Synthesis and properties of a series of beta-cyclodextrin/nitrone spin traps for improved superoxide detection - Aix-Marseille Université Access content directly
Journal Articles Organic & Biomolecular Chemistry Year : 2017

Synthesis and properties of a series of beta-cyclodextrin/nitrone spin traps for improved superoxide detection

Abstract

Three new DEPMPO-based spin traps have been designed and synthesized for improved superoxide detection, each carrying a cyclodextrin (CD) moiety but with a different alkyl chain on the phosphorus atom or with a long spacer arm. EPR spectroscopy allowed us to estimate the half-life of the superoxide spin adducts which is close to the value previously reported for CD-DEPMPO (t(1/2) approximate to 50-55 min under the conditions investigated). The spectra are typical of superoxide adducts (almost no features of the HO center dot adduct that usually forms with time for other nitrone spin traps such as DMPO) and we show that at 250 mu M, the new spin trap enables the reliable detection of superoxide by 1 scan at the position opposite to the corresponding spin trap without the CD moiety. The resistance of the spin adducts to a reduction process has been evaluated, and the superoxide spin adducts are sensitive to ascorbate and glutathione (GSH), but not to glutathione peroxidase/GSH, reflecting the exposed nature of the nitroxide moiety to the bulk solvent. To understand these results, 2D-ROESY NMR studies and molecular dynamics pointed to a shallow or surface self-inclusion of the nitrone spin traps and of nitroxide spin adducts presumably due to the high flexibility of the permethyl-beta-CD rim.
No file

Dates and versions

hal-01774184 , version 1 (23-04-2018)

Identifiers

Cite

Florent Poulhes, Egon Rizzato, Patrick Bernasconi, Roselyne Rosas, Stephane Viel, et al.. Synthesis and properties of a series of beta-cyclodextrin/nitrone spin traps for improved superoxide detection. Organic & Biomolecular Chemistry, 2017, 15 (30), pp.6358--6366. ⟨10.1039/c7ob00961e⟩. ⟨hal-01774184⟩
70 View
0 Download

Altmetric

Share

Gmail Facebook X LinkedIn More