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C4116

Sigma-Aldrich

Cyclopamine hydrate

≥98% (HPLC), solid, Hedgehog signaling pathway inhibitor

Synonym(s):

11-deoxojervine hydrate

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About This Item

Empirical Formula (Hill Notation):
C27H41NO2 · xH2O
CAS Number:
Molecular Weight:
411.62 (anhydrous basis)
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.77

product name

Cyclopamine hydrate, ≥98% (HPLC)

Assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: soluble ≥5 mg/mL
H2O: insoluble

storage temp.

2-8°C

SMILES string

O.C[C@@H]1CN[C@H]2[C@@H](C)[C@@]3(CC[C@H]4[C@@H]5CC=C6C[C@@H](O)CC[C@]6(C)[C@H]5CC4=C3C)O[C@@H]2C1

InChI

1S/C27H41NO2.H2O/c1-15-11-24-25(28-14-15)17(3)27(30-24)10-8-20-21-6-5-18-12-19(29)7-9-26(18,4)23(21)13-22(20)16(27)2;/h5,15,17,19-21,23-25,28-29H,6-14H2,1-4H3;1H2/t15-,17+,19-,20-,21-,23-,24+,25-,26-,27-;/m0./s1

InChI key

KDAGJRDPNXDDSB-HBYCUIHISA-N

Gene Information

human ... EBP(10682)

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General description

Cyclopamine is a steroidal alkaloid, extracted from Veratrum californicum. It prevents tumor cell growth and invasiveness in vitro and in vivo.

Application

Cyclopamine hydrate has been used:
  • as a sonic hedgehog (Shh) inhibitor in various experiments
  • to explore the effects of stress stimulation on the proliferation and differentiation of fibrochondrocytes
  • to study its influence on ocular vessel patterning

Biochem/physiol Actions

Cyclopamine is a Hedgehog signaling pathway inhibitor; inhibits the growth of medulloblastoma cells.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Carlos Andrés Chacón-Martínez et al.
The EMBO journal, 36(2), 151-164 (2016-12-13)
Understanding how complex tissues are formed, maintained, and regenerated through local growth, differentiation, and remodeling requires knowledge on how single-cell behaviors are coordinated on the population level. The self-renewing hair follicle, maintained by a distinct stem cell population, represents an
Regulatory Mechanisms of the Ihh/PTHrP Signaling Pathway in Fibrochondrocytes in Entheses of Pig Achilles Tendon
Han X, et al.
Stem Cells International, 2016 (2016)
Ectodysplasin A regulates epithelial barrier function through sonic hedgehog signalling pathway
Li S, et al.
Journal of Cellular and Molecular Medicine, 22(1), 230-240 (2018)
Loss of pancreas upon activated Wnt signaling is concomitant with emergence of gastrointestinal identity
Munoz-Bravo JL, et al
Testing, 11(10), e0164714-e0164714 (2016)
Introduction to Cancer Metastasis (2016)

Articles

Cancer stem cell media, spheroid plates and cancer stem cell markers to culture and characterize CSC populations.

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n proliferating cells, the cell cycle consists of four phases. Gap 1 (G1) is the interval between mitosis and DNA replication that is characterized by cell growth. Replication of DNA occurs during the synthesis (S) phase, which is followed by a second gap phase (G2) during which growth and preparation for cell division occurs. Together, these three stages comprise the interphase phase of the cell cycle. Interphase is followed by the mitotic (M) phase.

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