Insights into the mechanism of inhibition of tryptophan 2,3-dioxygenase by isatin derivatives

References

• Dounay AB, Tuttle JB, Verhoest PR. Challenges and opportunities in the discovery of new therapeutics targeting the kynurenine pathway. J Med Chem 2015;58:8762–82.
   PubMed Web of Science ®Google Scholar
• Stone TW, Darlington LG. Endogenous kynurenines as targets for drug discovery and development. Nat Rev Drug Discov 2002;1:609–20.
   PubMed Web of Science ®Google Scholar
• Muller AJ, DuHadaway JB, Donover PS, et al. Inhibition of indoleamine 2,3-dioxygenase, an immunoregulatory target of the cancer suppression gene Bin1, potentiates cancer chemotherapy. Nat Med 2005;11:312–19.
   PubMed Web of Science ®Google Scholar
• Opitz CA, Litzenburger UM, Sahm F, et al. An endogenous tumour-promoting ligand of the human aryl hydrocarbon receptor. Nature 2011;478:197–203.
   PubMed Web of Science ®Google Scholar
• Dolusic E, Frederick R. Indoleamine 2,3-dioxygenase inhibitors: a patent review (2008–2012). Exp Opin Therap Pat 2013;23:1367–81.
   PubMed Web of Science ®Google Scholar
• Peng YH, Ueng SH, Tseng CT, et al. Important hydrogen bond networks in indoleamine 2,3-dioxygenase 1 (IDO1) inhibitor design revealed by crystal structures of imidazoleisoindole derivatives with IDO1. J Med Chem 2016;59:282–93.
   PubMed Web of Science ®Google Scholar
• Malachowski WP, Winters M, DuHadaway JB, et al. O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1. Eur J Med Chem 2016;108:564–76.
   PubMed Web of Science ®Google Scholar
• Lin SY, Yeh TK, Kuo CC, et al. Phenyl benzenesulfonylhydrazides exhibit selective indoleamine 2,3-dioxygenase inhibition with potent in vivo pharmacodynamic activity and antitumor efficacy. J Med Chem 2016;59:419–30.
   PubMed Web of Science ®Google Scholar
• Liu X, Shin N, Koblish HK, et al. Selective inhibition of IDO1 effectively regulates mediators of antitumor immunity. Blood 2010;115:3520–30.
   PubMed Web of Science ®Google Scholar
• Dolusic E, Larrieu P, Moineaux L, et al. Tryptophan 2,3-dioxygenase (TDO) inhibitors: 3-(2-(pyridyl)ethenyl)indoles as potential anticancer immunomodulators. J Med Chem 2011;54:5320–34.
   PubMed Web of Science ®Google Scholar
• Banerjee M, Middya S, Shrivastava R, et al. Inhibitors of the kynurenine pathway. Google Patents; 2014.
   Google Scholar
• Kumar S, Waldo J, Jaipuri F, Mautino M. Tricyclic compounds as inhibitors of immunosuppression mediated by tryptophan metabolization. Google Patents; 2014.
   Google Scholar
• Cowley P, Wise A. Tryptophan-2,3-dioxygenase (TDO) and/or indolamine-2,3-dioxygenase (IDO) inhibitors and their use. Google Patents; 2015.
   Google Scholar
• Reinhard JF Jr, Flanagan EM, Madge DJ, et al. Effects of 540C91 [(E)-3-[2-(4′-pyridyl)-vinyl]-1H-indole], an inhibitor of hepatic tryptophan dioxygenase, on brain quinolinic acid in mice. Biochem Pharmacol 1996;51:159–63.
   PubMed Web of Science ®Google Scholar
• Salter M, Hazelwood R, Pogson CI, et al. The effects of a novel and selective inhibitor of tryptophan 2,3-dioxygenase on tryptophan and serotonin metabolism in the rat. Biochem Pharmacol 1995;49:1435–42.
   PubMed Web of Science ®Google Scholar
• Pantouris G, Mowat CG. Antitumour agents as inhibitors of tryptophan 2,3-dioxygenase. Biochem Biophys Res Commun 2014;443:28–31.
   PubMed Web of Science ®Google Scholar
• Pilotte L, Larrieu P, Stroobant V, et al. Reversal of tumoral immune resistance by inhibition of tryptophan 2,3-dioxygenase. Proc Natl Acad Sci USA 2012;109:2497–502.
   PubMed Web of Science ®Google Scholar
• Pandeya SN, Smitha S, Jyoti M, Sridhar SK. Biological activities of isatin and its derivatives. Acta Pharm 2005;55:27–46.
   PubMedGoogle Scholar
• Vine KL, Matesic L, Locke JM, et al. Cytotoxic and anticancer activities of isatin and its derivatives: a comprehensive review from 2000–2008. Anticancer Agents Med Chem 2009;9:397–414.
   PubMed Web of Science ®Google Scholar
• Samlowski WE, Vogelzang NJ. Emerging drugs for the treatment of metastatic renal cancer. Exp Opin Emerg Drugs 2007;12:605–18.
   PubMed Web of Science ®Google Scholar
• Gillam EM, Notley LM, Cai H, et al. Oxidation of indole by cytochrome P450 enzymes. Biochemistry 2000;39:13817–24.
   PubMed Web of Science ®Google Scholar
• Pantouris G, Serys M, Yuasa HJ, et al. Human indoleamine 2,3-dioxygenase-2 has substrate specificity and inhibition characteristics distinct from those of indoleamine 2,3-dioxygenase-1. Amino Acids 2014;46:2155–63.
   PubMed Web of Science ®Google Scholar
• Trott O, Olson AJ. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 2010;31:455–61.
   PubMed Web of Science ®Google Scholar
• Sugimoto H, Oda S, Otsuki T, et al. Crystal structure of human indoleamine 2,3-dioxygenase: catalytic mechanism of O2 incorporation by a heme-containing dioxygenase. Proc Natl Acad Sci USA 2006;103:2611–16.
   PubMed Web of Science ®Google Scholar
• Biasini M, Bienert S, Waterhouse A, et al. SWISS-MODEL: modelling protein tertiary and quaternary structure using evolutionary information. Nucleic Acids Res 2014;42:W252–8.
   PubMed Web of Science ®Google Scholar
• Forouhar F, Anderson JL, Mowat CG, et al. Molecular insights into substrate recognition and catalysis by tryptophan 2,3-dioxygenase. Proc Natl Acad Sci USA 2007;104:473–8.
   PubMed Web of Science ®Google Scholar
• Huang W, Gong Z, Li J, Ding J. Crystal structure of Drosophila melanogaster tryptophan 2,3-dioxygenase reveals insights into substrate recognition and catalytic mechanism. J Struct Biol 2013;181:291–9.
   PubMed Web of Science ®Google Scholar
• Laskowski RA, Swindells MB. LigPlot+: multiple ligand-protein interaction diagrams for drug discovery. J Chem Inf Model 2011;51:2778–86.
   PubMed Web of Science ®Google Scholar
• DeLano WL. The PyMOL molecular graphics system. Palo Alto (CA): DeLano Scientific; 2002.
   Google Scholar
• Chauhan N, Thackray SJ, Rafice SA, et al. Reassessment of the reaction mechanism in the heme dioxygenases. J Am Chem Soc 2009;131:4186–7.
   PubMed Web of Science ®Google Scholar
• Tojo S, Kohno T, Tanaka T, et al. Crystal structures and structure-activity relationships of imidazothiazole derivatives as IDO1 inhibitors. ACS Med Chem Lett 2014;5:1119–23.
   PubMed Web of Science ®Google Scholar