61361-17-9

Upstream product

• 16649-50-6 N-tert-Butylhydroxylamine 
• 619-66-9 4-Carboxybenzaldehyde 
• 57497-39-9 N-tertbutylhydroxylamine hydrochloride 

Downstream Products

• 688063-78-7 N-tert-butyl-α-4-(2,5-dioxopyrrolidin-1-ylphenyl ester)nitrone 
• 1201892-99-0 (Z)-N-(4-(carboxymethylcarbamoyl)benzylidene)-2-methylpropan-2-amine oxide 

Relevant academic research and scientific papers

NOVEL ANTIOXIDANTS AND METHODS OF TREATMENT

Formula 1 is an antioxidant compound, wherein R, R1, or D is an antioxidant substituent; R and D are each independently selected from hydrogen or groups containing cysteine, thiols, disulfides, amino acids, amines, amides, or carboxylic acids; when one of

Fluorinated amphiphilic amino acid derivatives as antioxidant carriers: A new class of protective agents

The use of classical antioxidants is limited by their low bioavailabilities, and therefore, high doses are usually required to display significant protective activity. In a recent article (J. Med. Chem. 2003, 46, 5230) we showed that the ability of the α-phenyl-N-tert-butylnitrone (PBN) to restore the viability of ATPase-deficient human skin fibroblasts was greatly enhanced by grafting it on a fluorinated amphiphilic carrier. With the aim of extending this concept to other antioxidants, we present here the design, the synthesis, and the physicochemical measurements of a new series of fluorinated amphiphilic antioxidant derivatives. The hydroxyl radical scavenging activity and the radical reducing potency of these newly designed compounds were respectively demonstrated in an ABTS competition and an ABTS.+ reduction assay. We also showed that the protective effects of amphiphilic antioxidants derived from PBN, Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2- carboxylic acid) or lipoic acid (5-[1,2]-dithiolan-3-ylpentanoic acid) in primary cortical mixed cell cultures exposed to oxidotoxins are greatly improved compared to their parent compounds in the following rank-order: (1) PBN, (2) Trolox, and (3) lipoic acid. In contrast, the protective activity of indole-3-propionic acid was slightly decreased by grafting it on the amphiphilic carrier. Similar observations were made in in vivo experiments using aquatic invertebrate microorganisms, called rotifers, which were exposed to lethal concentrations of nonselective (H2O2) and mitochondria-selective (doxorubicin) oxidotoxins. The conclusion of these studies is that fluorinated amphiphilic PBN, Trolox, and lipoic acid derivatives exhibit very potent protective activities in in vitro and in vivo experiments. The findings demonstrated herein therefore strongly suggest that the amphiphilic character enhances the bioavailability of the antioxidants and allows for a selective targeting of mitochondria.

2-Substituted and 4-substituted aryl nitrone compounds

The present invention provides aryl nitrones, compositions comprising the same and methods of their use for the treatment or prevention of oxidative, ischemic, ischemia/reperfusion-related and chemokine mediated conditions.