6BIO

CHF 160.00
In stock
AG-MR-C0019-M01010 mgCHF 160.00
AG-MR-C0019-M05050 mgCHF 640.00
More Information
Product Details
Synonyms BIO; 6-Bromoindirubin-3'-oxime
Product Type Chemical
Properties
Formula

C16H10BrN3O2

MW 356.2
CAS 667463-62-9
Purity Chemicals ≥99% (NMR)
Appearance Dark red solid.
Solubility Soluble in DMSO or ethanol.
Reconstitution Stock solutions can be made up to 10mM in DMSO.
Identity Determined by 1H-NMR.
InChi Key DDLZLOKCJHBUHD-WAVHTBQISA-N
Smiles O\N=C1\C(\NC2=CC=CC=C\12)=C1\C(=O)NC2=C1C=CC(Br)=C2
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry.
Protect from light.
Protect from light and moisture.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • Potent, reversible and ATP-competitive glycogen synthase kinase-3α/β (GSK-3α/β) 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.
Product References
  1. GSK-3-selective inhibitors derived from Tyrian purple indirubins: L. Meijer, et al.; Chem. Biol. 10, 1255 (2003)
  2. 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)
  3. 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)
  4. The GSK-3 inhibitor BIO promotes proliferation in mammalian cardiomyocytes: A.S. Tseng, et al.; Chem. Biol. 13, 957 (2006)
  5. 7-Bromoindirubin-3'-oxime induces caspase-independent cell death: J. Ribas, et al.; Oncogene 25, 6304 (2006)
  6. Indirubin, the red shade of indigo: L. Meijer, et al. (Editors): In «Life in Progress», Station Biologique, Roscoff, 297 pp. (2006)
  7. Indirubin derivatives inhibit malignant lymphoid cell proliferation: A. Chebel, et al.; Leuk. Lymphoma 50, 2049 (2009)
  8. 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)
  9. Anticancer effects and antimetastatic mechanisms of novel indirubin derivatives: C.A. Kressirer; Diss. Ludwig-Maximilians-Universitaet Munchen, (2010)
  10. 6-Bromoindirubin-3'-Oxime Inhibits JAK/STAT3 Signaling and Induces Apoptosis of Human Melanoma Cells: L. Liu, et al.; Cancer Res. 71, 3972 (2011)
  11. Inhibition of Tat-mediated HIV-1 replication and neurotoxicity by novel GSK3-beta inhibitors: K. Kehn-Hall, et al.; Virology 415, 56 (2011)
  12. Induction of discrete apoptotic pathways by bromo-substituted indirubin derivatives in invasive breast cancer cells: K.A. Nicolaou, et al.; BBRC 425, 76 (2012)
  13. From Tyrian purple to kinase modulators: naturally halogenated indirubins and synthetic analogues: K. Vougogiannopoulou & A.L. Skaltsounis; Planta Med. 78, 1518 (2012)
  14. Pleiotrophin suppression of receptor protein tyrosine phosphatase-β/ζ maintains the self-renewal competence of fetal human oligodendrocyte progenitor cells: C.R. McClain, et al.; J. Neurosci. 32, 15066 (2012)
  15. Novel inverse binding mode of indirubin derivatives yields improved selectivity for DYRK kinases: V. Myrianthopoulos, et al.; ACS Med. Chem. Lett 4, 22 (2013)
  16. Indirubin Derivative 6BIO Suppresses Metastasis: S. Braig, et al.; Cancer Res. 73, 6004 (2013)
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