BIO

ChemicalBook > CAS DataBase List > BIO

Product Name: BIO
CAS No.: 667463-62-9
Chemical Name: BIO
Synonyms: Z E;6BIO;CS-1934;MLS2052;GSK 3 IX;MLS 2052;BIO (SM04554);BIO USP/EP/BP;GSK3 Inhibitor IX1;BIO(GSK-3 Inhibitor IX
CBNumber: CB5496994
Molecular Formula: C16H10BrN3O2
Formula Weight: 356.17
MOL File: 667463-62-9.mol

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BIO Property

Melting point:: 300°C(lit.)
Boiling point:: 554.3±50.0 °C(Predicted)
Density: 1.80±0.1 g/cm3(Predicted)
RTECS: NM3241900
storage temp.: 2-8°C
solubility: DMSO: >5 mg/mL
form: solid
pka: 9.56±0.20(Predicted)
color: dark red
Sensitive: Air & Light Sensitive
Stability:: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months.

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36
WGK Germany: 3
HS Code: 29339900

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 361550
Product name: GSK-3 Inhibitor IX
Packaging: 1mg
Price: $159
Updated: 2024/03/01

Sigma-Aldrich

Product number: 361550
Product name: GSK-3 Inhibitor IX
Packaging: 10mg
Price: $490
Updated: 2024/03/01

Sigma-Aldrich

Product number: 361552
Product name: InSolution GSK-3 Inhibitor IX - CAS 667463-62-9 - Calbiochem
Packaging: 500μg
Price: $144
Updated: 2024/03/01

TCI Chemical

Product number: B4006
Product name: (2'Z,3'E)-6-Bromoindirubin-3'-oxime
Purity: >95.0%(HPLC)
Packaging: 5mg
Price: $104
Updated: 2024/03/01

TCI Chemical

Product number: B4006
Product name: (2'Z,3'E)-6-Bromoindirubin-3'-oxime
Purity: >95.0%(HPLC)
Packaging: 25mg
Price: $359
Updated: 2024/03/01

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BIO Chemical Properties,Usage,Production

Description

BIO is a cell-permeable bis-indolo (indirubin) compound that acts as a highly potent, selective, reversible, and ATP-competitive inhibitor of GSK3α/β (IC₅₀ = 5 nM). Its specificity has been tested against various cyclin-dependent kinases (CDKs) (IC₅₀s = 83, 300, 320, and 10,000 nM for Cdk5/p25, Cdk2/A, Cdk1/B, and Cdk4/D₁, respectively). BIO was also tested for its specificity towards many other commonly studied kinases (IC₅₀ ≥10 μM), including MAP kinases, PKA, PKC isoforms, PKG, CK, and IRTK. Inhibition of GSK by BIO has been shown to result in the activation of the Wnt signaling pathway and sustained pluripotency in human and mouse embryonic stem cells (ESCs). BIO is reported to maintain self-renewal in human and mouse ESCs as well as induce the differentiation of neonatal cardiomyocytes.

Uses

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)

Definition

ChEBI: 6-bromoindirubin-3'-oxime is a member of the class of biindoles that is indirubin substituted at position 6 by a bromo group and in which the keto group at position 3' has undergone condensation with hydroxylamine to form the corresponding oxime. It has a role as an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor and an EC 2.7.11.26 (tau-protein kinase) inhibitor. It is a ketoxime, an organobromine compound, a member of oxindoles and a biindole.

General Description

A cell-permeable, highly potent, selective, reversible, and ATP-competitive inhibitor of GSK-3α/β (IC₅₀ = 5 nM). Specificity was confirmed using various Cdk′s (IC₅₀ = 83 nM for Cdk5/p25, 300 nM for Cdk2/cyclin A, 320 nM for Cdk1/cyclin B, and 10 μM for Cdk4/cyclin D1), MAP kinases, PKA, PKC isoforms, PKG, CK, and IRTK (IC₅₀ ≥ 10 μM). Inhibition of GSK by BIO has been shown to result in the activation of the Wnt signaling pathway and sustained pluripotency of human and murine embryonic stem cells (ESCs).

Biological Activity

Potent and selective, ATP-competitive glycogen synthase kinase-3 (GSK-3) inhibitor (IC 50 values are 5, 83, 300, 320 and > 10 000 nM at GSK-3, CDK5/p25, CDK2/cyclin A, CDK1/cyclin B and other common kinases respectively). Maintains self-renewal and pluripotency in embryonic stem cells via activation of the Wnt signaling pathway in vitro .

Biochem/physiol Actions

Cell permeable: yes

Enzyme inhibitor

These protein kinase inhibitors (FWBIO = 356.19 g/mol; CAS 667463-62-9; Solubility: 70 mg/mL DMSO, <1mg/mL H2O), also known as BIO, 6BIO, and systematically as 6-bromo-3-[(3E)-1,3-dihydro-3-(hydroxyimino)-2Hindol- 2-ylidene]-1,3-dihydro-(3Z)-2H-indol-2-one, targets glycogen synthase kinase-3 (or GSK-3), with an IC50 value of 5 nM for α and β forms. BIO also shows greater than 16x selectivity over CDK5 and is also a weaker pan-JAK inhibitor, with IC50 values of 30 nM, 1.5 μM, 8.0 μM, and 0.5 μM for TYK2, JAK1, JAK2 and JAK3. (See the structural related inhibitor 1-Azakenpaullone) BIO, but not 1-methyl-BIO, closely mimicked Wnt signaling in Xenopus embryos. BIO-induced apoptosis of human melanoma cells is associated with reduced phosphorylation of JAKs and STAT3 in both dose- and time-dependent manners. Consistent with inhibition of STAT3 signaling, expression of the anti-apoptotic protein Mcl- 1 was down-regulated. Maintaining Embryonic Stem Cells Pluripotency: Human and mouse embryonic stem cells (ESCs) self-renew indefinitely while maintaining the ability to generate all three germ-layer derivatives. Importantly, Wnt pathway activation by BIO is sufficient to maintain the undifferentiated phenotype in both types of ESCs and sustains expression of the pluripotent state-specific transcription factors Oct-3/4, Rex-1 and Nanog. Such results suggest that BIO and related GSK-3-specific inhibitors may off practical advantages in regenerative medicine. Bio can also participate in controlling the proliferative capability of the highly differentiated cardiomyocytes. Activation of Wnt/β-catenin and inhibition of Notch signaling pathways, as mediated by simultaneous co-application of BIO and the γ-secretase inhibitor N-[(3,5-difluorophenyl)acetyl]-L-alanyl-2- phenylglycine-1,1-dimethylethyl ester (or DAPT), efficiently induces intestinal differentiation of ESCs cultured on feeder cells. These findings that Wnt and Notch signaling function to pattern the anterior-posterior axis of the DE and control intestinal differentiation. 6-Bromoindirubin-3'- acetoxime: This cell-permeable BIO analogue (FWBIO-acetoxime = 398.21 g/mol; CAS 667463-85-6) is active against herpes simplex virus-1 (HSV-1) infection in human oral epithelial cells, the latter representing a natural target cell type. BIO-acetoxime reduces viral yields and the expression of different classes of viral proteins. BIO-acetoxime may suppress viral gene expression and protect oral epithelial cells from HSV-1 infection. Tyrian Purple: BIO’s indirubin nucleus is related to the famous Tyrian purple dye that the Phoenicians isolated from the gastropod mollusk Hexaplex trunculus and gained favor in antiquity, because it did not fade, actually becoming more brilliant upon weathering and exposure to sunlight. The inhibitory properties of BIO suggest that 6-bromoindirubin provides a new scaffold for the development of selective and potent pharmacological inhibitors of GSK- 3.

in vivo

study showed bio activated maternal wnt signaling pathway in xenopus embryos. it caused a hyper dorso-anteriorization at the expense of trunk and tail in a dose-response manner. it also activated the dorsal genes (siamois and chordin) ectopically. [1]

storage

+4°C

References

1) Meijer et al. (2003), GSK-3-selective inhibitors derived from Tyrian purple indirubins; Chem. Biol., 10 1255 2) Tseng et al. (2006), The GSK-3 inhibitor BIO promotes proliferation in mammalian cardiomyocytes; Chem. Biol., 13 957 3) Chebel et al. (2009), Indirubin derivatives inhibit malignant lymphoid cell proliferation; Leuk. Lymphoma, 50 2049

BIO Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from BIO manufacturers

Career Henan Chemical Co

Product: BIO 667463-62-9
Price: US $1.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 100kg
Release date: 2019-07-05

667463-62-9, BIORelated Search:

Indirubin Zidovudine KU-55933 (ATM Kinase Inhibitor) Y27632 (hydrochloride) BKM120 (NVP-BKM120, Buparlisib) xav-939 2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-3-NITRO- Olaparib EPA QUAZINONE 2-[2-[4-(4-NITROBENZYLOXY)PHENYL]ETHYL]ISOTHIOUREA MESYLATE Nicardipine hydrochloride CHOLESTEROL ESTERASE FARNESENE Ethylamine ESTETROL (-)-Varitriol

GSK-3 Inhibitor IX - CAS 667463-62-9 - Calbiochem

InSolution GSK-3 Inhibitor IX - CAS 667463-62-9 - Calbiochem

GSK-3 Inhibitor IX (BIO)

CS-1934

(2'Z,3'E)-6-Bromoindirubin-3'-oxim

BIO - GSK-3 inhibitor IX | 6-Bromoindirubin-3'-oxime

2H-Indol-2-one, 6-broMo-3-[(3E)-1,3-dihydro-3-(hydroxyiMino)-2H-indol-2-ylidene]-1,3-dihydro-, (3Z)-

6BIO

6-bromoindirubin-3-oxime

GSK3 Inhibitor IX1

BIO(GSK-3 Inhibitor IX

BIO (SM04554)

InSolution? GSK-3 Inhibitor IX

GSK 3 Inhibitor IX (MLS 2052,6BIO)

(2E,3E)-6'-Bromo-3-(hydroxyimino)-[2,3'-biindolinylidene]-2'-one

GSK 3 Inhibitor IX (6-Bromoindirubin-3'-oxime

GSK 3 INHIBITOR IX (6-BROMOINDIRUBIN-3'-OXIME; BIO)

6BIO;6-BIO;GSK 3 IX;GSK 3 INHIBITOR IX;MLS 2052;MLS2052;GSK-3 INHIBITOR IX; 6-BROMOINDIRUBIN-3-OXIME

GSK 3 IX

MLS 2052

MLS2052

(2'Z,3'E)-6-Bromoindirubin-3'-oxime &gt

Z E

BIO USP/EP/BP

MLS-2052 (GSK-3 Inhibitor IX

(2Z,3E)-6'-Bromo-3-(hydroxyimino)-[2,3'-biindolinylidene]-2'-one

GSK 3 Inhibitor IX,Cyclin dependent kinase,Apoptosis,Inhibitor,Glycogen synthase kinase-3,CDK,MLS2052,Glycogen synthase kinase 3,MLS-2052,GSK-3,inhibit

(2'Z,3'E)-6-Bromoindirubin-3'-oxime

(2Z,3E)-6'-Bromo-3-(hydroxyimino)-[2,3'-biindolinylidene]-2'-one

667463-62-9

C16H10BrN3O6

Inhibitors

Intracellular Signaling

Akt

mTOR

PI3K