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ProductsBack/Cyclopamine [4449-51-8]
Chemical Structure
Chemical Structure
Chemical Structure

Cyclopamine [4449-51-8]

Research Use Only
AG-CN2-0028
AdipoGen Life Sciences
CAS Number4449-51-8
DownloadMSDS
Product group Chemicals
Estimated Purity>98%
Molecular Weight411.6
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Cyclopamine
  • Delivery Days Customer
    10
  • CAS Number
    4449-51-8
  • Certification
    Research Use Only
  • Estimated Purity
    >98%
  • Hazard Information
    Warning
  • Molecular Formula
    C27H41NO2
  • Molecular Weight
    411.6
  • Scientific Description
    Cell permeable steroidal alkaloid. Specific sonic hedgehog (Shh) signaling pathway inhibitor. Directly interacts/inhibits Smo (smoothened) [1-4]. Teratogenic [1] and antitumor compound. Inhibits tumor cell growth and progression. Shows selective activity against Shh-dependent tumors [5-11]. Blocks abnormal cell growth associated with oncogenic mutations of Ptch and Smo in fibroblasts [2]. Arrests cell cycle at G0/G1 [6]. Apoptosis inducer [8]. - Chemical. CAS: 4449-51-8. Formula: C27H41NO2. MW: 411.6. Isolated from Veratrum californicum. Cell permeable steroidal alkaloid. Specific sonic hedgehog (Shh) signaling pathway inhibitor. Directly interacts/inhibits Smo (smoothened). Teratogenic and antitumor compound. Inhibits tumor cell growth and progression. Shows selective activity against Shh-dependent tumors. Blocks abnormal cell growth associated with oncogenic mutations of Ptch and Smo in fibroblasts. Arrests cell cycle at G0/G1. Apoptosis inducer.
  • SMILES
    [H][C@@]12C[C@H](C)CN[C@@]1([H])[C@@H](C)[C@@]1(CC[C@]3([H])C(C[C@@]4([H])[C@@]3([H])CC=C3C[C@@H](O)CC[C@]43C)=C1C)O2
  • Storage Instruction
    -20°C,2°C to 8°C
  • UNSPSC
    12352200

References

  • The teratogenic Veratrum alkaloid cyclopamine inhibits sonic hedgehog signal transduction: J.P. Incardona, et al.; Development 125, 3553 (1998)
  • Pancreas development is promoted by cyclopamine, a hedgehog signaling inhibitor: S.K. Kim & D.A. Melton; PNAS 95, 13036 (1998)
  • Effects of oncogenic mutations in Smoothened and Patched can be reversed by cyclopamine: J. Taipale, et al; Nature 406, 1005 (2000)
  • Inhibition of Hedgehog signaling by direct binding of cyclopamine to Smoothened: J.K. Chen, et al.; Genes Dev. 16, 2743 (2002)
  • Hedgehog signalling in colorectal tumour cells: induction of apoptosis with cyclopamine treatment: D. Qualtrough, et al.; Int. J. Cancer 110, 831 (2004)
  • The hedgehog pathway inhibitor cyclopamine increases levels of p27, and decreases both expression of IGF-II and activation of Akt in PC-3 prostate cancer cells: R.J. Levitt, et al.; Cancer Lett. 255, 300 (2007)
  • Cyclopamine-mediated hedgehog pathway inhibition depletes stem-like cancer cells in glioblastoma: E.E. Bar, et al.; Stem Cells 25, 2524 (2007)
  • The hedgehog inhibitor cyclopamine induces apoptosis in leukemic cells in vitro: J. Warzecha, et al.; Leuk. Lymph. 49, 2383 (2008)
  • Cyclopamine inhibition of human breast cancer cell growth independent of Smoothened (Smo): X. Zhang, et al.; Breast Cancer Res. Treat. 115, 505 (2009)
  • Cyclopamine and hedgehog signaling: chemistry, biology, medical perspectives: P. Heretsch, et al.; Chem. Int. Ed. Engl. 49, 3418 (2010) (Review)