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Merck

B1686

Sigma-Aldrich

BIO

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

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C16H10BrN3O2
Número de CAS:
Peso molecular:
356.17
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

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

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

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.

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Visite la Librería de documentos

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.
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)
Xiang Qiu et al.
World journal of gastroenterology, 21(26), 8061-8072 (2015-07-18)
To investigate the therapeutic effects of lutein against non-alcoholic fatty liver disease (NAFLD) and the related underlying mechanism. After 9 d of acclimation to a constant temperature-controlled room (20 °C-22 °C) under 12 h light/dark cycles, male Sprague-Darley rats were randomly divided
Julia Helberg et al.
Materials (Basel, Switzerland), 12(14) (2019-07-18)
The mycelium of the edible mushroom Pleurotus ostreatus can be used for diverse technical applications, such as packaging materials or wastewater treatment, besides the more obvious use for nutrition. While P. ostreatus usually grows on sawdust, wood or similar materials
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)

Artículos

Naive pluripotent stem cells cultured in vitro using specialized media and inhibitors mimic "ground-state" cells from blastocysts.

Naive pluripotent stem cells cultured in vitro using specialized media and inhibitors mimic "ground-state" cells from blastocysts.

Naive pluripotent stem cells cultured in vitro using specialized media and inhibitors mimic "ground-state" cells from blastocysts.

Naive pluripotent stem cells cultured in vitro using specialized media and inhibitors mimic "ground-state" cells from blastocysts.

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