title: Evaluation of glucose-linked nitroxide radicals for use as an in vivo spin-label probe.
abstract: In vivo incorporation and reduction abilities of 4-carboxy-2,2,6,6-tetramethylpiperidine-1-oxyl (4-carboxy-TEMPO) (1), 3-carboxy-2,2,5,5-tetramethylpyrroline-1-oxyl (3-carboxy-dehydro-PROXYL, 3-carboxy-DPRO) (2), 4-hydroxy-TEMPO and 3-hydroxymethyl-DPRO O-β-D-glucosides (3 and 5), and newly designed forms of 6-O-(TEMPO-4-carbonyl and DPRO-3-carbonyl)-D-glucose (4 and 6) were evaluated using white radish sprouts. For each of these compounds, electron spin resonance (ESR) spectrometry was used to measure two effects: the rate of in vitro reduction via the addition of ascorbic acid; and, the rate of successful incorporation into radish sprouts for a reduction to the corresponding hydroxyl amine. DPRO-radicals 2, 5, and 6 were detected significantly more than TEMPO-radicals 1, 3, and 4 in vitro and in vivo for both experiments. Four glucose-linked nitroxide radicals were reduced faster than the glucose-non-linked ones in the in vitro experiment, but were nonetheless detected more each time in radish sprouts due to the absorbability. Glucose ester-linked radicals 4 and 6 were detected more than glycosides 3 and 5, which suggests that glucose ester-linked DPRO-radical 6 is the best for use as a spin-label probe that a plant will incorporate.
authors: Graduate School of Science and Engineering, Yamagata University, Jonan 4-3-16, Yonezawa-shi, Yamagata 992-8510, Japan. Electronic address: shingo-s@yz.yamagata-u.ac.jp.
authors: Shingo
authors: S
authors: Sato
authors: Graduate School of Science and Engineering, Yamagata University, Jonan 4-3-16, Yonezawa-shi, Yamagata 992-8510, Japan.
authors: Masaki
authors: M
authors: Yamaguchi
authors: Graduate School of Science and Engineering, Yamagata University, Jonan 4-3-16, Yonezawa-shi, Yamagata 992-8510, Japan.
authors: Akio
authors: A
authors: Nagai
authors: Department of Chemistry and Chemical Sciences, Faculty of Engineering, Yamagata University, Jonan 4-3-16, Yonezawa-shi, Yamagata 992-8510, Japan.
authors: Ryo
authors: R
authors: Onuma
authors: Department of Chemistry and Chemical Sciences, Faculty of Engineering, Yamagata University, Jonan 4-3-16, Yonezawa-shi, Yamagata 992-8510, Japan.
authors: Misaki
authors: M
authors: Saito
authors: Department of Chemistry and Chemical Sciences, Faculty of Engineering, Yamagata University, Jonan 4-3-16, Yonezawa-shi, Yamagata 992-8510, Japan.
authors: Rina
authors: R
authors: Sugawara
authors: Department of Chemistry and Chemical Sciences, Faculty of Engineering, Yamagata University, Jonan 4-3-16, Yonezawa-shi, Yamagata 992-8510, Japan.
authors: Sayaka
authors: S
authors: Shinohara
authors: Department of Chemistry and Chemical Sciences, Faculty of Engineering, Yamagata University, Jonan 4-3-16, Yonezawa-shi, Yamagata 992-8510, Japan.
authors: Eriko
authors: E
authors: Okabe
authors: Graduate School of Science and Engineering, Yamagata University, Jonan 4-3-16, Yonezawa-shi, Yamagata 992-8510, Japan.
authors: Tomohiro
authors: T
authors: Ito
authors: Graduate School of Science and Engineering, Yamagata University, Jonan 4-3-16, Yonezawa-shi, Yamagata 992-8510, Japan.
authors: Tateaki
authors: T
authors: Ogata
mesh_terms: D003497:Cyclic N-Oxides / Q000737:chemistry; D004578:Electron Spin Resonance Spectroscopy; D018525:Germination; D005947:Glucose / Q000737:chemistry*; D007700:Kinetics; D009589:Nitrogen Oxides / Q000138:chemical synthesis / Q000737:chemistry*; D018515:Plant Leaves / Q000378:metabolism; D031224:Raphanus / Q000254:growth & development; D012996:Solutions; D013113:Spin Labels; D013997:Time Factors
chemical_list: D003497:Cyclic N-Oxides; D009589:Nitrogen Oxides; D012996:Solutions; D013113:Spin Labels; C039900:nitroxyl; D005947:Glucose; C003959:TEMPO
keywords: Ascorbic acid; ESR spectrometry; Glucose-linked nitroxide; Incorporation; Reduction; White radish sprout