C60 and Water-Soluble Fullerene Derivatives as Antioxidants Against Radical-Initiated Lipid Peroxidation
Resource
Journal of Medicinal Chemistry 42 (22): 4614-4620
Journal
Journal of Medicinal Chemistry
Journal Volume
42
Journal Issue
22
Pages
4614-4620
Date Issued
1999
Date
1999
Author(s)
Wang, I Chen
Tai, Lin Ai
Lee, Don Dar
Kanakamma, P. P.
Shen, Clifton K. F.
Cheng, Chien Hong
Hwang, Kuo Chu
Abstract
C(60), vitamin E, and three C(60) derivatives (polar 1 and water-soluble C(3)/D(3)C(60)s) were examined for their antioxidant effects on prevention of lipid peroxidation induced by superoxide and hydroxyl radicals. The protection effect on lipid peroxidation was found to be in the sequence: C(60) >/= vitamin E > 1 > none, for liposoluble antioxidants, and C(3)C(60) >> D(3)C(60) > none, for water-soluble ones. Fluorescence quenching of PyCH(2)COOH (Py = pyrene) by both C(3)- and D(3)C(60)s shows that the Stern-Volmer constant, K(SV), is about the same for both quenchers in aqueous solution. Upon addition of liposomes, the fluorescence quenching becomes more efficient: 5-fold higher in K(SV) for C(3)C(60) than for D(3)C(60). When Py(CH(2))(n)()COOH (n = 1, 3, 5, 9, or 15) was incorporated in lipid membranes, the K(SV)s all were small and nearly equal for D(3)C(60) but were quite large and different for C(3)C(60) with the sequence: n = 1 < 3 < 5 < 9 < 15. The better protection effect of C(3)C(60) on lipid peroxidation than that of D(3)C(60) is attributed to its stronger interaction with membranes. Overall, the antioxidation abilities of the compounds examined were rationalized in terms of the number of reactive sites, the location of antioxidant in lipid membranes, and the strength of interactions between antioxidants and membranes.
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journal article
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