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[CAS NO. 4449-51-8] Cyclopamine

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Catalog:	HY-17024
Brand:	MCE
CAS:	4449-51-8

Overview

MDL	MFCD09878269
Molecular Weight	411.62
Molecular Formula	C27H41NO2
SMILES	CC1=C2[C@@]([C@@]3([H])[C@]([C@@]4(C(C[C@@H](O)CC4)=CC3)C)([H])C2)([H])CC[C@@]15[C@@H]([C@@]6([H])[C@](C[C@H](C)CN6)([H])O5)C

For research use only. We do not sell to patients.

27 Publications Citing Use of MCE

[1]Nat Commun. 2022 Jul 13;13(1):4061.
[2]Cell Death Differ. 2021 Jul;28(7):2221-2237.
[3]Cell Death Dis. 2019 Sep 12;10(9):681.
[4]Pharmacol Res. 2021 Jan 26;105460.
[5]Int J Nanomedicine. 2017 Apr 20;12:3267-3280.
[6]Oxid Med Cell Longev. 09 Jul 2021.
[7]J Genet Genomics. 2018 May 20;45(5):237-246.
[8]FASEB J. 2018 Oct;32(10):5703-5715.
[9]Biochem Pharmacol. 2021 May 6;190:114593.
[10]J Cell Mol Med. 2021 Aug;25(16):8015-8027.
[11]J Cell Mol Med. 2021 Jun 2.
[12]iScience. 2019 Sep 27;19:1248-1259.
[13]Front Pharmacol. 2018 Jun 26;9:674.
[14]Cell Death Discov. 2021 May 18;7(1):115.
[15]Life Sci. 2017 Dec 15;191:82-89.
[16]Exp Cell Res. 2021 Jan 15;398(2):112420.
[17]Neural Regen Res. 2023 Jan 30.
[18]Exp Biol Med. 2020 Feb;245(3):213-220.
[19]Neurochem Res. 2016 Apr;41(4):687-95.
[20]J Appl Toxicol. 2023 Jan 7. doi: 10.1002/jat.4436.
[21]J Ovarian Res. 2022 Dec 30;15(1):141.
[22]Biochem Biophys Res Commun. 2020 May 28;526(2):314-320.
[23]Connect Tissue Res. 2020 Jun 10;1-11.
[24]Cancer Biother Radiopharm. 2021 Dec 31.
[25]Hematology. 2022 Dec;27(1):1-10.
[26]Mol Biol Rep. 2022 Dec 1.
[27]Research Square Print. 2022 May.

Summary

Cyclopamine is a Hedgehog ( Hh ) pathway antagonist with an IC ₅₀ of 46 nM in the Hh cell assay. Cyclopamine is also a selective Smo inhibitor.

IC50 & Target

Human Endogenous Metabolite

In Vitro

Treatment with small molecule Hh inhibitors such as HhAntag and the natural product Cyclopamine, both binding to Smo, induces tumor remission in a genetic mouse model of medulloblastoma ^[1] . Cyclopamine is a Hedgehog (Hh) pathway antagonist. Cyclopamine suppresses cell growth. Cyclopamine (3 μM) suppression of Hh pathway activity and growth in digestive tract tumour cell lines correlates with expression of PTCHmRNA ^[2] . Cyclopamine is a steroidal alkaloid that inhibits Hh signalling through direct interaction with Smo ^[3] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Cyclopamine causes durable regression of xenograft tumors. Tumors in Cyclopamine-treated animals, regress completely by 12 days ^[2] . Cyclopamine (1.2 mg) treatment blocks tumour formation of human pancreatic adenocarcinoma cells after transplantation into nude mice ^[3] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Appearance

Solid

Source

Plants
Liliaceae
Veratrum nigrum Linn.

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Solvent & Solubility

In Vitro:

Ethanol : 20 mg/mL ( 48.59 mM ; Need ultrasonic)

DMSO : 10 mg/mL ( 24.29 mM ; ultrasonic and warming and heat to 80°C)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	2.4294 mL	12.1471 mL	24.2943 mL
5 mM	0.4859 mL	2.4294 mL	4.8589 mL
10 mM	0.2429 mL	1.2147 mL	2.4294 mL

* Please refer to the solubility information to select the appropriate solvent.

In Vivo:

1.

Add each solvent one by one: 10% EtOH >> 90% corn oil

Solubility: ≥ 1.67 mg/mL (4.06 mM); Clear solution
2.

Add each solvent one by one: 10% DMSO >> 90% corn oil

Solubility: ≥ 1 mg/mL (2.43 mM); Clear solution
3.

Add each solvent one by one: 10% DMSO >> 40% PEG300 >> 5% Tween-80 >> 45% saline

Solubility: ≥ 0.5 mg/mL (1.21 mM); Clear solution
4.

Add each solvent one by one: 10% DMSO >> 40% PEG300 >> 5% Tween-80 >> 45% saline

Solubility: ≥ 0.5 mg/mL (1.21 mM); Clear solution

* All of the co-solvents are available by MCE.

References

[1] Peukert S, et al. Identification and structure-activity relationships of ortho-biphenyl carboxamides as potent Smoothened antagonists inhibiting the Hedgehog signaling pathway. Bioorg Med Chem Lett, 2009, 19(2), 328-331.
[2] Berman DM, et al. Widespread requirement for Hedgehog ligand stimulation in growth of digestive tract tumours. Nature, 2003, 425(6960), 846-851.
[3] Thayer SP, et al. Hedgehog is an early and late mediator of pancreatic cancer tumorigenesis. Nature, 2003, 425(6960), 851-856.
[4] Ma W, et al. Reduced Smoothened level rescued Aβ-induced memory deficits and neuronal inflammation in animal models of Alzheimer's disease. J Genet Genomics. 2018 May 20;45(5):237-246.
[5] Qi Wan, et al. Overexpression of Laminin α4 Facilitates Proliferation and Migration of Fibroblasts in Knee Arthrofibrosis by Targeting Canonical Shh/Gli1 Signaling. Connect Tissue Res. 2020 May 24.

Synonyms

Spiro[9H-benzo[a]fluorene-9,2′(3′H)-furo[3,2-b]pyridin]-3-ol, 1,2,3,3′a,4,4′,5′,6,6′,6a,6b,7,7′,7′a,8,11,11a,11b-octadecahydro-3′,6′,10,11b-tetramethyl-, (2′R,3S,3′R,3′aS,6′S,6aS,6bS,7′aR,11aS,11bR)-

Cyclopamine

Veratraman-3-ol, 17,23-epoxy-, (3β,23β)-

Jervine, 11-deoxo-

(2′R,3S,3′R,3′aS,6′S,6aS,6bS,7′aR,11aS,11bR)-1,2,3,3′a,4,4′,5′,6,6′,6a,6b,7,7′,7′a,8,11,11a,11b-Octadecahydro-3′,6′,10,11b-tetramethylspiro[9H-benzo[a]fluorene-9,2′(3′H)-furo[3,2-b]pyridin]-3-ol

11-Deoxyjervine

11-Deoxojervine

(-)-Cyclopamine

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