Meisoindigo

Modify Date: 2024-01-02 08:57:07

Meisoindigo Structure
Meisoindigo structure
Common Name Meisoindigo
CAS Number 97207-47-1 Molecular Weight 276.289
Density 1.4±0.1 g/cm3 Boiling Point 482.0±45.0 °C at 760 mmHg
Molecular Formula C17H12N2O2 Melting Point 236-237ºC
MSDS N/A Flash Point 245.3±28.7 °C

 Use of Meisoindigo


Meisoindigo(Natura-α; N-Methylisoindigotin; Dian III), a derivative of Indigo naturalis, might induce apoptosis and myeloid differentiation of acute myeloid leukemia (AML).IC50 value:Target: apoptosis inducerin vitro: Meisoindigo inhibited the growth of leukemic cells by inducing marked apoptosis and moderate cell-cycle arrest at the G(0)/G(1) phase. It down-regulated anti-apoptotic Bcl-2, and up-regulated pro-apoptotic Bak and Bax and cell-cycle related proteins, p21and p27. Furthermore, it induced myeloid differentiation, as demonstrated by morphologic changes, up-regulation of CD11b, and increased nitroblue tetrazolium reduction activity in all cell lines tested. In addition, meisoindigo down-regulated the expression of human telomerase reverse transcriptase and enhanced the cytotoxicity of conventional chemotherapeutic agents, cytarabine and idarubicin. As with the results from cell lines, meisoindigo also induced apoptosis, up-regulated p21 and p27, and down-regulated Bcl-2 in primary AML cells [1]. meisoindigo effectively inhibits HT-29 cell proliferation (IC(50) 4.3 mmol/L), arrests HT-29 cells in G2/ M phase and induces HT-29 cell apoptosis. The downstream genes and proteins of GSK-3beta(ser(9)) expression level decrease [2].in vivo: The in vivo anti-leukemic activity of meisoindigo was also demonstrated by decreased spleen size in a dose-dependent manner [1]. Meisoindigo significantly inhibits the HT-29 xenograft tumors growth at the dose of 100 mg/kg. The mechanism of meisoindigo activity against HT-29 cells may be related to its inhibition of glycogen synthase kinase-3beta, GSK-3beta(ser(9)) phosphorylation in Wnt signaling pathway [2].

 Names

Name (3E)-1-methyl-3-(2-oxo-1H-indol-3-ylidene)indol-2-one
Synonym More Synonyms

 Meisoindigo Biological Activity

Description Meisoindigo(Natura-α; N-Methylisoindigotin; Dian III), a derivative of Indigo naturalis, might induce apoptosis and myeloid differentiation of acute myeloid leukemia (AML).IC50 value:Target: apoptosis inducerin vitro: Meisoindigo inhibited the growth of leukemic cells by inducing marked apoptosis and moderate cell-cycle arrest at the G(0)/G(1) phase. It down-regulated anti-apoptotic Bcl-2, and up-regulated pro-apoptotic Bak and Bax and cell-cycle related proteins, p21and p27. Furthermore, it induced myeloid differentiation, as demonstrated by morphologic changes, up-regulation of CD11b, and increased nitroblue tetrazolium reduction activity in all cell lines tested. In addition, meisoindigo down-regulated the expression of human telomerase reverse transcriptase and enhanced the cytotoxicity of conventional chemotherapeutic agents, cytarabine and idarubicin. As with the results from cell lines, meisoindigo also induced apoptosis, up-regulated p21 and p27, and down-regulated Bcl-2 in primary AML cells [1]. meisoindigo effectively inhibits HT-29 cell proliferation (IC(50) 4.3 mmol/L), arrests HT-29 cells in G2/ M phase and induces HT-29 cell apoptosis. The downstream genes and proteins of GSK-3beta(ser(9)) expression level decrease [2].in vivo: The in vivo anti-leukemic activity of meisoindigo was also demonstrated by decreased spleen size in a dose-dependent manner [1]. Meisoindigo significantly inhibits the HT-29 xenograft tumors growth at the dose of 100 mg/kg. The mechanism of meisoindigo activity against HT-29 cells may be related to its inhibition of glycogen synthase kinase-3beta, GSK-3beta(ser(9)) phosphorylation in Wnt signaling pathway [2].
Related Catalog
References

[1]. Lee CC, et al. 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.

[2]. Mingxin Z, et al. The antitumor activity of meisoindigo against human colorectal cancer HT-29 cells in vitro and in vivo. J Chemother. 2008 Dec;20(6):728-33.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 482.0±45.0 °C at 760 mmHg
Melting Point 236-237ºC
Molecular Formula C17H12N2O2
Molecular Weight 276.289
Flash Point 245.3±28.7 °C
Exact Mass 276.089874
PSA 49.41000
LogP 1.53
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.698

 Safety Information

HS Code 2933990090

 Precursor & DownStream

Precursor  3

DownStream  0

 Customs

HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 Synonyms

1-Methyl-1H,1'H-[3,3']biindolyliden-2,2'-dion
Meisoindigo
Biindolene deriv.
(E)-1-methyl-1H,1'H-[3,3']biindolylidene-2,2'-dione
2H-Indol-2-one, 3-(1,2-dihydro-2-oxo-3H-indol-3-ylidene)-1,3-dihydro-1-methyl-, (3E)-
(E)-1-Methyl-1H,1'H-[3,3']biindolyliden-2,2'-dion
HMS1593P16
1-methyl-1H,1'H-[3,3']biindolylidene-2,2'-dione
Dian III
Methylisoindigotin
N-methylisoindigo
N-Methylisoindigotin
(3E)-1-Methyl-3-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)-1,3-dihydro-2H-indol-2-one
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