Coumarins comprise a large class of natural-based and synthetic compounds containing a 2Hchromen2-one ring. Derivatives with hydroxy groups are able to donate a H, exhibiting antioxidant activities similar to phenols and quinones. In this work, 3-(pyridin-2-yl)coumarins with and without hydroxy group/s were prepared and their antioxidant ability and inhibition activity towards lipoxygenase enzymes were studied. The studied derivatives have shown potent lipoxygenase activities with IC50 in the mM range, with the radical scavenging properties tuneable according to the number and position of the hydroxy groups. The study of the protonation constants of the 3-(pyridin-2-yl)coumarins, carried out in aqueous solutions, helped in evaluating the absorption and the potential biological properties of the molecules, strongly affected by their protonation state and charge. The antioxidant properties and the way of enzymatic inhibition of the studied 3-(pyridin-2-yl)coumarins are discussed on the basis of the calculated specific thermochemical descriptors and molecular docking.

Hydroxylated 3-(pyridin-2-yl)coumarins as radical scavengers with potent lipoxygenase inhibitor activity

Sebastiano Masuri
Primo
Investigation
;
Maria Grazia Cabiddu
Secondo
Investigation
;
Enzo Cadoni
Penultimo
Methodology
;
Tiziana Pivetta
Ultimo
Supervision
2021-01-01

Abstract

Coumarins comprise a large class of natural-based and synthetic compounds containing a 2Hchromen2-one ring. Derivatives with hydroxy groups are able to donate a H, exhibiting antioxidant activities similar to phenols and quinones. In this work, 3-(pyridin-2-yl)coumarins with and without hydroxy group/s were prepared and their antioxidant ability and inhibition activity towards lipoxygenase enzymes were studied. The studied derivatives have shown potent lipoxygenase activities with IC50 in the mM range, with the radical scavenging properties tuneable according to the number and position of the hydroxy groups. The study of the protonation constants of the 3-(pyridin-2-yl)coumarins, carried out in aqueous solutions, helped in evaluating the absorption and the potential biological properties of the molecules, strongly affected by their protonation state and charge. The antioxidant properties and the way of enzymatic inhibition of the studied 3-(pyridin-2-yl)coumarins are discussed on the basis of the calculated specific thermochemical descriptors and molecular docking.
File in questo prodotto:
File Dimensione Formato  
d1nj01232k.pdf

Solo gestori archivio

Descrizione: Articolo principale
Tipologia: versione editoriale
Dimensione 4.2 MB
Formato Adobe PDF
4.2 MB Adobe PDF   Visualizza/Apri   Richiedi una copia
manuscript_revised_hydroxy.pdf

Open Access dal 29/06/2022

Descrizione: Articolo principale
Tipologia: versione post-print
Dimensione 1.71 MB
Formato Adobe PDF
1.71 MB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11584/313657
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 3
  • ???jsp.display-item.citation.isi??? 3
social impact