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Research Paper

Indirubin derivatives are potent and selective anti-Trypanosoma cruzi agents

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Pages 1658-1668 | Received 25 May 2018, Accepted 21 Sep 2018, Published online: 02 Nov 2018

References

  • Hotez PJ, Bottazzi ME, Franco-Paredes C, et al. The neglected tropical diseases of latin America and the caribbean: a review of disease burden and distribution and a roadmap for control and elimination. PLoS Negl Trop Dis. 2008;2:e300.
  • Coura JR, Junqueira AC, Fernandes O, et al. Emerging chagas disease in amazonian Brazil. Trends Parasitol. 2002;18:171–176.
  • WHO. Chagas disease (American trypanosomiasis). 2017.
  • Vougogiannopoulou K, Skaltsounis AL. From tyrian purple to kinase modulators: naturally halogenated indirubins and synthetic analogues. Planta medica. 2012;78:1515–1528.
  • Kalsi DS, Ward J, Lee R, et al. Purple urine bag syndrome: a rare spot diagnosis. Dis Markers. 2017;2017:9131872.
  • Gaboriaud-Kolar N, Vougogiannopoulou K, Skaltsounis AL. Indirubin derivatives: a patent review (2010 - present). Expert Opin Ther Pat. 2015;25:583–593.
  • Zhou A, Yan L, Lai F, et al. Design, synthesis and biological evaluation of novel indolin-2-ones as potent anticancer compounds. Bioorg Med Chem Lett. 2017;27:3326–3331.
  • Cheng X, Merz KH, Vatter S, et al. Identification of a water-soluble indirubin derivative as potent inhibitor of insulin-like growth factor 1 receptor through structural modification of the parent natural molecule. J Med Chem. 2017;60:4949–4962.
  • Choi SJ, Lee JE, Jeong SY, et al. 5,5ʹ-substituted indirubin-3ʹ-oxime derivatives as potent cyclin-dependent kinase inhibitors with anticancer activity. J Med Chem. 2010;53:3696–3706.
  • Jie C, Luo Z, Chen H, et al. Indirubin, a bisindole alkaloid from Isatis indigotica, reduces H1N1 susceptibility in stressed mice by regulating MAVS signaling. Oncotarget. 2017;8:105615–105629.
  • Medina-Moreno S, Dowling TC, Zapata JC, et al. Targeting of CDK9 with indirubin 3ʹ-monoxime safely and durably reduces HIV viremia in chronically infected humanized mice. PloS one. 2017;12:e0183425.
  • Clough BH, Zeitouni S, Krause U, et al. Rapid osteogenic enhancement of stem cells in human bone marrow using a glycogen-synthease-kinase-3-beta inhibitor improves osteogenic efficacy in vitro and in vivo. Stem Cells Transl Med. 2018;7(4):342–353.
  • 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.
  • Chen L, Huang C, Shentu J, et al. Indirubin derivative 7-bromoindirubin-3-oxime (7bio) attenuates abeta oligomer-induced cognitive impairments in mice. Front Mol Neurosci. 2017;10:393.
  • Toledo EM, Colombres M, Inestrosa NC. Wnt signaling in neuroprotection and stem cell differentiation. Prog Neurobiol. 2008;86:281–296.
  • Sekhon S, Koo J. Indirubin: a novel topical agent in the treatment of psoriasis. Br J Dermatol. 2018;178:21.
  • Qi T, Li H, Li S. Indirubin improves antioxidant and anti-inflammatory functions in lipopolysaccharide-challenged mice. Oncotarget. 2017;8:36658–36663.
  • 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;4:22–26.
  • Polychronopoulos P, Magiatis P, Skaltsounis AL, 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;47:935–946.
  • Vougogiannopoulou K, Ferandin Y, Bettayeb K, et al. Soluble 3ʹ,6-substituted indirubins with enhanced selectivity toward glycogen synthase kinase −3 alter circadian period. J Med Chem. 2008;51:6421–6431.
  • 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;1:60–67.
  • 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.
  • Efstathiou AG-KN, Myrianthopoulos V, Vougogiannopoulou K, et al. Indirubin analogues inhibit typanosoma brucei glycogen synthase kinase 3 short and T. brucei growth. submitted. 2018.
  • Stuart K, Brun R, Croft S, et al. Kinetoplastids: related protozoan pathogens, different diseases. J Clin Invest. 2008;118:1301–1310.
  • Heredia A, Natesan S, Le NM, et al. Indirubin 3ʹ-monoxime, from a Chinese traditional herbal formula, suppresses viremia in humanized mice infected with multidrug-resistant HIV. AIDS Res Hum Retroviruses. 2014;30:403–406.
  • Cheng X, Merz KH. The role of indirubins in inflammation and associated tumorigenesis. Adv Exp Med Biol. 2016;929:269–290.
  • Gaboriaud-Kolar N, Myrianthopoulos V, Vougogiannopoulou K, et al. Natural-based indirubins display potent cytotoxicity toward wild-type and t315i-resistant leukemia cell lines. J Natur Prod. 2016;79:2464–2471.
  • Broecker-Preuss M, Becher-Boveleth N, Gall S, et al. Induction of atypical cell death in thyroid carcinoma cells by the indirubin derivative 7-bromoindirubin-3ʹ-oxime (7BIO). Cancer Cell Inter. 2015;15:97.
  • 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. Cancer Biol Ther. 2012;13:1255–1261.
  • Xingi E, Smirlis D, Myrianthopoulos V, et al. 6-br-5methylindirubin-3ʹoxime (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 Parasitol. 2009;39:1289–1303.
  • Durieu E, Prina E, Leclercq O, et al. From drug screening to target deconvolution: a target-based drug discovery pipeline using leishmania casein kinase 1 isoform 2 to identify compounds with antileishmanial activity. Antimicrob Agents Chemother. 2016;60:2822–2833.
  • Grant KM, Dunion MH, Yardley V, et al. Inhibitors of leishmania mexicana CRK3 cyclin-dependent kinase: chemical library screen and antileishmanial activity. Antimicrob Agents Chemother. 2004;48:3033–3042.
  • Brancaglion GA, Toyota AE, Cardoso Machado JV, et al. In vitro and in vivo trypanocidal activities of 8-methoxy-3-(4-nitrobenzoyl)-6-propyl-2H-cromen-2-one, a new synthetic coumarin of low cytotoxicity against mammalian cells. Chem Biol Drug Des. 2018
  • MacLean LM, Thomas J, Lewis MD, et al. Development of trypanosoma cruzi in vitro assays to identify compounds suitable for progression in chagas’ disease drug discovery. PLoS Negl Trop Dis. 2018;12:e0006612.
  • Bastos TM, Barbosa MI, Da Silva MM, et al. Nitro/nitrosyl-ruthenium complexes are potent and selective anti-trypanosoma cruzi agents causing autophagy and necrotic parasite death. Antimicrob Agents Chemother. 2014;58:6044–6055.
  • Zong WX, Thompson CB. Necrotic death as a cell fate. Genes & Dev. 2006;20:1–15.
  • Juliany Cola Fernandes Rodrigues SHSaWdS. APOPTOSIS-LIKE DEATH IN PARASITIC PROTOZOA. Braz J morphol Sci. 2006;23:87–89.
  • Tessarolo LD, de Menezes R, Mello CP, et al. Nanoencapsulation of benznidazole in calcium carbonate increases its selectivity to trypanosoma cruzi. Parasitology. 2018;145:1191–1198.
  • Maya JD, Cassels BK, Iturriaga-Vasquez P, et al. Mode of action of natural and synthetic drugs against trypanosoma cruzi and their interaction with the mammalian host. Comp Biochem and Physiol Part A, Mol & Integr Physiol. 2007;146:601–620.
  • Manallack DT, Prankerd RJ, Yuriev E, et al. The significance of acid/base properties in drug discovery. Chem Soc Rev. 2013;42:485–496.
  • Sousa MC, Varandas R, Santos RC, et al. Antileishmanial activity of semisynthetic lupane triterpenoids betulin and betulinic acid derivatives: synergistic effects with miltefosine. PloS one. 2014;9:e89939.
  • Alirol E, Schrumpf D, Amici Heradi J, et al. Nifurtimox-eflornithine combination therapy for second-stage gambiense human African trypanosomiasis: medecins sans frontieres experience in the democratic republic of the congo. Clin Infect Dis: Off Publ Infect Dis Soc Am. 2013;56:195–203.
  • Ferandin Y, Bettayeb K, Kritsanida M, et al. 3ʹ-substituted 7-halogenoindirubins, a new class of cell death inducing agents. J Med Chem. 2006;49:4638–4649.
  • Meijer L, Skaltsounis AL, Magiatis P, et al. GSK-3-selective inhibitors derived from tyrian purple indirubins. Chem Biol. 2003;10:1255–1266.
  • Silva LHNV. Sobre uma cepa de Trypanosoma cruzi virulenta para o camundongo branco. Folia Clin Biol. 1953;20:191–207.
  • Brener Z. Therapeutic activity and criterion of cure on mice experimentally infected with trypanosoma cruzi. Rev Inst Med Trop Sao Paulo. 1962;4:389–396.