B1686
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
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
BIO, ≥98% (HPLC)
SMILES string
O\N=C1\C(Nc2ccccc12)=C3\C(=O)Nc4cc(Br)ccc34
InChI key
DDLZLOKCJHBUHD-WAVHTBQISA-N
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+
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
Quality Level
Related Categories
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.
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.
Packaging
air sensitive
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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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)
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)
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.
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
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
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