Naphthyl-functionalized acetamide derivatives: Promising agents for cholinesterase inhibition and antioxidant therapy in Alzheimer's disease

This study presents the synthesis and characterization of a series of 13 novel acetamides. These were subjected to Ellman's assay to determine the efficacy of the AChE and BChE inhibitors. Finally, we report their antioxidant activity as an alternative approach for the search for drugs to treat...

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Autores:: Camargo-Ayala, Lorena
Prent-Peñaloza, Luis
Osorio, Edison
Camargo-Ayala, Paola Andrea
Jimenez, Claudio A
Zúñiga-Arbalti, Felipe
Brito, Iván
Delgado, Gerzon E
Gutiérrez John Alexander
Polo-Cuadrado, Efraín

Tipo de recurso:: Article of investigation

Fecha de publicación:: 2024

Institución:: Universidad de Ibagué

Repositorio:: Repositorio Universidad de Ibagué

Idioma:: eng

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network_acronym_str	UNIBAGUE2
network_name_str	Repositorio Universidad de Ibagué
repository_id_str
dc.title.eng.fl_str_mv	Naphthyl-functionalized acetamide derivatives: Promising agents for cholinesterase inhibition and antioxidant therapy in Alzheimer's disease
title	Naphthyl-functionalized acetamide derivatives: Promising agents for cholinesterase inhibition and antioxidant therapy in Alzheimer's disease
spellingShingle	Naphthyl-functionalized acetamide derivatives: Promising agents for cholinesterase inhibition and antioxidant therapy in Alzheimer's disease Alzheimer Acetamida - Funcionalidades Alzheimer - Terapia antioxidante Acetamide compound Alzheimer's disease Antioxidant activity Cholinesterase inhibitor Crystallography
title_short	Naphthyl-functionalized acetamide derivatives: Promising agents for cholinesterase inhibition and antioxidant therapy in Alzheimer's disease
title_full	Naphthyl-functionalized acetamide derivatives: Promising agents for cholinesterase inhibition and antioxidant therapy in Alzheimer's disease
title_fullStr	Naphthyl-functionalized acetamide derivatives: Promising agents for cholinesterase inhibition and antioxidant therapy in Alzheimer's disease
title_full_unstemmed	Naphthyl-functionalized acetamide derivatives: Promising agents for cholinesterase inhibition and antioxidant therapy in Alzheimer's disease
title_sort	Naphthyl-functionalized acetamide derivatives: Promising agents for cholinesterase inhibition and antioxidant therapy in Alzheimer's disease
dc.creator.fl_str_mv	Camargo-Ayala, Lorena Prent-Peñaloza, Luis Osorio, Edison Camargo-Ayala, Paola Andrea Jimenez, Claudio A Zúñiga-Arbalti, Felipe Brito, Iván Delgado, Gerzon E Gutiérrez John Alexander Polo-Cuadrado, Efraín
dc.contributor.author.none.fl_str_mv	Camargo-Ayala, Lorena Prent-Peñaloza, Luis Osorio, Edison Camargo-Ayala, Paola Andrea Jimenez, Claudio A Zúñiga-Arbalti, Felipe Brito, Iván Delgado, Gerzon E Gutiérrez John Alexander Polo-Cuadrado, Efraín
dc.subject.armarc.none.fl_str_mv	Alzheimer Acetamida - Funcionalidades Alzheimer - Terapia antioxidante
topic	Alzheimer Acetamida - Funcionalidades Alzheimer - Terapia antioxidante Acetamide compound Alzheimer's disease Antioxidant activity Cholinesterase inhibitor Crystallography
dc.subject.proposal.eng.fl_str_mv	Acetamide compound Alzheimer's disease Antioxidant activity Cholinesterase inhibitor Crystallography
description	This study presents the synthesis and characterization of a series of 13 novel acetamides. These were subjected to Ellman's assay to determine the efficacy of the AChE and BChE inhibitors. Finally, we report their antioxidant activity as an alternative approach for the search for drugs to treat AD. These studies revealed that compounds 1a–1k and 2l–2m were obtained in moderate yield. Four amides (1h, 1j, 1k, and 2l) were selective for one of the enzymes (BChE); thus, those that inhibited BChE were more active than the positive control (galantamine) and showed better IC50 values (3.30–5.03 µM). The theoretical free binding energies calculated by MM-GBSA indicated that all inhibitors were more stable than rivastigmine, and the inhibition mechanisms involved the entire active site: peripheral anionic site, oxyanion hole, acyl-binding pockets, and catalytic site. We examined the cytotoxicity of compounds 1h, 1j, 1k, and 2l in human dermal cells and found that they did not exhibit any toxic effects under the tested conditions. Additionally, these compounds, which also inhibited BChE, displayed mixed inhibition and did not exhibit hemolytic effects on human erythrocytes. Furthermore, the ABTS and DPPH assays indicated that, although none of the compounds showed activity in the DPPH assay, the EC50 values for radical trapping by the ABTS method showed that compounds 1a, 1d, 1e, and 1g had EC50 values lower than 10 µg/mL, indicating their strong radical scavenging capacity. We also report the crystal structures of compounds 1c, 1d, 1f, and 1g, which are found in monoclinic crystal systems.
publishDate	2024
dc.date.issued.none.fl_str_mv	2024-12
dc.date.accessioned.none.fl_str_mv	2025-08-25T15:21:08Z
dc.date.available.none.fl_str_mv	2025-08-25T15:21:08Z
dc.type.none.fl_str_mv	Artículo de revista
dc.type.coar.none.fl_str_mv	http://purl.org/coar/resource_type/c_2df8fbb1
dc.type.coarversion.none.fl_str_mv	http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.content.none.fl_str_mv	Text
dc.type.driver.none.fl_str_mv	info:eu-repo/semantics/article
dc.type.version.none.fl_str_mv	info:eu-repo/semantics/publishedVersion
format	http://purl.org/coar/resource_type/c_2df8fbb1
status_str	publishedVersion
dc.identifier.citation.none.fl_str_mv	Camargo-Ayala, L., Prent-Peñaloza, L., Osorio, E., Camargo-Ayala, P., Jimenez, C., Zúñiga-Arbalti, F., Brito, I., Delgado, G., Gutiérrez, M. y Polo-Cuadrado, E. 2024. Naphthyl-functionalized acetamide derivatives: Promising agents for cholinesterase inhibition and antioxidant therapy in Alzheimer's disease. Bioorganic Chemistry, 153. DOI: 10.1016/j.bioorg.2024.107896
dc.identifier.doi.none.fl_str_mv	10.1016/j.bioorg.2024.107896
dc.identifier.eissn.none.fl_str_mv	10902120
dc.identifier.issn.none.fl_str_mv	00452068
dc.identifier.uri.none.fl_str_mv	https://hdl.handle.net/20.500.12313/5534
dc.identifier.url.none.fl_str_mv	https://www.sciencedirect.com/science/article/pii/S0045206824008010
identifier_str_mv	Camargo-Ayala, L., Prent-Peñaloza, L., Osorio, E., Camargo-Ayala, P., Jimenez, C., Zúñiga-Arbalti, F., Brito, I., Delgado, G., Gutiérrez, M. y Polo-Cuadrado, E. 2024. Naphthyl-functionalized acetamide derivatives: Promising agents for cholinesterase inhibition and antioxidant therapy in Alzheimer's disease. Bioorganic Chemistry, 153. DOI: 10.1016/j.bioorg.2024.107896 10.1016/j.bioorg.2024.107896 10902120 00452068
url	https://hdl.handle.net/20.500.12313/5534 https://www.sciencedirect.com/science/article/pii/S0045206824008010
dc.language.iso.none.fl_str_mv	eng
language	eng
dc.relation.citationstartpage.none.fl_str_mv	107896
dc.relation.citationvolume.none.fl_str_mv	153
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spelling	Camargo-Ayala, Lorena41c900ab-b356-4c05-8594-1f10c2d6c414-1Prent-Peñaloza, Luis75975bd9-cd4e-48b6-99cd-2cbb8f0b1dd9-1Osorio, Edisone6d834e4-46ca-40f0-ab7c-630a35856901-1Camargo-Ayala, Paola Andrea51909bee-c3db-4c2a-a2ed-101ca337237d-1Jimenez, Claudio A09e847f0-2d9b-49c4-86a3-9818ebcf7036-1Zúñiga-Arbalti, Felipe47f6f586-9b1b-40d8-915e-e87152af414a-1Brito, Iván26ac473f-3c45-4d5a-9701-4e0cf4753fa9-1Delgado, Gerzon Ec9c0c137-e521-463a-aa0b-0f98d8785b6e-1Gutiérrez John Alexander59b23fb9-8bb6-40b6-b03c-65bfbe88f0fc600Polo-Cuadrado, Efraínf8016ac0-3f43-4599-89b2-3d8e129cb357-12025-08-25T15:21:08Z2025-08-25T15:21:08Z2024-12This study presents the synthesis and characterization of a series of 13 novel acetamides. These were subjected to Ellman's assay to determine the efficacy of the AChE and BChE inhibitors. Finally, we report their antioxidant activity as an alternative approach for the search for drugs to treat AD. These studies revealed that compounds 1a–1k and 2l–2m were obtained in moderate yield. Four amides (1h, 1j, 1k, and 2l) were selective for one of the enzymes (BChE); thus, those that inhibited BChE were more active than the positive control (galantamine) and showed better IC50 values (3.30–5.03 µM). The theoretical free binding energies calculated by MM-GBSA indicated that all inhibitors were more stable than rivastigmine, and the inhibition mechanisms involved the entire active site: peripheral anionic site, oxyanion hole, acyl-binding pockets, and catalytic site. We examined the cytotoxicity of compounds 1h, 1j, 1k, and 2l in human dermal cells and found that they did not exhibit any toxic effects under the tested conditions. Additionally, these compounds, which also inhibited BChE, displayed mixed inhibition and did not exhibit hemolytic effects on human erythrocytes. Furthermore, the ABTS and DPPH assays indicated that, although none of the compounds showed activity in the DPPH assay, the EC50 values for radical trapping by the ABTS method showed that compounds 1a, 1d, 1e, and 1g had EC50 values lower than 10 µg/mL, indicating their strong radical scavenging capacity. We also report the crystal structures of compounds 1c, 1d, 1f, and 1g, which are found in monoclinic crystal systems.application/pdfCamargo-Ayala, L., Prent-Peñaloza, L., Osorio, E., Camargo-Ayala, P., Jimenez, C., Zúñiga-Arbalti, F., Brito, I., Delgado, G., Gutiérrez, M. y Polo-Cuadrado, E. 2024. Naphthyl-functionalized acetamide derivatives: Promising agents for cholinesterase inhibition and antioxidant therapy in Alzheimer's disease. Bioorganic Chemistry, 153. 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Chem. 23 (2010) 866–877, https://doi.org/ 10.1002/poc.1© 2024 Elsevier Inc.info:eu-repo/semantics/closedAccesshttp://purl.org/coar/access_right/c_14cbAtribución-NoComercial 4.0 Internacional (CC BY-NC 4.0)https://creativecommons.org/licenses/by-nc/4.0/https://www.sciencedirect.com/science/article/pii/S0045206824008010AlzheimerAcetamida - FuncionalidadesAlzheimer - Terapia antioxidanteAcetamide compoundAlzheimer's diseaseAntioxidant activityCholinesterase inhibitorCrystallographyNaphthyl-functionalized acetamide derivatives: Promising agents for cholinesterase inhibition and antioxidant therapy in Alzheimer's diseaseArtículo de revistahttp://purl.org/coar/resource_type/c_2df8fbb1http://purl.org/coar/version/c_970fb48d4fbd8a85Textinfo:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionPublicationLICENSElicense.txtlicense.txttext/plain; charset=utf-8134https://repositorio.unibague.edu.co/bitstreams/c9acfb21-b584-4284-a9a4-81d7e8d3febb/download2fa3e590786b9c0f3ceba1b9656b7ac3MD51TEXTArtículo.pdf.txtArtículo.pdf.txtExtracted texttext/plain2979https://repositorio.unibague.edu.co/bitstreams/62b4b530-b3c5-4a21-b762-8f4489698d7f/downloadfeb111c0f79240f08f0e30afabdbde11MD53THUMBNAILArtículo.pdf.jpgArtículo.pdf.jpgIM Thumbnailimage/jpeg20818https://repositorio.unibague.edu.co/bitstreams/8fffc176-d624-4aa1-99a6-50bf443894ab/download429dcd7769164737dc9d82310b3c50d1MD54ORIGINALArtículo.pdfArtículo.pdfapplication/pdf162366https://repositorio.unibague.edu.co/bitstreams/ad7438cf-f4e3-45d2-9d3a-34f444884991/download5c5b19a978f46a84ec22d0bbe93194b5MD5220.500.12313/5534oai:repositorio.unibague.edu.co:20.500.12313/55342025-09-12 11:40:29.376https://creativecommons.org/licenses/by-nc/4.0/© 2024 Elsevier Inc.https://repositorio.unibague.edu.coRepositorio Institucional Universidad de Ibaguébdigital@metabiblioteca.comQ3JlYXRpdmUgQ29tbW9ucyBBdHRyaWJ1dGlvbi1Ob25Db21tZXJjaWFsLU5vRGVyaXZhdGl2ZXMgNC4wIEludGVybmF0aW9uYWwgTGljZW5zZQ0KaHR0cHM6Ly9jcmVhdGl2ZWNvbW1vbnMub3JnL2xpY2Vuc2VzL2J5LW5jLW5kLzQuMC8=

Naphthyl-functionalized acetamide derivatives: Promising agents for cholinesterase inhibition and antioxidant therapy in Alzheimer's disease

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