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Increasing Polarity in Tacrine and Huprine Derivatives: Potent Anticholinesterase Agents for the Treatment of Myasthenia Gravis

descriptionPublicationkeyboard_double_arrow_right Article , Other literature type 11 Mar 2018 Spain, France, Italy, Spain English Publisher:MDPI AGJournal:Molecules, volume 23, page 634 (eissn: 1420-3049, Copyright policy )Funded by:ANR | SYNORG, ANR | Multi-click
Authors: Carles Galdeano; Nicolas Coquelle; Monika Cieslikiewicz-Bouet; Manuela Bartolini; Belén Pérez; M. Clos; Israel Silman; +4 Authors

doi: 10.3390/molecules23030634

pmid: 29534488

pmc: PMC6017698

handle: 2445/122306 , 11585/666770

Increasing Polarity in Tacrine and Huprine Derivatives: Potent Anticholinesterase Agents for the Treatment of Myasthenia Gravis

Abstract

Symptomatic treatment of myasthenia gravis is based on the use of peripherally-acting acetylcholinesterase (AChE) inhibitors that, in some cases, must be discontinued due to the occurrence of a number of side-effects. Thus, new AChE inhibitors are being developed and investigated for their potential use against this disease. Here, we have explored two alternative approaches to get access to peripherally-acting AChE inhibitors as new agents against myasthenia gravis, by structural modification of the brain permeable anti-Alzheimer AChE inhibitors tacrine, 6-chlorotacrine, and huprine Y. Both quaternization upon methylation of the quinoline nitrogen atom, and tethering of a triazole ring, with, in some cases, the additional incorporation of a polyphenol-like moiety, result in more polar compounds with higher inhibitory activity against human AChE (up to 190-fold) and butyrylcholinesterase (up to 40-fold) than pyridostigmine, the standard drug for symptomatic treatment of myasthenia gravis. The novel compounds are furthermore devoid of brain permeability, thereby emerging as interesting leads against myasthenia gravis.

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Spain, France, Italy, Spain
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Keywords

Models, Molecular, Malalties neuromusculars, [SDV.BBM.BS] Life Sciences [q-bio]/Biochemistry, Molecular Biology/Structural Biology [q-bio.BM], [CHIM.THER] Chemical Sciences/Medicinal Chemistry, 610, quinolinium compounds, Organic chemistry, Down-Regulation, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, GPI-Linked Proteins, Heterocyclic Compounds, 4 or More Rings, [SDV.BBM.BS]Life Sciences [q-bio]/Biochemistry, Article, copper-catalyzed azide-alkyne cycloaddition, Structure-Activity Relationship, QD241-441, Myasthenia Gravis, structural biology, Humans, triazoles, Molecular Structure, Molecular Biology/Structural Biology [q-bio.BM], Aminoacridines, acetylcholinesterase inhibitors; butyrylcholinesterase inhibitors; quinolinium compounds; triazoles; structural biology; copper-catalyzed azide-alkyne cycloaddition; click chemistry;, acetylcholinesterase inhibitors; butyrylcholinesterase inhibitors; quinolinium compounds; triazoles; structural biology; copper-catalyzed azide-alkyne cycloaddition; click chemistry, Triazoles, Acetilcolinesterasa, Neuromuscular diseases, acetylcholinesterase inhibitors, [SDV.SP.PHARMA] Life Sciences [q-bio]/Pharmaceutical sciences/Pharmacology, Butyrylcholinesterase, click chemistry, [SDV.SP.PHARMA]Life Sciences [q-bio]/Pharmaceutical sciences/Pharmacology, Acetylcholinesterase, Aminoquinolines, Tacrine, butyrylcholinesterase inhibitors, Cholinesterase Inhibitors

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popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
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influence
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impulse
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