131 results match your criteria dual-binding cholinesterase


Design, synthesis, and cholinesterase inhibition assay of liquiritigenin derivatives as anti-Alzheimer's activity.

Bioorg Med Chem Lett 2021 Aug 6:128306. Epub 2021 Aug 6.

Department of Physiology and Pathophysiology, Jiaxing University Medical College, Jiaxing 314001, China. Electronic address:

The marine environment is a rich resource for discovering functional materials, and seaweed is recognized for its potential use in biology and medicine. Liquiritigenin has been isolated and identified from Sargassum pallidum. To find new anti-Alzheimer's activity, we designed and synthesized thirty-two 7-prenyloxy-2,3-dihydroflavanone derivatives (3a-3p) and 5-hydroxy-7-prenyloxy-2,3-dihydro- flavanone derivatives (4a-4p) as cholinesterases inhibitors based on liquiritigenin as the lead compound. Read More

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"Clicking" fragment leads to novel dual-binding cholinesterase inhibitors.

Bioorg Med Chem 2021 Jul 7;42:116269. Epub 2021 Jun 7.

National Medicines Institute, Chełmska 30/34, 00-725 Warsaw, Poland; National Centre for Nuclear Research, 05-400 Otwock-Świerk, Poland.

Cholinesterase inhibitors are potent therapeutics in the treatment of Alzheimer's disease. Among them, dual binding ligands have recently gained a lot of attention. We discovered novel dual-binding cholinesterase inhibitors, using "clickable" fragments, which bind to either catalytic active site (CAS) or peripheral anionic site (PAS) of the enzyme. Read More

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Inhibitory activities of flavonoids from Eupatorium adenophorum against acetylcholinesterase.

Pestic Biochem Physiol 2020 Nov 9;170:104701. Epub 2020 Sep 9.

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China. Electronic address:

Fifteen flavonoids isolated from the Eupatorium adenophorum showed inhibitory activities against acetylcholinesterase (AChE) isolated from Caenorhabditis elegans and Spodoptera litura. Their IC values ranged from 12.54 to 89. Read More

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November 2020

Discovery of a New Donepezil-like Acetylcholinesterase Inhibitor for Targeting Alzheimer's Disease: Computational Studies with Biological Validation.

J Chem Inf Model 2020 10 8;60(10):4717-4729. Epub 2020 Oct 8.

Discovery Informatics Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu 180001, India.

Alzheimer's disorder is one of the most common worldwide health problems, and its prevalence continues to increase, thereby straining the healthcare budgets of both developed and developing countries. So far, donepezil is the only Food and Drug Administration-approved dual-binding site inhibitor of acetylcholinesterase (AChE) that can amplify the cholinergic activity and also decrease Aβ aggregation in Alzheimer patients. We report herein a new donepezil-like natural compound derivative (D1) as a convincing AChE inhibitor. Read More

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October 2020

Novel Acetylcholinesterase Inhibitors Based on Uracil Moiety for Possible Treatment of Alzheimer Disease.

Molecules 2020 Sep 12;25(18). Epub 2020 Sep 12.

Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, Arbuzov str. 8, 420088 Kazan, Russia.

In this study, novel derivatives based on 6-methyluracil and condensed uracil were synthesized, namely, 2,4-quinazoline-2,4-dione with ω-(-nitrilebenzylethylamino) alkyl chains at the N atoms of the pyrimidine ring. In this series of synthesized compounds, the polymethylene chains were varied from having tetra- to hexamethylene chains, and secondary NH, tertiary ethylamino, and quaternary ammonium groups were introduced into the chains. The molecular modeling of the compounds indicated that they could function as dual binding site acetylcholinesterase inhibitors, binding to both the peripheral anionic site and active site. Read More

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September 2020

Design and Microwave-Assisted Synthesis of Aza-Resveratrol Analogs with Potent Cholinesterase Inhibition.

CNS Neurol Disord Drug Targets 2020 ;19(8):630-641

INQUISUR-CONICET, Departamento de Química, Universidad Nacional del Sur, Bahía Blanca, Argentina.

Background: Currently approved Alzheimer's disease medications mainly comprise acetylcholinesterase inhibitors. Many of these inhibitors are either natural compounds or synthetic molecules inspired in natural compounds. Hybrid molecules that can interact with different target sites of the enzyme could lead to the discovery of effective multitarget drugs. Read More

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January 2020

New Hybrids of 4-Amino-2,3-polymethylene-quinoline and -Tolylsulfonamide as Dual Inhibitors of Acetyl- and Butyrylcholinesterase and Potential Multifunctional Agents for Alzheimer's Disease Treatment.

Molecules 2020 Aug 27;25(17). Epub 2020 Aug 27.

Department of Environmental Health Sciences, University of Michigan, Ann Arbor, MI 48109, USA.

New hybrid compounds of 4-amino-2,3-polymethylene-quinoline containing different sizes of the aliphatic ring and linked to -tolylsulfonamide with alkylene spacers of increasing length were synthesized as potential drugs for treatment of Alzheimer's disease (AD). All compounds were potent inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) with selectivity toward BChE. The lead compound 4-methyl-N-(5-(1,2,3,4-tetrahydro-acridin-9-ylamino)-pentyl)-benzenesulfonamide () exhibited an IC (AChE) = 0. Read More

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Synthesis and biological evaluation of novel quinazoline-triazole hybrid compounds with potential use in Alzheimer's disease.

Bioorg Med Chem Lett 2020 09 12;30(18):127404. Epub 2020 Jul 12.

Institute of Chemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Cau Giay, Hanoi, Viet Nam; Graduate University of Science and Technology, VAST, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Viet Nam. Electronic address:

A library of twelve quinazoline-triazole hybrid compounds were designed, synthesized and evaluated as a novel class of acetylcholinesterase inhibitors to treat Alzheimer's disease (AD). The biological assay results demonstrated the ability of several hybrid compounds to inhibit AChE enzyme (IC range = 0.2-83. Read More

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September 2020

Bi-functional sterically hindered phenol lipid-based delivery systems as potential multi-target agents against Alzheimer's disease via an intranasal route.

Nanoscale 2020 Jul;12(25):13757-13770

Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov str. 8, Kazan 420088, Russian Federation.

New lipid-based nanomaterials and multi-target directed ligands (MTDLs) based on sterically hindered phenol, containing a quaternary ammonium moiety (SHP-s-R, with s = 2,3) of varying hydrophobicity (R = CH2Ph and CnH2n+1, with n = 8, 10, 12, 16), have been prepared as potential drugs against Alzheimer's disease (AD). SHP-s-R are inhibitors of human cholinesterases with antioxidant properties. The inhibitory potency of SHP-s-R and selectivity ratio of cholinesterase inhibition were found to significantly depend on the length of the methylene spacer (s) and alkyl chain length. Read More

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New deferiprone derivatives as multi-functional cholinesterase inhibitors: design, synthesis and in vitro evaluation.

Eur J Med Chem 2020 Jul 25;198:112350. Epub 2020 Apr 25.

Department of Chimica e Tecnologia del Farmaco, Sapienza University of Rome, Piazzale Aldo Moro, 5, 00185, Rome, Italy. Electronic address:

In order to obtain multi-functional molecules for Alzheimer's disease, a series of deferiprone derivatives has been synthesized and evaluated in vitro with the hypothesis that they can restore the cholinergic tone and attenuate the dyshomeostasis of the metals mainly involved in the pathology. These compounds were designed as dual binding site AChE inhibitors: they possess an arylalkylamine moiety connected via an alkyl chain to a 3-hydroxy-4-pyridone fragment, to allow the simultaneous interaction with catalytic active site (CAS) and peripheral anionic site (PAS) of the enzyme. Deferiprone moiety and 2-aminopyridine, 2-aminopyrimidine or 2,4-diaminopyrimidine groups have been incorporated into these compounds, in order to obtain molecules potentially able to chelate bio-metals colocalized in Aβ plaques and involved in the generation of radical species. Read More

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Discovery of dual cation-π inhibitors of acetylcholinesterase: design, synthesis and biological evaluation.

Pharmacol Rep 2020 Jun 21;72(3):705-718. Epub 2020 Mar 21.

Department of Biotechnology and Bioinformatics, University of Hyderabad, Hyderabad, 500046, India.

Background: Alzheimer's disease (AD) is a widespread dementia-related disease affecting mankind worldwide. A cholinergic hypothesis is considered the most effective target for treating mild to moderate AD. Present study aims to identify new scaffolds for inhibiting acetylcholinesterase activity. Read More

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Design, synthesis and molecular modeling of isothiochromanone derivatives as acetylcholinesterase inhibitors.

Future Med Chem 2019 10 9;11(20):2687-2699. Epub 2019 Oct 9.

State Key Laboratory of Natural Medicines & Department of Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, PR China.

A series of novel isothio- and isoselenochromanone derivatives bearing -benzyl pyridinium moiety were designed, synthesized and evaluated as acetylcholinesterase (AChE) inhibitors. Most of the target compounds exhibited potent anti-AChE activities with IC values in nanomolar ranges. Among them, compound exhibited the most potent anti-AChE activity (IC = 2. Read More

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October 2019

Synthesis and AChE Inhibitory Activity of Novel Thiazolylhydrazone Derivatives.

Molecules 2019 Jun 28;24(13). Epub 2019 Jun 28.

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu Universty, 26470 Eskişehir, Turkey.

Alzheimer's disease (AD) is the most common of the degenerative brain diseases and is described together with the impairment of cognitive function. Patients with AD lose the capability to code new memories, and life conditions are extremely difficult. The development of new drugs in this area continues at a great pace. Read More

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Novel chromanone-dithiocarbamate hybrids as multifunctional AChE inhibitors with β-amyloid anti-aggregation properties for the treatment of Alzheimer's disease.

Bioorg Chem 2019 08 31;89:103027. Epub 2019 May 31.

National Pharmaceutical Engineering Center for Solid Preparation in Chinese Herbal Medicine, Jiangxi University of Traditional Chinese Medicine, Nanchang, PR China. Electronic address:

By connecting chromanone with dithiocarbamate moieties through flexible linkers, a series of hybrids as novel multifunctional AChE inhibitors have been designed and synthesized. Most of these compounds displayed strong and excellently selective inhibition to eeAChE as well as potent inhibition to self- and AChE-induced Aβ aggregation. Among them, compound 6c showed the best activity to inhibit eeAChE (IC = 0. Read More

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Design, Synthesis, and Cholinesterase Inhibition Assay of Coumarin-3-carboxamide-N-morpholine Hybrids as New Anti-Alzheimer Agents.

Chem Biodivers 2019 Jul 26;16(7):e1900144. Epub 2019 Jun 26.

Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, 1417653761, Iran.

A new series of coumarin-3-carboxamide-N-morpholine hybrids 5a-5l was designed and synthesized as cholinesterases inhibitors. The synthetic approach for title compounds was started from the reaction between 2-hydroxybenzaldehyde derivatives and Meldrum's acid to afford corresponding coumarin-3-carboxylic acids. Then, amidation of the latter compounds with 2-morpholinoethylamine or N-(3-aminopropyl)morpholine led to the formation of the compounds 5a-5l. Read More

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New evidence for dual binding site inhibitors of acetylcholinesterase as improved drugs for treatment of Alzheimer's disease.

Neuropharmacology 2019 09 25;155:131-141. Epub 2019 May 25.

Kazan Federal University, 18 Kremlyovskaya str, Kazan, 420008, Russia. Electronic address:

Profound synaptic dysfunction contributes to early loss of short-term memory in Alzheimer's disease. This study was set up to analyze possible neuroprotective effects of two dual binding site inhibitors of acetylcholinesterase (AChE), a new 6-methyluracil derivative, C-35, and the clinically used inhibitor donepezil. Crystal structure of the complex between human AChE and C-35 revealed tight contacts of ligand along the enzyme active site gorge. Read More

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September 2019

Synthesis of 2-(2-oxo-2H-chromen-4-yl)acetamides as potent acetylcholinesterase inhibitors and molecular insights into binding interactions.

Arch Pharm (Weinheim) 2019 Jul 24;352(7):e1800310. Epub 2019 May 24.

Department of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat Yai, Songkhla, Thailand.

Sixteen novel coumarin-based compounds are reported as potent acetylcholinesterase (AChE) inhibitors. The most active compound in this series, 5a (IC 0.04 ± 0. Read More

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Design, synthesis, evaluation and molecular modeling study of 4-N-phenylaminoquinolines for Alzheimer disease treatment.

Bioorg Med Chem Lett 2019 06 30;29(11):1325-1329. Epub 2019 Mar 30.

Department of Pharmacy Engineering, Tianjin University of Technology, Tianjin 300384, PR China. Electronic address:

Dual binding site acetylcholinesterase (AChE) inhibitors and butyrylcholinesterase (BChE) inhibitors have recently emerged as two classes of new anti-Alzheimer agents to positively modify the disease's course. In this work, a new series of 4-N-phenylaminoquinolines was synthesized and evaluated for their abilities to inhibit AChE and BChE. Compound 11b showed significant inhibitory activities on AChE and BChE with IC values of 0. Read More

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Design, Synthesis and Insecticide Activity of Novel Acetylcholinesterase Inhibitors: Triazolinone and Phthalimide Heterodimers.

Chem Pharm Bull (Tokyo) 2019 ;67(4):345-350

State Key Laboratory for Biology of Plant Diseases and Insect Pests, Institute of Plant Protection, Chinese Academy of Agricultural Sciences.

Based on the "cluster effect" and the structure characters of acetylcholinesterase (AChE; EC 3.1.1. Read More

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Highly potent and selective aryl-1,2,3-triazolyl benzylpiperidine inhibitors toward butyrylcholinesterase in Alzheimer's disease.

Bioorg Med Chem 2019 03 23;27(6):931-943. Epub 2018 Dec 23.

School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, Av. Café s/n, 14040-930 Ribeirão Preto, SP, Brazil. Electronic address:

Acetylcholinesterase (AChE) is the key enzyme targeted in Alzheimer's disease (AD) therapy, nevertheless butyrylcholinesterase (BuChE) has been drawing attention due to its role in the disease progression. Thus, we aimed to synthesize novel cholinesterases inhibitors considering structural differences in their peripheral site, exploiting a moiety replacement approach based on the potent and selective hAChE drug donepezil. Hence, two small series of N-benzylpiperidine based compounds have successfully been synthesized as novel potent and selective hBuChE inhibitors. Read More

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New Multitarget Hybrids Bearing Tacrine and Phenylbenzothiazole Motifs as Potential Drug Candidates for Alzheimer's Disease.

Molecules 2019 Feb 7;24(3). Epub 2019 Feb 7.

Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais 1, 1049-001 Lisboa, Portugal.

Research on neurodegenerative brain disorders, namely the age-dependent Alzheimer's disease (AD), has been intensified in the last decade due to the absence of a cure and the recognized increasing of life expectancy for populations. To address the multifactorial nature and complexity of AD, a multi-target-directed ligand approach was herein employed, by designing a set of six selected hybrids (⁻) that combine in the same entity two pharmacophores: tacrine (TAC) and 2-phenylbenzothiazole (PhBTA). The compounds contain a methoxy substituent at the PhBTA moiety and have a variable length linker between that and the TAC moiety. Read More

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February 2019

Design, synthesis and bioevaluation of tricyclic fused ring system as dual binding site acetylcholinesterase inhibitors.

Bioorg Chem 2019 03 23;83:336-347. Epub 2018 Oct 23.

Department of Chemistry, COMSATS University Islamabad, Abbottabad Campus, 22060, Pakistan. Electronic address:

Due to recently discovered non-classical acetylcholinesterase (AChE) function, dual binding-site AChE inhibitors have acquired a paramount attention of drug designing researchers. The unique structural arrangements of AChE peripheral anionic site (PAS) and catalytic site (CAS) joined by a narrow gorge, prompted us to design the inhibitors that can interact with dual binding sites of AChE. Eighteen homo- and heterodimers of desloratadine and carbazole (already available tricyclic building blocks) were synthesized and tested for their inhibition potential against electric eel acetylcholinesterase (eeAChE) and equine serum butyrylcholinesterase (eqBChE). Read More

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Novel tacrine-coumarin hybrids linked to 1,2,3-triazole as anti-Alzheimer's compounds: In vitro and in vivo biological evaluation and docking study.

Bioorg Chem 2019 03 28;83:303-316. Epub 2018 Oct 28.

Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran; Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran. Electronic address:

A new series of tacrine-coumarin hybrids linked to 1,2,3-triazole were designed, synthesized, and tested as potent dual binding site cholinesterase inhibitors (ChEIs) for the treatment of Alzheimer's disease (AD). Among them, compound 8e was the most potent anti-AChE derivative (IC = 27 nM) and compound 8m displayed the best anti-BChE activity (IC = 6 nM) much more active than tacrine and donepezil as the reference drugs. Compound 8e was also evaluated for its BACE1 inhibitory activity and neuroprotectivity against PC12 cells exposed to Aβ which indicated low activity. Read More

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Donepezil-melatonin hybrids as butyrylcholinesterase inhibitors: Improving binding affinity through varying mode of linking fragments.

Arch Pharm (Weinheim) 2018 Nov 5;351(11):e1800194. Epub 2018 Oct 5.

Faculty of Chemistry, University of Warsaw, Warsaw, Poland.

Hybrid inhibitors of acetyl- and butyrylcholinesterase are compounds that combine structural motifs of two different classical inhibitors, leading to a dual binding ligand. A rapidly growing collection of those compounds involves a wide diversity of structural motifs, but the way of linking two active fragments and its impact on the affinity toward cholinesterases usually remains beyond the extent of investigation. We present hereby a detailed analysis of this aspect using melatonin-donepezil hybrids. Read More

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November 2018

Coumarin-dithiocarbamate hybrids as novel multitarget AChE and MAO-B inhibitors against Alzheimer's disease: Design, synthesis and biological evaluation.

Bioorg Chem 2018 12 11;81:512-528. Epub 2018 Sep 11.

National Pharmaceutical Engineering Center for Solid Preparation in Chinese Herbal Medicine, Jiangxi University of Traditional Chinese Medicine, Nanchang 330006, PR China. Electronic address:

A series of new coumarin-dithiocarbamate hybrids were designed and synthesized as multitarget agents for the treatment of Alzheimer's disease. Most of them showed potent and clearly selective inhibition towards AChE and MAO-B. Among these compounds, compound 8f demonstrated the most potent inhibition to AChE with IC values of 0. Read More

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December 2018

Structure-based design, synthesis, and evaluation of structurally rigid donepezil analogues as dual AChE and BACE-1 inhibitors.

Bioorg Med Chem Lett 2018 09 11;28(17):2910-2913. Epub 2018 Jul 11.

Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt; School of Chemistry and Molecular Biosciences, University of Queensland, St Lucia 4072, Queensland, Australia.

A new series of structurally rigid donepezil analogues was designed, synthesized and evaluated as potential multi-target-directed ligands (MTDLs) against neurodegenerative diseases. The investigated compounds 10-13 displayed dual AChE and BACE-1 inhibitory activities in comparison to donepezil, the FDA-approved drug. The hybrid compound 13 bearing 2-aminoquinoline scaffold exhibited potent AChE inhibition (IC value of 14. Read More

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September 2018

Tacrine-coumarin and Tacrine-7-chloroquinoline Hybrids with Thiourea Linkers: Cholinesterase Inhibition Properties, Kinetic Study, Molecular Docking and Permeability Assay for Blood-brain Barrier.

Curr Alzheimer Res 2018 ;15(12):1096-1105

Biomedical Research Centre, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech Republic.

Background: The design of new heterodimeric dual binding site acetylcholinesterase inhibitors constitutes the main goal-directed to the development of new anticholinesterase agents with the expanded pharmacological profile. Multi-target compounds are usually designed by combining in a hybrid molecule with two or more pharmacophoric moieties that are known to enable interaction with the selected molecular targets.

Methods: All compounds were tested for their inhibitory activity on human AChE/BChE. Read More

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October 2019

A molecular approach in drug development for Alzheimer's disease.

Biomed Pharmacother 2018 Oct 11;106:553-565. Epub 2018 Jul 11.

School of Pharmacy and Applied Science, La Trobe Institute for Molecular Sciences, La Trobe University, Edwards Rd., Bendigo, 3550, Australia.

An increase in dementia numbers and global trends in population aging across the world prompts the need for new medications to treat the complex biological dysfunctions, such as neurodegeneration associated with dementia. Alzheimer's disease (AD) is the most common form of dementia. Cholinergic signaling, which is important in cognition, is slowly lost in AD, so the first line therapy is to treat symptoms with acetylcholinesterase inhibitors to increase levels of acetylcholine. Read More

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October 2018

An evaluation of neonicotinoids' potential to inhibit human cholinesterases: Protein-ligand docking and interaction profiling studies.

Authors:
Kerem Teralı

J Mol Graph Model 2018 09 17;84:54-63. Epub 2018 Jun 17.

Department of Medical Biochemistry, Faculty of Medicine, Near East University, Nicosia, 99138, North Cyprus. Electronic address:

Many so-called neuroactive insecticides target invertebrate neurotransmitter systems, including the cholinergic system. With their relatively low toxicity to vertebrates, neonicotinoids represent a new class of neuroactive insecticides that bind to nicotinic receptors for acetylcholine in the insect central nervous system and result in paralysis and eventual death due to receptor overstimulation. On the understanding that, today, cholinesterase inhibitors are used to obtain the symptomatic relief of Alzheimer disease (AD), the aforementioned direct cholinomimetic action of neonicotinoids could, perhaps, confer anti-AD drug-like attributes to these compounds. Read More

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September 2018

Rational design of carbamate-based dual binding site and central AChE inhibitors by a "biooxidisable" prodrug approach: Synthesis, in vitro evaluation and docking studies.

Eur J Med Chem 2018 Jul 1;155:171-182. Epub 2018 Jun 1.

Normandie Univ, UNIROUEN, INSA Rouen, CNRS, COBRA, 76000, Rouen, France. Electronic address:

Herein, we report a new class of dual binding site AChE inhibitor 4 designed to exert a central cholinergic activation thanks to a redox-activation step of a prodrug precursor 3. Starting from potent pseudo-irreversible quinolinium salts AChE inhibitors 2 previously reported, a new set of diversely substituted quinolinium salts 2a-p was prepared and assayed for their inhibitory activity against AChE. Structure-activity relationship (SAR) analysis of 2a-p coupled with molecular docking studies allowed us to determine which position of the quinolinium scaffold may be considered to anchor the phtalimide fragment presumed to interact with the peripheral anionic site (PAS). Read More

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