Evaluation of galantamine and deconstructed analogs as α7 nAChR and AChE ligands
Tài liệu tham khảo
Alzheimer’s Association, 2021, Alzheimer’s disease facts and figures, Alzheimer’s Dement., 17, 327
Stelzmann, 1995, An English translation of alzheimer’s 1907 paper, “über eine eigenartige erkankung der hirnrinde”, Clin. Anat., 8, 429, 10.1002/ca.980080612
Perry, 1995, Alteration in nicotine binding sites in Parkinson's disease, Lewy body dementia and Alzheimer's disease: Possible index of early neuropathology, Neuroscience, 64, 385, 10.1016/0306-4522(94)00410-7
Whitehouse, 1988, Reductions in acetylcholine and nicotine binding in several degenerative diseases, Arch. Neurol., 45, 722, 10.1001/archneur.1988.00520310028012
Davies, 1976, Selective loss of central cholinergic neurons in Alzheimer’s Disease, Lancet, 2, 1403, 10.1016/S0140-6736(76)91936-X
Perry, 1977, Neurotransmitter enzyme abnormalities in senile dementia. Choline acetyltransferase and glutamic acid decarboxylase activities in necropsy brain tissue, J. Neurol. Sci., 34, 247, 10.1016/0022-510X(77)90073-9
Davis, 1999, Cholinergic markers in elderly patients with early signs of Alzheimer disease, JAMA-J. Am. Med. Assoc., 281, 1401, 10.1001/jama.281.15.1401
Bartus, 1982, The cholinergic hypothesis of geriatric memory dysfunction, Science, 217, 408, 10.1126/science.7046051
Heinrich, 2004, Galanthamine from snowdrop—the development of a modern drug against Alzheimer’s disease from local Caucasian knowledge, J. Ethnopharmacol., 92, 147, 10.1016/j.jep.2004.02.012
Janssen, 2017, Galantamine, ChemTexts, 3, 1, 10.1007/s40828-017-0043-y
Schrattenholz, 1996, Agonist responses of neuronal nicotinic acetylcholine receptors are potentiated by a novel class of allosterically acting ligands, Mol. Pharmacol., 49, 1
Pereira, 1994, Physostigmine and galanthamine: Probes for a novel binding site on the alpha4 beta2 subtype of neuronal nicotinic acetylcholine receptors stably expressed in fibroblast cells, J. Pharmacol. Exp. Ther., 270, 768
Samochocki, 2003, Galantamine is an allosterically potentiating ligand of neuronal nicotinic but not of muscarinic acetylcholine receptors, J. Pharmacol. Exp. Ther., 305, 1024, 10.1124/jpet.102.045773
Maelicke, 2001, Allosteric sensitization of nicotinic receptors by galantamine, a new treatment strategy for Alzheimer’s disease, Biol. Psychiatry, 49, 279, 10.1016/S0006-3223(00)01109-4
Samochocki, 2000, Galantamine is an allosterically potentiating ligand of the human alpha4/beta2 nAChR, Acta. Neurol. Scand. Suppl., 176, 68, 10.1034/j.1600-0404.2000.00310.x
Maelicke, 2000, Allosterically potentiating ligands of nicotinic receptors as a treatment strategy for Alzheimer’s disease, Behav. Brain Res., 113, 199, 10.1016/S0166-4328(00)00214-X
Storch, 1995, Physostigmine, galanthamine and codeine act as ‘noncompetitive nicotinic receptor agonists’ on clonal rat pheochromocytoma cells, Eur. J. Pharmacol., 290, 207, 10.1016/0922-4106(95)00080-1
Harvey, 1995, The pharmacology of galanthamine and its analogues, Pharmacol. Ther., 68, 113, 10.1016/0163-7258(95)02002-0
Fang, 2014, Design, synthesis and biological evaluation of D-ring opened galantamine analogs as multifunctional anti-Alzheimer agents, Eur. J. Med. Chem., 76, 376, 10.1016/j.ejmech.2014.02.035
Herlem, 2003, Synthesis and structure-activity relationships of open D-Ring galanthamine analogues, Med. Chem. Lett., 13, 2389, 10.1016/S0960-894X(03)00397-4
Atanasova, 2015, Galantamine derivatives with indole moiety: Docking, design, synthesis and acetylcholinesterase inhibitory activity, Bioorg. Med. Chem., 23, 5382, 10.1016/j.bmc.2015.07.058
Jia, 2009, Design, synthesis and evaluation of galanthamine derivatives as acetylcholinesterase inhibitors, Eur. J. Med. Chem., 44, 772, 10.1016/j.ejmech.2008.04.018
Mary, 1998, Potent acetylcholinesterase inhibitors: design, synthesis, and structure–activity relationships of bis-interacting ligands in the galanthamine series, Bioorg. Med. Chem., 6, 1835, 10.1016/S0968-0896(98)00133-3
Jordis, 2001, 12H-[2]-Benzothiepino[6,5a,5-bc]benzofuran: Synthesis of a sulfur-analog of galanthamine, Heterocycles, 55, 1727, 10.3987/COM-01-9278
Berkov, 2008, N-Alkylated galanthamine derivatives: Potent acetylcholinesterase inhibitors from Leucojum aestivum, Bioorg. Med. Chem. Lett., 18, 2263, 10.1016/j.bmcl.2008.03.008
Guillou, 2000, Potent acetylcholinesterase inhibitors: Design, synthesis and structure–activity relationships of alkylene linked bis-galanthamine and galanthamine–galanthaminium salts, Bioorg. Med. Chem. Lett., 10, 637, 10.1016/S0960-894X(00)00059-7
Treu, 2002, Carbocyclic galanthamine analogues: Construction of the novel 6H-benzo[a]cyclohepta[hi]benzofuran ring system, Mendeleev Commun., 12, 52, 10.1070/MC2002v012n02ABEH001557
Poschalko, 2002, Synthesis of (±)-6H-benzofuro[3a,3,2, ef][3]benzazepine: An unnatural analog of (–)-galanthamine, Tetrahedron, 58, 1513, 10.1016/S0040-4020(01)01235-2
Vezenkov, 2009, Synthesis and characterization of new galanthamine derivatives comprising peptide moiety, Protein Pept. Lett., 16, 1024, 10.2174/092986609789055412
Han, 1992, Chemical and pharmacological characterization of galanthamine, an acetylcholinesterase inhibitor, and its derivatives. A potential application in Alzheimer’s disease?, Eur. J. Med. Chem., 27, 673, 10.1016/0223-5234(92)90087-H
Barniol-Xicota, 2014, Direct reductive alkylation of amine hydrochlorides with aldehyde bisulfite adducts, Tetrahedron Lett., 55, 2548, 10.1016/j.tetlet.2014.03.046
Thomsen, 1991, Inhibition of acetylcholinesterase activity in human brain tissue and erythrocytes by galanthamine, physostigmine and tacrine, Eur. J. Clin. Chem. Clin. Biochem., 29, 487
Darvesh, 2003, Inhibition of human cholinesterases by drugs used to treat Alzheimer disease, Alzheimer Dis. Assoc. Disord., 17, 117, 10.1097/00002093-200304000-00011
Cer, 2009, IC50-to-Ki: a web-based tool for converting IC50 to Ki values for inhibitors of enzyme activity and ligand binding, Nucleic acids Res, 37, W441, 10.1093/nar/gkp253
Texidó, 2005, Effect of galantamine on the human α7 neuronal nicotinic acetylcholine receptor, the Torpedo nicotinic acetylcholine receptor and spontaneous cholinergic synaptic activity, Br. J. Pharmacol., 145, 672, 10.1038/sj.bjp.0706221
Kowal, 2018, Galantamine is not a positive allosteric modulator of human α4β2 or α7 nicotinic acetylcholine receptors, Brit. J. Pharmacol., 175, 2911, 10.1111/bph.14329
Moraga-Nicolás, 2019, Galanthamine and other Amaryllidaceae related alkaloids are inhibitors of α7, α4β2 and α3β4 nicotinic acetylcholine receptors, Rev. Bras. Farmacogn., 29, 495, 10.1016/j.bjp.2019.04.003
Loesche, 2018, Unexpected AChE inhibitory activity of (2E)α, β-unsaturated fatty acids, Bioorg. Med. Chem. Lett., 28, 3315, 10.1016/j.bmcl.2018.09.013
Cheung, 2012, Structures of human acetylcholinesterase in complex with pharmacologically important ligands, J. Med. Chem., 55, 10282, 10.1021/jm300871x
Glennon, 1981, Synthesis and evaluation of novel alkylpiperazines as potential dopamine antagonists, J. Med. Chem., 24, 678, 10.1021/jm00138a007
Arnold, 1955, Synthetische stoffe mit uterotonischer wirkung ii. vom 3,4-dimethoxybenzylamin abgeleitete tertiäre amine, Collect. Czech. Chem. C., 20, 567, 10.1135/cccc19550567
Stedman, 1927, The isomeric hydroxybenzyldimethylamines, J. Chem. Soc., 1902, 10.1039/JR9270001902
Jung, 1988, Improved synthesis of 3-substituted 7-methoxybenzofurans. Useful intermediates for the preparation of morphine analogs of organic chemistry, J. Org. Chem., 53, 423, 10.1021/jo00237a037
So, 2012, Concise synthesis of 2-benzazepine derivatives and their biological activity, J. Org. Chem., 77, 4017, 10.1021/jo300380z
Pandit, 2009, Expedient reductive amination of aldehyde bisulfite adducts, Synthesis (Stuttg), 2009, 4032, 10.1055/s-0029-1217050
Joshi, 2004, A vertical flow chamber for Xenopus oocyte electrophysiology and automated drug screening, J. Neurosci. Methods, 132, 69, 10.1016/j.jneumeth.2003.09.002
Pecic, 2011, Nantenine as an acetylcholinesterase inhibitor: SAR, enzyme kinetics and molecular modeling investigations, J. Enzyme Inhib. Med. Chem., 26, 46, 10.3109/14756361003671078
