Effect of <i>N</i>-Amide Substitution on Antioxidative Activities of Melatonin Derivatives
Five <i>N</i>-amide substituted melatonin (MLT) derivatives were synthesized and evaluated for antioxidative activities, and compounds <b>9</b>−<b>12</b> showed higher electron spin resonance (ESR) response than MLT. 4-Bromobenzoyl and naphthoyl derivati...
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| Format: | Article |
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MDPI AG
2020-01-01
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| Series: | Scientia Pharmaceutica |
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| Online Access: | https://www.mdpi.com/2218-0532/88/1/3 |
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| author | Panyada Panyatip Nutjaree Pratheepawanit Johns Aroonsri Priprem Kouichi Nakagawa Ploenthip Puthongking |
| author_facet | Panyada Panyatip Nutjaree Pratheepawanit Johns Aroonsri Priprem Kouichi Nakagawa Ploenthip Puthongking |
| author_sort | Panyada Panyatip |
| collection | DOAJ |
| description | Five <i>N</i>-amide substituted melatonin (MLT) derivatives were synthesized and evaluated for antioxidative activities, and compounds <b>9</b>−<b>12</b> showed higher electron spin resonance (ESR) response than MLT. 4-Bromobenzoyl and naphthoyl derivatives (<b>10</b> and <b>11</b>) presented stronger hydroxyl radical inhibitory effect than MLT in Fenton reaction. The substitution at the <i>N1</i>-position on the MLT core structure with acetyl (<b>8</b>), benzoyl (<b>9</b>), 4-bromobenzoyl (<b>10</b>), and naphthoyl (<b>11</b>) and <i>N2</i>-substitution with 4-bromobenzoyl (<b>12</b>) decreased the reducing power of the derivatives in ferric reducing antioxidant power (FRAP) assay. Compounds <b>8</b>−<b>11</b> also presented lower antioxidant capacity than their parent compound in 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) disodium salt (ABTS) assay; whereas, compound <b>12</b> presented radical scavenging activity similarly to MLT. All aryl derivatives (<b>9</b>−<b>12</b>) showed higher ability to quench peroxyl radicals than MLT about three times, especially the benzoylated derivatives (<b>9</b> and <b>10</b>) that presented the highest ability in oxygen radical absorbance capacity (ORAC) assay. |
| first_indexed | 2024-04-11T11:54:53Z |
| format | Article |
| id | doaj.art-0fe537b6e7c942ba8d355ee0385167e9 |
| institution | Directory Open Access Journal |
| issn | 2218-0532 |
| language | English |
| last_indexed | 2024-04-11T11:54:53Z |
| publishDate | 2020-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Scientia Pharmaceutica |
| spelling | doaj.art-0fe537b6e7c942ba8d355ee0385167e92022-12-22T04:25:12ZengMDPI AGScientia Pharmaceutica2218-05322020-01-01881310.3390/scipharm88010003scipharm88010003Effect of <i>N</i>-Amide Substitution on Antioxidative Activities of Melatonin DerivativesPanyada Panyatip0Nutjaree Pratheepawanit Johns1Aroonsri Priprem2Kouichi Nakagawa3Ploenthip Puthongking4Graduate School, Khon Kaen University, Khon Kaen 40002, ThailandMelatonin Research Group, Faculty of Pharmaceutical Sciences, Khon Kaen University, Khon Kaen 40002, ThailandMelatonin Research Group, Faculty of Pharmaceutical Sciences, Khon Kaen University, Khon Kaen 40002, ThailandDivision of Regional Innovation, Graduate School of Health Sciences, Hirosaki University, 66-1 Hon-cho, Hirosaki, Aomori 036-8564, JapanMelatonin Research Group, Faculty of Pharmaceutical Sciences, Khon Kaen University, Khon Kaen 40002, ThailandFive <i>N</i>-amide substituted melatonin (MLT) derivatives were synthesized and evaluated for antioxidative activities, and compounds <b>9</b>−<b>12</b> showed higher electron spin resonance (ESR) response than MLT. 4-Bromobenzoyl and naphthoyl derivatives (<b>10</b> and <b>11</b>) presented stronger hydroxyl radical inhibitory effect than MLT in Fenton reaction. The substitution at the <i>N1</i>-position on the MLT core structure with acetyl (<b>8</b>), benzoyl (<b>9</b>), 4-bromobenzoyl (<b>10</b>), and naphthoyl (<b>11</b>) and <i>N2</i>-substitution with 4-bromobenzoyl (<b>12</b>) decreased the reducing power of the derivatives in ferric reducing antioxidant power (FRAP) assay. Compounds <b>8</b>−<b>11</b> also presented lower antioxidant capacity than their parent compound in 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) disodium salt (ABTS) assay; whereas, compound <b>12</b> presented radical scavenging activity similarly to MLT. All aryl derivatives (<b>9</b>−<b>12</b>) showed higher ability to quench peroxyl radicals than MLT about three times, especially the benzoylated derivatives (<b>9</b> and <b>10</b>) that presented the highest ability in oxygen radical absorbance capacity (ORAC) assay.https://www.mdpi.com/2218-0532/88/1/3melatonin<i>n</i>-amide derivativeradical scavengingelectron spin resonance |
| spellingShingle | Panyada Panyatip Nutjaree Pratheepawanit Johns Aroonsri Priprem Kouichi Nakagawa Ploenthip Puthongking Effect of <i>N</i>-Amide Substitution on Antioxidative Activities of Melatonin Derivatives Scientia Pharmaceutica melatonin <i>n</i>-amide derivative radical scavenging electron spin resonance |
| title | Effect of <i>N</i>-Amide Substitution on Antioxidative Activities of Melatonin Derivatives |
| title_full | Effect of <i>N</i>-Amide Substitution on Antioxidative Activities of Melatonin Derivatives |
| title_fullStr | Effect of <i>N</i>-Amide Substitution on Antioxidative Activities of Melatonin Derivatives |
| title_full_unstemmed | Effect of <i>N</i>-Amide Substitution on Antioxidative Activities of Melatonin Derivatives |
| title_short | Effect of <i>N</i>-Amide Substitution on Antioxidative Activities of Melatonin Derivatives |
| title_sort | effect of i n i amide substitution on antioxidative activities of melatonin derivatives |
| topic | melatonin <i>n</i>-amide derivative radical scavenging electron spin resonance |
| url | https://www.mdpi.com/2218-0532/88/1/3 |
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