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B1686

Sigma-Aldrich

BIO

≥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:
Molecular Weight:
356.17
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Pricing and availability is not currently available.

Product Name

BIO, ≥98% (HPLC)

Quality Level

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

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This Item
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BIO ≥98% (HPLC)

B1686

BIO

MitoCDNB ≥98% (HPLC)

SML2573

MitoCDNB

form

powder

form

powder

form

solid

form

powder

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

DMSO: >5 mg/mL

solubility

H2O: 2 mg/mL (clear solution, warmed)

solubility

DMSO: 5 mg/mL

solubility

H2O: 2 mg/mL, clear (warmed)

storage condition

protect from light

storage condition

-

storage condition

OK to freeze, protect from light

storage condition

-

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[1]
  • as a medium supplement in embryonic stem cells (ESCs)[2]
  • for the inhibition of glycogen synthase kinase 3 β (GSK-3β) in human dermal papilla cells (hDPCs)[3]

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.

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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    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.
    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
    Anchel De Jaime-Soguero et al.
    PLoS genetics, 13(3), e1006682-e1006682 (2017-03-28)
    Understanding the mechanisms regulating cell cycle, proliferation and potency of pluripotent stem cells guarantees their safe use in the clinic. Embryonic stem cells (ESCs) present a fast cell cycle with a short G1 phase. This is due to the lack
    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)
    Human placental extract exerts hair growth-promoting effects through the GSK-3beta signaling pathway in human dermal papilla cells
    Kwon TR, et al.
    International Journal of Molecular Medicine, 36(4), 1088-1096 (2015)

    Articles

    Naive pluripotent stem cells are located within the epiblast of mature blastocysts. These primitive “ground-state” cells may be cultured in vitro using specialized media and small molecule inhibitors.

    Cancer stem cell media, spheroid plates and cancer stem cell markers to culture and characterize CSC populations.

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