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402087

Sigma-Aldrich

7BIO - CAS 916440-85-2 - Calbiochem

Synonym(s):

(2ʹZ,3ʹE)-7-Bromoindirubin-3ʹ-oxime, Indirubin-3ʹ-monoxime, 7-Bromo, 7-Bromoindirubin-oxime

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About This Item

UNSPSC Code:
12352200

assay

≥97% (HPLC)

Quality Level

form

solid

color

deep black-red

solubility

DMSO: 50 mg/mL

General description

A cell-permeable 6-BIO (Cat. Nos. 361550 and 361552) structural isomer that acts as an ATP-competitive inhibitor of Flt3 (IC50 = 340 nM) and a caspase-independent, non-apoptotic cell death inducer (IC50 of cell survival ranges from 6.0 μM to 22.0 μM). Inhibition study against 75 other kinases reveals 10- to 80-fold selectivities over a group of 14 kinases, including TSF1, Aurora-A, and Aurora-B (IC50 = 3.3, 4.7, and 6.6 μM, respectively), up to 280-fold selectivities over a second group of 15 kinases, and little activity against the remaining 46 kinases of the panel (IC50 >100 μM).
A cell-permeable 6-BIO structural isomer that acts as an ATP-competitive inhibitor of Flt3 and a caspase-independent, non-apoptotic cell death inducer.

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

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Stefan Zahler et al.
Chemistry & biology, 14(11), 1207-1214 (2007-11-21)
Protein kinases are clinically relevant, attractive drug targets for cancer. One major problem with kinase inhibitors is broad promiscuity, causing off-target actions and side effects. In silico prediction of targets of a compound would immensely facilitate and accelerate drug development.
Yoan Ferandin et al.
Journal of medicinal chemistry, 49(15), 4638-4649 (2006-07-21)
Indirubins are kinase inhibitory bis-indoles that can be generated from various plant, mollusk, mammalian, and bacterial sources or chemically synthesized. We here report on the synthesis and biological evaluation of 3'-substituted 7-halogenoindirubins. Molecular modeling and kinase assays suggest that steric
J Ribas et al.
Oncogene, 25(47), 6304-6318 (2006-05-17)
Indirubin, an isomer of indigo, is a reported inhibitor of cyclin-dependent kinases (CDKs) and glycogen synthase kinase-3 (GSK-3) as well as an agonist of the aryl hydrocarbon receptor (AhR). Indirubin is the active ingredient of a traditional Chinese medicinal recipe
Vassilios Myrianthopoulos et al.
Journal of medicinal chemistry, 50(17), 4027-4037 (2007-08-02)
A variation of the bromine substitution from 6- to 7-position converts the glycogen synthase kinase-3alpha/beta-(GSK-3-alpha/beta) selective inhibitor 6-bromoindirubin-3'-oxime (6BIO) to a potent inhibitor of Aurora B and C kinases. The novel indirubin analogue 7-bromoindirubin-3'-oxime (7BIO) demonstrated unexpected selectivity against these

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