Skip to Content
MilliporeSigma
All Photos(1)

Documents

I0404

Sigma-Aldrich

Indirubin-3′-oxime

≥98% (HPLC), solid

Synonym(s):

Indirubin-3′-monoxime

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C16H11N3O2
CAS Number:
160807-49-8
Molecular Weight:
277.28
MDL number:
MFCD02683594
UNSPSC Code:
12352200
PubChem Substance ID:
24278483
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

solid

mol wt

277.28

solubility

DMSO: >10 mg/mL
H2O: insoluble

storage temp.

room temp

SMILES string

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+

InChI key

HBDSHCUSXQATPO-BGBJRWHRSA-N

Application

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

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.
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.

Features and Benefits

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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 5

1 of 5

SB 216763 >98% (HPLC)

Sigma-Aldrich

S3442

SB 216763

SKF-96365 ≥98% (HPLC), solid

Sigma-Aldrich

S7809

SKF-96365

Roscovitine ≥98% (TLC)

Sigma-Aldrich

R7772

Roscovitine

(−)-Epigallocatechin gallate ≥95%

Sigma-Aldrich

E4143

(−)-Epigallocatechin gallate

(Z)-4-Hydroxytamoxifen ≥98% Z isomer

Sigma-Aldrich

H7904

(Z)-4-Hydroxytamoxifen

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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service