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Amphiphilic NO‐Donor Antioxidants
Author(s) -
Chegaev Konstantin,
Lazzarato Loretta,
Rolando Barbara,
Marini Elisabetta,
Lopez Gloria V.,
Bertinaria Massimo,
Di Stilo Antonella,
Fruttero Roberta,
Gasco Alberto
Publication year - 2007
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.200600248
Subject(s) - chemistry , antioxidant , phospholipid , amphiphile , tbars , alkyl , organic chemistry , stereochemistry , vesicle , biochemistry , lipid peroxidation , membrane , copolymer , polymer
Models of amphiphilic NO‐donor antioxidants 24 – 26 were designed and synthesized. The products were obtained by linking a lipophilic tail (C 6 , C 8 , C 10 ) with a polar head constituted by the 2,6‐dimethoxyphenol antioxidant joined to the NO‐donor 3‐furoxancarboxamide substructure through a bridge containing a quaternary ammonium group. Compound 23 , containing the shortest C 2 ‐alkyl chain, was also studied as a reference. The antioxidant properties (TBARS and LDL oxidation assays) and the vasodilator properties of the compounds were studied in vitro. The ability of these products to interact with phospholipid vesicles was also investigated by NMR techniques. The results indicate that both activities are modulated by the ability of the compounds to accumulate on phospholipid layers.