6BIO

AdipoGen Life Sciences
Product Code: AG-MR-C0019
CodeSizePrice
AG-MR-C0019-M01010 mg£125.00
Quantity:
AG-MR-C0019-M05050 mg£425.00
Quantity:
Prices exclude any Taxes / VAT

Overview

Regulatory Status: RUO
Shipping:
-20°C
Storage:
-20°C

Images

1 / 1
Chemical Structure

Chemical Structure

Further Information

Alternate Names/Synonyms:
BIO; 6-Bromoindirubin-3'-oxime
Appearance:
Dark red solid.
CAS:
667463-62-9
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07
Handling Advice:
Keep cool and dry.Protect from light.Protect from light and moisture.
Hazards:
H315, H319, H335
InChi:
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+
InChiKey:
DDLZLOKCJHBUHD-WAVHTBQISA-N
Long Description:
Chemical. CAS: 667463-62-9. Formula: C16H10BrN3O2. MW: 356.2. Potent, reversible and ATP-competitive glycogen synthase kinase-3alpha/beta (GSK-3alpha/beta) inhibitor. JAK/STAT3 signaling inhibitor. Phosphoinositide-dependent kinase 1 (PDK1) inhibitor. Anticancer compound. Potent antiproliferative agent. Suppresses metastasis. Apoptosis inducer. Sustains pluripotency and self-renewal of human and mouse embryonic stem cells (ESCs) by activation of the Wnt signaling pathway. Anti-leishmanial (IC50 = 0.150µM). Proto-oncogene tyrosine-protein kinase receptor RET inhibitor (IC50=0.51µM). Inhibits HIV-1 transcription and protects against Tat induced neurotoxicity.
MDL:
MFCD08705318
Molecular Formula:
C16H10BrN3O2
Molecular Weight:
356.2
Package Type:
Vial
Precautions:
P261, P271, P280, P312
Product Description:
Potent, reversible and ATP-competitive glycogen synthase kinase-3alpha/beta (GSK-3alpha/beta) inhibitor. JAK/STAT3 signaling inhibitor. Phosphoinositide-dependent kinase 1 (PDK1) inhibitor. Anticancer compound. Potent antiproliferative agent. Suppresses metastasis. Apoptosis inducer. Sustains pluripotency and self-renewal of human and mouse embryonic stem cells (ESCs) by activation of the Wnt signaling pathway. Anti-leishmanial (IC50 = 0.150µM). Proto-oncogene tyrosine-protein kinase receptor RET inhibitor (IC50=0.51µM). Inhibits HIV-1 transcription and protects against Tat induced neurotoxicity.
Purity:
>99% (NMR)
Signal word:
Warning
SMILES:
ON=C1C(NC2=CC=CC=C12)=C1C(=O)NC2=C1C=CC(Br)=C2
Solubility Chemicals:
Soluble in DMSO or ethanol.
Transportation:
Non-hazardous
UNSPSC Category:
Protein Kinase Modulators
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.

References

GSK-3-selective inhibitors derived from Tyrian purple indirubins: L. Meijer, et al.; Chem. Biol. 10, 1255 (2003) | Structural basis for the synthesis of indirubins as potent and selective inhibitors of glycogen synthase kinase-3 and cyclin-dependent kinases: P. Polychronopoulos, et al.; J. Med. Chem. 47, 935 (2004) | Maintenance of pluripotency in human and mouse embryonic stem cells through activation of Wnt signaling by a pharmacological GSK-3-specific inhibitor: N. Sato, et al.; Nat. Med. 10, 55 (2004) | The GSK-3 inhibitor BIO promotes proliferation in mammalian cardiomyocytes: A.S. Tseng, et al.; Chem. Biol. 13, 957 (2006) | 7-Bromoindirubin-3'-oxime induces caspase-independent cell death: J. Ribas, et al.; Oncogene 25, 6304 (2006) | Indirubin, the red shade of indigo: L. Meijer, et al. (Editors): In ?Life in Progress?, Station Biologique, Roscoff, 297 pp. (2006) | Indirubin derivatives inhibit malignant lymphoid cell proliferation: A. Chebel, et al.; Leuk. Lymphoma 50, 2049 (2009) | 6-Br-5methylindirubin-3'oxime (5-Me-6-BIO) targeting the leishmanial glycogen synthase kinase-3 (GSK-3) short form affects cell-cycle progression and induces apoptosis-like death: Exploitation of GSK-3 for treating leishmaniasis: E. Xingi, et al.; Int. J. Parasit. 39, 1289 (2009) | Anticancer effects and antimetastatic mechanisms of novel indirubin derivatives: C.A. Kressirer; Diss. Ludwig-Maximilians-Universitaet Munchen, (2010) | 6-Bromoindirubin-3'-Oxime Inhibits JAK/STAT3 Signaling and Induces Apoptosis of Human Melanoma Cells: L. Liu, et al.; Cancer Res. 71, 3972 (2011) | Inhibition of Tat-mediated HIV-1 replication and neurotoxicity by novel GSK3-beta inhibitors: K. Kehn-Hall, et al.; Virology 415, 56 (2011) | Induction of discrete apoptotic pathways by bromo-substituted indirubin derivatives in invasive breast cancer cells: K.A. Nicolaou, et al.; BBRC 425, 76 (2012) | From Tyrian purple to kinase modulators: naturally halogenated indirubins and synthetic analogues: K. Vougogiannopoulou & A.L. Skaltsounis; Planta Med. 78, 1518 (2012) | Pleiotrophin suppression of receptor protein tyrosine phosphatase-beta/zeta maintains the self-renewal competence of fetal human oligodendrocyte progenitor cells: C.R. McClain, et al.; J. Neurosci. 32, 15066 (2012) | Novel inverse binding mode of indirubin derivatives yields improved selectivity for DYRK kinases: V. Myrianthopoulos, et al.; ACS Med. Chem. Lett 4, 22 (2013) | Indirubin Derivative 6BIO Suppresses Metastasis: S. Braig, et al.; Cancer Res. 73, 6004 (2013)

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