Novel coumarin derivatives as potential tyrosinase inhibitors: Synthesis, binding analysis and biological evaluation
A novel series of thirty coumarin derivatives (4a ∼ r, 5a ∼ l) constituted by coumarin and cinnamic acid/benzoic acid through oxime linkage were synthesized and evaluated for their potential anti-tyrosinase activity. Among them, compound 5l exhibited outstanding anti-tyrosinase activity with IC50 of...
| Main Authors: | , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2023-06-01
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| Series: | Arabian Journal of Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535223001867 |
| _version_ | 1797846355246317568 |
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| author | Li Lu Xin Zhang Yu Kang Zhuang Xiong Kun Zhang Xuetao Xu Liping Bai Hongguang Li |
| author_facet | Li Lu Xin Zhang Yu Kang Zhuang Xiong Kun Zhang Xuetao Xu Liping Bai Hongguang Li |
| author_sort | Li Lu |
| collection | DOAJ |
| description | A novel series of thirty coumarin derivatives (4a ∼ r, 5a ∼ l) constituted by coumarin and cinnamic acid/benzoic acid through oxime linkage were synthesized and evaluated for their potential anti-tyrosinase activity. Among them, compound 5l exhibited outstanding anti-tyrosinase activity with IC50 of 3.04 ± 0.01 μM compared to 14.13 ± 0.80 μM of kojic acid. Kinetic study revealed compound 5l to be a reversible and uncompetitive tyrosinase inhibitor. 3D fluorescence and CD spectra results showed treatment of compound 5l lead to the conformational changes of tyrosinase. Molecular docking revealed the binding between compound 5l and tyrosinase. Furthermore, compound 5l inhibited melanin content and cellular tyrosinase activity both in B16F10 cells and zebrafish model with no toxicity effect. Taken together, our findings suggested that compound 5l could be used as potential candidate to relieve tyrosinase-related hyperpigmentation. |
| first_indexed | 2024-04-09T17:54:37Z |
| format | Article |
| id | doaj.art-647cf2cd0c02411bb3d2c0a186c2844e |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-04-09T17:54:37Z |
| publishDate | 2023-06-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-647cf2cd0c02411bb3d2c0a186c2844e2023-04-15T05:52:05ZengElsevierArabian Journal of Chemistry1878-53522023-06-01166104724Novel coumarin derivatives as potential tyrosinase inhibitors: Synthesis, binding analysis and biological evaluationLi Lu0Xin Zhang1Yu Kang2Zhuang Xiong3Kun Zhang4Xuetao Xu5Liping Bai6Hongguang Li7School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR ChinaSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR ChinaSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR ChinaSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR ChinaSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR ChinaSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR China; Corresponding authors.State Key Laboratory of Quality Research in Chinese Medicine, Macau Institute for Applied Research in Medicine and Health, Guang dong-Hong Kong-Macao Joint Laboratory of Respiratory Infectious Disease, Macau University of Science and Technology, Macau 999078, PR China; Corresponding authors.School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR China; Corresponding authors.A novel series of thirty coumarin derivatives (4a ∼ r, 5a ∼ l) constituted by coumarin and cinnamic acid/benzoic acid through oxime linkage were synthesized and evaluated for their potential anti-tyrosinase activity. Among them, compound 5l exhibited outstanding anti-tyrosinase activity with IC50 of 3.04 ± 0.01 μM compared to 14.13 ± 0.80 μM of kojic acid. Kinetic study revealed compound 5l to be a reversible and uncompetitive tyrosinase inhibitor. 3D fluorescence and CD spectra results showed treatment of compound 5l lead to the conformational changes of tyrosinase. Molecular docking revealed the binding between compound 5l and tyrosinase. Furthermore, compound 5l inhibited melanin content and cellular tyrosinase activity both in B16F10 cells and zebrafish model with no toxicity effect. Taken together, our findings suggested that compound 5l could be used as potential candidate to relieve tyrosinase-related hyperpigmentation.http://www.sciencedirect.com/science/article/pii/S1878535223001867TyrosinaseMelanogenesisCoumarinCinnamic acid |
| spellingShingle | Li Lu Xin Zhang Yu Kang Zhuang Xiong Kun Zhang Xuetao Xu Liping Bai Hongguang Li Novel coumarin derivatives as potential tyrosinase inhibitors: Synthesis, binding analysis and biological evaluation Arabian Journal of Chemistry Tyrosinase Melanogenesis Coumarin Cinnamic acid |
| title | Novel coumarin derivatives as potential tyrosinase inhibitors: Synthesis, binding analysis and biological evaluation |
| title_full | Novel coumarin derivatives as potential tyrosinase inhibitors: Synthesis, binding analysis and biological evaluation |
| title_fullStr | Novel coumarin derivatives as potential tyrosinase inhibitors: Synthesis, binding analysis and biological evaluation |
| title_full_unstemmed | Novel coumarin derivatives as potential tyrosinase inhibitors: Synthesis, binding analysis and biological evaluation |
| title_short | Novel coumarin derivatives as potential tyrosinase inhibitors: Synthesis, binding analysis and biological evaluation |
| title_sort | novel coumarin derivatives as potential tyrosinase inhibitors synthesis binding analysis and biological evaluation |
| topic | Tyrosinase Melanogenesis Coumarin Cinnamic acid |
| url | http://www.sciencedirect.com/science/article/pii/S1878535223001867 |
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