Development of potent reversible selective inhibitors of butyrylcholinesterase as fluorescent probes

References

• Wang J, Gu BJ, Masters CL, et al. A systemic view of Alzheimer disease — insights from amyloid-β metabolism beyond the brain. Nat Rev Neurol 2017;13:612–23.
   PubMed Web of Science ®Google Scholar
• Crous-Bou M, Minguillón C, Gramunt N, et al. Alzheimer’s disease prevention: from risk factors to early intervention. Alzheimers Res Ther 2017;9:71.
   PubMed Web of Science ®Google Scholar
• Masters CL, Bateman R, Blennow K, et al. Alzheimer's disease. Nat Rev Dis Primers 2015;1:15056.
   PubMed Web of Science ®Google Scholar
• Dubois B, Feldman HH, Jacova C, et al. Advancing research diagnostic criteria for Alzheimer's disease: the IWG-2 criteria. Lancet Neurol 2014;13:614–29.
   PubMed Web of Science ®Google Scholar
• Weller J, Budson A. Current understanding of Alzheimer’s disease diagnosis and treatment. 1000Res 2018;7:1161.
   Google Scholar
• Darvesh S, Hopkins DA, Geula C. Neurobiology of butyrylcholinesterase. Nat Rev Neurol 2003;4:131–8.
   Web of Science ®Google Scholar
• Macdonald IR, Maxwell SP, Reid GA, et al. Quantification of butyrylcholinesterase activity as a sensitive and specific biomarker of Alzheimer's disease. J Alzheimers Dis 2017;58:491–504.
   PubMed Web of Science ®Google Scholar
• Saltmarsh JR, Boyd AE, Rodriguez OP, et al. Synthesis of fluorescent probes directed to the active site gorge of acetylcholinesterase. Bioorg Med Chem Lett 2000;10:1523–6.
   PubMed Web of Science ®Google Scholar
• Huang X, Lee B, Johnson G, et al. Novel assay utilizing fluorochrome-tagged physostigmine (Ph-F) to in-situ detect active acetylcholinesterase (AChE) induced during apoptosis. Cell Cycle 2005;4:140–7.
   PubMed Web of Science ®Google Scholar
• Amitai G, Ashani Y, Gafni A, et al. New fluorescent organophosphates as probes for studying aging-induced conformational changes in inhibited acetylcholinesterase. Neurochem Int 1980;2:199–204.
   Google Scholar
• Chao S, Krejci E, Bernard V, et al. A selective and sensitive near-infrared fluorescent probe for acetylcholinesterase imaging. ChemComm 2016;52:11599–602.
   PubMed Web of Science ®Google Scholar
• Elsinghorst PW, Härtig W, Goldhammer S, et al. A gorge-spanning, high-affinity cholinesterase inhibitor to explore β-amyloid plaques. Org Biomol Chem 2009;7:3940–6.
   PubMed Web of Science ®Google Scholar
• Yang S-H, Sun Q, Xiong H, et al. Discovery of a butyrylcholinesterase-specific probe via a structure-based design strategy. Chem Comm 2017;53:3952–5.
   PubMed Web of Science ®Google Scholar
• Liu S-Y, Xiong H, Yang J-Q, et al. Discovery of butyrylcholinesterase-activated near-infrared fluorogenic probe for live-cell and in vivo imaging. ACS Sens 2018;3:2118–28.
   PubMed Web of Science ®Google Scholar
• Brus B, Košak U, Turk S, et al. Discovery, biological evaluation, and crystal structure of a novel nanomolar selective butyrylcholinesterase inhibitor. J Med Chem 2014;57:8167–79.
   PubMed Web of Science ®Google Scholar
• Košak U, Brus B, Knez D, et al. Development of an in-vivo active reversible butyrylcholinesterase inhibitor. Sci Rep 2016;6:39495.
   PubMed Web of Science ®Google Scholar
• Košak U, Brus B, Knez D, et al. The magic of crystal-structure-based inhibitor optimization: development of a butyrylcholinesterase inhibitor with picomolar affinity and in-vivo activity. J Med Chem 2018;61:119–39.
   PubMed Web of Science ®Google Scholar
• Ellman GL, Courtney KD, Andres V, et al. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961;7:88–95.
   PubMed Web of Science ®Google Scholar
• Kosak U, Knez D, Coquelle N, et al. N-Propargylpiperidines with naphthalene-2-carboxamide or naphthalene-2-sulfonamide moieties: potential multifunctional anti-Alzheimer's agents. Bioorg Med Chem 2017;25:633–45.
   PubMed Web of Science ®Google Scholar
• Bevc S, Konc J, Stojan J, et al. ENZO: a web tool for derivation and evaluation of kinetic models of enzyme catalyzed reactions. PLoS ONE 2011;6:e22265.
   PubMed Web of Science ®Google Scholar
• Stojan J. The significance of low substrate concentration measurements for mechanistic interpretation in cholinesterases. Chem-Biol Interact 2013;203:44–50.
   PubMed Web of Science ®Google Scholar
• Stojan J. Rapid mechanistic evaluation and parameter estimation of putative inhibitors in a single-step progress-curve analysis: the case of horse butyrylcholinesterase. Molecules 2017;22:1248.
   Web of Science ®Google Scholar
• Kuzmič P. Application of the Van Slyke–Cullen irreversible mechanism in the analysis of enzymatic progress curves. Anal Biochem 2009;394:287–9.
   PubMed Web of Science ®Google Scholar
• Stojan J. The mechanism and benefit of human butyrylcholinesterase activation by what would otherwise be inhibitors. Chem-Biol Interact 2019;308:350–6.
   PubMed Web of Science ®Google Scholar
• Nachon F, Nicolet Y, Viguié N, et al. Engineering of a monomeric and low-glycosylated form of human butyrylcholinesterase. Eur J Biochem 2002;269:630–7.
   PubMedGoogle Scholar
• Brazzolotto X, Wandhammer M, Ronco C, et al. Human butyrylcholinesterase produced in insect cells: huprine-based affinity purification and crystal structure. Febs J 2012;279:2905–16.
   PubMed Web of Science ®Google Scholar
• Kabsch W. Integration, scaling, space-group assignment and post-refinement. Acta Cryst D 2010;66:133–44.
   PubMed Web of Science ®Google Scholar
• Vonrhein C, Flensburg C, Keller P, et al. Data processing and analysis with the autoPROC toolbox. Acta Cryst D 2011;67:293–302.
   PubMedGoogle Scholar
• Adams PD, Afonine PV, Bunkoczi G, et al. PHENIX: a comprehensive Python-based system for macromolecular structure solution. Acta Cryst D 2010;66:213–21.
   PubMed Web of Science ®Google Scholar
• Moriarty NW, Grosse-Kunstleve RW, Adams PD. Electronic ligand builder and optimization workbench (eLBOW): a tool for ligand coordinate and restraint generation. Acta Cryst D 2009;65:1074–80.
   PubMed Web of Science ®Google Scholar
• Schuttelkopf AW, van Aalten DM. PRODRG: a tool for high-throughput crystallography of protein-ligand complexes. Acta Crystallogr D Biol Crystallogr 2004;60:1355–63.
   PubMed Web of Science ®Google Scholar
• Emsley P, Lohkamp B, Scott WG, et al. Features and development of Coot. Acta Cryst D 2010;66:486–501.
   PubMed Web of Science ®Google Scholar
• Sakai H, Hirano T, Mori S, et al. 6-Arylcoumarins as novel nonsteroidal type progesterone antagonists: an example with receptor-binding-dependent fluorescence. J Med Chem. 2011;54(20):2055–7065.
   Google Scholar
• Eugenio Vázquez M, Rothman DM, Imperiali B. A new environment-sensitive fluorescent amino acid for Fmoc-based solid phase peptide synthesis. Org Biomol Chem 2004;2:1965–6.
   PubMed Web of Science ®Google Scholar
• Goodey NM, Alapa MT, Hagmann DF, et al. Development of a fluorescently labeled thermostable DHFR for studying conformational changes associated with inhibitor binding. Biochem Biophys Res Commun 2011;413:442–7.
   PubMed Web of Science ®Google Scholar
• Ikeda M, Yoshii T, Matsui T, et al. Montmorillonite − supramolecular hydrogel hybrid for fluorocolorimetric sensing of polyamines. J Am Chem Soc 2011;133:1670–3.
   PubMed Web of Science ®Google Scholar
• Bissantz C, Kuhn B, Stahl M. A medicinal chemist’s guide to molecular interactions. J Med Chem 2010;53:5061–84.
   PubMed Web of Science ®Google Scholar
• Rostovtsev VV, Green LG, Fokin VV, et al. A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes. Angew Chem Int 2002;41:2596–9.
   PubMed Web of Science ®Google Scholar
• Tornøe CW, Christensen C, Meldal M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J Org Chem 2002;67:3057–64.
   PubMed Web of Science ®Google Scholar
• Koelle GB, Friedenwald JS. A histochemical method for localizing cholinesterase activity. Proc Soc Exp Biol Med 1949;70:617–22.
   PubMed Web of Science ®Google Scholar
• Darvesh S, Grantham DL, Hopkins DA. Distribution of butyrylcholinesterase in the human amygdala and hippocampal formation. J Comp Neurol 1998;393:374–90.
   PubMed Web of Science ®Google Scholar
• Geula C, Nagykery N. Butyrylcholinesterase activity in the rat forebrain and upper brainstem: postnatal development and adult distribution. Exp Neurol 2007;204:640–57.
   PubMed Web of Science ®Google Scholar