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B1686

BIO

Name: BIO
Brand: SIGMA

≥98% (HPLC), powder, GSK-3α/β inhibitor

Synonym(s):

(2’Z,3’E)-6-Bromoindirubin-3′-oxime, 6-BIO, 6BIO

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About This Item

Empirical Formula (Hill Notation):

C₁₆H₁₀BrN₃O₂

CAS Number:

667463-62-9

Molecular Weight:

356.17

UNSPSC Code:

12352200

PubChem Substance ID:

24724412

NACRES:

NA.77

MDL number:

MFCD08705318

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

Storage condition:

protect from light

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Properties

Product Name

BIO, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

dark red

solubility

DMSO: >5 mg/mL

shipped in

wet ice

storage temp.

2-8°C

SMILES string

O\N=C1\C(Nc2ccccc12)=C3\C(=O)Nc4cc(Br)ccc34

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/h1-7,18,22H,(H,19,21)/b15-13-,20-14+

InChI key

DDLZLOKCJHBUHD-WAVHTBQISA-N

Description

Application

6-bromoindirubin-3′-oxime (BIO) has been used:

in MTT 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) cell proliferation assay
as a medium supplement in embryonic stem cells (ESCs)
for the inhibition of glycogen synthase kinase 3 β (GSK-3β) in human dermal papilla cells (hDPCs)

Biochem/physiol Actions

6-bromoindirubin-3′-oxime (BIO) is a potent, reversible and ATP-competitive GSK-3α/β inhibitor and the first pharmacological agent shown to maintain self-renewal in human and mouse embryonic stem cells. Human embryonic stem cells (hESCs) are maintained in the undifferentiated state through treatment with a GSK-3 inhibitor, BIO, under a feeder-free condition.

BIO is a potent, selective, reversible, and ATP-competitive GSK-3α/β inhibitor.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the GSK-3 page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Packaging

air sensitive

Legal Information

Product is sold for research and laboratory purposes in vitro and may not be used for any in vivo or therapeutic uses in humans, veterinary applications, or to make chemical derivatives.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Gimap5-dependent inactivation of GSK3β is required for CD4

Andrew R Patterson et al.

Nature communications, 9(1), 430-430 (2018-02-01)

GTPase of immunity-associated protein 5 (Gimap5) is linked with lymphocyte survival, autoimmunity, and colitis, but its mechanisms of action are unclear. Here, we show that Gimap5 is essential for the inactivation of glycogen synthase kinase-3β (GSK3β) following T cell activation.

Small molecule AT7867 proliferates PDX1-expressing pancreatic progenitor cells derived from human pluripotent stem cells.

Azuma Kimura et al.

Stem cell research, 24, 61-68 (2017-08-27)

While pancreatic islet transplantation achieves insulin independence in type 1 diabetes (T1D) patients, its widespread application is limited by donor tissue scarcity. Pancreatic progenitor cells (PPCs) give rise to all cell types in the pancreas during development. PPCs derived from

Disconnect between alcohol-induced alterations in chromatin structure and gene transcription in a mouse embryonic stem cell model of exposure

Veazey K, et al.

Alcohol, 60(23), 121-133 (2017)

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Global Trade Item Number

SKU	GTIN
B1686-25MG	04061832444529
B1686-5MG	04061833426319