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I0404

Sigma-Aldrich

Indirubin-3′-oxime

≥98% (HPLC), solid

Sinonimo/i:

Indirubin-3′-monoxime

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About This Item

Formula empirica (notazione di Hill):
C16H11N3O2
Numero CAS:
160807-49-8
Peso molecolare:
277.28
Numero MDL:
MFCD02683594
Codice UNSPSC:
12352200
ID PubChem:
24278483
NACRES:
NA.77

Livello qualitativo

100

Saggio

≥98% (HPLC)

Forma fisica

solid

PM

277.28

Solubilità

DMSO: >10 mg/mL
H2O: insoluble

Temperatura di conservazione

room temp

Stringa SMILE

O\N=C1\C(Nc2ccccc12)=C3\C(=O)Nc4ccccc34

InChI

1S/C16H11N3O2/c20-16-13(9-5-1-3-7-11(9)18-16)15-14(19-21)10-6-2-4-8-12(10)17-15/h1-8,17,21H,(H,18,20)/b15-13-,19-14+
HBDSHCUSXQATPO-BGBJRWHRSA-N

Applicazioni

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

Azioni biochim/fisiol

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.
Indirubin-3′-oxime mediates apoptosis in Jurkat T cells and has anti-tumor functionality. Indirubin-3′-oxime inhibits Y box binding protein 1 (YB1) translocation, contributing to anticancer functionality. Indirubin-3′-oxime decreases expression of estrogen-related receptor γ (ERRγ) and peroxisome proliferator-activated receptor-γ co-activator-1α (PGC1α) in human neuroblastoma, leading to cell cycle arrest and mitochondrial dysfunction.

Caratteristiche e vantaggi

This compound is featured on the CDKs and GSK-3 pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

Certificati d'analisi (COA)

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Indirubin-3'-oxime induces mitochondrial dysfunction and triggers growth inhibition and cell cycle arrest in human neuroblastoma cells.
Liao XM and Leung KN
Oncology Reports, 29(1), 371-379 (2013)
Dynamic modulation of innate immune response by varying dosages of LPS in human monocytic cells.
Morris M, et al.
The Journal of Biological Chemistry, 289(31), 21584-21590 (2014)
Mechanism responsible for inhibitory effect of indirubin 3?-oxime on anticancer agent-induced YB-1 nuclear translocation in HepG2 human hepatocellular carcinoma cells.
Tanaka T, et al.
Experimental Cell Research, 370(2), 454-460 (2018)
Semi-synthesis of indirubin-3′-oxime from Strobilanthes cusia leaves, its acute and sub-chronic toxicity, in vitro and in vivo antitumor activity in Lewis lung carcinoma bearing mice.
Cuong NM, et al.
Journal of Pharmacognosy and Phytochemistry, 5(4), 205-205 (2016)
Ming-Yang Lee et al.
European journal of pharmacology, 839, 57-65 (2018-09-30)
Cholangiocarcinoma (CCA) is one of the most serious of all cancers and a major public health problem. CCA is an extremely invasive cancer, and the survival rate for CCA patients is only 24 months after diagnosis. Although surgery and chemotherapy
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