its exit from the endoplasmic reticulum. Suppresses both the ShhNp-induced pathway activity and SmoA1-induced reporter activity. Shown to sensitize human glioma cells to TRAIL-induced apoptosis. Also available as a 1 mM solution in DMSO (Cat. No. 239807).

Biochem/physiol Actions

Cell permeable: yes
Primary Target
Hh signaling in Shh-light2 assay
Product does not compete with ATP.
Reversible: no
Target IC50: 20 nM against Hedgehog (Hh) signaling in Shh-LIGHT2 assay; 50 nM in p2Ptch-/-cells; 500 nM in SmoA1-LIGHT cells

Packaging

Packaged under inert gas

Warning

Toxicity: Harmful (C)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 2 weeks at -20°C.

Other Notes

Siegelin, M.D. et al. 2009. Neurobiol. Dis.34, 259.
Watkins, D.N., et al. 2003. Nature422, 313.
Berman, D.M., et al. 2002. Science297, 1559.
Chen, J.K., et al. 2002. Proc. Natl. Acad. Sci. USA99, 14071.
Chen, J.K., et al. 2002. Genes Dev.16, 2743.
Frank-Kamenetsky, M., et al. 2002. J. Biol.1, 10.
Taipale, J., et al. 2000. Nature406, 1005.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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