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Synthesis and Evaluation of the Acetylcholinesterase Inhibitory Activities of Some Flavonoids Derived from Naringenin
Alzheimer's disease (AD) is an irreversible neurodegenerative disease that affects many older people adversely. AD has been putting a huge socioeconomic burden on the healthcare systems of many developed countries with aging populations. The need for new therapies that can halt or reverse the p...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Hindawi
2021
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8651387/ https://www.ncbi.nlm.nih.gov/pubmed/34887704 http://dx.doi.org/10.1155/2021/4817900 |
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author | Tran, The-Huan Vo, Thi-Thu-Hien Vo, Thi-Quynh-Nhi Cao, Thi-Cam-Nhung Tran, Thai-Son |
author_facet | Tran, The-Huan Vo, Thi-Thu-Hien Vo, Thi-Quynh-Nhi Cao, Thi-Cam-Nhung Tran, Thai-Son |
author_sort | Tran, The-Huan |
collection | PubMed |
description | Alzheimer's disease (AD) is an irreversible neurodegenerative disease that affects many older people adversely. AD has been putting a huge socioeconomic burden on the healthcare systems of many developed countries with aging populations. The need for new therapies that can halt or reverse the progression of the disease is now extremely great. A research approach in the finding new treatment for AD that has attracted much interest from scientists for a long time is the reestablishment of cholinergic transmission through inhibition of acetylcholinesterase (AChE). Naringenin is a flavonoid with the potential inhibitory activity against AChE. From naringenin, many other flavonoid derivatives, such as flavanones and chalcones, can be synthesized. In this study, by applying the Williamson method, nine flavonoid derivatives were synthesized, including four flavanones and five chalcones. The evaluation of AChE inhibitory activity by the Ellman method showed that there were four substances (2, 4, 5, and 7) with relatively good biological activities (IC(50) < 100 μM), and these biological activities were better than that of naringenin. The molecular docking revealed that strong interactions with amino acid residue Ser200 of the catalytic triad and those of the peripheral region of the enzyme were crucial for strong effects against AChE. Compound 7 had the strongest AChE inhibitory activity (IC(50) 13.0 ± 1.9 μM). This substance could be used for further studies. |
format | Online Article Text |
id | pubmed-8651387 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | Hindawi |
record_format | MEDLINE/PubMed |
spelling | pubmed-86513872021-12-08 Synthesis and Evaluation of the Acetylcholinesterase Inhibitory Activities of Some Flavonoids Derived from Naringenin Tran, The-Huan Vo, Thi-Thu-Hien Vo, Thi-Quynh-Nhi Cao, Thi-Cam-Nhung Tran, Thai-Son ScientificWorldJournal Research Article Alzheimer's disease (AD) is an irreversible neurodegenerative disease that affects many older people adversely. AD has been putting a huge socioeconomic burden on the healthcare systems of many developed countries with aging populations. The need for new therapies that can halt or reverse the progression of the disease is now extremely great. A research approach in the finding new treatment for AD that has attracted much interest from scientists for a long time is the reestablishment of cholinergic transmission through inhibition of acetylcholinesterase (AChE). Naringenin is a flavonoid with the potential inhibitory activity against AChE. From naringenin, many other flavonoid derivatives, such as flavanones and chalcones, can be synthesized. In this study, by applying the Williamson method, nine flavonoid derivatives were synthesized, including four flavanones and five chalcones. The evaluation of AChE inhibitory activity by the Ellman method showed that there were four substances (2, 4, 5, and 7) with relatively good biological activities (IC(50) < 100 μM), and these biological activities were better than that of naringenin. The molecular docking revealed that strong interactions with amino acid residue Ser200 of the catalytic triad and those of the peripheral region of the enzyme were crucial for strong effects against AChE. Compound 7 had the strongest AChE inhibitory activity (IC(50) 13.0 ± 1.9 μM). This substance could be used for further studies. Hindawi 2021-11-30 /pmc/articles/PMC8651387/ /pubmed/34887704 http://dx.doi.org/10.1155/2021/4817900 Text en Copyright © 2021 The-Huan Tran et al. https://creativecommons.org/licenses/by/4.0/This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Research Article Tran, The-Huan Vo, Thi-Thu-Hien Vo, Thi-Quynh-Nhi Cao, Thi-Cam-Nhung Tran, Thai-Son Synthesis and Evaluation of the Acetylcholinesterase Inhibitory Activities of Some Flavonoids Derived from Naringenin |
title | Synthesis and Evaluation of the Acetylcholinesterase Inhibitory Activities of Some Flavonoids Derived from Naringenin |
title_full | Synthesis and Evaluation of the Acetylcholinesterase Inhibitory Activities of Some Flavonoids Derived from Naringenin |
title_fullStr | Synthesis and Evaluation of the Acetylcholinesterase Inhibitory Activities of Some Flavonoids Derived from Naringenin |
title_full_unstemmed | Synthesis and Evaluation of the Acetylcholinesterase Inhibitory Activities of Some Flavonoids Derived from Naringenin |
title_short | Synthesis and Evaluation of the Acetylcholinesterase Inhibitory Activities of Some Flavonoids Derived from Naringenin |
title_sort | synthesis and evaluation of the acetylcholinesterase inhibitory activities of some flavonoids derived from naringenin |
topic | Research Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8651387/ https://www.ncbi.nlm.nih.gov/pubmed/34887704 http://dx.doi.org/10.1155/2021/4817900 |
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