Synthesis, In Vitro, and In Silico Analysis of the Antioxidative Activity of Dapsone Imine Derivatives
Dapsone (DDS) is an antibacterial drug with well-known antioxidant properties. However, the antioxidant behavior of its derivatives has not been well explored. In the present work, the antioxidant activity of 10 dapsone derivatives 4-substituted was determined by an evaluation in two in vitro models...
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MDPI AG
2021-09-01
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| author | Ricardo Guzmán-Ávila Mayra Avelar Edgar A. Márquez Julio C. Rivera-Leyva José R. Mora Virginia Flores-Morales Jesús Rivera-Islas |
| author_facet | Ricardo Guzmán-Ávila Mayra Avelar Edgar A. Márquez Julio C. Rivera-Leyva José R. Mora Virginia Flores-Morales Jesús Rivera-Islas |
| author_sort | Ricardo Guzmán-Ávila |
| collection | DOAJ |
| description | Dapsone (DDS) is an antibacterial drug with well-known antioxidant properties. However, the antioxidant behavior of its derivatives has not been well explored. In the present work, the antioxidant activity of 10 dapsone derivatives 4-substituted was determined by an evaluation in two in vitro models (DPPH radical scavenging assay and ferric reducing antioxidant power). These imine derivatives <b>1</b>–<b>10</b> were obtained through condensation between DDS and the corresponding aromatic aldehydes 4-substuited. Three derivatives presented better results than DDS in the determination of DPPH (<b>2</b>, <b>9</b>, and <b>10</b>). Likewise, we have three compounds with better reducing activity than dapsone (<b>4</b>, <b>9</b>, and <b>10</b>). In order to be more insight, the redox process, a conceptual DFT analysis was carried out. Molecular descriptors such as electronic distribution, the total charge accepting/donating capacity (I/A), and the partial charge accepting/donating capacity (ω<sup>+</sup>/ω<sup>−</sup>) were calculated to analyze the relative donor-acceptor capacity through employing a donor acceptor map (DAM). The DFT calculation allowed us to establish a relationship between GAP<sub>HOMO-LUMO</sub> and DAM with the observed antioxidant effects. According to the results, we concluded that compounds <b>2</b> and <b>3</b> have the lowest <i>R<sub>a</sub></i> values, representing a good antioxidant behavior observed experimentally in DPPH radical capturing. On the other hand, derivatives <b>4</b>, <b>9</b>, and <b>10</b> display the best reducing capacity activity with the highest ω<sup>−</sup> and <i>R<sub>d</sub></i> values. Consequently, we propose these compounds as the best antireductants in our DDS imine derivative series. |
| first_indexed | 2024-03-10T06:54:39Z |
| format | Article |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T06:54:39Z |
| publishDate | 2021-09-01 |
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| record_format | Article |
| series | Molecules |
| spelling | doaj.art-0b2b1aae6b524334b5bb2ed2e9f3321f2023-11-22T16:32:03ZengMDPI AGMolecules1420-30492021-09-012619574710.3390/molecules26195747Synthesis, In Vitro, and In Silico Analysis of the Antioxidative Activity of Dapsone Imine DerivativesRicardo Guzmán-Ávila0Mayra Avelar1Edgar A. Márquez2Julio C. Rivera-Leyva3José R. Mora4Virginia Flores-Morales5Jesús Rivera-Islas6Laboratorio 4, Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Cuernavaca 62209, MexicoLaboratorio de Síntesis Asimétrica y Bioenergética (LSAyB), Ingeniería Química (UACQ), Universidad Autónoma de Zacatecas, Campus XXI Km 6 Carr. Zac-Gdl, Zacatecas 98160, MexicoGrupo de Investigación en Química y Biología, Departamento de Química y Biología, Universidad del Norte, Km 5 vía Puerto Colombia 1569, Barranquilla Atlántico 081007, ColombiaLaboratorio 4, Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Cuernavaca 62209, MexicoGrupo de Química Computacional y Teórica (QCT-USFQ), Departamento de Ingeniería Química, Universidad San Francisco de Quito, Diego de Robles y Vía Interoceánica, Quito 170901, EcuadorLaboratorio de Síntesis Asimétrica y Bioenergética (LSAyB), Ingeniería Química (UACQ), Universidad Autónoma de Zacatecas, Campus XXI Km 6 Carr. Zac-Gdl, Zacatecas 98160, MexicoLaboratorio 4, Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Cuernavaca 62209, MexicoDapsone (DDS) is an antibacterial drug with well-known antioxidant properties. However, the antioxidant behavior of its derivatives has not been well explored. In the present work, the antioxidant activity of 10 dapsone derivatives 4-substituted was determined by an evaluation in two in vitro models (DPPH radical scavenging assay and ferric reducing antioxidant power). These imine derivatives <b>1</b>–<b>10</b> were obtained through condensation between DDS and the corresponding aromatic aldehydes 4-substuited. Three derivatives presented better results than DDS in the determination of DPPH (<b>2</b>, <b>9</b>, and <b>10</b>). Likewise, we have three compounds with better reducing activity than dapsone (<b>4</b>, <b>9</b>, and <b>10</b>). In order to be more insight, the redox process, a conceptual DFT analysis was carried out. Molecular descriptors such as electronic distribution, the total charge accepting/donating capacity (I/A), and the partial charge accepting/donating capacity (ω<sup>+</sup>/ω<sup>−</sup>) were calculated to analyze the relative donor-acceptor capacity through employing a donor acceptor map (DAM). The DFT calculation allowed us to establish a relationship between GAP<sub>HOMO-LUMO</sub> and DAM with the observed antioxidant effects. According to the results, we concluded that compounds <b>2</b> and <b>3</b> have the lowest <i>R<sub>a</sub></i> values, representing a good antioxidant behavior observed experimentally in DPPH radical capturing. On the other hand, derivatives <b>4</b>, <b>9</b>, and <b>10</b> display the best reducing capacity activity with the highest ω<sup>−</sup> and <i>R<sub>d</sub></i> values. Consequently, we propose these compounds as the best antireductants in our DDS imine derivative series.https://www.mdpi.com/1420-3049/26/19/5747dapsone iminesdapsone-derivativesantioxidant in vitro |
| spellingShingle | Ricardo Guzmán-Ávila Mayra Avelar Edgar A. Márquez Julio C. Rivera-Leyva José R. Mora Virginia Flores-Morales Jesús Rivera-Islas Synthesis, In Vitro, and In Silico Analysis of the Antioxidative Activity of Dapsone Imine Derivatives Molecules dapsone imines dapsone-derivatives antioxidant in vitro |
| title | Synthesis, In Vitro, and In Silico Analysis of the Antioxidative Activity of Dapsone Imine Derivatives |
| title_full | Synthesis, In Vitro, and In Silico Analysis of the Antioxidative Activity of Dapsone Imine Derivatives |
| title_fullStr | Synthesis, In Vitro, and In Silico Analysis of the Antioxidative Activity of Dapsone Imine Derivatives |
| title_full_unstemmed | Synthesis, In Vitro, and In Silico Analysis of the Antioxidative Activity of Dapsone Imine Derivatives |
| title_short | Synthesis, In Vitro, and In Silico Analysis of the Antioxidative Activity of Dapsone Imine Derivatives |
| title_sort | synthesis in vitro and in silico analysis of the antioxidative activity of dapsone imine derivatives |
| topic | dapsone imines dapsone-derivatives antioxidant in vitro |
| url | https://www.mdpi.com/1420-3049/26/19/5747 |
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