Dopamine-Mediated Vanillin Multicomponent Derivative Synthesis via Grindstone Method: Application of Antioxidant, Anti-Tyrosinase, and Cytotoxic Activities
Arunadevi Mani,1 Anis Ahamed,2 Daoud Ali,3 Saud Alarifi,3 Idhayadhulla Akbar1 1Research Department of Chemistry, Nehru Memorial College (Affiliated to Bharathidasan University), Puthanampatti -621007, Tiruchirappalli District, Tamil Nadu, India; 2Department of Botany & Microbiology, College...
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| Format: | Article |
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Dove Medical Press
2021-02-01
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| Series: | Drug Design, Development and Therapy |
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| Online Access: | https://www.dovepress.com/dopamine-mediated-vanillin-multicomponent-derivative-synthesis-via-gri-peer-reviewed-article-DDDT |
| _version_ | 1819171618632499200 |
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| author | Mani A Ahamed A Ali D Alarifi S Akbar I |
| author_facet | Mani A Ahamed A Ali D Alarifi S Akbar I |
| author_sort | Mani A |
| collection | DOAJ |
| description | Arunadevi Mani,1 Anis Ahamed,2 Daoud Ali,3 Saud Alarifi,3 Idhayadhulla Akbar1 1Research Department of Chemistry, Nehru Memorial College (Affiliated to Bharathidasan University), Puthanampatti -621007, Tiruchirappalli District, Tamil Nadu, India; 2Department of Botany & Microbiology, College of Sciences, King Saud University (KSU), Riyadh, Saudi Arabia; 3Department of Zoology, College of Sciences, King Saud University (KSU), Riyadh, 11451, Saudi ArabiaCorrespondence: Idhayadhulla Akbar Tel +91-9994265115Email a.idhayadhulla@gmail.comPurpose: 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 (1H and 13C) 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 (H2O2), 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 (IC50:11.02μg/mL) the DPPH-scavenging activity to a greater extent than the standard BHT (IC50:25.17μg/mL), and showed high activity in H2O2 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 (IC50=10.63 μg/mL), than kojic acid (IC50=21.52μg/mL), and was more cytotoxic (GI50 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.Keywords: Mannich base, grindstone chemistry, antioxidant, anti-tyrosinase activity, cytotoxicity |
| first_indexed | 2024-12-22T19:54:09Z |
| format | Article |
| id | doaj.art-556b9249a9b34ac7b1be43979eeac6a0 |
| institution | Directory Open Access Journal |
| issn | 1177-8881 |
| language | English |
| last_indexed | 2024-12-22T19:54:09Z |
| publishDate | 2021-02-01 |
| publisher | Dove Medical Press |
| record_format | Article |
| series | Drug Design, Development and Therapy |
| spelling | doaj.art-556b9249a9b34ac7b1be43979eeac6a02022-12-21T18:14:27ZengDove Medical PressDrug Design, Development and Therapy1177-88812021-02-01Volume 1578780262385Dopamine-Mediated Vanillin Multicomponent Derivative Synthesis via Grindstone Method: Application of Antioxidant, Anti-Tyrosinase, and Cytotoxic ActivitiesMani AAhamed AAli DAlarifi SAkbar IArunadevi Mani,1 Anis Ahamed,2 Daoud Ali,3 Saud Alarifi,3 Idhayadhulla Akbar1 1Research Department of Chemistry, Nehru Memorial College (Affiliated to Bharathidasan University), Puthanampatti -621007, Tiruchirappalli District, Tamil Nadu, India; 2Department of Botany & Microbiology, College of Sciences, King Saud University (KSU), Riyadh, Saudi Arabia; 3Department of Zoology, College of Sciences, King Saud University (KSU), Riyadh, 11451, Saudi ArabiaCorrespondence: Idhayadhulla Akbar Tel +91-9994265115Email a.idhayadhulla@gmail.comPurpose: 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 (1H and 13C) 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 (H2O2), 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 (IC50:11.02μg/mL) the DPPH-scavenging activity to a greater extent than the standard BHT (IC50:25.17μg/mL), and showed high activity in H2O2 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 (IC50=10.63 μg/mL), than kojic acid (IC50=21.52μg/mL), and was more cytotoxic (GI50 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.Keywords: Mannich base, grindstone chemistry, antioxidant, anti-tyrosinase activity, cytotoxicityhttps://www.dovepress.com/dopamine-mediated-vanillin-multicomponent-derivative-synthesis-via-gri-peer-reviewed-article-DDDTmannich basegrindstone chemistryantioxidantanti-tyrosinase activitycytotoxicity |
| spellingShingle | Mani A Ahamed A Ali D Alarifi S Akbar I Dopamine-Mediated Vanillin Multicomponent Derivative Synthesis via Grindstone Method: Application of Antioxidant, Anti-Tyrosinase, and Cytotoxic Activities Drug Design, Development and Therapy mannich base grindstone chemistry antioxidant anti-tyrosinase activity cytotoxicity |
| title | Dopamine-Mediated Vanillin Multicomponent Derivative Synthesis via Grindstone Method: Application of Antioxidant, Anti-Tyrosinase, and Cytotoxic Activities |
| title_full | Dopamine-Mediated Vanillin Multicomponent Derivative Synthesis via Grindstone Method: Application of Antioxidant, Anti-Tyrosinase, and Cytotoxic Activities |
| title_fullStr | Dopamine-Mediated Vanillin Multicomponent Derivative Synthesis via Grindstone Method: Application of Antioxidant, Anti-Tyrosinase, and Cytotoxic Activities |
| title_full_unstemmed | Dopamine-Mediated Vanillin Multicomponent Derivative Synthesis via Grindstone Method: Application of Antioxidant, Anti-Tyrosinase, and Cytotoxic Activities |
| title_short | Dopamine-Mediated Vanillin Multicomponent Derivative Synthesis via Grindstone Method: Application of Antioxidant, Anti-Tyrosinase, and Cytotoxic Activities |
| title_sort | dopamine mediated vanillin multicomponent derivative synthesis via grindstone method application of antioxidant anti tyrosinase and cytotoxic activities |
| topic | mannich base grindstone chemistry antioxidant anti-tyrosinase activity cytotoxicity |
| url | https://www.dovepress.com/dopamine-mediated-vanillin-multicomponent-derivative-synthesis-via-gri-peer-reviewed-article-DDDT |
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