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Article

Synthesis of Coumarin Derivatives: A New Class of Coumarin-Based G Protein-Coupled Receptor Activators and Inhibitors

by
Zhe Fu
1,
Linjie Zhang
1,
Sijin Hang
1,
Shiyi Wang
2,
Na Li
1,
Xiaojing Sun
1,
Zian Wang
1,
Ruilong Sheng
3,
Fang Wang
4,
Wenhui Wu
1 and
Ruihua Guo
1,5,6,*
1
College of Food Science and Technology, Shanghai Ocean University, Shanghai 201306, China
2
AIEN Institute, Shanghai Ocean University, Shanghai 201306, China
3
CQM—Centro de Química da Madeira, Campus da Penteada, Universidade da Madeira, 9000-390 Funchal, Portugal
4
School Basic Medicine, Shanghai University of Medicine and Health Science, Shanghai 201318, China
5
Laboratory of Quality and Safety Risk Assessment for Aquatic Product on Storage and Preservation, Ministry of Agriculture, Shanghai 201306, China
6
Engineering Research Center of Aquatic-Product Processing & Preservation, Shanghai 201306, China
*
Author to whom correspondence should be addressed.
Polymers 2022, 14(10), 2021; https://doi.org/10.3390/polym14102021
Submission received: 14 March 2022 / Revised: 29 April 2022 / Accepted: 4 May 2022 / Published: 15 May 2022
(This article belongs to the Special Issue Bio-Based and Biodegradable Polymeric Composites: Synthesis, Characterization and Applications)
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Abstract

To expand the range of daphnetin-based inhibitors/activators used for targeting G protein-coupled receptors (GPCRs) in disease treatment, twenty-five coumarin derivatives 1–25, including 7,8-dihydroxycoumarin and 7-hydroxycoumarin derivatives with various substitution patterns/groups at C3-/4- positions, were synthesized via mild Pechmann condensation and hydroxyl modification. The structures were characterized by 1H NMR, 13C NMR and ESI-MS. Their inhibition or activation activities relative to GPCRs were evaluated by double-antibody sandwich ELISA (DAS–ELISA) in vitro. The results showed that most of the coumarin derivatives possessed a moderate GPCR activation or inhibitory potency. Among them, derivatives 14, 17, 18, and 21 showed a remarkable GPCR activation potency, with EC50 values of 0.03, 0.03, 0.03, and 0.02 nM, respectively. Meanwhile, derivatives 4, 7, and 23 had significant GPCR inhibitory potencies against GPCRs with IC50 values of 0.15, 0.02, and 0.76 nM, respectively. Notably, the acylation of hydroxyl groups at the C-7 and C-8 positions of 7,8-dihydroxycoumarin skeleton or the etherification of the hydroxyl group at the C-7 position of the 7-hydroxycoumarin skeleton could successfully change GPCRs activators into inhibitors. This work demonstrated a simple and efficient approach to developing coumarin derivatives as remarkable GPCRs activators and inhibitors via molecular diversity-based synthesis.
Keywords: coumarin; G protein-coupled receptors; synthesis; structure–activity relationships coumarin; G protein-coupled receptors; synthesis; structure–activity relationships
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MDPI and ACS Style

Fu, Z.; Zhang, L.; Hang, S.; Wang, S.; Li, N.; Sun, X.; Wang, Z.; Sheng, R.; Wang, F.; Wu, W.; et al. Synthesis of Coumarin Derivatives: A New Class of Coumarin-Based G Protein-Coupled Receptor Activators and Inhibitors. Polymers 2022, 14, 2021. https://doi.org/10.3390/polym14102021

AMA Style

Fu Z, Zhang L, Hang S, Wang S, Li N, Sun X, Wang Z, Sheng R, Wang F, Wu W, et al. Synthesis of Coumarin Derivatives: A New Class of Coumarin-Based G Protein-Coupled Receptor Activators and Inhibitors. Polymers. 2022; 14(10):2021. https://doi.org/10.3390/polym14102021

Chicago/Turabian Style

Fu, Zhe, Linjie Zhang, Sijin Hang, Shiyi Wang, Na Li, Xiaojing Sun, Zian Wang, Ruilong Sheng, Fang Wang, Wenhui Wu, and et al. 2022. "Synthesis of Coumarin Derivatives: A New Class of Coumarin-Based G Protein-Coupled Receptor Activators and Inhibitors" Polymers 14, no. 10: 2021. https://doi.org/10.3390/polym14102021

APA Style

Fu, Z., Zhang, L., Hang, S., Wang, S., Li, N., Sun, X., Wang, Z., Sheng, R., Wang, F., Wu, W., & Guo, R. (2022). Synthesis of Coumarin Derivatives: A New Class of Coumarin-Based G Protein-Coupled Receptor Activators and Inhibitors. Polymers, 14(10), 2021. https://doi.org/10.3390/polym14102021

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