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INDIRUBIN-3'-MONOXIME

CAS No.
160807-49-8
Chemical Name:
INDIRUBIN-3'-MONOXIME
Synonyms
-monoxime;Indirubin-3;INDIRUBIN-3'-OXIME;Indirubine-3'-oxime;Indirubin-3'-monoxime;INDIRUBIN-3'-MONOXIME;INDIRUBIN-3’-MONOOXIME;3-(Hydroxyimino)-[2,3'-biindolinylidene]-2'-one;3-(Hydroxyimino)-[2,3'-biindolinylidene]-2'-one;Indirubin-3-monoxime - CAS 160807-49-8 - Calbiochem
CBNumber:
CB1325944
Molecular Formula:
C16H11N3O2
Molecular Weight:
277.28
MDL Number:
MFCD02683594
MOL File:
160807-49-8.mol
MSDS File:
SDS
Last updated:2023-06-30 15:45:59

INDIRUBIN-3'-MONOXIME Properties

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
FDA UNII X6CSG51MBQ

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H332-H335
Precautionary statements  P261-P280-P305+P351+P338
WGK Germany  3

INDIRUBIN-3'-MONOXIME price More Price(36)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich I0404 Indirubin-3′-oxime ≥98% (HPLC), solid 160807-49-8 1mg $192 2024-03-01 Buy
Sigma-Aldrich 402085 Indirubin-3?-monoxime 160807-49-8 1mg $201 2024-03-01 Buy
Alfa Aesar J67459 Indirubin-3'-oxime, 98% 160807-49-8 5mg $180.65 2024-03-01 Buy
Alfa Aesar J67459 Indirubin-3'-oxime, 98% 160807-49-8 10mg $200 2021-12-16 Buy
Cayman Chemical 13314 Indirubin-3?-monoxime ≥98% 160807-49-8 1mg $48 2024-03-01 Buy
Product number Packaging Price Buy
I0404 1mg $192 Buy
402085 1mg $201 Buy
J67459 5mg $180.65 Buy
J67459 10mg $200 Buy
13314 1mg $48 Buy

INDIRUBIN-3'-MONOXIME Chemical Properties,Uses,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

INDIRUBIN-3'-MONOXIME Suppliers

Global( 116)Suppliers
Supplier Tel Email Country ProdList Advantage
ATK CHEMICAL COMPANY LIMITED
+undefined-21-51877795 ivan@atkchemical.com China 32686 60
Hubei xin bonus chemical co. LTD
86-13657291602 linda@hubeijusheng.com CHINA 22968 58
Alchem Pharmtech,Inc.
8485655694 sales@alchempharmtech.com United States 63711 58
career henan chemical co
+86-0371-86658258 15093356674; factory@coreychem.com China 29826 58
SHANGHAI T&W PHARMACEUTICAL CO., LTD.
+86-021-61551413 +8618813727289 contact@trustwe.com China 5738 58
Tianjin Xinshengjiahe Science & Technology Development Co,.Ltd
+86-86-22-87899925 +86-8618522618860 18522618860@163.com China 694 58
HANGZHOU CLAP TECHNOLOGY CO.,LTD
86-571-88216897,88216896 13588875226 sales@hzclap.com CHINA 6313 58
ANHUI WITOP BIOTECH CO., LTD
+8615255079626 eric@witopchemical.com China 23556 58
Dayang Chem (Hangzhou) Co.,Ltd.
571-88938639 +8617705817739 info@dycnchem.com CHINA 52867 58
InvivoChem
+1-708-310-1919 +1-13798911105 sales@invivochem.cn United States 6393 58

View Lastest Price from INDIRUBIN-3'-MONOXIME manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
INDIRUBIN-3'-MONOXIME pictures 2020-02-01 INDIRUBIN-3'-MONOXIME
160807-49-8
US $3.00 / KG 1KG 98% 100KG Career Henan Chemical Co
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 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