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Merck

361550

BIO

≥97% (HPLC), solid, GSK-3GSK-3α/β inhibitor, Calbiochem

Synonym(s):

GSK-3 Inhibitor IX, BIO, (2ʹ Z,3ʹ E)-6-Bromoindirubin-3ʹ-oxime, BIO, (2ʹZ,3ʹE)-6-Bromoindirubin-3ʹ-oxime

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About This Item

Empirical Formula (Hill Notation):
C16H10BrN3O2
CAS Number:
667463-62-9
Molecular Weight:
356.17
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD08705318

Key Documents

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Product Name

GSK-3 Inhibitor IX, BIO, CAS 667463-62-9, is a cell-permeable, highly potent, selective, reversible, and ATP-competitive inhibitor of GSK-3α/β (IC50 = 5 nM). Maintains self-renewal in human & mouse embryonic stem cells.

SMILES string

Brc1cc2c(cc1)\C(=C3\Nc4c(cccc4)C\3N=O)\C(=O)N2

InChI

1S/C16H10BrN3O2/c17-8-5-6-9-12(7-8)19-16(21)13(9)15-14(20-22)10-3-1-2-4-11(10)18-15/h1-7,14,18H,(H,19,21)/b15-13-

InChI key

WFRDXNRAUPBBTO-SQFISAMPSA-N

assay

≥97% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, protect from light

color

purple

solubility

DMSO: 5 mg/mL

shipped in

wet ice

Quality Level

100

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General description

The small molecule, 6-bromoindirubin-3′-oxime (BIO) serves as a specific inhibitor of glycogen synthase kinase-3 (GSK-3). It can sustain self-renewal and pluripotency in both human and mouse embryonic stem cells (ESCs). Treating ESCs with BIO increases β-catenin activity, suggesting that the activation of canonical Wnt signaling plays a key role in preserving the stem cell characteristics. BIO can also induce adult mammalian cardiomyocytes to dedifferentiate and enter mitosis. In addition to its effects on stem cells, the GSK-3 inhibitor IX (BIO) has the ability to elevate the expression of caspase-3 and caspase-8 proteins, leading to the induction of apoptosis in glioblastoma (GBM) cells. This GSK-3 inhibitor also triggers G2/M cell cycle arrest in GBM cells.

Application

BIO has been used as a GSK-3 inhibitor:
  • in aortic valve interstitial cells (VICs) culture to induce osteogenesis in VICs
  • to treat VICs to study its effects on RUNX2, GSK-3β, and p-SMAD protein expression
  • and a Wnt pathway activator to study the effect of Wnt and bone morphogenetic protein (BMP) pathways on Saos-2 using differentiation markers Dlx5, Runx2 and Msx2

Biochem/physiol Actions

Cell permeable: yes
Product competes with ATP.
Reversible: yes

Packaging

Packaged under inert gas

Legal Information

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

Disclaimer

Toxicity: Carcinogenic / Teratogenic (D)

Storage Class

11 - Combustible Solids

wgk

WGK 3

Certificates of Analysis (COA)

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Zhongde Ye et al.
NPJ aging and mechanisms of disease, 7(1), 4-4 (2021-02-10)
MicroRNAs play an important role in the regulation of T cell development, activation, and differentiation. One of the most abundant microRNAs in lymphocytes is miR-181a, which controls T cell receptor (TCR) activation thresholds in thymic selection as well as in
Verónica Uribe-Etxebarria et al.
Cells, 9(3) (2020-03-12)
Dental pulp stem cells (DPSCs) from adult teeth show the expression of a very complete repertoire of stem pluripotency core factors and a high plasticity for cell reprogramming. Canonical Wnt and Notch signaling pathways regulate stemness and the expression of

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