Stauprimide

Inhibits NME2 nuclear translocation; primes ESCs for differentiation CAS# 154589-96-5

Stauprimide

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Quality Control of Stauprimide

Number of papers citing our products

Chemical structure

Stauprimide

3D structure

Chemical Properties of Stauprimide

Cas No. 154589-96-5 SDF Download SDF
PubChem ID 46245328 Appearance Powder
Formula C35H28N4O5 M.Wt 584.62
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in DMSO > 10 mM
Chemical Name N-[(2S,3R,4R,6R)-3-methoxy-2-methyl-16,18-dioxo-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14,19,21,23,25,27-nonaen-4-yl]-N-methylbenzamide
SMILES CC12C(C(CC(O1)N3C4=CC=CC=C4C5=C6C(=C7C8=CC=CC=C8N2C7=C53)C(=O)NC6=O)N(C)C(=O)C9=CC=CC=C9)OC
Standard InChIKey MQCCJEYZKWZQHU-MPRCCEKMSA-N
Standard InChI 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Stauprimide

DescriptionSmall molecule that primes embryonic stem cells (ESCs) for differentiation. Interacts with NME2 and inhibits its nuclear translocation. Increases the efficiency of directed differentiation of mouse and human ESCs in vitro.

Stauprimide Dilution Calculator

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Preparing Stock Solutions of Stauprimide

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.7105 mL 8.5526 mL 17.1051 mL 34.2103 mL 42.7628 mL
5 mM 0.3421 mL 1.7105 mL 3.421 mL 6.8421 mL 8.5526 mL
10 mM 0.1711 mL 0.8553 mL 1.7105 mL 3.421 mL 4.2763 mL
50 mM 0.0342 mL 0.1711 mL 0.3421 mL 0.6842 mL 0.8553 mL
100 mM 0.0171 mL 0.0855 mL 0.1711 mL 0.3421 mL 0.4276 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Stauprimide

Stauprimide Priming of Human Embryonic Stem Cells toward Definitive Endoderm.[Pubmed:24518969]

Cell J. 2014 Feb 3;16(1):63-72. Epub 2014 Feb 3.

OBJECTIVE: In vitro production of a definitive endoderm (DE) is an important issue in stem cell-related differentiation studies and it can assist with the production of more efficient endoderm derivatives for therapeutic applications. Despite tremendous progress in DE differentiation of human embryonic stem cells (hESCs), researchers have yet to discover universal, efficient and cost-effective protocols. MATERIALS AND METHODS: In this experimental study, we have treated hESCs with 200 nM of Stauprimide (Spd) for one day followed by activin A (50 ng/ml; A50) for the next three days (Spd-A50). In the positive control group, hESCs were treated with Wnt3a (25 ng/ml) and activin A (100 ng/ml) for the first day followed by activin A for the next three days (100 ng/ml; W/A100-A100). RESULTS: Gene expression analysis showed up regulation of DE-specific marker genes (SOX17, FOXA2 and CXCR4) comparable to that observed in the positive control group. Expression of the other lineage specific markers did not significantly change (p<0.05). We also obtained the same gene expression results using another hESC line. The use of higher concentrations of Spd (400 and 800 nM) in the Spd-A50 protocol caused an increase in the expression SOX17 as well as a dramatic increase in mortality rate of the hESCs. A lower concentration of activin A (25 ng/ml) was not able to up regulate the DE-specific marker genes. Then, A50 was replaced by inducers of definitive endoderm; IDE1/2 (IDE1 and IDE2), two previously reported small molecule (SM) inducers of DE, in our protocol (Spd-IDE1/2). This replacement resulted in the up regulation of visceral endoderm (VE) marker (SOX7) but not DE-specific markers. Therefore, while the Spd-A50 protocol led to DE production, we have shown that IDE1/2 could not fully replace activin A in DE induction of hESCs. CONCLUSION: These findings can assist with the design of more efficient chemically-defined protocols for DE induction of hESCs and lead to a better understanding of the different signaling networks that are involved in DE differentiation of hESCs.

A small molecule primes embryonic stem cells for differentiation.[Pubmed:19427291]

Cell Stem Cell. 2009 May 8;4(5):416-26.

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 lack of highly efficient methods for lineage-specific differentiation. Using a high-content screen, we have identified a small molecule, named Stauprimide, that increases the efficiency of the directed differentiation of mouse and human ESCs in synergy with defined extracellular signaling cues. Affinity-based methods revealed that Stauprimide interacts with NME2 and inhibits its nuclear localization. This, in turn, leads to downregulation of c-Myc, a key regulator of the pluripotent state. Thus, our findings identify a chemical tool that primes ESCs for efficient differentiation through a mechanism that affects c-Myc expression, and this study points to an important role for NME2 in ESC self-renewal.

Description

Stauprimide is a staurosporine analog that promotes embryonic stem cell (ESC) differentiation. Stauprimide is a non-broad spectrum inhibitor that binds to the MYC transcription factor NME2 and blocks its nuclear localization in ESCs, which results in down-regulation of MYC transcription.

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