Meisoindigo
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MedKoo CAT#: 100622

CAS#: 97207-47-1

Description: Meisoindigo, also known as N-Methylisoindigotin and Dian III, is an apoptosis inducer and potential agent for AML. Meisoindigo has been a routine therapeutic agent in the clinical treatment of chronic myelogenous leukemia (CML) in China since the 1980s. Meisoindigo is a promising agent with in vitro and in vivo activity against human acute myeloid leukemia.


Chemical Structure

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Meisoindigo
CAS# 97207-47-1

Theoretical Analysis

MedKoo Cat#: 100622
Name: Meisoindigo
CAS#: 97207-47-1
Chemical Formula: C18H14N2O2
Exact Mass: 290.10553
Molecular Weight: 290.31
Elemental Analysis: C, 74.47; H, 4.86; N, 9.65; O, 11.02

Price and Availability

Size Price Availability Quantity
10.0mg USD 150.0 Same day
25.0mg USD 250.0 Same day
50.0mg USD 450.0 Same day
100.0mg USD 750.0 Same day
200.0mg USD 1250.0 Same day
500.0mg USD 1950.0 Same day
1.0g USD 2950.0 Same day
2.0g USD 3950.0 2 Weeks
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Synonym: Methyl isoindigotin; N-Methylisoindigotin; Meisoindigo; Dian III.

IUPAC/Chemical Name: (E)-1,1'-dimethyl-[3,3'-biindolinylidene]-2,2'-dione

InChi Key: QNOCRUSVMMAKSC-CCEZHUSRSA-N

InChi Code: 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)/b15-14+

SMILES Code: CN(C1=CC=CC=C1/C2=C3C(NC4=C\3C=CC=C4)=O)C2=O

Appearance: Red solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 290.31 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Huang M, Lin HS, Lee YS, Ho PC. Evaluation of meisoindigo, an indirubin derivative: in vitro antileukemic activity and in vivo pharmacokinetics. Int J Oncol. 2014 Oct;45(4):1724-34. doi: 10.3892/ijo.2014.2548. PubMed PMID: 25050545.

2: Huang M, Goh LT, Ho PC. Identification of stereoisomeric metabolites of meisoindigo in rat liver microsomes by achiral and chiral liquid chromatography/tandem mass spectrometry. Drug Metab Dispos. 2008 Nov;36(11):2171-84. doi: 10.1124/dmd.108.021956. PubMed PMID: 18710897.

3: Zhang HJ, Zhang Y, Jin J, Zhou WQ, Chen XG. [Mechanism about therapeutic effect of meisoindigo on psoriasis via down-regulation of the TLR4-TAK-NF-kappaB pathways]. Yao Xue Xue Bao. 2013 Apr;48(4):503-7. Chinese. PubMed PMID: 23833936.

4: Wang XJ, Yin SM, Ma LP, Nie DN, Xie SF, Li YQ. [Immuno-regulatory effect of 3'-meisoindigo in mice of various germlines]. Zhong Yao Cai. 2010 Jul;33(7):1124-9. Chinese. PubMed PMID: 21137371.

5: Liu BC, Xiao ZJ. [Effect on bcr-abl signaling pathway and the mechanisms of apoptosis induction by meisoindigo in K562 cells]. Zhonghua Xue Ye Xue Za Zhi. 2008 Dec;29(12):815-8. Chinese. PubMed PMID: 19176035.

6: Mingxin Z, Yan L, Hongbo W, Jianhua Z, Hongyan L, He L, Hongqi X, Sen Z, Xiaoguang C. 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. PubMed PMID: 19129071.

7: Huang M, Choo LW, Ho PC. Characterization of metabolites of meisoindigo in male and female rat kidney microsomes by high-performance liquid chromatography coupled with positive electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom. 2008 Dec;22(23):3835-45. doi: 10.1002/rcm.3805. PubMed PMID: 18980268.

8: 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. doi: 10.3109/10428191003672115. PubMed PMID: 20233051.

9: Zuo MX, Li Y, Zhou JH, Wang HB, Chen XG. [Effect of Meisoindigo on Wnt signal pathway in K562 and HL-60 cells]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2010 Jun;18(3):579-82. Chinese. PubMed PMID: 20561405.

10: Ye B, Xiong X, Deng X, Gu L, Wang Q, Zeng Z, Gao X, Gao Q, Wang Y. Meisoindigo, but not its core chemical structure indirubin, inhibits zebrafish interstitial leukocyte chemotactic migration. Pharm Biol. 2017 Dec;55(1):673-679. PubMed PMID: 27981893.

11: Huang M, Ho PC. Identification of metabolites of meisoindigo in rat, pig and human liver microsomes by UFLC-MS/MS. Biochem Pharmacol. 2009 Apr 15;77(8):1418-28. doi: 10.1016/j.bcp.2009.01.012. PubMed PMID: 19426681.

12: Wang Y, Zhu XF, Xiao ZJ, Wang HH, Zhou JM, Mei YP, Deng R, Jiang WQ, Liu ZC. [Inducement effect of Meisoindigo on apoptosis of leukemia cell line HL-60 and its mechanism]. Ai Zheng. 2005 Dec;24(12):1464-8. Chinese. PubMed PMID: 16351793.

13: Xiao Z, Wang Y, Lu L, Li Z, Peng Z, Han Z, Hao Y. Anti-angiogenesis effects of meisoindigo on chronic myelogenous leukemia in vitro. Leuk Res. 2006 Jan;30(1):54-9. PubMed PMID: 15982734.

14: Huang M, Lee YS, Ho PC. Identification of circulatory and excretory metabolites of meisoindigo in rat plasma, urine and feces by high-performance liquid chromatography coupled with positive electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom. 2010 Mar;24(6):729-41. doi: 10.1002/rcm.4434. PubMed PMID: 20169560.

15: Xiao Z, Hao Y, Liu B, Qian L. Indirubin and meisoindigo in the treatment of chronic myelogenous leukemia in China. Leuk Lymphoma. 2002 Sep;43(9):1763-8. Review. PubMed PMID: 12685829.

16: Meng Z, Li WY, Hou LY, Xue HM, Xia Y, Guo HX, Deng QL. [Effects of meisoindigo on the expression of globin gene in vitro]. Zhonghua Er Ke Za Zhi. 2004 Mar;42(3):184-7. Chinese. PubMed PMID: 15144711.

17: Song L, Qian L. [Apoptosis inducing effect of meisoindigo on K562 cells]. Zhongguo Zhong Xi Yi Jie He Za Zhi. 1999 Jun;19(6):353-5. Chinese. PubMed PMID: 11783201.

18: Wee XK, Yang T, Go ML. Exploring the anticancer activity of functionalized isoindigos: synthesis, drug-like potential, mode of action and effect on tumor-induced xenografts. ChemMedChem. 2012 May;7(5):777-91. doi: 10.1002/cmdc.201200018. PubMed PMID: 22416043.

19: Xiao Z, Qian L, Liu B, Hao Y. Meisoindigo for the treatment of chronic myelogenous leukaemia. Br J Haematol. 2000 Nov;111(2):711-2. PubMed PMID: 11122126.

20: Liu XM, Wang LG, Li HY, Ji XJ. Induction of differentiation and down-regulation of c-myb gene expression in ML-1 human myeloblastic leukemia cells by the clinically effective anti-leukemia agent meisoindigo. Biochem Pharmacol. 1996 Jun 14;51(11):1545-51. PubMed PMID: 8630096.



Additional Information

Methyl isoindigotin was approved for treating cancers in China. Methyl isoindigotin is an orally bioavailable anticancer drug, which belongs to anti-metabolite drugs.