Stemolecule™ KAAD-Cyclopamine

Stemolecule™ KAAD-Cyclopamine

Stemolecule™ KAAD-Cyclopamine is a sonic hedgehog antagonist known to target Smoothened¹. Hedgehog signaling is involved in embryogenesis as well as cancer progression². KAAD-Cyclopamine has been utilized to halt the migration or proliferation of a variety of cancer cells (e.g. esophageal³, gastrointestinal⁴, hepatic⁵ and pancreatic⁶ cancer).

References

1. Pasca di Magliano, M., Hebrok, M. (2003) Hedgehog signalling in cancer formation and maintenance. Nat Rev Cancer 3: 903-11.
2. Jiang, J., Hui, C.C. (2008) Hedgehog signaling in development and cancer. Dev Cell 15: 801-12.
3. Ma, X., Chen, K., Huang, S., Zhang, X., Adegboyega, P.A., Evers, B.M., Zhang, H., Xie, J. (2005) Frequent activation of the hedgehog pathway in advanced gastric adenocarcinomas. Carcinogenesis 26: 1698-705.
4. Ma, X., Sheng, T., Zhang, Y., Zhang, X., He, J., Huang, S., Chen, K., Sultz, J., Adegboyega, P.A., Zhang, H., Xie, J. (2006) Hedgehog signaling is activated in subsets of esophageal cancers. Int J Cancer 118: 139-48.
5. Sicklick, J.K., Li, Y.X., Jayaraman, A., Kannangai, R., Qi, Y., Vivekanandan, P., Ludlow, J.W., Owzar, K., Chen, W., Torbenson, M.S., Diehl, A.M. (2006) Dysregulation of the Hedgehog pathway in human hepatocarcinogenesis. Carcinogenesis 27: 748-57.
6. Cheng, W.T., Xu, K., Tian, D.Y., Zhang, Z.G., Liu, L.J., Chen, Y. (2009) Role of Hedgehog signaling pathway in proliferation and invasiveness of hepatocellular carcinoma cells. Int J Oncol 34: 829-36.

For research use only. Not for use in diagnostic procedures. Not for resale.

Stemolecule™ KAAD-Cyclopamine

Alternate Names	3-Keto-N-(aminoethyl-aminocaproyl-dihydrocinnamoyl)cyclopamine; Cyclopamine-KAAD; Shh Signaling Antagonist II; N-[2-[(3'R,7'aR)-3',6',10,11b-tetramethyl-3-oxospiro[1,2,4,6,6a,6b,7,8, 11,11a-decahydrobenzo[a]fluorene-9,2'-3,3a,5,6,7,7a-hexahydrofuro[3, 2-b]pyridine]-4'-yl]ethyl]-6-(3-phenylpropanoylamino)hexanamide
Chemical Formula	C44H63N3O4
Structure
Molecular Weight	697.99
CAS Number	306387-90-6
Purity	95%
Formulation	Pale yellow solid
Solubility	Soluble in DMSO (100 mM), ethanol (1.4 mM), or methanol (1.4 mM). For a 1 mM concentrated stock solution, reconstitute the compound by adding 143 µl of DMSO to the entire contents of the vial. Note: for most cells, the maximum tolerance to DMSO is <0.5%.
Storage	Store at 4°C. Protect from light. Following reconstitution, store aliquots at -20°C.
Stability	Stock solutions stable at -20°C for 6 months.
Quality Control	The purity of KAAD-Cyclopamine was determined by HPLC analysis. The accurate mass and structure of KAAD-Cyclopamine was determined by mass spectrometry and NMR, respectively. Cellular toxicity of KAAD-Cyclopamine was tested on mouse embryonic stem cells.
References	Pasca di Magliano, M., Hebrok, M. (2003) Hedgehog signalling in cancer formation and maintenance. Nat Rev Cancer 3: 903-11. Jiang, J., Hui, C.C. (2008) Hedgehog signaling in development and cancer. Dev Cell 15: 801-12. Ma, X., Chen, K., Huang, S., Zhang, X., Adegboyega, P.A., Evers, B.M., Zhang, H., Xie, J. (2005) Frequent activation of the hedgehog pathway in advanced gastric adenocarcinomas. Carcinogenesis 26: 1698-705. Ma, X., Sheng, T., Zhang, Y., Zhang, X., He, J., Huang, S., Chen, K., Sultz, J., Adegboyega, P.A., Zhang, H., Xie, J. (2006) Hedgehog signaling is activated in subsets of esophageal cancers. Int J Cancer 118: 139-48. Sicklick, J.K., Li, Y.X., Jayaraman, A., Kannangai, R., Qi, Y., Vivekanandan, P., Ludlow, J.W., Owzar, K., Chen, W., Torbenson, M.S., Diehl, A.M. (2006) Dysregulation of the Hedgehog pathway in human hepatocarcinogenesis. Carcinogenesis 27: 748-57. Cheng, W.T., Xu, K., Tian, D.Y., Zhang, Z.G., Liu, L.J., Chen, Y. (2009) Role of Hedgehog signaling pathway in proliferation and invasiveness of hepatocellular carcinoma cells. Int J Oncol 34: 829-36.

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