Novel antioxidant agents deriving from molecular combination of Vitamin C and NO-donor moieties.
In this paper, we describe a new class of products in which NO-donor moieties are linked to either the 3-OH (4a-f) or 2-OH group (7a-c) of ascorbic acid (ASA). Log Ps and pK(a)s of these products were experimentally evaluated. All the compounds were tested for their antioxidant activity on lipidic peroxidation induced by Fe(3+)-ADP/NADPH in lipids of microsomal membranes of rat hepatocytes. Only 3-O series displays antioxidant activity and it seems to be principally dependent on the lipophilicity. Both series trigger in vitro NO-dependent vasodilator properties.
Cena
Clara
C
Dipartimento di Scienza e Tecnologia del Farmaco, Università degli Studi di Torino, Via Pietro Giuria 9, I-10125 Torino, Italy.
Chegaev
Konstantin
K
Balbo
Silvia
S
Lazzarato
Loretta
L
Rolando
Barbara
B
Giorgis
Marta
M
Marini
Elisabetta
E
Fruttero
Roberta
R
Gasco
Alberto
A
D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry* / Q000145:classification; D001013:Aorta, Thoracic / Q000187:drug effects; D001205:Ascorbic Acid / Q000138:chemical synthesis* / Q000737:chemistry / Q000145:classification; D004305:Dose-Response Relationship, Drug; D015227:Lipid Peroxidation / Q000187:drug effects; D008055:Lipids / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008861:Microsomes / Q000187:drug effects; D015394:Molecular Structure; D020030:Nitric Oxide Donors / Q000138:chemical synthesis* / Q000737:chemistry / Q000145:classification; D051381:Rats; D017208:Rats, Wistar; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013997:Time Factors
D000975:Antioxidants; D008055:Lipids; D020030:Nitric Oxide Donors; D001205:Ascorbic Acid