| Identification | Back Directory | [Name]
Meisoindigo | [CAS]
97207-47-1 | [Synonyms]
CS-1454
Dian III
Natura-α
MEISOINDIGO
Meisoindigo, >96%
Meisoindigo, >=98%
Methylisoindigotin
Meisoindigo(Natura-
N-methylisoindigotin
Meisoindigo USP/EP/BP
Methylisoindigotin Meisoindigo
DIAN III; N-METHYLISOINDIGOTIN; NATURA-Α
1-METHYL-3,3'-BIINDOLE-2,2'(1H,1'H)-DIONE
1-methyl-3-(2-oxo-1H-indol-3-ylidene)indol-2-one
(3E)-1-methyl-3-(2-oxo-1H-indol-3-ylidene)indol-2-one
3-(1,2-dihydro-2-oxo-3h-indol-3-ylidene)-1,3-dihydro-1-methyl-2h-indol-2-one
2H-Indol-2-one, 3-(1,2-dihydro-2-oxo-3H-indol-3-ylidene)-1,3-dihydro-1-methyl-
Meisoindigo 3-(1,2-Dihydro-2-oxo-3H-indol-3-ylidene)-1,3-dihydro-1-methyl-2H-indol-2-one | [EINECS(EC#)]
200-256-5 | [Molecular Formula]
C17H12N2O2 | [MDL Number]
MFCD05988503 | [MOL File]
97207-47-1.mol | [Molecular Weight]
276.29 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [Description]
Meisoindigo is a derivative of indirubin (Item No. 14155) that has anticancer activity.1 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 (Item No. 16069) and idarubicin (Item No. 14176). 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.2 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
| [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]
Meisoindigo (Dian III; 50-150?mg/kg; IP; daily; for 14 days) has anti-leukemic activity in?vivo[1].
Meisoindigo (2, 4, 8, 12 mg/kg; IP; before MCAO and 2 h after reperfusion) significantly reduces infarct volume, ameliorates neurological deficits 3 days after middle cerebral artery occlusion (MCAO) in Wild-type C57BL/6J mice (25-30 g). Meisoindigo reduces edema and lowers AQP4 expression in the brain[2].
| Animal Model: | NOD/SCID mice, 6-8 weeks old, with HL-60 leukemic cells[1] | | Dosage: | 50, 100, 150?mg/kg | | Administration: | IP; daily; for 14 days | | Result: | Had anti-leukemic activity in?vivo.
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| [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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