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Merck
CN

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
MDL number:
MFCD08705318
UNSPSC Code:
12352200
NACRES:
NA.77

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.

Quality Level

100

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

storage temp.

2-8°C

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

Related Categories

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 Code

11 - Combustible Solids

WGK

WGK 3

Certificates of Analysis (COA)

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Miki Tokuoka et al.
PLoS genetics, 19(9), e1010953-e1010953 (2023-09-27)
How gene regulatory networks (GRNs) encode gene expression dynamics and how GRNs evolve are not well understood, although these problems have been studied extensively. We created a digital twin that accurately reproduces expression dynamics of 13 genes that initiate expression
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
Matthew Harder et al.
Developmental biology, 448(2), 136-146 (2018-10-06)
The gene regulatory networks underlying Ciona notochord fate specification and differentiation have been extensively investigated, but the regulatory basis for regionalized expression within the notochord is not understood. Here we identify three notochord-expressed genes, C11.331, C12.115 and C8.891, with strongly
Yanfei Deng et al.
Cellular reprogramming, 22(4), 217-225 (2020-07-17)
Wnt/β-Catenin signaling pathway plays an important role in maintaining self-renewal and pluripotency of human and mouse embryonic stem cells (ESCs). Activation of Wnt/β-Catenin signaling pathway by glycogen synthase kinase-3 (GSK3) inhibitor, the Wnt signaling agonist, could maintain the pluripotency of
Laura Menendez et al.
Nature protocols, 8(1), 203-212 (2013-01-05)
Multipotent neural crest stem cells (NCSCs) have the potential to generate a wide range of cell types including melanocytes; peripheral neurons; and smooth muscle, bone, cartilage and fat cells. This protocol describes in detail how to perform a highly efficient
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