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

Florent Poulhes 1 Egon Rizzato 1 Patrick Bernasconi Roselyne Rosas 2 Stephane Viel 1 Laszlo Jicsinszky 3 Antal Rockenbauer 4 David Bardelang 1 Didier Siri 1 Anouk Gaudel-Siri 1 Hakim Karoui 1 Micael Hardy 1 Olivier Ouari 5
1 ICR - Institut de Chimie Radicalaire
2 AMU SPEC - Spectropôle - Aix Marseille Université
3 Cyclolab recherche et développement, PO Box 435, H-1525 Budapest, Hongrie
4 Institute of Materials and Environmental Chemistry [Budapest]
5 LCP - Laboratoire Chimie Provence
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.
Keywords : conjugate cyclic nitrone depmpo epr inclusion in-vivo metabolic stability radical adducts resonance trapping properties
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Submitted on : Monday, April 23, 2018 - 2:41:42 PM
Last modification on : Friday, January 7, 2022 - 3:53:28 AM

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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 and Biomolecular Chemistry, Royal Society of Chemistry, 2017, 15 (30), pp.6358--6366. ⟨10.1039/c7ob00961e⟩. ⟨hal-01774184⟩

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