title: Amphiphilic NO-donor antioxidants.
abstract: 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.
authors.affiliation: Dipartimento di Scienza e Tecnologia del Farmaco, Università degli Studi di Torino, Via Pietro Giuria 9, 10125 Torino, Italy.
authors.forename: Konstantin
authors.initials: K
authors.lastname: Chegaev
authors.forename: Loretta
authors.initials: L
authors.lastname: Lazzarato
authors.forename: Barbara
authors.initials: B
authors.lastname: Rolando
authors.forename: Elisabetta
authors.initials: E
authors.lastname: Marini
authors.forename: Gloria V
authors.initials: GV
authors.lastname: Lopez
authors.forename: Massimo
authors.initials: M
authors.lastname: Bertinaria
authors.forename: Antonella
authors.initials: A
authors.lastname: Di Stilo
authors.forename: Roberta
authors.initials: R
authors.lastname: Fruttero
authors.forename: Alberto
authors.initials: A
authors.lastname: Gasco
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis / Q000494:pharmacology*; D015195:Drug Design; D020128:Inhibitory Concentration 50; D008077:Lipoproteins, LDL / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008956:Models, Chemical; D020030:Nitric Oxide Donors / Q000138:chemical synthesis / Q000494:pharmacology*; D010084:Oxidation-Reduction; D010743:Phospholipids / Q000378:metabolism; D000644:Quaternary Ammonium Compounds / Q000737:chemistry / Q000494:pharmacology*; D051381:Rats; D017208:Rats, Wistar; D013329:Structure-Activity Relationship; D013501:Surface-Active Agents / Q000138:chemical synthesis / Q000494:pharmacology; D017392:Thiobarbituric Acid Reactive Substances / Q000378:metabolism; D014664:Vasodilation / Q000187:drug effects* / Q000502:physiology
chemical_list: D000975:Antioxidants; D008077:Lipoproteins, LDL; D020030:Nitric Oxide Donors; D010743:Phospholipids; D000644:Quaternary Ammonium Compounds; D013501:Surface-Active Agents; D017392:Thiobarbituric Acid Reactive Substances