Synthesis and Preliminary Biological Evaluations of Ionic and Nonionic Amphiphilic α-Phenyl-N-tert-butylnitrone Derivatives

Citations Over TimeTop 10% of 2003 papers

Abstract

In this study we report the synthesis of a series of new amphiphilic compounds derived from alpha-phenyl-N-tert-butylnitrone (PBN). The nitrone function was fitted into the core of the molecule between its polar and apolar groups. The polar head consisted of a lactobionamide, an ammonium, or a carboxylate group. The hydrophobic part consisted of a hydro- or a perfluorocarbon chain. The hydrophobic chain was linked to the tert-butyl group of the PBN derivatives using an urethane, a thioether, or an amide bond. The impact of these different parameters on the hydrophilic lipophilic balance of these compounds and their spin trap activity were studied. The various ESR measurements indicated that the aromatic and tert-butyl functional groups of PBN did not affect its spin trap properties. Moreover, these compounds were found to increase the viability of cultured human skin fibroblasts harboring the neurogenic ataxia retinitis pigmentosa mutation and presenting a severe ATPase deficiency.

Related Papers

• → Solid-State Supramolecular Chemistry of a Benzylpyridine-Functionalized Zwitterion: Polymorphism, Interconversion, and Porosity(2015)8 cited
• → Gas-Phase Zwitterions in the Absence of a Net Charge(2004)48 cited
• → Polymorphism and Host–Guest Chemistry of a Phenylpyridine-Functionalized Zwitterion(2020)1 cited
• → THE IONIZATION OF 5‐HYDROXYTRYPTAMINE AND RELATED COMPOUNDS AND AN APPRAISAL OF METHODS FOR THE ESTIMATION OF ZWITTERION CONSTANTS(1980)6 cited
• → The zwitterion isomer of orthosilicic acid and its role in neutral pH dimerization from density functional theory.(2021)