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StaupriMide

Product Name
StaupriMide
CAS No.
154589-96-5
Chemical Name
StaupriMide
Synonyms
Stauprimide;Stauprimide-d5;benzaMide deriv.;N-Benzoyl-7-oxostaurosporine;Stauprimide - CAS 154589-96-5 - Calbiochem;N-[(9S,10R,11R,13R)-2,3,10,11,12,13-hexahydro-10-methoxy-9-methyl-1,3-dioxo-9,13-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-11-yl]-N-methyl benzamide;Benzamide, N-[(9S,10R,11R,13R)-2,3,10,11,12,13-hexahydro-10-methoxy-9-methyl-1,3-dioxo-9,13-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-11-yl]-N-methyl-;[9S-(9α,10β,11β,13α)]-N-(2,3,10,11,12,13-Hexahydro-10-methoxy-9-methyl-1,3-dioxo-9,13-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-11-yl)-N-methylbenzamide;N-((5S,6R,7R,9S)-6-Methoxy-5-methyl-14,16-dioxo-6,7,8,9,15,16-hexahydro-5H,14H-17-oxa-4b,9a,15-triaza-5,9-methanodibenzo[b,h]cyclonona[jkl]cyclopenta[e]-as-indacen-7-yl)-N-methylbenzamide
CBNumber
CB32518818
Molecular Formula
C35H28N4O5
Formula Weight
584.62
MOL File
154589-96-5.mol
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StaupriMide Property

Density 
1.52±0.1 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
DMSO: >20mg/mL
pka
9.51±0.70(Predicted)
form 
Yellow solid
color 
white to beige
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.
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Safety

WGK Germany 
3
HS Code 
2934999090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
S2951
Product name
Stauprimide
Purity
≥98% (HPLC)
Packaging
1mg
Price
$214
Updated
2024/03/01
Sigma-Aldrich
Product number
569393
Product name
Stauprimide - CAS 154589-96-5 - Calbiochem
Packaging
500μg
Price
$246
Updated
2024/03/01
Cayman Chemical
Product number
15398
Product name
Stauprimide
Purity
≥98%
Packaging
500μg
Price
$50
Updated
2024/03/01
Cayman Chemical
Product number
15398
Product name
Stauprimide
Purity
≥98%
Packaging
1mg
Price
$85
Updated
2024/03/01
Sigma-Aldrich
Product number
S2951
Product name
Stauprimide
Purity
≥98% (HPLC)
Packaging
5mg
Price
$855
Updated
2024/03/01
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StaupriMide Chemical Properties,Usage,Production

Description

Stauprimide is a small molecule that increases the efficiency of mouse and human embryonic stem cell differentiation in conjunction with lineage specification cues (EC50 = 0.3 μM). It specifically inhibits the nuclear localization of NME2, which results in the suppression of c-Myc, a key regulator of pluripotency.

Uses

Labelled Stauprimide (S684700). It is an enhancer stem cell differentiation into endoderm.

Uses

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.

Uses

Stauprimide is a semi-synthetic analogue of the staurosporine family of indolocarbazoles. Stauprimide was first published in 1994 as part of an extensive structure-activity investigation to improve the selective inhibition of protein kinase C as potential antitumour agents. Stauprimide increases the efficiency of the directed differentiation of mouse and human embryonic stem cells in synergy with defined extracellular signalling cues. Stauprimide interacts with NME2 (PUF) transcription factor to down-regulate c-Myc expression, leading to differentiation of stem cells.

General Description

A cell-permeable ESCs (Embryonic Stem Cells) EMT (Epithelial-Mesenchymal Transition) inducer that is reported to prime/sensitize human and murine ESC cultures for much more enhanced/efficient differentiation into progenitor cells of multiple lineages, including Activin A- (Cat. No. 114700) induced definitive endoderm differentiation (60% differentiation from murine R1 ESCs with 5 ng/ml Activin A and 200 nM Spd), ATRA- (Cat. No. 554720) induced neuronal progenitor differentiation, and BMP-4- (Cat. No. 203642) induced mesoderm differentiation, under suboptimal lineage specifying stimuli concentrations and often serum-free conditions, while Spd sensitization alone does not induce any ESCs differentiation. Spd is shown to interact with NME2/DNPK B/PUF and prevent NME2 nuclear localization and c-myc transcription in murine R1 ESC cultures (46% and 85% drop in c-myc mRNA in 24 h, respectively, with 200 nM and 500 nM Spd), which accounts for, at least in part, its EMT induction activity. Although a structural analog of the broad-spectrum kinase inhibitors Staurosporine (Cat. Nos. 569396 and 569397) and UCN-01 (Cat. No. 539644), Spd exhibits significant kinase inhibitory activities only at elevated concentrations, but not at concentrations ≤500 nM typically used in EMT induction.

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.

storage

-20°C

References

1) Zhu et al. (2009), A small molecule primes embryonic stem cells for differentiation; Cell Stem Cell, 4 416 2) Zaret et al. (2009), Using small molecules to great effect in stem cell differentiation; Cell Stem Cell, 4 373 3) Bouvard et al. (2017) Small molecule selectively suppresses MYC transcription in cancer cells; Proc. Natl. Acad. Sci. USA 114 3497

StaupriMide Preparation Products And Raw materials

Raw materials

Preparation Products

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StaupriMide Suppliers

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Aurisco Pharmaceutical (Tianjin) Inc.
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154589-96-5, StaupriMideRelated Search:

KY0211 Dexamethasone IWP-2 Troglitazone

  • Stauprimide
  • [9S-(9α,10β,11β,13α)]-N-(2,3,10,11,12,13-Hexahydro-10-methoxy-9-methyl-1,3-dioxo-9,13-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-11-yl)-N-methylbenzamide
  • N-Benzoyl-7-oxostaurosporine
  • benzaMide deriv.
  • Stauprimide - CAS 154589-96-5 - Calbiochem
  • Benzamide, N-[(9S,10R,11R,13R)-2,3,10,11,12,13-hexahydro-10-methoxy-9-methyl-1,3-dioxo-9,13-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-11-yl]-N-methyl-
  • Stauprimide-d5
  • N-((5S,6R,7R,9S)-6-Methoxy-5-methyl-14,16-dioxo-6,7,8,9,15,16-hexahydro-5H,14H-17-oxa-4b,9a,15-triaza-5,9-methanodibenzo[b,h]cyclonona[jkl]cyclopenta[e]-as-indacen-7-yl)-N-methylbenzamide
  • N-[(9S,10R,11R,13R)-2,3,10,11,12,13-hexahydro-10-methoxy-9-methyl-1,3-dioxo-9,13-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-11-yl]-N-methyl benzamide
  • 154589-96-5
  • C35H28N4O5
  • C35H23D5N4O5
  • Antibiotic
  • Chiral Reagents
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Isotope Labelled Compounds