Indirubin E804 | CAS#854171-35-0 | Indirubin synthetic derivative

MedKoo Cat#: 463274 | Name: Indirubin E804

Description:

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

Indirubin E804 is a synthetic derivative of natural indirubin. It has been shown to significantly inhibit the growth of human glioblastoma cells lines via induction of differentiation and apoptosis.

Chemical Structure

Indirubin E804

CAS#854171-35-0

Theoretical Analysis

MedKoo Cat#: 463274

Name: Indirubin E804

CAS#: 854171-35-0

Chemical Formula: C20H19N3O4

Exact Mass: 365.1376

Molecular Weight: 365.39

Elemental Analysis: C, 65.74; H, 5.24; N, 11.50; O, 17.51

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Indirubin E804; Indirubin E 804; Indirubin E-804; E-804; E804; E 804; Indirubin E804; Indirubin E 804; Indirubin E-804;

IUPAC/Chemical Name

(2Z,3Z)-3-((3,4-dihydroxybutoxy)imino)-[2,3'-biindolinylidene]-2'-one

InChi Key

RKUMZEVCWKZXFV-YQSYOFKPSA-N

InChi Code

InChI=1S/C20H19N3O4/c24-11-12(25)9-10-27-23-18-14-6-2-4-8-16(14)21-19(18)17-13-5-1-3-7-15(13)22-20(17)26/h1-8,12,21,24-25H,9-11H2,(H,22,26)/b19-17-,23-18-

SMILES Code

OCC(CCO/N=C1\C(Nc2c1cccc2)=C3C(Nc4c\3cccc4)=O)O

Appearance

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

Shelf Life

>3 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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 365.39 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.

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

1: Wang R, Liu K, Zhang Y, Chen X, Wang X. Evaluation of the Developmental Toxicity Induced by E804 in Zebrafish Embryos. Front Pharmacol. 2020 Feb 14;11:32. doi: 10.3389/fphar.2020.00032. PMID: 32116709; PMCID: PMC7033426. 2: Scobie MR, Houke HR, Rice CD. Modulation of glioma-inflammation crosstalk profiles in human glioblastoma cells by indirubin-3'-(2,3 dihydroxypropyl)-oximether (E804) and 7-bromoindirubin-3'-oxime (7BIO). Chem Biol Interact. 2019 Oct 1;312:108816. doi: 10.1016/j.cbi.2019.108816. Epub 2019 Sep 7. PMID: 31505164. 3: Dixon-Clarke SE, Shehata SN, Krojer T, Sharpe TD, von Delft F, Sakamoto K, Bullock AN. Structure and inhibitor specificity of the PCTAIRE-family kinase CDK16. Biochem J. 2017 Feb 20;474(5):699-713. doi: 10.1042/BCJ20160941. PMID: 28057719; PMCID: PMC5317395. 4: Kwok HH, Poon PY, Fok SP, Ying-Kit Yue P, Mak NK, Chan MC, Peiris JS, Wong RN. Anti-inflammatory effects of indirubin derivatives on influenza A virus- infected human pulmonary microvascular endothelial cells. Sci Rep. 2016 Jan 6;6:18941. doi: 10.1038/srep18941. PMID: 26732368; PMCID: PMC4702174. 5: Zhang Y, Du Z, Zhuang Z, Wang Y, Wang F, Liu S, Wang H, Feng H, Li H, Wang L, Zhang X, Hao A. E804 induces growth arrest, differentiation and apoptosis of glioblastoma cells by blocking Stat3 signaling. J Neurooncol. 2015 Nov;125(2):265-75. doi: 10.1007/s11060-015-1917-8. Epub 2015 Sep 19. PMID: 26386687. 6: Ichimaru Y, Saito H, Uchiyama T, Metori K, Tabata K, Suzuki T, Miyairi S. Indirubin 3'-(O-oxiran-2-ylmethyl)oxime: a novel anticancer agent. Bioorg Med Chem Lett. 2015 Apr 1;25(7):1403-6. doi: 10.1016/j.bmcl.2015.02.053. Epub 2015 Feb 28. PMID: 25765906. 7: Heshmati N, Cheng X, Dapat E, Sassene P, Eisenbrand G, Fricker G, Müllertz A. In vitro and in vivo evaluations of the performance of an indirubin derivative, formulated in four different self-emulsifying drug delivery systems. J Pharm Pharmacol. 2014 Nov;66(11):1567-75. doi: 10.1111/jphp.12286. Epub 2014 Jun 24. PMID: 24961657. 8: Mok CK, Kang SS, Chan RW, Yue PY, Mak NK, Poon LL, Wong RN, Peiris JS, Chan MC. Anti-inflammatory and antiviral effects of indirubin derivatives in influenza A (H5N1) virus infected primary human peripheral blood-derived macrophages and alveolar epithelial cells. Antiviral Res. 2014 Jun;106:95-104. doi: 10.1016/j.antiviral.2014.03.019. Epub 2014 Apr 6. PMID: 24717263. 9: Heshmati N, Wagner B, Cheng X, Scholz T, Kansy M, Eisenbrand G, Fricker G. Physicochemical characterization and in vitro permeation of an indirubin derivative. Eur J Pharm Sci. 2013 Nov 20;50(3-4):467-75. doi: 10.1016/j.ejps.2013.08.021. Epub 2013 Aug 28. PMID: 23994641. 10: Heshmati N, Cheng X, Eisenbrand G, Fricker G. Enhancement of oral bioavailability of E804 by self-nanoemulsifying drug delivery system (SNEDDS) in rats. J Pharm Sci. 2013 Oct;102(10):3792-9. doi: 10.1002/jps.23696. Epub 2013 Aug 11. PMID: 23934779. 11: Babcock AS, Anderson AL, Rice CD. Indirubin-3'-(2,3 dihydroxypropyl)-oximether (E804) is a potent modulator of LPS-stimulated macrophage functions. Toxicol Appl Pharmacol. 2013 Jan 1;266(1):157-66. doi: 10.1016/j.taap.2012.10.011. Epub 2012 Oct 26. PMID: 23107598; PMCID: PMC3525808. 12: Shin EK, Kim JK. Indirubin derivative E804 inhibits angiogenesis. BMC Cancer. 2012 May 3;12:164. doi: 10.1186/1471-2407-12-164. PMID: 22554053; PMCID: PMC3488320. 13: Nam S, Scuto A, Yang F, Chen W, Park S, Yoo HS, Konig H, Bhatia R, Cheng X, Merz KH, Eisenbrand G, Jove R. Indirubin derivatives induce apoptosis of chronic myelogenous leukemia cells involving inhibition of Stat5 signaling. Mol Oncol. 2012 Jun;6(3):276-83. doi: 10.1016/j.molonc.2012.02.002. Epub 2012 Feb 17. PMID: 22387217; PMCID: PMC3361532. 14: Chan YK, Kwok HH, Chan LS, Leung KS, Shi J, Mak NK, Wong RN, Yue PY. An indirubin derivative, E804, exhibits potent angiosuppressive activity. Biochem Pharmacol. 2012 Mar 1;83(5):598-607. doi: 10.1016/j.bcp.2011.12.003. Epub 2011 Dec 9. PMID: 22178720. 15: Miyoshi K, Takaishi M, Digiovanni J, Sano S. Attenuation of psoriasis-like skin lesion in a mouse model by topical treatment with indirubin and its derivative E804. J Dermatol Sci. 2012 Jan;65(1):70-2. doi: 10.1016/j.jdermsci.2011.10.001. Epub 2011 Oct 8. PMID: 22051056. 16: Zhou J, Bi C, Janakakumara JV, Liu SC, Chng WJ, Tay KG, Poon LF, Xie Z, Palaniyandi S, Yu H, Glaser KB, Albert DH, Davidsen SK, Chen CS. Enhanced activation of STAT pathways and overexpression of survivin confer resistance to FLT3 inhibitors and could be therapeutic targets in AML. Blood. 2009 Apr 23;113(17):4052-62. doi: 10.1182/blood-2008-05-156422. Epub 2009 Jan 14. PMID: 19144991. 17: Xu F, Mukhopadhyay S, Sehgal PB. Live cell imaging of interleukin-6-induced targeting of "transcription factor" STAT3 to sequestering endosomes in the cytoplasm. Am J Physiol Cell Physiol. 2007 Oct;293(4):C1374-82. doi: 10.1152/ajpcell.00220.2007. Epub 2007 Aug 1. PMID: 17670892. 18: Jakobs S, Merz KH, Vatter S, Eisenbrand G. Molecular targets of indirubins. Int J Clin Pharmacol Ther. 2005 Dec;43(12):592-4. doi: 10.5414/cpp43592. PMID: 16372530. 19: Nam S, Buettner R, Turkson J, Kim D, Cheng JQ, Muehlbeyer S, Hippe F, Vatter S, Merz KH, Eisenbrand G, Jove R. Indirubin derivatives inhibit Stat3 signaling and induce apoptosis in human cancer cells. Proc Natl Acad Sci U S A. 2005 Apr 26;102(17):5998-6003. doi: 10.1073/pnas.0409467102. Epub 2005 Apr 18. PMID: 15837920; PMCID: PMC1087919.