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Chemical Compound Review

AC1NSWUD     (2Z)-2-(2-oxo-1H-indol-3- ylidene)-1H-indol...

Synonyms: SureCN9899338, BSPBio_001110, BMK1-G9, Ambotz479-41-4, CHEBI:150286, ...
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Disease relevance of Indirubin


High impact information on Indirubin

  • The crystal structure of CDK2 in complex with indirubin derivatives shows that indirubin interacts with the kinase's ATP-binding site through van der Waals interactions and three hydrogen bonds [1].
  • Indirubin, the active constituent of a Chinese antileukaemia medicine, inhibits cyclin-dependent kinases [1].
  • Indirubin derivatives inhibit Stat3 signaling and induce apoptosis in human cancer cells [2].
  • The antiapoptotic proteins Mcl-1 and Survivin, which are encoded in target genes of Stat3, were down-regulated by indirubin derivatives, followed by induction of apoptosis [2].
  • This effect is mimicked by the structurally independent inhibitors of GSK-3, FRAT1, and indirubin [6].

Chemical compound and disease context of Indirubin


Biological context of Indirubin


Anatomical context of Indirubin


Associations of Indirubin with other chemical compounds


Gene context of Indirubin

  • The potency of indirubin was comparable to that of TCDD in a CYP1B1-promoter-driven luciferase assay, when MCF-7 cells were co-exposed to the AhR ligands together with the CYP inhibitor, ellipticine [15].
  • These enhancing effects of indirubin and indigo were not observed in AhR knock-out mice [23].
  • CYP1A1 and CYP1A2 mRNAs were induced by as little as 1 pM of indirubin, whereas they were not induced by 10 pM of TCDD [12].
  • In addition, indirubin induced marked IL-8 release by the cells during differentiation and the cells differentiated with indirubin had typical neutrophilic properties, deformed nuclei and granules [16].
  • Our results suggest that indirubin and indigo act as inducers for cytochrome P450 1A1/2 mediated by AhR in mammals in vivo [23].

Analytical, diagnostic and therapeutic context of Indirubin

  • Here we compared gene expression changes in HepG2 cells exposed to 10 nM of indirubin or TCDD using nylon-membrane-based cDNA arrays with 1176 genes to elucidate the toxic differences at the transcriptional level [12].
  • The binding force between them was rather weak, as indirubin molecules were easily released during the precipitation with alcohol or the gel filtration [24].
  • Evidence from TLC, NMR spectroscopy, absorption spectrum analysis and solubility behaviour suggested that the blue pigment was indigo and the pink pigment was indirubin, a structural isomer of indigo [25].


  1. Indirubin, the active constituent of a Chinese antileukaemia medicine, inhibits cyclin-dependent kinases. Hoessel, R., Leclerc, S., Endicott, J.A., Nobel, M.E., Lawrie, A., Tunnah, P., Leost, M., Damiens, E., Marie, D., Marko, D., Niederberger, E., Tang, W., Eisenbrand, G., Meijer, L. Nat. Cell Biol. (1999) [Pubmed]
  2. Indirubin derivatives inhibit Stat3 signaling and induce apoptosis in human cancer cells. Nam, S., Buettner, R., Turkson, J., Kim, D., Cheng, J.Q., Muehlbeyer, S., Hippe, F., Vatter, S., Merz, K.H., Eisenbrand, G., Jove, R. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  3. Indirubins inhibit glycogen synthase kinase-3 beta and CDK5/p25, two protein kinases involved in abnormal tau phosphorylation in Alzheimer's disease. A property common to most cyclin-dependent kinase inhibitors? Leclerc, S., Garnier, M., Hoessel, R., Marko, D., Bibb, J.A., Snyder, G.L., Greengard, P., Biernat, J., Wu, Y.Z., Mandelkow, E.M., Eisenbrand, G., Meijer, L. J. Biol. Chem. (2001) [Pubmed]
  4. 7-Bromoindirubin-3'-oxime induces caspase-independent cell death. Ribas, J., Bettayeb, K., Ferandin, Y., Knockaert, M., Garrof??-Ochoa, X., Totzke, F., Sch??chtele, C., Mester, J., Polychronopoulos, P., Magiatis, P., Skaltsounis, A.L., Boix, J., Meijer, L. Oncogene (2006) [Pubmed]
  5. Characterization of a forest soil metagenome clone that confers indirubin and indigo production on Escherichia coli. Lim, H.K., Chung, E.J., Kim, J.C., Choi, G.J., Jang, K.S., Chung, Y.R., Cho, K.Y., Lee, S.W. Appl. Environ. Microbiol. (2005) [Pubmed]
  6. Lithium blocks the c-Jun stress response and protects neurons via its action on glycogen synthase kinase 3. Hongisto, V., Smeds, N., Brecht, S., Herdegen, T., Courtney, M.J., Coffey, E.T. Mol. Cell. Biol. (2003) [Pubmed]
  7. Anti-mitotic properties of indirubin-3'-monoxime, a CDK/GSK-3 inhibitor: induction of endoreplication following prophase arrest. Damiens, E., Baratte, B., Marie, D., Eisenbrand, G., Meijer, L. Oncogene (2001) [Pubmed]
  8. 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. Liu, X.M., Wang, L.G., Li, H.Y., Ji, X.J. Biochem. Pharmacol. (1996) [Pubmed]
  9. Indigo production by naphthalene-degrading bacteria. Bhushan, B., Samanta, S.K., Jain, R.K. Lett. Appl. Microbiol. (2000) [Pubmed]
  10. Indirubin enhances tumor necrosis factor-induced apoptosis through modulation of nuclear factor-kappaB signaling pathway. Sethi, G., Ahn, K.S., Sandur, S.K., Lin, X., Chaturvedi, M.M., Aggarwal, B.B. J. Biol. Chem. (2006) [Pubmed]
  11. Antitumor activity of novel indirubin derivatives in rat tumor model. Kim, S.A., Kim, Y.C., Kim, S.W., Lee, S.H., Min, J.J., Ahn, S.G., Yoon, J.H. Clin. Cancer Res. (2007) [Pubmed]
  12. Comparison of gene expression patterns between 2,3,7,8-tetrachlorodibenzo-p-dioxin and a natural arylhydrocarbon receptor ligand, indirubin. Adachi, J., Mori, Y., Matsui, S., Matsuda, T. Toxicol. Sci. (2004) [Pubmed]
  13. Molecular mechanisms of indirubin and its derivatives: novel anticancer molecules with their origin in traditional Chinese phytomedicine. Eisenbrand, G., Hippe, F., Jakobs, S., Muehlbeyer, S. J. Cancer Res. Clin. Oncol. (2004) [Pubmed]
  14. Inhibition of RANTES expression by indirubin in influenza virus-infected human bronchial epithelial cells. Mak, N.K., Leung, C.Y., Wei, X.Y., Shen, X.L., Wong, R.N., Leung, K.N., Fung, M.C. Biochem. Pharmacol. (2004) [Pubmed]
  15. Transient induction of cytochromes P450 1A1 and 1B1 in MCF-7 human breast cancer cells by indirubin. Spink, B.C., Hussain, M.M., Katz, B.H., Eisele, L., Spink, D.C. Biochem. Pharmacol. (2003) [Pubmed]
  16. Indirubin, a Chinese anti-leukaemia drug, promotes neutrophilic differentiation of human myelocytic leukaemia HL-60 cells. Suzuki, K., Adachi, R., Hirayama, A., Watanabe, H., Otani, S., Watanabe, Y., Kasahara, T. Br. J. Haematol. (2005) [Pubmed]
  17. Indirubin inhibits inflammatory reactions in delayed-type hypersensitivity. Kunikata, T., Tatefuji, T., Aga, H., Iwaki, K., Ikeda, M., Kurimoto, M. Eur. J. Pharmacol. (2000) [Pubmed]
  18. Generation of new protein kinase inhibitors utilizing cytochrome p450 mutant enzymes for indigoid synthesis. Guengerich, F.P., Sorrells, J.L., Schmitt, S., Krauser, J.A., Aryal, P., Meijer, L. J. Med. Chem. (2004) [Pubmed]
  19. Characterization of dark liver pigment observed in rats after subchronic dosing of the beta3-adrenergic receptor agonist LY368842. He, M.M., Barbuch, R.J., Abraham, T.L., Lindsay, T.J., Jackson, D.A., Ackermann, B.L., Wilke, A.V., Jensen, C.B. Chem. Res. Toxicol. (2003) [Pubmed]
  20. Identification of an indigo precursor from leaves of Isatis tinctoria (Woad). Maugard, T., Enaud, E., Choisy, P., Legoy, M.D. Phytochemistry (2001) [Pubmed]
  21. Novel indole S,O-bisdesmoside, calanthoside, the precursor glycoside of tryptanthrin, indirubin, and isatin, with increasing skin blood flow promoting effects, from two Calanthe species (Orchidaceae). Yoshikawa, M., Murakami, T., Kishi, A., Sakurama, T., Matsuda, H., Nomura, M., Matsuda, H., Kubo, M. Chem. Pharm. Bull. (1998) [Pubmed]
  22. Protein engineering of toluene ortho-monooxygenase of Burkholderia cepacia G4 for regiospecific hydroxylation of indole to form various indigoid compounds. Rui, L., Reardon, K.F., Wood, T.K. Appl. Microbiol. Biotechnol. (2005) [Pubmed]
  23. Aryl hydrocarbon receptor-mediated induction of microsomal drug-metabolizing enzyme activity by indirubin and indigo. Sugihara, K., Kitamura, S., Yamada, T., Okayama, T., Ohta, S., Yamashita, K., Yasuda, M., Fujii-Kuriyama, Y., Saeki, K., Matsui, S., Matsuda, T. Biochem. Biophys. Res. Commun. (2004) [Pubmed]
  24. Studies on the mechanism of indirubin action in the treatment of chronic granulocytic leukemia. V. Binding between indirubin and DNA and identification of the type of binding. Wu, G.Y., Liu, J.Z., Fang, F.D., Zuo, J. Sci. Sin., Ser. B, Chem. Biol. Agric. Med. Earth Sci. (1982) [Pubmed]
  25. Identification of indigo-related pigments produced by Escherichia coli containing a cloned Rhodococcus gene. Hart, S., Koch, K.R., Woods, D.R. J. Gen. Microbiol. (1992) [Pubmed]
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