Journal Article Reactivity of 2,2-Diphenyl-1-picrylhydrazyl Solubilized in Water by β-Cyclodextrin and Its Methylated Derivative

Nakanishi, Ikuo  ,  Ohkubo, Kei  ,  Kamibayashi, Masato  ,  Ogawa, Yukihiro  ,  Ozawa, Toshihiko  ,  Matsumoto, Kenichiro  ,  Fukuzumi, Shunichi

1 ( 12 )  , pp.3367 - 3370 , 2016-08 , Wiley-VCH
A stable radical, 2,2-diphenyl-1-picrylhydrazyl (DPPH), frequently used as a reactivity model of reactive oxygen species, was successfully solubilized in water by forming an inclusion complex with beta-cyclodextrin (b-CD), but the yield was less than 1%. When b-CD was replaced with 2,6-di-O-methyl-beta-cyclodextrin (DM-b-CD), the solubility of DPPH in water improved significantly. However, the reactivity of DM-b-CD-solubilized DPPH toward water-soluble antioxidants, such as ascorbate, Trolox, and caffeic acid, was significantly lower than that of b-CD-solubilized DPPH due to the steric hindrance of the methyl groups in DM-b-CD. Therefore, b-CD-solubilized DPPH is suitable for evaluating the innate activity of water-soluble antioxidants.

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