Synthesis and in vitro acetylcholinesterase and butyrylcholinesterase inhibitory potential of hydrazide based Schiff bases

Rahim, Fazal; Ullah, Hayat; Taha, Muhammad; Wadood, Abdul; Javed, Muhammad Tariq; Rehman, Wajid; Nawaz, Mohsan; Ashraf, Muhammad; Ali, Muhammad; Sajid, Muhammad; Ali, Farman; Khan, Muhammad Naseem; Khan, Khalid Mohammed

doi:10.1016/j.bioorg.2016.07.005

Cited by 96 publications

(36 citation statements)

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“…The molecular docking study was performed via MOE to predict the binding mode of β-sitosterol in the active sites of AChE and BChE as inhibitor ( Rahim et al, 2016 ). The three dimensional structure of β-sitosterol was built using builder tool of MOE software and was protonated and energy minimized.…”

Section: Behavioral Assessmentsmentioning

confidence: 99%

Anti-Alzheimer’s Studies on β-Sitosterol Isolated from Polygonum hydropiper L.

et al. 2017

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The family Polygonaceae is known for its traditional use in the management of various neurological disorders including Alzheimer’s disease (AD). In search of new anti-AD drugs, β-sitosterol isolated from Polygonum hydropiper was subjected to in vitro, in vivo, behavioral and molecular docking studies to confirm its possibility as a potential anti-Alzheimer’s agent. The in vitro AChE, BChE inhibitory potentials of β-sitosterol were investigated following Ellman’s assay. The antioxidant activity was tested using DPPH, ABTS and H2O2 assays. Behavioral studies were performed on a sub-strain of transgenic mice using shallow water maze (SWM), Y-maze and balance beam tests. β-sitosterol was tested for in vivo inhibitory potentials against cholinesterase’s and free radicals in the frontal cortex (FC) and hippocampus (HC). The molecular docking study was performed to predict the binding mode of β-sitosterol in the active sites of AChE and BChE as inhibitor. Considerable in vitro and in vivo cholinesterase inhibitory effects were observed in the β-sitosterol treated groups. β-sitosterol exhibited an IC50 value of 55 and 50 μg/ml against AChE and BChE respectively. Whereas, the activity of these enzymes were significantly low in FC and HC homogenates of transgenic animals. Molecular docking studies also support the binding of β-sitosterol with the target enzyme and further support the in vitro and in vivo results. In the antioxidant assays, the IC50 values were observed as 140, 120, and 280 μg/ml in the DPPH, ABTS and H2O2 assays respectively. The free radicals load in the brain tissues was significantly declined in the β-sitosterol treated animals as compared to the transgenic-saline treated groups. In the memory assessment and coordination tasks including SWM, Y-maze and balance beam tests, β-sitosterol treated transgenic animals showed gradual improvement in working memory, spontaneous alternation behavior and motor coordination. These results conclude that β-sitosterol is a potential compound for the management of memory deficit disorders like AD.

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Section: Behavioral Assessmentsmentioning

confidence: 99%

Anti-Alzheimer’s Studies on β-Sitosterol Isolated from Polygonum hydropiper L.

et al. 2017

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“…ESIPT fluorophores 1 – 4 were synthesized via simple Schiff base condensation reaction between HBH and different aldehydes (Scheme a, S1) . Amine precursor, HBH, was synthesized by reacting hydrazine and methyl salicylate.…”

Section: Resultsmentioning

confidence: 99%

Easily Accessible Schiff Base ESIPT Molecules with Tunable Solid State Fluorescence: Mechanofluorochromism and Highly Selective Co²⁺ Fluorescence Sensing

et al. 2020

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Schiff base molecules of 1–4 ((E)‐N′‐benzylidene‐2‐hydroxybenzohydrazide derivatives) showed structure controlled solid state fluorescence tuning, reversible stimuli induced fluorescence switching and highly selective Co2+ sensing. The strong intramolecular H‐bonding between imine and amine facilitates excited state intramolecular proton transfer (ESIPT) and large red shifted solid state fluorescence. Positional isomers and substitutional change tuned the solid state fluorescence (460 to 605 nm). The substituents and positions control stimuli‐induced fluorescence switching. ESIPT fluorophores showed strong fluorescence in DMF (Φf=0.057 to 0.35 compared to quinine sulphate). ESIPT fluorophores (2–4) exhibited highly selective fluorescence sensing of Co2+ ions without significant interference from other metal ions. Concentration dependent studies of fluorophores show the detection limit (LOD) of 54 nM that is much lower than the Environmental Protection Agency (EPA) guideline value (1.7 μM) in drinking water. Solid state fluorescence of ESIPT fluorophores have been made use to fabricate solid fluorescence assay (PVA polymer composite thin films) and demonstrated highly selective fluorescence sensing of Co2+ upon dipping into aqueous metal ions solution. Thus, the present studies demonstrate the versatility of Schiff base molecules for developing ESIPT fluorophores for stimuli responsive materials and highly selective fluorescence sensing both in solution and solid state.

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“…The AchE interactions with protein give rise to a complex AchE–Aβ, which causes neurotoxicity. AchE is present in the brain, muscles, and cholinergic neurons while BchE is present in intestine, liver, kidneys, heart, lungs, and serum [ 8 , 9 ]. It plays a main role in the breakdown of ester containing compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Benzimidazole–Based Analogs as Anti Alzheimer’s Disease Compounds and Their Molecular Docking Studies

et al. 2020

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We synthesized 10 analogs of benzimidazole-based thiosemicarbazide 1 (a–j) and 13 benzimidazole-based Schiff bases 2 (a–m), and characterized by various spectroscopic techniques and evaluated in vitro for acetylcholinesterase (AchE) and butyrylcholinesterase (BchE) inhibition activities. All the synthesized analogs showed varying degrees of acetylcholinesterase and butyrylcholinesterase inhibitory potentials in comparison to the standard drug (IC50 = 0.016 and 4.5 µM. Amongst these analogs 1 (a–j), compounds 1b, 1c, and 1g having IC50 values 1.30, 0.60, and 2.40 µM, respectively, showed good acetylcholinesterase inhibition when compared with the standard. These compounds also showed moderate butyrylcholinesterase inhibition having IC50 values of 2.40, 1.50, and 2.40 µM, respectively. The rest of the compounds of this series also showed moderate to weak inhibition. While amongst the second series of analogs 2 (a–m), compounds 2c, 2e, and 2h having IC50 values of 1.50, 0.60, and 0.90 µM, respectively, showed moderate acetylcholinesterase inhibition when compared to donepezil. Structure Aactivity Relation of both synthesized series has been carried out. The binding interactions between the synthesized analogs and the enzymes were identified through molecular docking simulations.

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Synthesis and in vitro acetylcholinesterase and butyrylcholinesterase inhibitory potential of hydrazide based Schiff bases

Cited by 96 publications

References 44 publications

Anti-Alzheimer’s Studies on β-Sitosterol Isolated from Polygonum hydropiper L.

Anti-Alzheimer’s Studies on β-Sitosterol Isolated from Polygonum hydropiper L.

Easily Accessible Schiff Base ESIPT Molecules with Tunable Solid State Fluorescence: Mechanofluorochromism and Highly Selective Co²⁺ Fluorescence Sensing

Synthesis of Benzimidazole–Based Analogs as Anti Alzheimer’s Disease Compounds and Their Molecular Docking Studies

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Synthesis and in vitro acetylcholinesterase and butyrylcholinesterase inhibitory potential of hydrazide based Schiff bases

Cited by 96 publications

References 44 publications

Anti-Alzheimer’s Studies on β-Sitosterol Isolated from Polygonum hydropiper L.

Anti-Alzheimer’s Studies on β-Sitosterol Isolated from Polygonum hydropiper L.

Easily Accessible Schiff Base ESIPT Molecules with Tunable Solid State Fluorescence: Mechanofluorochromism and Highly Selective Co2+ Fluorescence Sensing

Synthesis of Benzimidazole–Based Analogs as Anti Alzheimer’s Disease Compounds and Their Molecular Docking Studies

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Easily Accessible Schiff Base ESIPT Molecules with Tunable Solid State Fluorescence: Mechanofluorochromism and Highly Selective Co²⁺ Fluorescence Sensing