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Reactivity of 2,2‐Diphenyl‐1‐picrylhydrazyl Solubilized in Water by β ‐Cyclodextrin and Its Methylated Derivative
Author(s) -
Nakanishi Ikuo,
Ohkubo Kei,
Kamibayashi Masato,
Ogawa Yukihiro,
Ozawa Toshihiko,
Matsumoto Ken–Ichiro,
Fukuzumi Shunichi
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600745
Subject(s) - chemistry , dpph , reactivity (psychology) , solubility , solubilization , cyclodextrin , trolox , caffeic acid , organic chemistry , antioxidant , medicinal chemistry , steric effects , biochemistry , medicine , alternative medicine , pathology
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 β ‐cyclodextrin ( β ‐CD), but the yield was less than 1 %. When β ‐CD was replaced with 2,6‐di‐ O ‐methyl‐ β ‐cyclodextrin (DM‐ β ‐CD), the solubility of DPPH • in water improved significantly. However, the reactivity of DM‐ β ‐CD‐solubilized DPPH • toward water‐soluble antioxidants, such as ascorbate, Trolox, and caffeic acid, was significantly lower than that of β ‐CD‐solubilized DPPH • due to the steric hindrance of the methyl groups in DM‐ β ‐CD. Therefore, β ‐CD‐solubilized DPPH • is suitable for evaluating the innate activity of water‐soluble antioxidants.
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