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Original Article

Water-Soluble Hexasulfobutyl[60]fullerene Inhibit Low-Density Lipoprotein Oxidation in Aqueous and Lipophilic Phases

Yuan-Teh Lee^*, Long-Yong Chiang, Wei-Jao Chen^* and Hsiu-Ching Hsu^*,1

^* Department of Internal Medicine (Cardiology) and the
Center for Condensed Matter Sciences, National Taiwan University, Taipei, Taiwan

Oxidative modification of low-density lipoprotein (LDL) plays a pivotal role in the pathogenesis of atherosclerosis. Increasing the resistance of LDL to oxidation may therefore mitigate, or even prevent, atherosclerosis. A new water-soluble C₆₀ derivative, hexasulfobutyl[60]fullerene [C₆₀ - (CH₂CH₂CH₂CH₂-SO₃Na)₆; FC₄S], consisting of 6 sulfobutyl moieties covalently bound onto the C₆₀ cage is a potent free radical scavenger. This study explored the antioxidative effect of sulfobutylated fullerene derivatives (FC₄S) on LDL oxidation. FC₄S was found to be effective in protecting LDL against oxidation induced by either Cu²⁺ or azo peroxyl radicals generated initially in the aqueous or lipophilic phase, respectively. Levels of the oxidative products, conjugated diene and thiobarbituric acid-reactive substances, and the relative electrophoresis mobility of the LDL were decreased. The addition of 20 µM FC₄S at the early stage of oxidation increased the kinetic lag time from 69 ± 11 to 14 ± 10 min (P < 0.05) and decreased the propagation rate from 17.1 ± 2.6 to 6.3 ± 1.0 mOD/min (P < 0.005). Persistent suppression of peroxidation reaction was observed upon further addition of FC₄S after full consumption of all endogenous antioxidants during the propagation period. Intravenous injection of hypercholesterolemic rabbits with FC₄S (1 mg/kg/day) efficiently decreased atheroma formation. Data substantiate the use of FC₄S as an excellent hydrophilic antioxidant in protecting atheroma formation, via removing free radicals, in either aqueous or lipophilic phase.