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C-8700 Cyclopamine, Free Base, >99%

[11-Deoxyjervine]

M.W. 411.62

C27H41NO2

[4449-51-8] RTECS:  GY0750000

M.I. 14:  10201

SPECIAL HAZARD:  TERATOGEN.  Gloves and mask should be worn when using this compound.  Care must be taken to prevent contact through all routes of exposure.  Women of childbearing age should be extremely careful in handling cyclopamine!

Storage:  Store at or below -20 ºC.  Solubility:  See below.  Disposal:  A

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• Cyclopamine blocks activation of the Hedgehog response pathway associated with mutations that either activate the proto-oncogene Smoothened (Smo) or inactivate the tumour suppressor Patched (Ptch) both of which encode multipass transmembrane proteins.  Furthermore, it has been demonstrated that the inhibitory effect of cyclopamine results from its direct binding to the Smo heptahelical protein bundle.  Taipale, J., et al.  "Effects of oncogenic mutations in Smoothened and Patched can be reversed by cyclopamine."  Nature 406:  944-945 (2000).  Chen, J.K., et al.  "Inhibition of Hedgehog signaling by direct binding of cyclopamine to Smoothened."  Genes & Dev. 16:  2743-2748 (2002).

• Induces chick embryo malformations associated with the interruption of Sonic hedgehog (Shh)-mediated dorsoventral patterning.  Incardona, J.P., et al.  "The teratogenic Veratrum alkaloid cyclopamine inhibits sonic hedgehog signal transduction."  Development. 125:  3553-3562 (1998).

• Displays anti-tumor properties.  It has been shown to induce apoptosis in both colorectal adenoma- and carcinoma-derived cell lines and in skin basal cell carcinomas.  Qualtrough, D., et al.  "Hedgehog signalling in colorectal tumour cells: induction of apoptosis with cyclopamine treatment."  Int J Cancer. 110:  831-837 (2004).  Tabs, S., and Avci, O.  "Induction of the differentiation and apoptosis of tumor cells in vivo with efficiency and selectivity."  Eur J Dermatol. 14:  96-102 (2004).

• Pregnant cattle, goats, or sheep who graze on the corn lily plant, Veratrum californicum, at the 14th day of gestation (for sheep) can give birth to deformed offspring with a characteristic single eye in the middle of the forehead.  [For example, view www.cybergoat.com/cyclopia/cyclopia.htm.]

  This type of birth defect recalls one of the most unforgettable images in all of mythology, namely Homer's Cyclops (for which cyclopamine was named).  If plants containing cyclopamine or a similar compound existed in the Mediterranean area in ancient times, it would then seem likely that the Cyclops was not merely a product of Homer's imagination but rather was based on known, naturally-occurring birth defects in animals.  Alternatively, this type of birth defect might arise from spontaneous mutation, as may have been the case for a kitten recently reported:  www.samtsai.com/p131.

• CYCLOPAMINE SOLUBILITY: Ethanol is the best cyclopamine solvent for biological use.  A 2% solution (20 mg/mL) can be prepared by warming the cyclopamine in ethanol to 50-60 ºC; boiling is neither necessary nor recommended.  Upon cooling, the cyclopamine remains in solution at room temperature, even if left for several days.  However, storage at -20 ºC is recommended, and at this temperature the cyclopamine will crystallize out of solution.  Upon thawing, the mixture will need to be heated again to redissolve the cyclopamine.

  Methanol and DMSO can also be used as cyclopamine solvents, but solubility in methanol is only about 0.7% (7 mg/mL) at best, and solubility in DMSO is about 0.4% (4 mg/mL).  Substantial heating is again needed to achieve solution with methanol or DMSO, but once the cyclopamine is dissolved it will remain in solution if kept at room temperature.  Storage in either solvent at the recommended -20 ºC will also cause crystallization, as noted above for ethanol, and reheating is necessary after thawing in order to achieve full dissolution.

  Methanol is less desirable than the other two solvents because it is the most volatile; merely standing open in air will lead to slow volume loss and consequent artefactual increase in concentration of the solution.  DMSO is the least volatile solvent and is preferred if a stock solution need only be 4 mg/mL or less.  Ethanol is a compromise between volatility and achievable concentration.

• We notice that another vendor, Toronto Research Chemicals (TRC-Canada), publishes an advertising claim that they are "the pirimary source" of cyclopamine, specifically that "TRC is the Primary Manufacturer" of cyclopamine.  We believe this claim is simply false, and is very misleading to researchers.  LC Labs manufactures its own cyclopamine, and we are aware of many other primary manufacturers worldwide.  Thus, while TRC-Canada may be "a" primary manufacturer of cyclopamine, they are certainly not "the" primary manufacturer.

• Sold for laboratory or manufacturing purposes only; not for human, veterinary, food, or household use.