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

Ikuo Nakanishi; Kei Ohkubo; Masato Kamibayashi; Yukihiro Ogawa; Toshihiko Ozawa; Ken Ichiro Matsumoto; Shunichi Fukuzumi

doi:10.1002/slct.201600745

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

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

Department of Chemistry & Nanoscience

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

8 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	3367-3370
Number of pages	4
Journal	ChemistrySelect
Volume	1
Issue number	12
DOIs	https://doi.org/10.1002/slct.201600745
State	Published - 1 Aug 2016

Bibliographical note

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

antioxidants
cyclodextrins
kinetics
radical reactions
radicals

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@article{04866cafd1904ec0888565506933ca0d,

title = "Reactivity of 2,2-Diphenyl-1-picrylhydrazyl Solubilized in Water by β-Cyclodextrin and Its Methylated Derivative",

abstract = "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.",

keywords = "antioxidants, cyclodextrins, kinetics, radical reactions, radicals",

author = "Ikuo Nakanishi and Kei Ohkubo and Masato Kamibayashi and Yukihiro Ogawa and Toshihiko Ozawa and Matsumoto, {Ken Ichiro} and Shunichi Fukuzumi",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2016",

month = aug,

day = "1",

doi = "10.1002/slct.201600745",

language = "English",

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T1 - Reactivity of 2,2-Diphenyl-1-picrylhydrazyl Solubilized in Water by β-Cyclodextrin and Its Methylated Derivative

AU - Nakanishi, Ikuo

AU - Ohkubo, Kei

AU - Kamibayashi, Masato

AU - Ogawa, Yukihiro

AU - Ozawa, Toshihiko

AU - Matsumoto, Ken Ichiro

AU - Fukuzumi, Shunichi

PY - 2016/8/1

Y1 - 2016/8/1

N2 - 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.

AB - 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.

KW - antioxidants

KW - cyclodextrins

KW - kinetics

KW - radical reactions

KW - radicals

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DO - 10.1002/slct.201600745

M3 - Article

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SN - 2365-6549

VL - 1

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JO - ChemistrySelect

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IS - 12

ER -

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

Abstract

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Keywords

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