INDIRUBIN-3'-MONOXIME

ChemicalBook > CAS DataBase List > INDIRUBIN-3'-MONOXIME

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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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