The catalytic role of N-hydroxyphthalimide (NHPI) in promoting free-radical hydrogen atom transfer (HAT) reactions, well-documented for processes of industrial and synthetic interest, is here investigated for the first time in a biological environment. While NHPI by itself did not show any bioactivity, selected NHPI-derivatives (NHPIDs) revealed the ability to activate the intracellular formation of reactive oxygen species (ROS), causing the depletion of glutathione (GSH) levels and an increase in oxidative stress (OS). The evident bioactivity of some of these derivatives resulted in a significant reduction of the viability in osteosarcoma MG-63, suggesting a new, potential role of NHPIDs as pro-oxidant drugs. The key role of the N-OH group in promoting oxidative stress is demonstrated.

N-Hydroxyphthalimide catalysts as bioactive pro-oxidants

TARSINI, PAOLO;CANDIANI, GABRIELE;PUNTA, CARLO
2016

Abstract

The catalytic role of N-hydroxyphthalimide (NHPI) in promoting free-radical hydrogen atom transfer (HAT) reactions, well-documented for processes of industrial and synthetic interest, is here investigated for the first time in a biological environment. While NHPI by itself did not show any bioactivity, selected NHPI-derivatives (NHPIDs) revealed the ability to activate the intracellular formation of reactive oxygen species (ROS), causing the depletion of glutathione (GSH) levels and an increase in oxidative stress (OS). The evident bioactivity of some of these derivatives resulted in a significant reduction of the viability in osteosarcoma MG-63, suggesting a new, potential role of NHPIDs as pro-oxidant drugs. The key role of the N-OH group in promoting oxidative stress is demonstrated.
RSC ADVANCES
Chemical Engineering (all); Chemistry (all)
File in questo prodotto:
File Dimensione Formato  
2016-RSC Advances-Pro-oxidants.pdf

accesso aperto

Descrizione: ARTICOLO PRINCIPALE
: Post-Print (DRAFT o Author’s Accepted Manuscript-AAM)
Dimensione 520.69 kB
Formato Adobe PDF
520.69 kB 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: http://hdl.handle.net/11311/1000357
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 2
  • ???jsp.display-item.citation.isi??? 2
social impact