Cyclopamine

Catalog No.S1146 Synonyms: 11-deoxojervine

For research use only.

Cyclopamine (11-deoxojervine) is a specific Hedgehog (Hh) signaling pathway antagonist of Smoothened (Smo) with IC50 of 46 nM in TM3Hh12 cells.

Cyclopamine Chemical Structure

CAS No. 4449-51-8

Selleck's Cyclopamine has been cited by 102 publications

Purity & Quality Control

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Biological Activity

Description Cyclopamine (11-deoxojervine) is a specific Hedgehog (Hh) signaling pathway antagonist of Smoothened (Smo) with IC50 of 46 nM in TM3Hh12 cells.
Targets
Smoothened [1]
(TM3Hh12 cells)
46 nM
In vitro

Cyclopamine inhibits the Hedgehog signaling pathway with an IC50 of 46 nM, and blocks the activity of human Smo receptor expressed in CHO-K1 cells in [3H]Hh-Ag binding assay with an IC50 of 280 nM. [1] Cyclopamine significantly inhibits Hedgehog pathway activity in a dose-dependent manner in gut-derived tumor cell lines expressing Patched (PTCH) mRNA, and induces growth inhibition of those tumor cell lines by 75-95% at the concentration of 3 μM, but ineffective towards the colon tumor cells without PTCH mRNA expression, suggesting the effects of Cyclopamine treatment are Hedgehog pathway related rather than generally cytotoxic. [2] By blocking Hedgehog signaling through direct interaction with Smo, Cyclopamine (10 μM) inhibits the proliferation of SMOhigh Cyclopamine-responsive cell lines L3.6sl and Panc 05.04 by 75-80%, and increases the apoptosis by 2.5- to 3.5-fold, without affecting the BxPC3-SMOlow cell line. [3] Cyclopamine treatment significantly decreases of Snail mRNA and increasea E-cadherin transcripts in the E3LZ10.7 cell line. Independent of inhibition of cell growth, Cyclopamine treatment significantly inhibits the invasive phenotype of Hedgehog-dependent L3.6pl cells, causing a >500-fold reduction in the number of transmigrating cells, but not that of the Hedgehog-independent cell line Panc-1. [4]

Cell Data
Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
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HAL-01 NHPmb29Iem:5dHigTY5pcWKrdHnvckBCe3OjeR?= NH\TT3NKSzVyPUO3PU45OzhizszN NESwXHc9[SC2YYLn[ZQ:L1:kbHHub{chcHKnZk2nbJR1eHN8Lz;3e5cv\WKrLnHjMpVsN2OqZX3icE9kd22yb4Xu[H9z\XCxcoTfZ4Fz\C:FSFXNRmwzPTRzMkmvK|5USU6JRWK8M4E,
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CHO NGC0ToxHfW6ldHnvckBie3OjeR?= M{C4O2FvfGGpb37pd5Qh[WO2aY\peJkh[XRiaIXtZY4hW22xIILlZ4VxfG:{IHX4dJJme3OnZDDpckBEUE9iY3XscJMh[nliW{PIYWhpNUGpIHLpcoRqdmdiYYPzZZktKEmFNUCgQUAxNjJ6IN88UU4> M2TLTVxiKHSjcnfleF0oZ2KuYX7rK{BpemWoPTfoeJRxezpxL4D1Zo1m\C6wY3LpMo5tdS6waXiu[493NzF7MEmxOVU6Lz5zOUC5NVU2QTxxYU6=
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Shh-light2 M2nJO2Z2dmO2aX;uJIF{e2G7 NHHBRmRKdmirYnn0bY9vKG:oIGPtc{1u\WSrYYTl[EBJcCC|aXfuZYxqdmdiaX6gbJVu[W5iU3joMYxq\2i2MjDj[YxteyCkeTDseYNq\mW{YYPlJJJmeG:{dHXyJIdmdmViYYPzZZktKEmFNUCgQUAxNjNizszNMi=> MnTlQIEhfGG{Z3X0QUdg[myjbnunJIhz\WZ;J3j0eJB{Qi9xcIXicYVlNm6lYnmucoxuNm6raD7nc5YwOjJ{Nki1OVEoRjJ{Mk[4OVUyRC:jPh?=
M210B4 MnrQSpVv[3Srb36gZZN{[Xl? MWWyOEBpenN? MnrDTY5pcWKrdHnvckBw\iCKZXTn[Yhw\yC|aXfuZYxqdmdiaX6gcY92e2ViTUKxNGI1KGOnbHzzJIF{e2W|c3XkJIF{KGSxd37y[Yd2dGG2aX;uJI9nKFC2Y3igcXJPSSCneIDy[ZN{cW:wIHHmeIVzKDJ2IHjyd{BjgSCUVD3QR3Ih[W6jbInzbZMtKEmFNUCgQUAxNjR|IN88UU4> NW\ybJppRGFidHHy[4V1RSehYnzhcosoKGi{ZX[9K4h1fHC|Oj:vdJVjdWWmLn7jZokvdmyvLn7pbE5od3ZxMkS5NFA4OTZpPkK0PVAxPzF4PD;hQi=>
Shh-Light 2 MlXaSpVv[3Srb36gZZN{[Xl? MViyJIRigXN? NF\CT4dCdnSjZ3;ubZN1KGGldHn2bZR6KGG2IGPtc{BqdiCvb4Xz[UBUcGhvTHnnbJQhOiClZXzsd{Bie3Onc4Pl[EBieyCrbnjpZol1cW:wIH;mJHNpcC2rbnT1Z4VlKEeuaUGtdoVxd3K2ZYKgZYN1cX[rdImgZYZ1\XJiMjDkZZl{KGK7IHT1ZYwudHWlaX\ldoF{\SC{ZYDvdpRmeiCpZX7lJI1mfGixZDygTWM2OCB;IECuOFg1KM7:TT6= NV[5eIxqRGFidHHy[4V1RSehYnzhcosoKGi{ZX[9K4h1fHC|Oj:vdJVjdWWmLn7jZokvdmyvLn7pbE5od3ZxMkOwOlM2OjJpPkKzNFY{PTJ{PD;hQi=>
Shh Light2 MknTSpVv[3Srb36gZZN{[Xl? Mof4TY5pcWKrdHnvckBw\iCVSFigbY4hdW:3c3WgV4hpKEyrZ3j0NkBk\WyuczDifUBIVElvcnXzdI9ve2m4ZTDmbZJm\my7IHz1Z4ln\XKjc3WgdoVxd3K2ZYKg[4Vv\SCjc4PhfUwhTUN3MDC9JFAvPSEQvF2u MWK8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8yQTNyOUC4NEc,OTl|MEmwPFA9N2F-
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C3H10T1/2 NHHSOFhHfW6ldHnvckBie3OjeR?= MlK3OkBpenN? NFjNRVJKdmirYnn0bY9vKG:oIGPBS{1qdmS3Y3XkJIRq\m[ncnXueIlifGmxbjDv[kBud3W|ZTDt[ZNmdmOqeX3hcEBxdHW{aYDveIVvfCCFM1ixNHQyNzJiY3XscJMhfG9iYXzrZYxqdmVicHjvd5Bp[XSjc3WgdI9{cXSrdnWgc4V{\W:kbHHzeJMh[W[2ZYKgOkBpenNuIFnDOVAhRSByLk[yJO69VS5? MlLCQIEhfGG{Z3X0QUdg[myjbnunJIhz\WZ;J3j0eJB{Qi9xcIXicYVlNm6lYnmucoxuNm6raD7nc5YwOjJ{Nki1OVEoRjJ{Mk[4OVUyRC:jPh?=
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medulloblastoma cells Mn\rRY51cXC{b3zp[oVz[XSrdnWgZZN{[Xl? NUDWRXp{SW62aYDyc4xq\mW{YYTpeoUh[WO2aY\peJkh[WejaX7zeEBud3W|ZTDt[YR2dGyxYnzhd5RwdWFiY3XscJMhcGG{Yn;ybY5oKGindHXyc5p6\2:3czDweINpOSCpZX7lJIJ6KE2WVDDhd5NigSxiRVO1NEA:KDFizszNMi=> NYrKW2g2RGFidHHy[4V1RSehYnzhcosoKGi{ZX[9K4h1fHC|Oj:vdJVjdWWmLn7jZokvdmyvLn7pbE5od3ZxMUe0NVc3OzFpPkG3OFE4PjNzPD;hQi=>
CHO NHGyVVFHfW6ldHnvckBie3OjeR?= NVXOTYdNSW62YXfvcol{fCCjY4Tpeol1gSCjdDDtc5V{\SCVbX:gdoVk\XC2b4Kg[ZhxemW|c3XkJIlvKEOKTzDj[YxteyCkeTDbN2heUGhvQXegZolv\GmwZzDhd5NigSxiSVO1NEA:KDFwMjFOwG0v M2XNRVxiKHSjcnfleF0oZ2KuYX7rK{BpemWoPTfoeJRxezpxL4D1Zo1m\C6wY3LpMo5tdS6waXiu[493NzF7MEmxOVU6Lz5zOUC5NVU2QTxxYU6=
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MEF NHPG[XVHfW6ldHnvckBie3OjeR?= MoDkTY5pcWKrdHnvckBw\iCVbX:gbY4hdW:3c3WgVJRkcC2mZX\pZ4lmdnRiTVXGJINmdGy|IHHzd4V{e2WmIHHzJIlvcGmkaYTpc44hd2ZiU3joMYlv\HWlZXSgS4xqOSC2cnHud4NzcXC2aX;uZYwh[WO2aY\peJktKEmFNUCgQUAyNjVizszNMi=> NFHpfmQ9[SC2YYLn[ZQ:L1:kbHHub{chcHKnZk2nbJR1eHN8Lz;weYJu\WRwbnPibU5vdG1wbnnoModwfi9{M{C3OFU1OSd-MkOwO|Q2PDF:L3G+
MEF MW\GeY5kfGmxbjDhd5NigQ>? MUGzNEBpenN? MW\Jcohq[mm2aX;uJI9nKFOvbzDpckBud3W|ZTDQeINpNWSnZnnjbYVvfCCPRV[gZ4VtdHNiYYPz[ZN{\WRiYYOgbY5pcWKrdHnvckBw\iCVaHitbY5lfWOnZDDHcIkuemW|cH;ud4l3\SCkZYTh[4Ft[WO2b4Pp[IF{\SCjY4Tpeol1gSCjZoTldkA{OCCqcoOgZpkhSmW2YVfMc{Bie3OjeTygTWM2OCB;IEGuPUDPxE1w NX7EflVoRGFidHHy[4V1RSehYnzhcosoKGi{ZX[9K4h1fHC|Oj:vdJVjdWWmLn7jZokvdmyvLn7pbE5od3ZxMkOwO|Q2PDFpPkKzNFc1PTRzPD;hQi=>
neural precursor cells NYH1[pl7SW62aYDyc4xq\mW{YYTpeoUh[XO|YYm= Ml\xRY51cXC{b3zp[oVz[XSrdnWgZYN1cX[rdImgZYdicW6|dDDtc5V{\SCwZYXyZYwheHKnY4Xyd49zKGOnbHzzJIJ6KGOxbH;ufUBnd3KvYYTpc44h[XO|YYmsJGVEPTBiPTCxN{41PCEQvF2u NYDNTFAzRGFidHHy[4V1RSehYnzhcosoKGi{ZX[9K4h1fHC|Oj:vdJVjdWWmLn7jZokvdmyvLn7pbE5od3ZxMUe0NVc3OzFpPkG3OFE4PjNzPD;hQi=>
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Assay
Methods Test Index PMID
Western blot Snail / E-cadherin / Slug / Vimentin ; Gli1 / TGF-β1 / CXCR4 ; NF-κB / Cyclin D1 / MMP2 / MMP9 26859575 26137001 23599805
Immunofluorescence PCNA / β-catenin ; Vimentin 28747625 24553082
In vivo Administration of Cyclopamine at dose of 50 mg/kg/day for 22 days eradicates the HUCCT1 xenografts in mice with no obvious adverse effects. [2] Cyclopamine treatment at dose of 1.2 mg for 7 days induces significant apoptosis of tumor cells and decreases the tumor mass by 50-60% in Panc 05.04- and L3.6sl-derived tumors, respectively, but not in the BxPC3-SMOlow tumors. [3] Administration of Cyclopamine alone profoundly inhibits tumor metastases in xenografts of E3LZ10.7 and L3.6pl, and completely abrogates metastases when in combination of gemcitabine. [4]

Protocol (from reference)

Kinase Assay:[1]
  • Hedgehog cell assay:

    This assay measures the end stage of the Hh signaling pathway, that is, the transcriptional modulation of Gli, using Luciferase as readout (Gli-Luc assay). Cyclopamine is prepared for assay by serial dilution in DMSO and then added to empty assay plates. TM3Hh12 cells (TM3 cells containing Hh-responsive reporter gene construct pTA-8xGli-Luc) are resuspended in F12 Ham's/DMEM (1:1) containing 5% FBS and 15 mM Hepes pH 7.3, added to assay plates and incubated with Cyclopamine for approximately 30 minutes at 37 °C in 5% CO2. 1 nM Hh-Ag 1.5 is then added to assay plates and incubated at 37 °C in the presence of 5% CO2. After 48 hours, either Bright-Glo or MTS reagent is added to the assay plates and luminescence or absorbance at 492 nm is determined. IC50 value, defined as the inflection point of the logistic curve, is determined by non-linear regression of the Gli-driven luciferase luminescence or absorbance signal from MTS assay vs log10 (concentration) of Cyclopamine using the R statistical software pack

Cell Research:[2]
  • Cell lines: SEG1, OE33, KYAE, KYSE180, SNU1, AGS, SNU16, NCI-N-87, HUCCT1, PANC1, PL5, PL6, BXPC3, HS766T, KYSE150, GBD1, DLD1, and HCT116
  • Concentrations: Dissolved in DMSO, final concentration 3 μM
  • Incubation Time: 4 days
  • Method: Cells are exposed to Cyclopamine in 96-well plates. Cell viability is measured by MTS (soluble tetrazolium salt) assay. Viable cell mass is determined by optical density measurements at 490 nm (OD490) at 2 and 4 days using the CellTiter96 colorimetric assay. Relative growth is calculated as OD (day 4)﹣OD (day 2)/OD (day 2).
  • (Only for Reference)
Animal Research:[2]
  • Animal Models: Athymic (nude) mice inoculated subcutaneously with HUCCT1 cells
  • Dosages: 50 mg/kg/day
  • Administration: Subcutaneous injection
  • (Only for Reference)

Solubility (25°C)

In vitro

DMF 10 mg/mL warmed
(24.29 mM)
Ethanol 2 mg/mL warmed
(4.85 mM)
DMSO Insoluble

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 411.62
Formula

C27H41NO2

CAS No. 4449-51-8
Storage 3 years -20°C powder
2 years -80°C in solvent
Smiles CC1CC2C(C(C3(O2)CCC4C5CC=C6CC(CCC6(C5CC4=C3C)C)O)C)NC1

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)

mg/kg g μL

Step 2: Enter the in vivo formulation (This is only the calculator, not formulation. Please contact us first if there is no in vivo formulation at the solubility Section.)

% DMSO % % Tween 80 % ddH2O
%DMSO %

Calculation results:

Working concentration: mg/ml;

Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )

Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.

Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.

Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such
as vortex, ultrasound or hot water bath can be used to aid dissolving.

Molarity Calculator

Mass Concentration Volume Molecular Weight

Tech Support

Answers to questions you may have can be found in the inhibitor handling instructions. Topics include how to prepare stock solutions, how to store inhibitors, and issues that need special attention for cell-based assays and animal experiments.

Handling Instructions

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Frequently Asked Questions

Question 1:
How to reconstitute the compound for in vivo use in mice?

Answer:
One paper dissolved this drug in DMSO, and diluted in saline: Berman DM, et al. Nature, 2003, 425(6960), 846-851. Alternatively, you can try this vehicle: 10% DMSO+30% PEG 300+5% Tween 80+ddH2O for P.O. When preparing the solution, please dissolve the compound in DMSO clearly first. Then add PEG300 and Tween, after they mixed well, dilute with water.

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