Coumarin-Resveratrol-Inspired Hybrids as Monoamine Oxidase B Inhibitors: 3-Phenylcoumarin versus trans-6-Styrylcoumarin

Marco Mellado, César González, Jaime Mella, Luis F. Aguilar, Ismail Celik, Fernanda Borges, Eugenio Uriarte, Giovanna Delogu, Dolores Viña, Maria J. Matos

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Monoamine oxidases (MAOs) are attractive targets in drug design. The inhibition of one of the isoforms (A or B) is responsible for modulating the levels of different neurotransmitters in the central nervous system, as well as the production of reactive oxygen species. Molecules that act selectively on one of the MAO isoforms have been studied deeply, and coumarin has been described as a promising scaffold. In the current manuscript we describe a comparative study between 3-phenylcoumarin (endo coumarin-resveratrol-inspired hybrid) and trans-6-styrylcoumarin (exo coumarin-resveratrol-inspired hybrid). Crystallographic structures of both compounds were obtained and analyzed. 3D-QSAR models, in particular CoMFA and CoMSIA, docking simulations and molecular dynamics simulations have been performed to support and better understand the interaction of these molecules with both MAO isoforms. Both molecules proved to inhibit MAO-B, with trans-6-styrylcoumarin being 107 times more active than 3-phenylcoumarin, and 267 times more active than trans-resveratrol.

Original languageEnglish
Article number928
JournalMolecules
Volume27
Issue number3
DOIs
StatePublished - 1 Feb 2022
Externally publishedYes

Keywords

  • 3-phenylcoumarin
  • 3D-QSAR models
  • Molecular docking
  • Molecular dynamics
  • Monoamine oxidase B inhibitors
  • Trans-6-styrylcoumarin
  • Trans-resveratrol

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