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Dopamine-Mediated Vanillin Multicomponent Derivative Synthesis via Grindstone Method: Application of Antioxidant, Anti-Tyrosinase, and Cytotoxic Activities
| Content Provider | Scilit |
|---|---|
| Author | Mani, Arunadevi Ahamed, Anis Ali, Daoud Alarifi, Saud Akbar, Idhayadhulla |
| Copyright Year | 2021 |
| Abstract | Purpose: This study aimed to determine the extent of contribution of dopamine to antioxidant and anti-tyrosinase activities, by dopamine addition to vanillin. This study achieved the synthesis of dopamine-associated vanillin Mannich base derivatives prepared via a one-step reaction involving a green chemistry approach, and investigation of antioxidant and anti-tyrosinase activities. Methods: Novel one-pot synthesis of Mannich base dopamine-connected vanillin ( 1a-l) derivatives can be achieved via green chemistry without using a catalyst. Newly-prepared compounds were characterised with FTIR and NMR $(^{1}$H and$ ^{13}$C) spectra, mass spectra, and elemental analyses. In total, 12 compounds ( 1a-l) were synthesised and their antioxidant and anti-tyrosinase activities evaluated. Antioxidant activities of 2,2-diphenyl-1-picrylhydrazyl (DPPH), nitric oxide (NO), hydrogen peroxide $(H_{2}O_{2}$), and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), and diammonium assays, $ABTS^{•+}$ radical scavenging, and linoleic acid peroxidation were used to screen all synthesised compounds ( 1a-l) for anti-tyrosinase activities and cytotoxicity against MCF-7 and Vero cell lines;. Results: The compound 1k inhibited $(IC_{50}$:11.02μg/mL) the DPPH-scavenging activity to a greater extent than the standard BHT $(IC_{50}$:25.17μg/mL), and showed high activity in $H_{2}O_{2}$ and NO scavenging assays. Compound 1e was more potent (96.21%) against ABTS and compound 1k was more potent (95.28%) against 2,2ʹ-azobis(2-amidinopropane)dihydrochloride antioxidant than the standard trolox. All synthesised compounds were screened for anti-tyrosinase inhibitory activity. Compound 1e had higher activity against tyrosinase $(IC_{50}$=10.63 μg/mL), than kojic acid $(IC_{50}$=21.52μg/mL), and was more cytotoxic $(GI_{50}$ 0.01μM) against MCF-7 cell line than the doxorubicin standard and other tested compounds. Conclusion: In this study, all compounds were found to possess significant antioxidant and anti-tyrosinase activities. Compounds 1e and 1k performed well, compared with other compounds, in all assays. In addition, this study successfully identified several promising molecules that exhibited antioxidant and anti-tyrosinase activities. |
| Related Links | https://www.dovepress.com/getfile.php?fileID=66939 |
| Ending Page | 802 |
| Page Count | 16 |
| Starting Page | 787 |
| e-ISSN | 11778881 |
| DOI | 10.2147/dddt.s288389 |
| Journal | Drug design, development and therapy |
| Volume Number | 15 |
| Language | English |
| Publisher | Informa UK Limited |
| Publisher Date | 2021-02-01 |
| Access Restriction | Open |
| Subject Keyword | Journal: Drug Design, Development and Therapy Integrative and Complementary Medicine Mannich Base Grindstone Chemistry Antioxidant Anti-tyrosinase Activity Cytotoxicity |
| Content Type | Text |
| Resource Type | Article |
