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INDIRUBIN-3'-MONOXIME

Product Name
INDIRUBIN-3'-MONOXIME
CAS No.
160807-49-8
Chemical Name
INDIRUBIN-3'-MONOXIME
Synonyms
-oxime;-monoxime;Indirubin-3;Indirubin-3′INDIRUBIN-3'-OXIME;Indirubine-3'-oxime;Indirubin-3'-monoxime;INDIRUBIN-3'-MONOXIME;INDIRUBIN-3’-MONOOXIME;3-(Hydroxyimino)-[2,3'-biindolinylidene]-2'-one
CBNumber
CB1325944
Molecular Formula
C16H11N3O2
Formula Weight
277.28
MOL File
160807-49-8.mol
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INDIRUBIN-3'-MONOXIME Property

Melting point:
247-249°C
Boiling point:
532.2±50.0 °C(Predicted)
Density 
1.50
storage temp. 
room temp
solubility 
DMSO: >10 mg/mL
form 
solid
pka
8.66±0.20(Predicted)
color 
Dark red or brown
Stability:
Light Sensitive
CAS DataBase Reference
160807-49-8
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Safety

WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

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

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

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

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
I0404
Product name
Indirubin-3′-oxime
Purity
≥98% (HPLC), solid
Packaging
1mg
Price
$192
Updated
2024/03/01
Sigma-Aldrich
Product number
402085
Product name
Indirubin-3?-monoxime
Packaging
1mg
Price
$201
Updated
2024/03/01
Alfa Aesar
Product number
J67459
Product name
Indirubin-3'-oxime, 98%
Packaging
5mg
Price
$180.65
Updated
2024/03/01
Alfa Aesar
Product number
J67459
Product name
Indirubin-3'-oxime, 98%
Packaging
10mg
Price
$200
Updated
2021/12/16
Cayman Chemical
Product number
13314
Product name
Indirubin-3?-monoxime
Purity
≥98%
Packaging
1mg
Price
$48
Updated
2024/03/01
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INDIRUBIN-3'-MONOXIME Chemical Properties,Usage,Production

Description

Indirubin-3’-oxime is a potent inhibitor of glycogen synthase kinase 3β (GSK3β; IC50 = 22 nM). As GSK3β phosphorylates tau protein, indirubin-3’-oxime prevents tau phosphorylation both in vitro and in vivo at Alzheimer’s disease-relevant sites. It also inhibits cyclin-dependent kinases (CDKs) at higher concentrations, including Cdk1/cyclin B (IC50 = 180 nM), Cdk2/cyclin A (IC50 ~500 nM), Cdk2/cyclin E (IC50 = 250nM), Cdk4/cyclin D1 (IC50 = 3.3 μM) and Cdk5/p35 (IC50 = 100 nM). Indirubin-3’-oxime reversibly inhibits the proliferation of many cells types, arresting cycling in the G2/M phase.

Chemical Properties

Dark Red Solid

Uses

Indirubin-3′-oxime has been used in the inhibition of glycogen synthase kinase 3 in human monocytic cell line, THP-1.

Uses

A potent inhibitor of GSK-3? (IC50=22nM). Also inhibits CDK1 (IC50=180nM) and CDK (IC50=100nM). It reversibly arrests asynchronous HBL-100 cells at G2. It induces apoptosis in the mammary carcinoma cell line MCF-7 (10üM).

Definition

ChEBI: Indirubin-3'-monoxime is a member of the class of biindoles that is indirubin 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 2.7.11.22 (cyclin-dependent kinase) inhibitor, an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor, an osteogenesis regulator, a neuroprotective agent and an anti-obesity agent. It is a member of oxindoles, a bisindole, a ring assembly, a ketoxime and an alkaloid.

Biological Activity

Protein kinase inhibitor: inhibits cyclin-dependent kinases (IC 50 = 0.18-3.33 μ M) and GSK-3 β (IC 50 = 0.19 μ M). Inhibits CDK5- and GSK-3 β -mediated tau phosphorylation, a process over-active in Alzheimer disease states. Also inhibits AMPK, LCK and SGK. Induces cell cycle arrest and inhibits cell proliferation.

Biochem/physiol Actions

Indirubin-3′-oxime is a cyclin-dependent kinase inhibitor which functions by competing with ATP for binding to the catalytic subunit; exhibits antiproliferative activity leading to G2/M arrest in many cell lines and G1/S arrest in Jurkat cells.

storage

Store at RT

References

1) Leclerc?et al. (2001),?Indirubins inhibit glycogen synthase kinase-3 beta and CDK5/p25, two protein kinases involved in abnormal tau phosphorylation in Alzheimer’s disease. A property common to most cyclin-dependent kinase inhibitors?; J. Biol. Chem.,?276?251 2) Damiens?et al. (2001),?Anti-mitotic properties of indirubin-3′-monoximine, a CDK/GSK-3 inhibitor: induction of endoreplication following prophase arrest; Oncogene,?20?3786 3) Kim?et al. (2011),?Indirubin-3′-monoxime, a derivative of a chinese antileukemia medicine, inhibits angiogenesis; J. Cell. Biochem.,?112?1384 4) Ding?et al. (2010),?Indirubin-3′-monoxime rescues spatial memory deficits and attenuates beta-amyloid-associated neuropathology in a mouse model of Alzheimer’s disease; Neurobiol. Dis.,?39?156

INDIRUBIN-3'-MONOXIME Preparation Products And Raw materials

Raw materials

Preparation Products

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INDIRUBIN-3'-MONOXIME Suppliers

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View Lastest Price from INDIRUBIN-3'-MONOXIME manufacturers

Career Henan Chemical Co
Product
INDIRUBIN-3'-MONOXIME 160807-49-8
Price
US $3.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
100KG
Release date
2020-01-29

160807-49-8, INDIRUBIN-3'-MONOXIMERelated Search:

PD 173074 Apigenin 17-AAG BORRELIDIN RP107 (S)-CR8 KENPAULLONE Alsterpaullone Indirubin 1-METHYL-BIO (2'Z,3'E)-6-BROMOINDIRUBIN-3'-OXIME INDIRUBIN-3'-MONOXIME-5-SULPHONIC ACID INDIRUBIN-3'-MONOXIME, 5-IODO- (2'Z,3'E)-6-BROMOINDIRUBIN-3'-ACETOXIME INDIRUBIN-3'-MONOXIME

  • 3-[1,3-DIHYDRO-3-(HYDROXYIMINO)-2H-INDOL-2-YLIDENE]-1,3-DIHYDRO-2H-INDOL-2-ONE
  • INDIRUBIN-3'-MONOXIME
  • INDIRUBIN-3'-OXIME
  • Indirubine-3'-oxime
  • INDIRUBIN-3’-MONOOXIME
  • Indirubin-3
  • 3-(Hydroxyimino)-[2,3'-biindolinylidene]-2'-one
  • Indirubin-3-monoxime - CAS 160807-49-8 - Calbiochem
  • 2H-Indol-2-one, 3-[1,3-dihydro-3-(hydroxyimino)-2H-indol-2-ylidene]-1,3-dihydro-
  • -monoxime
  • Indirubin-3'-monoxime
  • 3-(Hydroxyimino)-[2,3'-biindolinylidene]-2'-one
  • -oxime
  • Indirubin-3&#8242
  • Indirubin-3''-monoxime, GSK3beta inhibitor. CDK inhibitor.
  • 160807-49-8
  • Apoptosis and Cell Cycle
  • BioChemical
  • Cell Biology
  • Cell Signaling and Neuroscience
  • Cell Cycle
  • Cell Cycle Regulators
  • Intracellular Signaling
  • Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes
  • Inhibitors
  • Protein Kinase