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MedKoo Cat#: 100622 | Name: Meisoindigo
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Meisoindigo
Meisoindigo
CAS#97207-47-1

Theoretical Analysis

MedKoo Cat#: 100622

Name: Meisoindigo

CAS#: 97207-47-1

Chemical Formula: C18H14N2O2

Exact Mass: 290.1055

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
10mg USD 110.00 Ready to ship
25mg USD 220.00 Ready to ship
50mg USD 385.00 Ready to ship
100mg USD 685.00 Ready to ship
200mg USD 1,250.00 Ready to ship
500mg USD 1,950.00 Ready to ship
1g USD 2,950.00 Ready to ship
2g USD 3,950.00 2 weeks
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Related CAS #
No Data
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
More Info
Methyl isoindigotin was approved for treating cancers in China. Methyl isoindigotin is an orally bioavailable anticancer drug, which belongs to anti-metabolite drugs.     
Biological target:
Meisoindigo (Dian III), a derivative of Indirubin (HY-N0117), halts the cell cycle at the G0/G1 phase and induces apoptosis in primary acute myeloid leukemia (AML) cells.
In vitro activity:
It was confirmed whether TLR4 is a major molecular target of meisoindigo. The LPS was applied, a special agonist of TLR4 signaling, to further verify this hypothesis. The suitable time of OGD and greatest dose of meisoindigo in HT-22 and BV2 were determined by CCK-8 kits (Supplementary Figure S2). Compared to the OGD/R group, the expression of TLR4 and its downstream target NF-κB p65 was increased after LPS treatment both in HT-22 and BV2 (P < 0.01) (Figures 10,11).. However, their expressions were downregulated by co-treatment with LPS and Meisoindigo, compared with LPS only. The expressions of NLRP3 inflammasome-associated proteins were detected, including NLRP3, ASC, CL-caspase-1 and IL-1β, which was mediated by TLR4/NF-κB pathway and upregulated after LPS stimulation, were also inhibited by co-treatment LPS and Meisoindigo both in HT22 and BV2 (P < 0.05) (Figures 10,11). The results mean that meisoindigo had great inhibitory effects on inflammatory activation in both hippocampal neurons (HT-22) and microglia (BV2) via suppressing TLR4/NF-kB pathway. In addition, it was found that LPS stimulation resulted in M1 polarization of microglia (BV2) after OGD/R, but co-treatment of meisoindigo with LPS could significantly promoted the M1 microglia shifting to M2 microglia (P < 0.05) (Figure 11). These results strongly indicate that protective effect of meisoindigo on CIRI through inhibiting NLRP3 inflammasome and blocking M1 polarization may occur via downregulation of the TLR4 pathway. Front Cell Neurosci. 2019; 13: 553. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6930809/
In vivo activity:
This study was designed to discover effective and safe compounds that can inhibit leukocyte chemotactic migration, thus providing possible novel therapeutic strategy for treating inflammatory diseases. A transgenic zebrafish model (Tg:zlyz-EGFP line) was used to visualize the process of leukocyte chemotactic migration. It was identified that the hit compound meisoindigo (25 μM, 50 μM, 75 μM) can significantly inhibit zebrafish leukocyte chemotactic migration in a dose-dependent manner (p = 0.01, p = 0.0006, p < 0.0001). Also, it was found that meisoindigo did not affect the process of leukocyte reverse migration (p = 0.43). Furthermore, the results unexpectedly showed that indirubin, the core structure of meisoindigo, had no significant effect on zebrafish leukocyte chemotactic migration (p = 0.6001). Additionally, the results revealed that meisoindigo exerts no effect on the Akt or Erk-mediated signalling pathway. The results suggest that meisoindigo, but not indirubin, is effective for inhibiting leukocyte chemotactic migration, thus providing a potential therapeutic agent for treating inflammatory diseases. Pharm Biol. 2017; 55(1): 673–679. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6130669/
Solvent mg/mL mM
Solubility
DMSO 36.0 124.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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
Formulation protocol:
1. Ye Y, Jin T, Zhang X, Zeng Z, Ye B, Wang J, Zhong Y, Xiong X, Gu L. Meisoindigo Protects Against Focal Cerebral IschemiaReperfusion Injury by Inhibiting NLRP3 Inflammasome Activation and Regulating Microglia/Macrophage Polarization via TLR4/NFκB Signaling Pathway. Front Cell Neurosci. 2019 Dec 16;13:553. doi: 10.3389/fncel.2019.00553. PMID: 31920554; PMCID: PMC6930809. 2. Zhou Y, Ye Y, Zhu X, Jin T, Yi W, Gu L, Xiong X. Meisoindigo inhibits cellular proliferation via down-regulation of the PI3K/Akt pathway and induces cellular apoptosis in glioblastoma U87 cells. Acta Biochim Pol. 2021 May 23;68(2):309-315. doi: 10.18388/abp.2020_5581. PMID: 34022786. 3. 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. doi: 10.1080/13880209.2016.1238949. PMID: 27981893; PMCID: PMC6130669.
In vitro protocol:
1. Ye Y, Jin T, Zhang X, Zeng Z, Ye B, Wang J, Zhong Y, Xiong X, Gu L. Meisoindigo Protects Against Focal Cerebral IschemiaReperfusion Injury by Inhibiting NLRP3 Inflammasome Activation and Regulating Microglia/Macrophage Polarization via TLR4/NFκB Signaling Pathway. Front Cell Neurosci. 2019 Dec 16;13:553. doi: 10.3389/fncel.2019.00553. PMID: 31920554; PMCID: PMC6930809. 2. Zhou Y, Ye Y, Zhu X, Jin T, Yi W, Gu L, Xiong X. Meisoindigo inhibits cellular proliferation via down-regulation of the PI3K/Akt pathway and induces cellular apoptosis in glioblastoma U87 cells. Acta Biochim Pol. 2021 May 23;68(2):309-315. doi: 10.18388/abp.2020_5581. PMID: 34022786.
In vivo protocol:
1. 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. doi: 10.1080/13880209.2016.1238949. PMID: 27981893; PMCID: PMC6130669. 2. . Ye Y, Jin T, Zhang X, Zeng Z, Ye B, Wang J, Zhong Y, Xiong X, Gu L. Meisoindigo Protects Against Focal Cerebral IschemiaReperfusion Injury by Inhibiting NLRP3 Inflammasome Activation and Regulating Microglia/Macrophage Polarization via TLR4/NFκB Signaling Pathway. Front Cell Neurosci. 2019 Dec 16;13:553. doi: 10.3389/fncel.2019.00553. PMID: 31920554; PMCID: PMC6930809.
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.