Design and development of some phenyl benzoxazole derivatives as a potent acetylcholinesterase inhibitor with antioxidant property to enhance learning and memory

Srivastava, Pavan; Tripathi, Prem Prakash; Sharma, Piyoosh; Nand, Sachchida; Singh, Surya Pratap; Srivastava, Rakesh K.; Shankar, Sharmila; Shrivastava, Sushant K.

doi:10.1016/j.ejmech.2018.11.049

Cited by 112 publications

(47 citation statements)

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“…However, molecules L46, L66 and L68 demonstrated excellent binding affinity and interaction with the enzyme acetylcholinesterase, higher than that found for the temephos molecule. Validations were used as parameters for molecules that are complexed in the PDB, which do not present such groups and have effectiveness in the inhibition of the enzyme acetylcholinesterase according to Srivastava et al [46], who performed design and development of some phenyl benzoxazole derivatives as potent acetylcholinesterase (AChE) inhibitors by in vivo and ex vivo analyses, and revealed the true nature and competitive type of the AChE inhibition among their analyzed molecules, even though they did not have a phosphorus atom and sulfur neither.…”

Section: Resultsmentioning

confidence: 99%

Hierarchical Virtual Screening of Potential Insectides Inhibitors of Acetylcholinesterase and Juvenile Hormone from Temephos

et al. 2019

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Aedes aegypti (Linnaeus, 1762; Diptera: Culicidae) is the main vector transmitting viral diseases such as dengue fever, dengue haemorrhagic fever, urban yellow fever, zika and chikungunya. Worldwide, especially in the Americas and Brazil, many cases of dengue have been reported in recent years, which have shown significant growth. The main control strategy is the elimination of the vector, carried out through various education programs, to change human habits, but the most usual is biological control, together with environmental management and chemical control. The most commonly insecticide used is temephos (an organophosphorus compound), but Aedes aegypti populations have shown resistance and the product is highly toxic, so we chose it as a template molecule to perform a ligand-based virtual screening in the ChemBrigde (DIVERSet-CL subcollection) database, searching for derivatives with similarity in shape (ROCS) and electrostatic potential (EON). Thus, fourty-five molecules were filtered based on their pharmacokinetic and toxicological properties and 11 molecules were selected by a molecular docking study, including binding affinity and mode of interaction. The L46, L66 and L68 molecules show potential inhibitory activity for both the insect (−9.28, −10.08 and −6.78 Kcal/mol, respectively) and human (−6.05, 6.25 and 7.2 Kcal/mol respectively) enzymes, as well as the juvenile hormone protein (−9.2; −10.96 and −8.16 kcal/mol, respectively), showing a significant difference in comparison to the template molecule temephos. Molecules L46, L66 and L68 interacted with important amino acids at each catalytic site of the enzyme reported in the literature. Thus, the molecules here investigated are potential inhibitors for both the acetylcholinesterase enzymes and juvenile hormone protein–from insect and humans, characterizing them as a potential insecticide against the Aedes aegypti mosquito.

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Section: Resultsmentioning

confidence: 99%

Hierarchical Virtual Screening of Potential Insectides Inhibitors of Acetylcholinesterase and Juvenile Hormone from Temephos

et al. 2019

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“…The acute oral toxicity study was performedas per OECD guidelines 423 on healthy female Wistar rats (37)(38)(39). The results showed no adverse effects up to the dose of 500 mg/kg ofCFA5.…”

Section: Acute Oral Toxicity Studymentioning

confidence: 99%

Design and Development of Multifunctional Hybrids of Ferulic Acid and 1,3,4-Oxadiazoles for the Treatment of Alzheimer’s Disease

Tripathi¹,

Choubey²,

Seth³

et al. 2020

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“…To date, while the complexity of neurodegeneration continues to be explored and recognized, AD has been characterized in part by excessive extracellular beta-amyloid (Aβ) plaque accumulation, the presence of intracellular tau-containing neurofibrillary tangles, and neuroinflammation in the brain (Erika et al, 2018;Rai et al, 2020;Knopman et al, 2021;Singh et al, 2021). In the brains of patients with AD, synaptic loss can precede neurodegeneration, brain tissue gradually shrinks, which, in turn, leads to a decline in memory and learning abilities of patients, eventually causing dementia (Blennow et al, 2006;Srivastava et al, 2019;Tripathi et al, 2019). Synaptic alterations are actually a critical part of neurodegeneration that are strongly correlated with the morphological lesions of AD, neurotoxicities of tau and Aβ, and cognitive impairment, which induce various neurotoxic effects such as increased inflammation, increased oxidative pressure, and subsequently damages the nerve synapses of the brain (Jack et al, 2019;Srivastava et al, 2019;Knopman et al, 2021).…”

Section: Introductionmentioning

confidence: 99%

“…In the brains of patients with AD, synaptic loss can precede neurodegeneration, brain tissue gradually shrinks, which, in turn, leads to a decline in memory and learning abilities of patients, eventually causing dementia ( Blennow et al, 2006 ; Srivastava et al, 2019 ; Tripathi et al, 2019 ). Synaptic alterations are actually a critical part of neurodegeneration that are strongly correlated with the morphological lesions of AD, neurotoxicities of tau and Aβ, and cognitive impairment, which induce various neurotoxic effects such as increased inflammation, increased oxidative pressure, and subsequently damages the nerve synapses of the brain ( Jack et al, 2019 ; Srivastava et al, 2019 ; Knopman et al, 2021 ). These factors gradually alter the microenvironment system of the brain, which becomes unconducive to the survival of nerve cells.…”

Section: Introductionmentioning

confidence: 99%

Effects of α-Lipoic Acid on Phagocytosis of Oligomeric Beta-Amyloid1–42 in BV-2 Mouse Microglial Cells

Chang

et al. 2022

Front. Aging Neurosci.

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Background and objectives: This study aimed to investigate the enhancing effect of vitamin-like alpha-lipoic acid (ALA) on phagocytosis of oligomeric beta-amyloid (oAβ)1–42 in BV-2 mouse microglial cells.Methods: An in vitro model was established to investigate phagocytosis of oAβ1–42 in BV-2 cells. Transmission electron microscopy images indicated that the morphology of prepared oAβ1–42 was spherical particles. BV-2 cells treated with ALA were incubated with 5(6)-carboxyfluorescein-labeled oAβ1–42 (FAM-oAβ1–42) for 24 h, followed by flow cytometer analysis, western blotting, real-time quantitative PCR, and immunocytochemistry (ICC) analysis to assess the in vitro phagocytosis ability of oAβ1–42.Results: Alpha-lipoic acid significantly increased messenger RNA (mRNA) expression of the CD36 receptor in BV-2 cells. ICC analysis showed that ALA significantly elevated CD36 protein expression in BV-2 cells both with and without oAβ1–42 treatment. Results from the flow cytometry analysis indicated that the CD36 receptor inhibitor significantly attenuated ALA-promoted phagocytosis of FAM-oAβ1–42 in BV-2 cells. Moreover, ICC analysis revealed that ALA caused the translocation of peroxisome proliferator-activated receptor-γ (PPAR-γ), which is known to regulate the expression of CD36 mRNA in BV-2 cells. ALA also elevated both the mRNA and protein expression of cyclooxygenase-2 (COX-2), which is a key enzyme involved in the synthesis of 15-deoxy-Δ12,14-prostaglandin J2 in BV-2 cells.Conclusion: We postulated that ALA enhances oAβ1–42 phagocytosis by upregulating the COX-2/15-deoxy-Δ12,14-prostaglandin J2/PPAR-γ/CD36 pathway in BV-2 cells. Finally, future studies should be conducted with an in vivo study to confirm the findings.

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Design and development of some phenyl benzoxazole derivatives as a potent acetylcholinesterase inhibitor with antioxidant property to enhance learning and memory

Cited by 112 publications

References 54 publications

Hierarchical Virtual Screening of Potential Insectides Inhibitors of Acetylcholinesterase and Juvenile Hormone from Temephos

Hierarchical Virtual Screening of Potential Insectides Inhibitors of Acetylcholinesterase and Juvenile Hormone from Temephos

Design and Development of Multifunctional Hybrids of Ferulic Acid and 1,3,4-Oxadiazoles for the Treatment of Alzheimer’s Disease

Effects of α-Lipoic Acid on Phagocytosis of Oligomeric Beta-Amyloid1–42 in BV-2 Mouse Microglial Cells

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