Design of donecopride, a dual serotonin subtype 4 receptor agonist/acetylcholinesterase inhibitor with potential interest for Alzheimer's disease treatment

Proceedings of the National Academy of Sciences of the United States of America

Volumn 111, Issue 36, 2014, Pages E3825-E3830

  Lecoutey, Cédric ^a   Hedou, Damien ^a   Freret, Thomas ^b   Giannoni, Patrizia ^c   Gaven, Florence ^c   Since, Marc ^a   Bouet, Valentine ^b   Ballandonne, Céline ^a   Corvaisier, Sophie ^a,b   Fréon, Aurélie Malzert ^a   Mignani, Serge ^a   Cresteil, Thierry ^d   Boulouard, Michel ^b   Claeysen, Sylvie ^c   Rochais, Christophe ^a   Dallemagne, Patrick ^a  

^a CENTRE D ETUDES ET DE RECHERCHE SUR LE MÉDICAMENT DE NORMANDIE   (France)

^b UNIVERSITÉ DE CAEN   (France)

^c INSTITUT DE GÉNOMIQUE FONCTIONNELLE   (France)

^d CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 AMINO 5 CHLORO 2 METHOXYPHENYL) 3 (1 BUTYL 4 PIPERIDINYL) 1 PROPANONE; AMYLOID BETA PROTEIN; ANILINE DERIVATIVE; CHOLINESTERASE INHIBITOR; CYCLOSPORIN; DONECOPRIDE; ERG1 POTASSIUM CHANNEL; LIGAND; PIPERIDINE DERIVATIVE; POTASSIUM CHANNEL HERG; RHODAMINE 123; SEROTONIN 4 AGONIST; SEROTONIN 4 RECEPTOR;

ALZHEIMER DISEASE; ANIMAL; BRAIN; CHEMISTRY; CHLOROCEBUS AETHIOPS; COGNITION; COS 1 CELL LINE; DRUG DESIGN; DRUG EFFECTS; KINETICS; METABOLISM; MOUSE; PATHOPHYSIOLOGY; PERMEABILITY; SECRETION (PROCESS); SOLUBILITY; TASK PERFORMANCE;

ALZHEIMER DISEASE; AMYLOID BETA-PEPTIDES; ANILINE COMPOUNDS; ANIMALS; BRAIN; CERCOPITHECUS AETHIOPS; CHOLINESTERASE INHIBITORS; COGNITION; COS CELLS; CYCLOSPORINE; DRUG DESIGN; ETHER-A-GO-GO POTASSIUM CHANNELS; KINETICS; LIGANDS; MICE; PERMEABILITY; PIPERIDINES; RECEPTORS, SEROTONIN, 5-HT4; RHODAMINE 123; SEROTONIN 5-HT4 RECEPTOR AGONISTS; SOLUBILITY; TASK PERFORMANCE AND ANALYSIS;

EID: 84907001204     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1410315111     Document Type: Article

References (46)

1. 4receptor agonists, RS 67333 and RS 67506, in vitro and in vivo. Br J Pharmacol 115(8):1387-1392.
2. Gómez-Lázaro E, et al. (2012) Effects of a putative antidepressant with a rapid onset of action in defeatedmice with different coping strategies. Prog Neuropsychopharmacol Biol Psychiatry 38(2):317-327.
3. Lucas G, et al. (2010) Selective serotonin reuptake inhibitors potentiate the rapid anti-depressant-like effects of serotonin4 receptor agonists in the rat. PLoS ONE 5(2):e9253.
4. 4)) receptor agonists are putative antidepressants with a rapid onset of action. Neuron 55(5):712-725.
5. 4receptor stimulation on basal and electrically evoked release of acetylcholine from guinea-pig myenteric plexus. Naunyn Schmiedebergs Arch Pharmacol 345(3):270-275.
6. 4receptor stimulation facilitates acetylcholine release in rat frontal cortex. Neuroreport 5(10):1230-1232.
7. 4receptor-mediated modulation of 5-HT release in the rat hippocampus in vivo. Br J Pharmacol 117(7):1475-1480.
8. 4receptors exert a state-dependent facilitatory control in vivo on nigrostriatal, but not mesoaccumbal, dopaminergic function. Eur J Neurosci 13(5):889-898.
9. 4) receptors in cholinergic function associated with cognitive processes: Behavioral, electrophysiological, and neurochemical studies. J Pharmacol Exp Ther 296(3):676-682.
10. 4receptor activation on GABA release from guinea pig hippocampal slices. Neuroreport 13(17):2177-2180.
11. 4) receptor agonist, into the nucleus basalis magnocellularis of the rat. Learn Mem 10(5):420-426.
12. 4) receptor agonist RS67333 and paroxetine on hippocampal extracellular 5-HT levels. Neurosci Lett 476(2):58-61.
13. Steward LJ, et al. (1996) Ability of 5-HT4 receptor ligands to modulate rat striatal dopamine release in vitro and in vivo. Br J Pharmacol 117(1):55-62.
14. Hotte M, Dauphin F, Freret T, Boulouard M, Levallet G (2012) A biphasic and brain-region selective down-regulation of cyclic adenosine monophosphate concentrations supports object recognition in the rat. PLoS ONE 7(2):e32244.
15. 4receptor-induced improvement of object recognition memory in the rat. Psychopharmacology (Berl) 202(1-3):125-139.
16. 4receptors. Neuropharmacology 41(7):844-853.
17. 4receptors, enhances place and object recognition in young adult and old rats. Prog Neuropsychopharmacol Biol Psychiatry 27(1):185-195.
18. 4receptor ligands in rat spatial navigation. Neuropharmacology 36(4-5):689-696.
19. Musiał A, Bajda M, Malawska B (2007) Recent developments in cholinesterases inhibitors for Alzheimer's disease treatment. Curr Med Chem 14(25):2654-2679.
20. Anand P, Singh B (2013) A review on cholinesterase inhibitors for Alzheimer's disease. Arch Pharm Res 36(4):375-399.
21. Yuede CM, Dong H, Csernansky JG (2007) Anti-dementia drugs and hippocampal-dependent memory in rodents. Behav Pharmacol 18(5-6):347-363.
22. 4receptors inhibits secretion of β-amyloid peptides and increases neuronal survival. Exp Neurol 203(1):274-278.
23. 4receptor and Alzheimer's disease: The amyloid connection. Exp Neurol 205(2):325-329.
24. 4receptor agonists: Application as amyloid cascade modulators and potential therapeutic utility in Alzheimer's disease. J Med Chem 52(8):2214-2225.
25. Inestrosa NC, et al. (1996) Acetylcholinesterase accelerates assembly of amyloid-β-peptides into Alzheimer' s fibrils: Possible role of the peripheral site of the enzyme. Neuron 16(4):881-891.
26. 4) receptor activation (RS67333) on object recognition in mice. Behav Brain Res 230(1):304-308.
27. Cavalli A, et al. (2008) Multi-target-directed ligands to combat neurodegenerative diseases. J Med Chem 51(3):347-372.
28. Morphy R, Rankovic Z (2006) The physicochemical challenges of designing multiple ligands. J Med Chem 49(16):4961-4970.
29. Sopkova-de Oliveira Santos J, et al. (2010) Virtual screening discovery of new acetylcholinesterase inhibitors issued from CERMN chemical library. J Chem Inf Model 50(3):422-428.
30. 4partial agonist clinical candidates for the treatment of Alzheimer's disease. J Med Chem 55(21):9240-9254.
31. Bai S, et al. (2014) Synthesis and structure-activity relationship studies of conformationally flexible tetrahydroisoquinolinyl triazole carboxamide and triazole substituted benzamide analogues as σ2 receptor ligands. J Med Chem 57(10):4239-4251.
32. Rosenberry TL, Mallender WD, Thomas PJ, Szegletes T (1999) A steric blockade model for inhibition of acetylcholinesterase by peripheral site ligands and substrate. Chem Biol Interact 119-120:85-97.
33. Sugimoto H, Yamanishi Y, Iimura Y, Kawakami Y (2000) Donepezil hydrochloride (E2020) and other acetylcholinesterase inhibitors. Curr Med Chem 7(3):303-339.
34. Maillet M, et al. (2003) Crosstalk between Rap1 and Rac regulates secretion of sAPPalpha. Nat Cell Biol 5(7):633-639.
35. Cochet M, et al. (2013) 5-HT4 receptors constitutively promote the non-amyloidogenic pathway of APP cleavage and interact with ADAM10. ACS Chem Neurosci 4(1):130-140.
36. 4receptor agonist, prevents amyloidogenesis and behavioral deficits in the 5XFAD mouse model of Alzheimer's disease. Front Aging Neurosci 5:96.
37. Bard B, Martel S, Carrupt PA (2008) High throughput UV method for the estimation of thermodynamic solubility and the determination of the solubility in biorelevant media. Eur J Pharm Sci 33(3):230-240.
38. Avdeef A, et al. (2007) PAMPA-critical factors for better predictions of absorption. J Pharm Sci 96(11):2893-2909.
39. Moser PC, et al. (2002) SL65.0155, a novel 5-hydroxytryptamine(4) receptor partial agonist with potent cognition-enhancing properties. J Pharmacol Exp Ther 302(2):731-741.
40. Sheline YI, et al. (2014) An antidepressant decreases CSF Aβ production in healthy individuals and in transgenic AD mice. Sci Transl Med 6(236):236re4.
41. Cirrito JR, et al. (2011) Serotonin signaling is associated with lower amyloid-β levels and plaques in transgenic mice and humans. Proc Natl Acad Sci USA 108(36):14968-14973.
42. Fowler SW, et al. (2014) Genetic modulation of soluble Aβ rescues cognitive and synaptic impairment in a mouse model of Alzheimer's disease. J Neurosci 34(23):7871-7885.
43. 2creceptors stimulate amyloid precursor protein ectodomain secretion. J Biol Chem 271(8):4188-4194.
44. Rosini M, Simoni E, Minarini A, Melchiorre C (2014) Multi-target design strategies in the context of Alzheimer's disease: Acetyl-cholinesterase inhibition and NMDA receptor antagonism as the diving forces. Neurochem Res, 10.1007/s11064-014-1250-1.
45. Citron M (2010) Alzheimer's disease: Strategies for disease modification. Nat Rev Drug Discov 9(5):387-398.
46. Ellman GL, Courtney KD, Andres V, Jr, Feather-Stone RM (1961) A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 7:88-95.