Potent acetylcholinesterase inhibitors: Synthesis, biological assay and docking study of nitro acridone derivatives

Parveen, Mehtab; Aslam, Afroz; Nami, Shahab A.A.; Malla, Ali Mohammed; Alam, Mahboob; Lee, Dong‐Ung; Rehman, Sumbul; Silva, P. S. Pereira; Silva, M. Ramos

doi:10.1016/j.jphotobiol.2016.05.028

Cited by 26 publications

(10 citation statements)

References 39 publications

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“…The cells were grown in standard conditions: IMDM basic medium supplemented with L-glutamine, 25 mM HEPES, fetal bovine serum, and gentamicin in an incubator at 37 °C and 5% CO 2 . 9-Acridone and 4-carboxy-9(10 H )acridone were synthesized according to the literature methods [ 23 , 24 ]. The spectra for synthesized compounds can be found in the Supplementary Materials .…”

Section: Methodsmentioning

confidence: 99%

Design and Synthesis of New Acridone-Based Nitric Oxide Fluorescent Probe

et al. 2021

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Nitric oxide (NO) is an important signaling molecule involved in a wide range of physiological and pathological processes. Fluorescent imaging is a useful tool for monitoring NO concentration, which could be essential in various biological and biochemical studies. Here, we report the design of a novel small-molecule fluorescent probe based on 9(10H)acridone moiety for nitric oxide sensing. 7,8-Diamino-4-carboxy-10-methyl-9(10H)acridone reacts with NO in aqueous media in the presence of O2, yielding a corresponding triazole derivative with fivefold increased fluorescence intensity. The probe was shown to be capable of nitric oxide sensing in living Jurkat cells.

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Section: Methodsmentioning

confidence: 99%

Design and Synthesis of New Acridone-Based Nitric Oxide Fluorescent Probe

et al. 2021

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“…Ligands with the lowest predicted binding energies were considered the most active compounds. The AChE and BChE crystals were selected for docking on their quality, ligand presence and use in literature [18][19][20][21][22][23][24]. For AChE, the selected proteins are: PDB: 4EY4 [25], PDB: 4EY7 [25]; PDB: 4BDT [26], and PDB: 4M0F [27].…”

Section: Molecular Dockingmentioning

confidence: 99%

Phenethyl Esters and Amide of Ferulic Acid, Hydroferulic Acid, Homovanillic Acid, and Vanillic Acid: Synthesis, Free Radicals Scavenging Activity, and Molecular Modeling as Potential Cholinesterases Inhibitors

Selka

Moutombi

Cormier

et al. 2020

Molbank

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As ferulic acid was reported to be involved in novel potential mechanisms associated with Alzheimer’s disease (AD) therapy, five closely related phenethyl esters and amide of this natural product were synthesized and screened for their free radicals scavenging activity. Ferulic acid and its analogue′s absorption, distribution, metabolism, and excretion (ADME) properties were predicted. All compounds obey Lipinski′s rules. Moreover, all evaluated compounds seem to present a high oral bioavailability and blood–brain barrier (BBB) permeation which is crucial for Alzheimer′s disease drug candidates. Molecular docking of analogues 4 and 8 with acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) showed interactions with the residues of the catalytic triad of AChE and BChE. In addition to their interactions with the anionic subsite, hydroferulic acid phenethyl ester 4 and homovanillic acid phenethyl ester 8 may have potential as inhibitors of AChE and BChE, respectively.

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“…Acridone is a unique alkaloid known to possess several biological activities including anti-cancer [ 40 ], anti-microbial [ 41 ], anti-pruritic [ 42 ] and anti-viral [ 43 ] activities. Moreover, some acridone derivatives have been shown to inhibit AChE activity [ 44 ]. Hence, acridone alkaloids might be a potential compound for AD treatment.…”

Section: Introductionmentioning

confidence: 99%

Multi-Target Actions of Acridones from Atalantia monophylla towards Alzheimer’s Pathogenesis and Their Pharmacokinetic Properties

et al. 2021

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Ten acridones isolated from Atalantia monophylla were evaluated for effects on Alzheimer’s disease pathogenesis including antioxidant effects, acetylcholinesterase (AChE) inhibition, prevention of beta-amyloid (Aβ) aggregation and neuroprotection. To understand the mechanism, the type of AChE inhibition was investigated in vitro and binding interactions between acridones and AChE or Aβ were explored in silico. Drug-likeness and ADMET parameters were predicted in silico using SwissADME and pKCSM programs, respectively. All acridones showed favorable drug-likeness and possessed multifunctional activities targeting AChE function, Aβ aggregation and oxidation. All acridones inhibited AChE in a mixed-type manner and bound AChE at both catalytic anionic and peripheral anionic sites. In silico analysis showed that acridones interfered with Aβ aggregation by interacting at the central hydrophobic core, C-terminal hydrophobic region, and the key residues 41 and 42. Citrusinine II showed potent multifunctional action with the best ADMET profile and could alleviate neuronal cell damage induced by hydrogen peroxide and Aβ1-42 toxicity.

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Potent acetylcholinesterase inhibitors: Synthesis, biological assay and docking study of nitro acridone derivatives

Cited by 26 publications

References 39 publications

Design and Synthesis of New Acridone-Based Nitric Oxide Fluorescent Probe

Design and Synthesis of New Acridone-Based Nitric Oxide Fluorescent Probe

Phenethyl Esters and Amide of Ferulic Acid, Hydroferulic Acid, Homovanillic Acid, and Vanillic Acid: Synthesis, Free Radicals Scavenging Activity, and Molecular Modeling as Potential Cholinesterases Inhibitors

Multi-Target Actions of Acridones from Atalantia monophylla towards Alzheimer’s Pathogenesis and Their Pharmacokinetic Properties

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