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480743

Sigma-Aldrich

Neuronal Differentiation Inducer III

A cell-permeable isoxazole compound that selectively induces robust neuronal differentiation (Effective concentration = 20 µM) in various stem/progenitor cells.

Synonym(s):

Neuronal Differentiation Inducer III, Isx, N-Cyclopropyl-5-(thiophen-2-yl)isoxazole-3-carboxamide, N-Cyclopropyl-5-(thiophen-2-yl)isoxazole-3-carboxamide, Isx

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About This Item

Empirical Formula (Hill Notation):
C11H10N2O2S
CAS Number:
832115-62-5
Molecular Weight:
234.27
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

off-white

solubility

ethanol: 3 mg/mL
DMSO: 5 mg/mL

shipped in

ambient

storage temp.

2-8°C

InChI

1S/C11H10N2O2S/c14-11(12-7-3-4-7)8-6-9(15-13-8)10-2-1-5-16-10/h1-2,5-7H,3-4H2,(H,12,14)

InChI key

SYENTKHGMVKGAQ-UHFFFAOYSA-N

General description

A cell-permeable isoxazole compound that selectively induces robust neuronal differentiation (Effective concentration = 20 µM) in various stem/progenitor cells. Induces insulin expression, and activates ERK signaling and histone acetylation in MIN6 pancreatic β cells. The underlying excitation-neurogenesis signaling is comprised of, at least in part, an initial NMDA receptor- and L-type chanenels-mediated Ca2+ influx, followed by an activation of CaMKII, phosphorylation/nuclear export of the MEF2 repressor HDAC5, the subsequent de-repression of MEF2, and the eventual activation of the HDAC-MEF2 epigenetic/transcriptional regulatory network.

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Dioum, E.M., et al. 2011. Proc. Natl. Acad. Sci. USA108, 20713.
Zhang, L., et al. 2011. Differentiation81, 233.
Sadek, H., et al. 2008. Proc. Natl. Acad. Sci. USA105, 6063.
Schneider, J.W., et al. 2008. Nat. Chem. Biol.4, 408.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

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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Hesham Sadek et al.
Proceedings of the National Academy of Sciences of the United States of America, 105(16), 6063-6068 (2008-04-19)
The clinical success of stem cell therapy for myocardial repair hinges on a better understanding of cardiac fate mechanisms. We have identified small molecules involved in cardiac fate by screening a chemical library for activators of the signature gene Nkx2.5
Jay W Schneider et al.
Nature chemical biology, 4(7), 408-410 (2008-06-17)
We probed an epigenetic regulatory path from small molecule to neuronal gene activation. Isoxazole small molecules triggered robust neuronal differentiation in adult neural stem cells, rapidly signaling to the neuronal genome via Ca(2+) influx. Ca(2+)-activated CaMK phosphorylated and mediated nuclear
Ling Zhang et al.
Differentiation; research in biological diversity, 81(4), 233-242 (2011-03-23)
In the central nervous system (CNS), neural stem cells (NSCs) differentiate into neurons, astrocytes, and oligodendrocytes--these cell lineages are considered unidirectional and irreversible under normal conditions. The introduction of a defined set of transcription factors has been shown to directly
Elhadji M Dioum et al.
Proceedings of the National Academy of Sciences of the United States of America, 108(51), 20713-20718 (2011-12-07)
New drugs for preserving and restoring pancreatic β-cell function are critically needed for the worldwide epidemic of type 2 diabetes and the cure for type 1 diabetes. We previously identified a family of neurogenic 3,5-disubstituted isoxazoles (Isx) that increased expression

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