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Vol.4 , No. 5, Publication Date: Aug. 30, 2017, Page: 53-60
, with different chemical group characteristics, such as aliphatic (acetohydroxamic acid and butyryl hydroxamic acid), aromatic (benzohydroxamic acid and phenylalanine hydroxamic acid) and amino acid (glycine hydroxamic acid and alanine hydroxamic acid). It was observed that these HAD compounds present very promising activity as acetylcholinesterase (AChE) inhibitors and as antioxidants. The aliphatic HAD demonstrated to have a higher inhibitory activity of AChE than amino acid or aromatic HAD. As for the antioxidant activity, a high antioxidant potential was found for all the compounds with EC<sub>50</sub> values ranging from 0.19 µM to 1.65 µM. Aiming these applications, a biocatalysis approach was used to obtain these HADs with optimal reactional conditions. In this study, reverse micelles with immobilized <i>Pseudomonas aeruginosa</i> intact cells containing amidase were used as a biocatalyst to catalyze the acyltransferase reaction of the corresponding substrate amide and hydroxylamine to obtain various HAD and this was achieved for the first time with yields of approximately 100 %.&picture=http://www.aascit.org/aascit/decorators/img/journal/919.jpg)
| [1] | Marisa Bernardo, Área Departamental de Engenharia Química, Instituto Superior de Engenharia de Lisboa, R. Conselheiro Emídio Navarro, Lisboa, Portugal; Centro de Química e Bioquímica da Faculdade de Ciências da Universidade de Lisboa, Campo Grande, Lisboa, Portugal. |
| [2] | Telma Reis, Área Departamental de Engenharia Química, Instituto Superior de Engenharia de Lisboa, R. Conselheiro Emídio Navarro, Lisboa, Portugal; Centro de Química e Bioquímica da Faculdade de Ciências da Universidade de Lisboa, Campo Grande, Lisboa, Portugal. |
| [3] | Miguel Minhalma, Centro de Física e Engenharia de Materiais Avançados, Instituto Superior Técnico, Universidade de Lisboa, Lisboa, Portugal. |
| [4] | Amin Karmali, Área Departamental de Engenharia Química, Instituto Superior de Engenharia de Lisboa, R. Conselheiro Emídio Navarro, Lisboa, Portugal; Chemical Engineering and Biotechnology Research Center of ISEL and CITAB-UTAD, R. Conselheiro Emídio Navarro, Lisboa, Portugal. |
| [5] | Maria Luísa Serralheiro, Centro de Química e Bioquímica da Faculdade de Ciências da Universidade de Lisboa, Campo Grande, Lisboa, Portugal. |
| [6] | Rita Pacheco, Área Departamental de Engenharia Química, Instituto Superior de Engenharia de Lisboa, R. Conselheiro Emídio Navarro, Lisboa, Portugal; Centro de Química e Bioquímica da Faculdade de Ciências da Universidade de Lisboa, Campo Grande, Lisboa, Portugal. |
In this study were investigated, the synthesis, acetylcholinesterase inhibition and antioxidant activity of a series of hydroxamic acid derivatives (HAD), with different chemical group characteristics, such as aliphatic (acetohydroxamic acid and butyryl hydroxamic acid), aromatic (benzohydroxamic acid and phenylalanine hydroxamic acid) and amino acid (glycine hydroxamic acid and alanine hydroxamic acid). It was observed that these HAD compounds present very promising activity as acetylcholinesterase (AChE) inhibitors and as antioxidants. The aliphatic HAD demonstrated to have a higher inhibitory activity of AChE than amino acid or aromatic HAD. As for the antioxidant activity, a high antioxidant potential was found for all the compounds with EC50 values ranging from 0.19 µM to 1.65 µM. Aiming these applications, a biocatalysis approach was used to obtain these HADs with optimal reactional conditions. In this study, reverse micelles with immobilized Pseudomonas aeruginosa intact cells containing amidase were used as a biocatalyst to catalyze the acyltransferase reaction of the corresponding substrate amide and hydroxylamine to obtain various HAD and this was achieved for the first time with yields of approximately 100 %.
Keywords
Hydroxamic Acid Derivatives (HAD), Acetylcholinesterase Inhibitors, Antioxidant Potential, Pseudomonas aeruginosa, Biocatalysis
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