Structural concept of nitroxide as a lipid peroxidation inhibitor

Toshihide Yamasaki; Yuko Ito; Fumiya Mito; Kana Kitagawa; Yuta Matsuoka; Mayumi Yamato; Ken Ichi Yamada

doi:10.1021/jo200361p

Structural concept of nitroxide as a lipid peroxidation inhibitor

Toshihide Yamasaki, Yuko Ito, Fumiya Mito, Kana Kitagawa, Yuta Matsuoka, Mayumi Yamato, Ken Ichi Yamada

Molecular Bioinformatics

Research output: Contribution to journal › Article › peer-review

24 Citations (Scopus)

Abstract

Nitroxides have antioxidative activities toward lipid peroxidation, but the influence of steric factors is not known. We synthesized alkyl-substituted nitroxides at the α-position of the N-O moiety to enhance lipophilicity and the bulk effect. There was good correlation between the IC₅₀ and lipophilicity (log P_o/w) of nitroxides with use of the thiobarbituric acid-reactive substances (TBARS) assay. Furthermore, an inhibitory effect on the TBARS assay was dependent upon the number and length of alkyl groups, though nitroxides had almost identical lipophilicity.

Original language	English
Pages (from-to)	4144-4148
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	76
Issue number	10
DOIs	https://doi.org/10.1021/jo200361p
Publication status	Published - May 20 2011

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo200361p

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AU - Yamasaki, Toshihide

AU - Ito, Yuko

AU - Mito, Fumiya

AU - Kitagawa, Kana

AU - Matsuoka, Yuta

AU - Yamato, Mayumi

AU - Yamada, Ken Ichi

PY - 2011/5/20

Y1 - 2011/5/20

N2 - Nitroxides have antioxidative activities toward lipid peroxidation, but the influence of steric factors is not known. We synthesized alkyl-substituted nitroxides at the α-position of the N-O moiety to enhance lipophilicity and the bulk effect. There was good correlation between the IC50 and lipophilicity (log Po/w) of nitroxides with use of the thiobarbituric acid-reactive substances (TBARS) assay. Furthermore, an inhibitory effect on the TBARS assay was dependent upon the number and length of alkyl groups, though nitroxides had almost identical lipophilicity.

AB - Nitroxides have antioxidative activities toward lipid peroxidation, but the influence of steric factors is not known. We synthesized alkyl-substituted nitroxides at the α-position of the N-O moiety to enhance lipophilicity and the bulk effect. There was good correlation between the IC50 and lipophilicity (log Po/w) of nitroxides with use of the thiobarbituric acid-reactive substances (TBARS) assay. Furthermore, an inhibitory effect on the TBARS assay was dependent upon the number and length of alkyl groups, though nitroxides had almost identical lipophilicity.

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Structural concept of nitroxide as a lipid peroxidation inhibitor

Abstract

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