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S2951

Sigma-Aldrich

Stauprimide

≥98% (HPLC)

Synonym(s):

N-Benzoyl-7-oxo Staurosporine

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About This Item

Empirical Formula (Hill Notation):
C35H28N4O5
CAS Number:
154589-96-5
Molecular Weight:
584.62
UNSPSC Code:
12352200
PubChem Substance ID:
329824527
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: >20 mg/mL

originator

Novartis

storage temp.

−20°C

SMILES string

CO[C@@H]1[C@@H](CC2O[C@]1(C)n3c4ccccc4c5c6C(=O)NC(=O)c6c7c8ccccc8n2c7c35)N(C)C(=O)c9ccccc9

InChI

1S/C35H28N4O5/c1-35-31(43-3)23(37(2)34(42)18-11-5-4-6-12-18)17-24(44-35)38-21-15-9-7-13-19(21)25-27-28(33(41)36-32(27)40)26-20-14-8-10-16-22(20)39(35)30(26)29(25)38/h4-16,23-24,31H,17H2,1-3H3,(H,36,40,41)/t23-,24+,31-,35+/m1/s1

InChI key

MQCCJEYZKWZQHU-JTPSWESPSA-N

Application

Stauprimide may be used to study the signaling involved in differentiation of stem cells.

Biochem/physiol Actions

Stauprimide is an enhancer stem cell differentiation into endoderm. In vitro differentiation of embryonic stem cells is of great interest to regenerative medicine, and current protocols are labor-intensive and expensive. Small molecules that induce or enhance differentiation are highly desired. High-content screening identified compounds that enhance endodermal differentiation in the presence of low levels of Activin A. Stauprimide increased definitive endodermal markers but not markers for visceral/parietal endoderm or mesoderm. Stauprimide-differentiated cells could be further differentiated into hepatocytes. Stauprimide treatment during differentiation decreased the concentration of Activin A required for definitive endoderm formation, and it eliminated the need for serum. The mechanism of action of stauprimide is to sensitize cells for differentiation. Stauprimide enabled differentiation into other cell lineages under varying differentiation conditions, including neurons, hematopoietic mesoderm, beating cardiac myocytes, and skeletal muscle. The cellular target of stauprimide was determined to be inhibition of NME2 transcription factor translocation to the nucleus, leading to down-regulation of c-Myc expression.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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Shoutian Zhu et al.
Cell stem cell, 4(5), 416-426 (2009-05-12)
Embryonic stem cells (ESCs) are an attractive source of cells for disease modeling in vitro and may eventually provide access to cells/tissues for the treatment of many degenerative diseases. However, applications of ESC-derived cell types are largely hindered by the
Kenneth S Zaret
Cell stem cell, 4(5), 373-374 (2009-05-12)
Several recent reports, including two Cell Stem Cell papers (Zhu et al., 2009 [this issue]; Borowiak et al., 2009), screened small molecule libraries for compounds that promote embryonic stem cell differentiation. Their combined success helps bypass challenges associated with using

Articles

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