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Article

Synthesis and In Vitro Screening of Novel Heterocyclic β-d-Gluco- and β-d-Galactoconjugates as Butyrylcholinesterase Inhibitors

1
Department of Chemistry, Faculty of Science, University of Zagreb, HR-10001 Zagreb, Croatia
2
Biochemistry and Organic Analytical Chemistry Unit, Institute for Medical Research and Occupational Health, P.O. Box 291, HR-10001 Zagreb, Croatia
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(15), 2833; https://doi.org/10.3390/molecules24152833
Received: 26 June 2019 / Revised: 1 August 2019 / Accepted: 3 August 2019 / Published: 4 August 2019
(This article belongs to the Special Issue Cholinesterase Inhibitors)
The development of selective butyrylcholinesterase (BChE) inhibitors may improve the treatment of Alzheimer’s disease by increasing lower synaptic levels of the neurotransmitter acetylcholine, which is hydrolysed by acetylcholinesterase, as well as by overexpressed BChE. An increase in the synaptic levels of acetylcholine leads to normal cholinergic neurotransmission and improved cognitive functions. A series of 14 novel heterocyclic β-d-gluco- and β-d-galactoconjugates were designed and screened for inhibitory activity against BChE. In the kinetic studies, 4 out of 14 compounds showed an inhibitory effect towards BChE, with benzimidazolium and 1-benzylbenzimidazolium substituted β-d-gluco- and β-d-galacto-derivatives in a 10–50 micromolar range. The analysis performed by molecular modelling indicated key residues of the BChE active site, which contributed to a higher affinity toward the selected compounds. Sugar moiety in the inhibitor should enable better blood–brain barrier permeability, and thus increase bioavailability in the central nervous system of these compounds. View Full-Text
Keywords: anticholinesterase; butyrylcholinesterase; glucose; galactose; heterocycles anticholinesterase; butyrylcholinesterase; glucose; galactose; heterocycles
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MDPI and ACS Style

Baumann, K.; Kordić, L.; Močibob, M.; Šinko, G.; Tomić, S. Synthesis and In Vitro Screening of Novel Heterocyclic β-d-Gluco- and β-d-Galactoconjugates as Butyrylcholinesterase Inhibitors. Molecules 2019, 24, 2833. https://doi.org/10.3390/molecules24152833

AMA Style

Baumann K, Kordić L, Močibob M, Šinko G, Tomić S. Synthesis and In Vitro Screening of Novel Heterocyclic β-d-Gluco- and β-d-Galactoconjugates as Butyrylcholinesterase Inhibitors. Molecules. 2019; 24(15):2833. https://doi.org/10.3390/molecules24152833

Chicago/Turabian Style

Baumann, Krešimir, Lorena Kordić, Marko Močibob, Goran Šinko, and Srđanka Tomić. 2019. "Synthesis and In Vitro Screening of Novel Heterocyclic β-d-Gluco- and β-d-Galactoconjugates as Butyrylcholinesterase Inhibitors" Molecules 24, no. 15: 2833. https://doi.org/10.3390/molecules24152833

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