Issue 32, 2020

Fluoxetine scaffold to design tandem molecular antioxidants and green catalysts

Abstract

Fluoxetine finds application in the treatment of depression and mood disorders. This selective serotonin-reuptake inhibitor (SSRI) also contrasts oxidative stress by direct ROS scavenging, modulation of the endogenous antioxidant defense system, and/or enhancement of the serotonin antioxidant capacity. We synthesised some fluoxetine analogues incorporating a selenium nucleus, thus expanding its antioxidant potential by enabling a hydroperoxides-inactivating, glutathione peroxidase (GPx)-like activity. Radical scavenging and peroxidatic activity were combined in a water-soluble, drug-like, tandem antioxidant molecule. Selenofluoxetine derivatives were reacted with H2O2 in water, and the mechanistic details of the reaction were unravelled combining nuclear magnetic resonance (NMR), electrospray ionisation-mass spectrometry (ESI-MS) and quantum chemistry calculations. The observed oxidation–elimination process led to the formation of seleninic acid and cinnamylamine in a trans-selective manner. This mechanism is likely to be extended to other substrates for the preparation of unsaturated cinnamylamines.

Graphical abstract: Fluoxetine scaffold to design tandem molecular antioxidants and green catalysts

Supplementary files

Article information

Article type
Paper
Submitted
19 apr 2020
Accepted
07 mai 2020
First published
15 mai 2020
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2020,10, 18583-18593

Fluoxetine scaffold to design tandem molecular antioxidants and green catalysts

G. Ribaudo, M. Bortoli, A. Ongaro, E. Oselladore, A. Gianoncelli, G. Zagotto and L. Orian, RSC Adv., 2020, 10, 18583 DOI: 10.1039/D0RA03509B

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