TY - JOUR
T1 - The lipoic acid analogue 1,2-diselenolane-3-pentanoic acid protects human low density lipoprotein against oxidative modification mediated by copper ion
AU - Matsugo, Seiichi
AU - Yan, Liang Jun
AU - Konishi, Tetsuya
AU - Youn, Hong Duk
AU - Lodge, John K.
AU - Ulrich, Heinz
AU - Packer, Lester
N1 - Funding Information:
This work was supported by the National Institute of Health (DK 50430).
PY - 1997/11/26
Y1 - 1997/11/26
N2 - 1,2-Diselenolane-3-pentanoic acid, in which the sulfur atoms of α-lipoic acid are replaced with selenium, displayed markedly different antioxidant properties when compared to α-lipoic acid. 1,2-Diselenolane-3-pentanoic acid was unable to inhibit protein oxidative modification of human low density lipoprotein (LDL) and bovine serum albumin induced by copper ion or hydroxyl radical, whereas α-lipoic acid showed significant protection. However, 1,2-diselenolane-3-pentanoic acid was able to inhibit the formation of lipid peroxidation products in LDL after oxidation by copper, while α-lipoic acid did not. Hence the diselenium compound exerts its effects in a lipophilic environment whilst lipoic acid exerts its effects in a hydrophilic environment. These differences in antioxidant activities of the two compounds may be explained, at least in part, by their differing partition coefficients.
AB - 1,2-Diselenolane-3-pentanoic acid, in which the sulfur atoms of α-lipoic acid are replaced with selenium, displayed markedly different antioxidant properties when compared to α-lipoic acid. 1,2-Diselenolane-3-pentanoic acid was unable to inhibit protein oxidative modification of human low density lipoprotein (LDL) and bovine serum albumin induced by copper ion or hydroxyl radical, whereas α-lipoic acid showed significant protection. However, 1,2-diselenolane-3-pentanoic acid was able to inhibit the formation of lipid peroxidation products in LDL after oxidation by copper, while α-lipoic acid did not. Hence the diselenium compound exerts its effects in a lipophilic environment whilst lipoic acid exerts its effects in a hydrophilic environment. These differences in antioxidant activities of the two compounds may be explained, at least in part, by their differing partition coefficients.
UR - http://www.scopus.com/inward/record.url?scp=0031587413&partnerID=8YFLogxK
U2 - 10.1006/bbrc.1997.7711
DO - 10.1006/bbrc.1997.7711
M3 - Article
C2 - 9398652
AN - SCOPUS:0031587413
SN - 0006-291X
VL - 240
SP - 819
EP - 824
JO - Biochemical and Biophysical Research Communications
JF - Biochemical and Biophysical Research Communications
IS - 3
ER -