A potent inhibitor of hedgehog signaling
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Cyclopamine-KAAD

Item No. 20943

Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[6-[[2-[(3'R,3'aS,6'S,6aS,6bS,7'aR,2'R,11aS,11bR)-1,2,3,3',3'a,4,5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-octadecahydro-3',6',10,11b-tetramethyl-3-oxospiro[9H-benzo[a]fluorene-9,2'(4'H)-furo[3,2-b]pyridin]-4'-yl]ethyl]amino]-6-oxohexyl]-benzenepropanamide
CAS Number
306387-90-6
Molecular Formula
C44H63N3O4
Formula Weight
698.0
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly solubleMethanol: Slightly soluble
SMILES
CC1=C2[C@](CC[C@@]31O[C@@](C[C@H](C)CN4CCNC(CCCCCNC(CCC5=CC=CC=C5)=O)=O)([H])[C@]4([H])[C@H]3C)([H])[C@]6([H])CC=C7CC(CC[C@]7(C)[C@@]6([H])C2)=O
InChi Code
InChI=1S/C44H63N3O4/c1-29-25-39-42(47(28-29)24-23-46-40(49)13-9-6-10-22-45-41(50)17-14-32-11-7-5-8-12-32)31(3)44(51-39)21-19-35-36-16-15-33-26-34(48)18-20-43(33,4)38(36)27-37(35)30(44)2/h5,7-8,11-12,15,29,31,35-36,38-39,42H,6,9-10,13-14,16-28H2,1-4H3
InChi Key
WDHRPWOAMDJICD-FOAQWNCLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    500 µg

    $528

    Add

    1 mg

    $956

    Add
    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    Product Description

    Cyclopamine-KAAD is a potent inhibitor of hedgehog signaling with an IC50 value of 20 nM in a Shh-LIGHT2 assay.1 It blocks binding of BODIPY-cyclopamine to cells expressing Smoothened (Smo) in a dose-dependent manner. Cyclopamine-KAAD is cell-permeable and binds to SmoA1 to promote its exit from the endoplasmic reticulum. It inhibits the invasion and migration (45.9 and 43.3% inhibition, respectively) of Bel-7402 hepatocarcinoma cells and decreases the expression of nuclear glioma-associated oncogene 1 (Gli1) and cytosolic MMP-9, pERK1, and pERK2 proteins in a dose-dependent manner.2 Cyclopamine-KAAD also increases TRAIL-mediated cell death in NCH82 and NCH89 human glioblastoma cultures and upregulates expression of the death receptors DR4 and DR5 in LN229 and U251 glioma cells.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chen, J.K., Taipale, J., Cooper, M.K., et al. Inhibition of Hedgehog signaling by direct binding of cyclopamine to Smoothened. Genes Dev. 16(21), 2743-2748 (2002).

    2. Lu, J.T., Zhao, W.D., He, W., et al. Hedgehog signaling pathway mediates invasion and metastasis of hepatocellular carcinoma via ERK pathway. Acta Pharmacol. Sin. 33(5), 691-700 (2012).

    3. Siegelin, M.D., Siegelin, Y., Habel, A., et al. KAAD-cyclopamine augmented TRAIL-mediated apoptosis in malignant glioma cells by modulating the intrinsic and extrinsic apoptotic pathway. Neurobiol. Dis. 34(2), 259-266 (2009).