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Tytuł pozycji:

Effect of relative configuration of TEMPO-type nitroxides on ascorbate reduction.

Tytuł:
Effect of relative configuration of TEMPO-type nitroxides on ascorbate reduction.
Autorzy:
Azuma R; Laboratory of Biophysical Chemistry, Kobe Pharmaceutical University, 4-19-1 Motoyamakita-machi, Higashinada-ku, Kobe, 658-8558, Japan.
Yamasaki T; Laboratory of Biophysical Chemistry, Kobe Pharmaceutical University, 4-19-1 Motoyamakita-machi, Higashinada-ku, Kobe, 658-8558, Japan.
Emoto MC; Department of Clinical Laboratory Science, School of Medical Technology, Health Sciences University of Hokkaido, Sapporo, Hokkaido, 002-8072, Japan.
Sato-Akaba H; Department of Systems Innovation, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka, 560-8531, Japan.
Sano K; Laboratory of Biophysical Chemistry, Kobe Pharmaceutical University, 4-19-1 Motoyamakita-machi, Higashinada-ku, Kobe, 658-8558, Japan.
Munekane M; Laboratory of Biophysical Chemistry, Kobe Pharmaceutical University, 4-19-1 Motoyamakita-machi, Higashinada-ku, Kobe, 658-8558, Japan.
Fujii HG; Advanced Research Promotion Center, Health Sciences University of Hokkaido, Ishikari, Hokkaido, 061-0293, Japan.
Mukai T; Laboratory of Biophysical Chemistry, Kobe Pharmaceutical University, 4-19-1 Motoyamakita-machi, Higashinada-ku, Kobe, 658-8558, Japan. Electronic address: .
Źródło:
Free radical biology & medicine [Free Radic Biol Med] 2023 Jan; Vol. 194, pp. 114-122. Date of Electronic Publication: 2022 Nov 26.
Typ publikacji:
Journal Article; Research Support, Non-U.S. Gov't
Język:
English
Imprint Name(s):
Publication: Tarrytown, NY : Elsevier Science
Original Publication: New York : Pergamon, c1987-
MeSH Terms:
Cyclic N-Oxides*
Ascorbic Acid*
Mice ; Animals ; Electron Spin Resonance Spectroscopy/methods ; Nitrogen Oxides ; Spin Labels ; Oxidation-Reduction
Contributed Indexing:
Keywords: Ascorbate; Diastereomers; Electron paramagnetic resonance; Electron spin resonance; Imaging; In vivo; Nitroxide; Radicals; Reduction
Substance Nomenclature:
GFQ4MMS07W (nitroxyl)
0 (Cyclic N-Oxides)
PQ6CK8PD0R (Ascorbic Acid)
0 (Nitrogen Oxides)
0 (Spin Labels)
Entry Date(s):
Date Created: 20221128 Date Completed: 20230109 Latest Revision: 20230114
Update Code:
20240105
DOI:
10.1016/j.freeradbiomed.2022.11.033
PMID:
36442586
Czasopismo naukowe
2,2,6,6-Tetramethylpiperidin-N-oxyl (TEMPO)-type nitroxides are susceptible to bioreduction, leading to a loss of radical properties. Although it has been reported that the steric and electronic environments around the N-O moiety of nitroxides affect the reduction, how the relative configuration of nitroxide derivatives alters it is unclear. In this study, we investigated the effect of diastereomers on the radical properties of C2- and C4-disubstituted TEMPO-type nitroxides. We succeeded in isolating the diastereomers of the studied nitroxides for the first time. In addition, we compared the reactivities of nitroxide derivatives with different substituents at the C2 and C4 positions toward ascorbate reduction. We found that the bulky substituents at both C2 and C4 and the electronic effect of C4 affected the reduction of the isomers. C2- and C4-disubstituted nitroxides were administered to mice for electron spin resonance imaging to assess bioreduction in the brain. Similar to the reactivity to reduction in vitro, a difference in the bioreduction of diastereomers was observed in brain tissues. Our research strongly indicates that bioreduction can be controlled by changing the relative configuration, which can be used in the design of nitroxide derivatives for biological applications.
Competing Interests: Declaration of competing interests None.
(Copyright © 2022 Elsevier Inc. All rights reserved.)

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