CAS 97207-47-1|Meisoindigo

Introduction：Basic information about CAS 97207-47-1|Meisoindigo, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Meisoindigo BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Customs
6. Synonyms

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	/	Flash Point	245.3±28.7 °C

Names

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

Meisoindigo BiologicalActivity

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	Signaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>Cancer
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.

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

Signaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>Cancer

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
InChIKey	XZYXCQXTKOYHGK-UHFFFAOYSA-N
SMILES	Cn1c(O)c(C2=c3ccccc3=NC2=O)c2ccccc21

Safety Information

HS Code	2933990090

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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