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239804 Cyclopamine-KAAD - Calbiochem

239804
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Overview

Replacement Information

Key Spec Table

Empirical Formula
C₄₄H₆₃N₃O₄

Pricing & Availability

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239804-500UGCN
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      Glass bottle 500 μg
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      Description
      OverviewA 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).
      Catalogue Number239804
      Brand Family Calbiochem®
      Synonyms3-Keto-N-(aminoethyl-aminocaproyl-dihydrocinnamoyl)cyclopamine, KAAD-Cyclopamine, Shh Signaling Antagonist II
      References
      ReferencesSiegelin, M.D. et al. 2009. Neurobiol. Dis. 34, 259.
      Watkins, D.N., et al. 2003. Nature 422, 313.
      Berman, D.M., et al. 2002. Science 297, 1559.
      Chen, J.K., et al. 2002. Proc. Natl. Acad. Sci. USA 99, 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. Nature 406, 1005.
      Product Information
      ATP CompetitiveN
      FormPale yellow solid
      Hill FormulaC₄₄H₆₃N₃O₄
      Chemical formulaC₄₄H₆₃N₃O₄
      ReversibleN
      Structure formula ImageStructure formula Image
      Quality LevelMQ100
      Applications
      Biological Information
      Primary TargetHh signaling in Shh-light2 assay
      Primary Target IC<sub>50</sub>20 nM against Hedgehog (Hh) signaling in Shh-LIGHT2 assay; 50 nM in p2Ptch-/-cells; 500 nM in SmoA1-LIGHT cells
      Purity≥70% by HPLC (sum of two isomers)
      Physicochemical Information
      Cell permeableY
      Dimensions
      Materials Information
      Toxicological Information
      Safety Information according to GHS
      Safety Information
      R PhraseR: 20/21/22

      Harmful by inhalation, in contact with skin and if swallowed.
      S PhraseS: 22-36/37

      Do not breathe dust.
      Wear suitable protective clothing and gloves.
      Product Usage Statements
      Storage and Shipping Information
      Ship Code Shipped with Blue Ice or with Dry Ice
      Toxicity Harmful
      Storage -20°C
      Protect from Light Protect from light
      Do not freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 2 weeks at -20°C.
      Packaging Information
      Packaged under inert gas Packaged under inert gas
      Transport Information
      Supplemental Information
      Specifications

      Documentation

      Cyclopamine-KAAD - Calbiochem SDS

      Title

      Safety Data Sheet (SDS) 

      Cyclopamine-KAAD - Calbiochem Certificates of Analysis

      TitleLot Number
      239804

      References

      Reference overview
      Siegelin, M.D. et al. 2009. Neurobiol. Dis. 34, 259.
      Watkins, D.N., et al. 2003. Nature 422, 313.
      Berman, D.M., et al. 2002. Science 297, 1559.
      Chen, J.K., et al. 2002. Proc. Natl. Acad. Sci. USA 99, 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. Nature 406, 1005.

      Citations

      Title
    • Siegelin, M.D. et al. 2009. Neurobiol. Dis. 34, 259.
    • Data Sheet

      Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

      Revision27-February-2012 RFH
      Synonyms3-Keto-N-(aminoethyl-aminocaproyl-dihydrocinnamoyl)cyclopamine, KAAD-Cyclopamine, Shh Signaling Antagonist II
      DescriptionA 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.
      FormPale yellow solid
      Intert gas (Yes/No) Packaged under inert gas
      Chemical formulaC₄₄H₆₃N₃O₄
      Structure formulaStructure formula
      Purity≥70% by HPLC (sum of two isomers)
      SolubilityDMSO (5 mg/ml), Ethanol (1 mg/ml), or Methanol (1 mg/ml)
      Storage -20°C
      Protect from light
      Do Not Freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 2 weeks at -20°C.
      Toxicity Harmful
      ReferencesSiegelin, M.D. et al. 2009. Neurobiol. Dis. 34, 259.
      Watkins, D.N., et al. 2003. Nature 422, 313.
      Berman, D.M., et al. 2002. Science 297, 1559.
      Chen, J.K., et al. 2002. Proc. Natl. Acad. Sci. USA 99, 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. Nature 406, 1005.
      Citation
    • Siegelin, M.D. et al. 2009. Neurobiol. Dis. 34, 259.