Synthesis, Biological Evaluation and Docking Studies of Chalcone and Flavone Analogs as Antioxidants and Acetylcholinesterase Inhibitors
Several oxidative processes are related to a wide range of human chronic and degenerative diseases, like Alzheimer’s disease, which also has been related to cholinergic processes. Therefore, search for new or improved antioxidant molecules with acetylcholinesterase activity is essential to offer alt...
| Autores principales: | , , , , , , , , , |
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| Formato: | Artículo |
| Lenguaje: | inglés |
| Publicado: |
2019
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| Materias: | |
| Acceso en línea: | http://eprints.uanl.mx/15807/1/9.pdf |
| _version_ | 1824414387069255680 |
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| author | Díaz Rubio, Laura Hernández Martínez, Rufina Estolano Cobián, Arturo Chávez Velasco, Daniel Salazar Aranda, Ricardo Waksman de Torres, Noemí Rivero, Ignacio García González, Víctor Ramos, Marco Córdova Guerrero, Iván |
| author_facet | Díaz Rubio, Laura Hernández Martínez, Rufina Estolano Cobián, Arturo Chávez Velasco, Daniel Salazar Aranda, Ricardo Waksman de Torres, Noemí Rivero, Ignacio García González, Víctor Ramos, Marco Córdova Guerrero, Iván |
| author_sort | Díaz Rubio, Laura |
| collection | Repositorio Institucional |
| description | Several oxidative processes are related to a wide range of human chronic and degenerative diseases, like Alzheimer’s disease, which also has been related to cholinergic processes. Therefore, search for new or improved antioxidant molecules with acetylcholinesterase activity is essential to offer alternative chemotherapeutic agents to support current drug therapies. A series of chalcone (2a–2k) and flavone (3a–3k) analogs were synthesized, characterized, and evaluated as acetylcholinesterase (AChE) inhibitors, and antioxidant agents using 1,1-diphenyl-2-picrylhydrazyl (DPPH•), 2-20-azino-bis-(3-ethylbenzothiazoline-6-sulfonate) (ABTS•), and β-carotene/linoleic acid bleaching assay. Compounds more active were 3j and 2k in DPPH with EC50 of 1 × 10−8 and 5.4 × 10−3 µg/mL, respectively; 2g and 3i in ABTS (1.14 × 10−2 and 1.9 × 10−3 µg/mL); 2e, 2f, 3f, 2j, and 3j exceeded the α-tocopherol control in the β-carotene assay (98–99% of antioxidant activity). At acetylcholinesterase inhibition assay, flavones were more active than chalcones; the best results were compounds 2d and 3d (IC50 21.5 and 26.8 µg/mL, respectively), suggesting that the presence of the nitro group enhances the inhibitory activity. The docking of these two structures were made to understand their interactions with the AChE receptor. Although further in vivo testing must be performed, our results represent an important step towards the identification of improved antioxidants and acetylcholinesterase inhibitors. |
| format | Article |
| id | eprints-15807 |
| institution | UANL |
| language | English |
| publishDate | 2019 |
| record_format | eprints |
| spelling | eprints-158072022-03-12T15:26:53Z http://eprints.uanl.mx/15807/ Synthesis, Biological Evaluation and Docking Studies of Chalcone and Flavone Analogs as Antioxidants and Acetylcholinesterase Inhibitors Díaz Rubio, Laura Hernández Martínez, Rufina Estolano Cobián, Arturo Chávez Velasco, Daniel Salazar Aranda, Ricardo Waksman de Torres, Noemí Rivero, Ignacio García González, Víctor Ramos, Marco Córdova Guerrero, Iván QR Microbiología Several oxidative processes are related to a wide range of human chronic and degenerative diseases, like Alzheimer’s disease, which also has been related to cholinergic processes. Therefore, search for new or improved antioxidant molecules with acetylcholinesterase activity is essential to offer alternative chemotherapeutic agents to support current drug therapies. A series of chalcone (2a–2k) and flavone (3a–3k) analogs were synthesized, characterized, and evaluated as acetylcholinesterase (AChE) inhibitors, and antioxidant agents using 1,1-diphenyl-2-picrylhydrazyl (DPPH•), 2-20-azino-bis-(3-ethylbenzothiazoline-6-sulfonate) (ABTS•), and β-carotene/linoleic acid bleaching assay. Compounds more active were 3j and 2k in DPPH with EC50 of 1 × 10−8 and 5.4 × 10−3 µg/mL, respectively; 2g and 3i in ABTS (1.14 × 10−2 and 1.9 × 10−3 µg/mL); 2e, 2f, 3f, 2j, and 3j exceeded the α-tocopherol control in the β-carotene assay (98–99% of antioxidant activity). At acetylcholinesterase inhibition assay, flavones were more active than chalcones; the best results were compounds 2d and 3d (IC50 21.5 and 26.8 µg/mL, respectively), suggesting that the presence of the nitro group enhances the inhibitory activity. The docking of these two structures were made to understand their interactions with the AChE receptor. Although further in vivo testing must be performed, our results represent an important step towards the identification of improved antioxidants and acetylcholinesterase inhibitors. 2019-07-26 Article PeerReviewed text en cc_by_nc_nd http://eprints.uanl.mx/15807/1/9.pdf http://eprints.uanl.mx/15807/1.haspreviewThumbnailVersion/9.pdf Díaz Rubio, Laura y Hernández Martínez, Rufina y Estolano Cobián, Arturo y Chávez Velasco, Daniel y Salazar Aranda, Ricardo y Waksman de Torres, Noemí y Rivero, Ignacio y García González, Víctor y Ramos, Marco y Córdova Guerrero, Iván (2019) Synthesis, Biological Evaluation and Docking Studies of Chalcone and Flavone Analogs as Antioxidants and Acetylcholinesterase Inhibitors. Applied sciences, 9 (3). pp. 1-20. ISSN 2076-3417 http://doi.org/10.3390/app9030410 doi:10.3390/app9030410 |
| spellingShingle | QR Microbiología Díaz Rubio, Laura Hernández Martínez, Rufina Estolano Cobián, Arturo Chávez Velasco, Daniel Salazar Aranda, Ricardo Waksman de Torres, Noemí Rivero, Ignacio García González, Víctor Ramos, Marco Córdova Guerrero, Iván Synthesis, Biological Evaluation and Docking Studies of Chalcone and Flavone Analogs as Antioxidants and Acetylcholinesterase Inhibitors |
| thumbnail | https://rediab.uanl.mx/themes/sandal5/images/online.png |
| title | Synthesis, Biological Evaluation and Docking Studies of Chalcone and Flavone Analogs as Antioxidants and Acetylcholinesterase Inhibitors |
| title_full | Synthesis, Biological Evaluation and Docking Studies of Chalcone and Flavone Analogs as Antioxidants and Acetylcholinesterase Inhibitors |
| title_fullStr | Synthesis, Biological Evaluation and Docking Studies of Chalcone and Flavone Analogs as Antioxidants and Acetylcholinesterase Inhibitors |
| title_full_unstemmed | Synthesis, Biological Evaluation and Docking Studies of Chalcone and Flavone Analogs as Antioxidants and Acetylcholinesterase Inhibitors |
| title_short | Synthesis, Biological Evaluation and Docking Studies of Chalcone and Flavone Analogs as Antioxidants and Acetylcholinesterase Inhibitors |
| title_sort | synthesis biological evaluation and docking studies of chalcone and flavone analogs as antioxidants and acetylcholinesterase inhibitors |
| topic | QR Microbiología |
| url | http://eprints.uanl.mx/15807/1/9.pdf |
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