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Review

Indirubin derivatives: a patent review (2010 – present)

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Bibliography

  • Clark RJH, Cooksey CJ, Daniels MAM, et al. Indigo, woad, and Tyrian Purple: important vat dyes from antiquity to the present. Endeavour 1993;17:191-9
  • Epstein E, Nabors MW, Stowe BB. Origin of Indigo of Woad. Nature 1967;216:547-9
  • Wu E, Komolpis K, Wang H. Chemical Extraction of Indigo from Indigofera tinctoria while attaining biological integrity. Biotechnol Tech 1999;13:567-9
  • McGovern PE, Michel RH. Royal purple dye: the chemical reconstruction of the ancient mediterranean industry. Acc Chem Res 1990;23:152-8
  • Koren ZC. Archaeo-chemical analysis of royal purple on a darius i stone jar. Microchim Acta 2008;162:381-92
  • Oberthür C, Schneider B, Graf H, et al. The elusive indigo precursors in woad (isatis tinctoria l.) – identification of the major indigo precursor, isatan a, and a structure revision of isatan B. Chem Biodiv 2004;1:174-82
  • Gilbert KG, Hill DJ, Crespo C, et al. Qualitative analysis of indigo precursors from woad by hplc and hplc-ms. Phytochem Anal 2000;11:18-20
  • Maier W, Schumann B, Gröger D. Biosynthesis of Indoxyl Derivatives in Isatis tinctoria and Polygonum tinctorium. Phytochem 1990;29:817-19
  • Oberthür C, Graf H, Hamburger M. The content of indigo precursors in isatis tinctoria leaves ‚ a comparative study of selected accessions and post-harvest treatments. Phytochem 2004;65:3261-8
  • Cooksey CJ. Tyrian Purple: 6,6’-Dibromoindigo and Related Compounds. Molecules 2001;6:736-69
  • Lopez Chavez FJ, Chavez PR, Oyama K. Brominated precursors of tyrian purple (C.I. Natural Violet 1) from Plicopurpura pansa, Plicopurpura columellaris and Plicopurpura patula. Dyes Pigments 2009;83:7-13
  • Westley C, Benkendorff K. Sex-specific tyrian purple genesis: precursor and pigment distribution in the reproductive system of the marine mollusc dicathais orbita. J Chem Ecol 2008;34:44-56
  • Baker JT, Duke CC. Isolation from marine mollusks hypobranchial glands of 6-bromo-2,2-bis(methylthio)indolin-3-one and 6-bromo-2-(methylthio)indoleninone as alternative precursors to tyrian purple. Tetrahedron Lett 1973;27:2481-2
  • Fouquet H, Bielig H-J. Biological precursors and genesis of tyrian purple. Angew Chem Int Ed 1971;10:816-17
  • Guengerich FP, Sorrells JL, Schmitt S, et al. Generation of new protein kinase inhibitors utilizing cytochrome p450 mutant enzymes for indigoid synthesis. J Med Chem 2004;47:3236-41
  • Hoessel R, Leclerc S, Endicott JA, et al. Indirubin, the active constituent of a Chinese antileukaemia medicine, inhibits cyclin-dependent kinases. Nat Cell Biol 1999;1:60-7
  • Meijer L, Skaltsounis A-L, Magiatis P, et al. GSK-3 selective inhibitors derived from tyrian purple indirubins. Chem Biol 2003;10:1255-66
  • Jautelat R, Brumby T, Schäfer M, et al. From the insoluble dye indirubin towards highly active, soluble CDK2-inhibitors. ChemBioChem 2005;6:531-40
  • Beauchard A, Ferandin Y, Frere S, et al. Synthesis of novel 5-substituted indirubins as protein kinases inhibitors. Bioorg Med Chem 2006;14:6434-43
  • Polychronopoulos P, Magiatis P, Skaltsounis A-L, et al. Structural basis for the synthesis of indirubins as potent and selective inhibitors of glycogen synthase kinase-3 and cyclin-dependent kinases. J Med Chem 2004;47:935-46
  • Myrianthopoulos V, Kritsanida M, Gaboriaud-Kolar N, et al. Novel inverse binding mode of indirubin derivatives yields improved selectivity for dyrk kinases. ACS Med Chem Lett 2013;4:22-6
  • Choi SJ, Moon MJ, Lee SD, et al. Indirubin derivatives as potent FLT3 inhibitors with anti-proliferative activity of acute myeloid leukemic cells. Bioorg Med Chem Lett 2010;20:2033-7
  • Myrianthopoulos V, Magiatis P, Ferandin Y, et al. An integrated computational approach to the phenomenon of potent and selective inhibition of aurora kinases B and C by a Series of 7-substituted indirubins. J Med Chem 2007;50:4027-37
  • Nam S, Wen W, Schroeder A, et al. Dual inhibition of janus and src family kinases by novel indirubin derivative blocks constitutively-activated stat3 signaling associated with apoptosis of human pancreatic cancer cells. Mol Oncol 2013;7:369-78
  • Cheng X, Merz K-H, Vatter S, et al. 7,7′-Diazaindirubin—A small molecule inhibitor of casein kinase 2 in vitro and in cells. Bioorg Med Chem 2014;22:247-55
  • Ribas J, Bettayeb K, Ferandin Y, et al. 7-Bromoindirubin-3’-oxime induces caspase-independent cell death. Oncogene 2006;25:6304-18
  • Knockaert M, Blondel M, Bach S, et al. Independent actions on cyclin-dependent kinases and aryl hydrocarbon receptor mediate the antiproliferative effects of indirubins. Oncogene 2004;23:4400-12
  • Xingi E, Smirlis D, Myrianthopoulos V, et al. 6-Br-5-Methylindirubin-3’-Oxime (5-Me-6-BIO) targeting the leishmanial glycogen synthase kinase-3 (GSK-3) short form affects cell-cycle progression and induces apoptosis-like death: exploitation of gsk-3 for treating leishmaniasis. Int J Parasit 2009;39:1289-303
  • Efstathiou A, Gaboriaud-Kolar N, Smirlis D, et al. An inhibitor-driven study for enhancing the selectivity of indirubin derivatives towards leishmanial Glycogen Synthase Kinase-3 over leishmanial cdc2-related protein kinase 3. Parasit vectors 2014;7:234
  • Krivogorsky B, Grundt P, Yolken R, et al. Inhibition of Toxoplasma gondii by indirubin and tryptanthrin analogs. Antimicrob Agents Chemother 2008;52:4466-9
  • Jacquemin D, Preat J, Wathelet V, et al. Substitution and chemical environment effects on the absorption spectrum of indigo. J Chem Phys 2006;124:074104-12
  • Karapanagiotis I, de Villemereuil V, Magiatis P, et al. Identification of the coloring constituents of four natural indigoid dyes. J Liq Chrom Rel Technol 2006;29:1491-502
  • Anhui Shenjian Bio Engineering. Method for preparing indirubin. CN101648901; 2010
  • Zhengzhou Ruilong Pharmaceutical Co. Ltd. Method for countercurrent ultrasonic extraction of active ingredients from traditional Chinese medicine radix isatidis and folium isatidis. CN102973729; 2013
  • Chen HJ, Tsao HH, Lo JG, et al. Supercritical fluid extraction coupled with solvent-less spray collection mode for rapid separation of indirubin and tryptanthrin from folium isatidis. Sep Sci Technol 2011;46:972-7
  • Anhui Shenjian Bio Engineering. Method for effectively extracting indirubin from Chinese herbal medicine radix isatidis. CN101638375; 2010
  • Baeyer A. Ueber die verbindungen der indigogruppe. Ber Dtsch Chem Ges 1883;16:2188-204
  • Russell GA, Kaupp G. Reactions of resonance stabilized carbanions. xxxi. oxidation of carbanions. 4. oxidation of indoxyl to indigo in basic solution. J Am Chem Soc 1969;91:3851-9
  • Vougogiannopoulou K, Skaltsounis AL. From tyrian purple to kinase modulators: naturally halogenated indirubins and synthetic analogues. Planta Med 2012;78:1515-28
  • Gaboriaud-Kolar N, Nam S, Skaltsounis AL. A colorful history: the evolution of indigoids. Prog Chem Org Nat Prod 2014;99:69-145
  • City of Hope. Indirubin derivatives and uses thereof in treating chronic myelogenous leukemia. US0210834A1; 2013
  • CNRS. 7-substituted indirubin-3’oximes and their applications. US331327(A1); 2010
  • CNRS. 3’,6-substituted indirubins and their biological applications. US0136808A1; 2011
  • Jove R, Nam S, Horne D, et al. 5-bromo-indirubins. WO2014153023A1; 2014
  • Universitätsklinikum Jena. Use of indirubin derivatives for producing pluripotent stem cells. EP2518139A1; 2012
  • Kritsanida M, Magiatis P, Skaltsounis A-L, et al. Synthesis and antiproliferative activity of 7-Azaindirubin-3’-oxime, a 7-Aza isostere of the natural indirubin pharmacophore. J Nat Prod 2009;72:2199-202
  • Shanghai Jiao Tong University. 1’-thio-aza indirubin compound, application and preparation method thereof. CN101747339; 2012
  • China Pharmaceutical University. Preparation method and use of 1’-oxo-indirubin. CN103333161 A; 2013
  • BASF AG. Cytochrome p450 monooxygenases and their use for oxidizing organic compounds. US7960155; 2011
  • Industry-Academic Cooperation Foundation, Chosun University. Biological methods for producing high concentrated indirubin by the recombinant E. coli cells harboring a monooxygenase. KR0089212; 2010
  • Han GH, Gim GH, Kim W, et al. Enhanced indirubin production in recombinant Escherichia coli harboring a flavin-containing monooxygenase gene by cysteine supplementation. J Biotechnol 2013;164:179-87
  • Kyunsung University Industry Cooperation Foundation. Lee J, Kim H, Lolita ASP, Jeong Y. Recombinant microorganism containing cornebacterium induced indole oxygenase gene and method for preparing indirubin using same. WO060489; 2012
  • Industry foundation of Chonnam National University. Mining and improvement of isatin-generating enzyme, and their combined use with β-glucosidase for the production of natural indirubin. KR0037687; 2011
  • Industry foundation of Chonnam National University. The production method of natural indirubin from indican using wild type E. coli cells. KR101021789; 2011
  • Chongqing Academy of Chinese Medicine; Baptist University of Hong Kong; Institute of Medicina Plant Development, Chinese Academy of Medical Sciences; Shanghai University of Traditional Chinese Medicine. Method for preparing indirubin with indigoplant as raw materials. CN103468759; 2013
  • Chongqing Academy of Chinese Medicine; Baptist University of Hong Kong; Institute of Medicina Plant Development, Chinese Academy of Medical Sciences; Shanghai University of Traditional Chinese Medicine. Method for preparing indirubin with fresh folium isatidis as raw material. CN103509835; 2014
  • Anygen Co. Ltd. Indirubin-3’-oxime derivatives as potent cyclin dependent kinase inhibitors. US0295948 A1; 2012
  • Deininger MWN, Goldman JM, Melo JV. The molecular biology of chronic myeloid leukemia. Blood 2000;96:3343-56
  • Yuan H, Wang Z, Gao C, et al. BCR-ABL gene expression is required for its mutations in a novel KCL-22 cell culture model for acquired resistance of chronic myelogenous leukemia. J Biol Chem 2010;285:5085-96
  • Li S. Src kinase signaling in leukaemia. Int J Biochem Cell Biol 2007;39:1483-8
  • Yang J, Ikezoe T, Nishioka C, et al. Bcr-Abl activates AURKA and AURKB in chronic myeloid leukemia cells via AKT signaling. Int J Cancer 2014;134(5):1183-94
  • Samanta AK, Lin H, Sun T, et al. Janus kinase 2: a critical target in chronic myelogenous leukemia. Cancer Res 2006;66:6468-72
  • City of Hope. Indirubin derivatives, and uses thereof. US0275168A1; 2014
  • Levitzki A, Klein S. Signal transduction therapy of cancer. Mol Aspects Med 2010;31:287-329
  • Nihon University. Indirubin derivative having highly selective cytotoxicity for malignant tumors. US0200253A1; 2014
  • Braig S, Kressirer CA, Liebl J, et al. Indirubin derivative 6BIO suppresses metastasis. Cancer Res 2013;73:6004-12
  • Braig S, Bischoff F, Abhari BA, et al. The pleiotropic profile of the indirubin derivative 6BIO overcomes TRAIL resistance in cancer. Biochem Pharm 2014;91:157-67
  • Liu L, Nam S, Tian Y, et al. 6-Bromoindirubin-3’-Oxime Inhibits JAK/STAT3 Signaling and induces apoptosis of human melanoma cells. Cancer Res 2011;71:3972-9
  • Choi S-J, Lee J-E, Jeong S-Y, et al. 5,5’-Substituted Indirubin-3’-oxime derivatives as potent cyclin-dependent kinase inhibitors with anticancer activity. J Med Chem 2010;53:3696-706
  • Ross SA, Gulve EA, Wang M. Chemistry and biochemistry of type 2 diabetes. Chem Rev 2004;104:1255-82
  • Freyberg Z, Ferrando SJ, Javitch JA. Roles of the Akt/GSK-3 and wnt signaling pathways in schizophrenia and antipsychotic drug action. Am J Psychiatry 2010;167:388-96
  • Takenaka K, Kise Y, Miki H. GSK-3beta positively regulates hedgehog signaling through sufu in mammalian cells. Biochem Biophys Res Commun 2007;353:501-8
  • Manoukian AS, Woodgett JR. Role of glycogen synthase kinase-3 in cancer: regulation by wnts and other signaling pathways. Adv Cancer Res 2002;84:203-29
  • Ougolkov A, Fernandez-Zapico M, Bilim V, et al. Aberrant nuclear accumulation of glycogen synthase kinase-3beta in human pancreatic cancer: association with kinase activity and tumor dedifferentiation. Clin Cancer Res 2006;12:5074-81
  • Garcea G, Manson M, Neal C, et al. Glycogen synthase kinase-3 beta; a new target in pancreatic cancer? Curr Cancer Drug Targets 2007;7:209-15
  • Irby RB, Yeatman TJ. Role of Src expression and activation in human cancer. Oncogene 2000;19:5636-42
  • Giamas G, Man YL, Hirner H, et al. Kinases as targets in the treatment of solid tumors. Cell Signal 2010;22:984-1002
  • Übel C, Mousset S, Trufa D, et al. Establishing the role of tyrosine kinase 2 in cancer. OncoImmunology 2013;2:e22840
  • Nam S, Buettner R, Turkson J, et al. Indirubin derivatives inhibit Stat3 signaling and induce apoptosis in human cancer cells. PNAS 2005;102:5998-6003
  • Liu L, Gaboriaud N, Vougogianopoulou K, et al. MLS-2384, a new 6-bromoindirubin derivative with dual JAK/Src kinase inhibitory activity, suppresses growth of diverse cancer cells. Canc Biol Ther 2014;15:0-1
  • Liu L, Kritsanida M, Magiatis P, et al. A novel 7-bromoindirubin with potent anticancer activity suppresses survival of human melanoma cells associated with inhibition of STAT3 and Akt signaling. Canc Biol Ther 2012;13:1255-61
  • Toledo EM, Colombres M, Inestrosa NC. Wnt signaling in neuroprotection and stem cell differentiation. Prog Neurobiol 2008;86:281-96
  • Coni S, Infante P, Gulino A. Control of stem cells and cancer stem cells by hedgehog signaling: pharmacologic clues from pathway dissection. Biochem Pharm 2013;85:623-8
  • Rayasam GV, Tulasi VK, Sodhi R, et al. Glycogen synthase kinase-3: more than a namesake. British J Pharm 2009;156:885-98
  • Sato N, Meijer L, Skaltsounis L, et al. maintenance of pluripotency in human and mouse embryonic stem cells through activation of wnt signaling by a pharmacological GSK-3-specific inhibitor. Nat Med 2004;10:55-63
  • Sato H, Amagai K, Shimizukawa R, et al. Stable generation of serum- and feeder-free embryonic stem cell-derived mice with full germline-competency by using a gsk-3 specific inhibitor. Genesis 2009;47:414-22
  • INSERM. Methods and pharmaceutical compositions for inhibiting influenza viruses replication. WO2012136851A1; 2014
  • Vougogiannopoulou K, Ferandin Y, Bettayeb K, et al. Soluble 3’,6-substituted indirubins with enhanced selectivity toward glycogen synthase Kinase-3 alter circadian period. J Med Chem 2008;51:6421-31
  • Lai X-M. Indirubin particle and manufacturing method thereof. TW201402113; 2014
  • Shanghai University of Traditional Chinese Medicine. Supersaturated self-microemulsion as well as preparation method and application thereof. CN102228433; 2012
  • Heshmati N, Cheng X, Eisenbrand G, et al. Enhancement of oral bioavailability of E804 by self-nanoemulsifying drug delivery system (SNEDDS) in rats. J Pharm Sci 2013;102:3792-9
  • Phosphorex Inc. Nanoparticles of indirubin, derivatives thereof and methods of making and using same. WO192493; 2013
  • Ji XJ, Zhang FR, Lei JL, et al. Studies on the antineoplastic action and toxicity of synthetic indirubin. Pharmaceutica Sinica Acta 1981;16:146-8
  • Huaqiao University. Preparation method of indirubin derivative and product and application thereof. CN103627748(A); 2014

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