Inhibitory Activity of 4-Benzylidene Oxazolones Derivatives of Cinnamic Acid on Human Acetylcholinesterase and Cognitive Improvements in a Mouse Model

We synthesized seven (Z)-benzylidene-2-(E)-styryloxazol-5(4H)-ones derivatives of cinnamic acid and evaluated the ability of these compounds to inhibit human acetylcholinesterase (hAChE). The most potent compound was evaluated for cognitive improvement in short-term memory. The seven compounds rever...

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Published inMolecules (Basel, Switzerland) Vol. 28; no. 21; p. 7392
Main Authors Ramírez-Ruiz, Alma Marisol, Ávila-Cossío, Martha Elena, Estolano-Cobián, Arturo, Cornejo-Bravo, José Manuel, Martinez, Ana Laura, Córdova-Guerrero, Iván, Cota-Ramírez, Bibiana Roselly, Carranza-Ambriz, Krysta Paola, Rivero, Ignacio A., Serrano-Medina, Aracely
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 01.11.2023
Subjects
Alzheimer's disease
Amino acids
Analysis
cinnamic acid
Drugs
Enzyme kinetics
human acetylcholinesterase
inhibitory activity
oxazolones
Mexico
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Abstract We synthesized seven (Z)-benzylidene-2-(E)-styryloxazol-5(4H)-ones derivatives of cinnamic acid and evaluated the ability of these compounds to inhibit human acetylcholinesterase (hAChE). The most potent compound was evaluated for cognitive improvement in short-term memory. The seven compounds reversibly inhibited the hAChE between 51 and 75% at 300 μM, showed an affinity (Ki) from 2 to 198 μM, and an IC50 from 9 to 246 μM. Molecular docking studies revealed that all binding moieties are involved in the non-covalent interactions with hAChE for all compounds. In addition, in silico pharmacokinetic analysis was carried out to predict the compounds’ blood–brain barrier (BBB) permeability. The most potent inhibitor of hAChE significantly improved cognitive impairment in a modified Y-maze test (5 μmol/kg) and an Object Recognition Test (10 μmol/kg). Our results can help the rational design of hAChE inhibitors to work as potential candidates for treating cognitive disorders.
AbstractList We synthesized seven (Z)-benzylidene-2-(E)-styryloxazol-5(4H)-ones derivatives of cinnamic acid and evaluated the ability of these compounds to inhibit human acetylcholinesterase (hAChE). The most potent compound was evaluated for cognitive improvement in short-term memory. The seven compounds reversibly inhibited the hAChE between 51 and 75% at 300 μM, showed an affinity (K[sub.i]) from 2 to 198 μM, and an IC[sub.50] from 9 to 246 μM. Molecular docking studies revealed that all binding moieties are involved in the non-covalent interactions with hAChE for all compounds. In addition, in silico pharmacokinetic analysis was carried out to predict the compounds’ blood–brain barrier (BBB) permeability. The most potent inhibitor of hAChE significantly improved cognitive impairment in a modified Y-maze test (5 μmol/kg) and an Object Recognition Test (10 μmol/kg). Our results can help the rational design of hAChE inhibitors to work as potential candidates for treating cognitive disorders.
We synthesized seven (Z)-benzylidene-2-(E)-styryloxazol-5(4H)-ones derivatives of cinnamic acid and evaluated the ability of these compounds to inhibit human acetylcholinesterase (hAChE). The most potent compound was evaluated for cognitive improvement in short-term memory. The seven compounds reversibly inhibited the hAChE between 51 and 75% at 300 μM, showed an affinity (Ki) from 2 to 198 μM, and an IC50 from 9 to 246 μM. Molecular docking studies revealed that all binding moieties are involved in the non-covalent interactions with hAChE for all compounds. In addition, in silico pharmacokinetic analysis was carried out to predict the compounds’ blood–brain barrier (BBB) permeability. The most potent inhibitor of hAChE significantly improved cognitive impairment in a modified Y-maze test (5 μmol/kg) and an Object Recognition Test (10 μmol/kg). Our results can help the rational design of hAChE inhibitors to work as potential candidates for treating cognitive disorders.
Audience Academic
Author Serrano-Medina, Aracely
Ávila-Cossío, Martha Elena
Estolano-Cobián, Arturo
Rivero, Ignacio A
Ramírez-Ruiz, Alma Marisol
Martinez, Ana Laura
Carranza-Ambriz, Krysta Paola
Cornejo-Bravo, José Manuel
Córdova-Guerrero, Iván
Cota-Ramírez, Bibiana Roselly
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Snippet We synthesized seven (Z)-benzylidene-2-(E)-styryloxazol-5(4H)-ones derivatives of cinnamic acid and evaluated the ability of these compounds to inhibit human...
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SubjectTerms Alzheimer's disease
Amino acids
Analysis
cinnamic acid
Drugs
Enzyme kinetics
human acetylcholinesterase
inhibitory activity
oxazolones
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Title Inhibitory Activity of 4-Benzylidene Oxazolones Derivatives of Cinnamic Acid on Human Acetylcholinesterase and Cognitive Improvements in a Mouse Model
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Volume 28
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