Meisoindigo Chemical Properties

Melting point:

236-237°C

Boiling point:

482.0±45.0 °C(Predicted)

Density 

1.381±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

insoluble in H2O; insoluble in EtOH; ≥25.85 mg/mL in DMSO with ultrasonic

form 

powder to crystal

pka

11.62±0.20(Predicted)

color 

Orange to Brown to Dark red

InChI

InChI=1S/C17H12N2O2/c1-19-13-9-5-3-7-11(13)15(17(19)21)14-10-6-2-4-8-12(10)18-16(14)20/h2-9H,1H3,(H,18,20)

InChIKey

QNOCRUSVMMAKSC-UHFFFAOYSA-N

SMILES

N1(C)C2=C(C=CC=C2)C(=C2C3=C(NC2=O)C=CC=C3)C1=O

Safety Information

HS Code 

2933.79.1500

Meisoindigo Usage And Synthesis

Description

Meisoindigo is a derivative of indirubin that has anticancer activity. It inhibits the growth of NB4, HL-60, and U937 leukemia and primary acute myeloid leukemia (AML) cells when used at concentrations of 5 and 10 μM. It also halts the cell cycle at the G₀/G₁ phase and induces apoptosis in leukemia cell lines and primary AML cells, induces myeloid differentiation, and potentiates the effects of cytarabine and idarubicin . Meisoindigo (10 μM) also induces apoptosis, decreases adherence, and decreases the expression of vascular cell adhesion molecule-1 (VCAM-1) in ECV304 human vein endothelial cells. Meisoindigo (50-150 mg/kg per day) decreases spleen size in an HL-60 mouse xenograft model of AML in a dose-dependent manner.

Chemical Properties

mp 236-237°C

Uses

Meisoindigo is a 5-HT3 receptor antagonist prevents acute nausea and vomiting associated with emetogenic cancer chemotherapy

Uses

Meisoindigo shows strong anti-proliferation effect against gemcitabine-resistant Pancreatic ductal adenocarcinoma (PDACs).

Synthesis

GENERAL METHOD: A mixture of 1-methylisatin (1, 1.0 mmol), 2-indolone (2, 1.0 mmol) and zirconium tetrachloride (ZrCl4, 23 mg, 0.1 mmol) in anhydrous ethanol (5 mL) was heated under reflux conditions. The progress of the reaction was monitored by thin layer chromatography (TLC) and after complete disappearance of the reactants, which usually takes 8-12 h, the reaction mixture was slowly cooled to room temperature. The precipitated red solid was collected by filtration and washed with a small amount of anhydrous ethanol to give pure 1-methyl-[3,3'-bi-indolinylidene]-2,2'-dione (3).

in vivo

References

[1] lee cc, lin cp, lee yl, wang gc, cheng yc, liu he. meisoindigo is a promising agent with in vitro and in vivo activity against human acute myeloid leukemia. leuk lymphoma. 2010 may;51(5):897-905.

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