I0404

Indirubin-3′-oxime

≥98% (HPLC), solid

• Synonym(s): Indirubin-3′-monoxime
• 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

Properties

• 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

Description

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves