α-Phenyl-N-tert-butylnitrone-type derivatives bound to β-cyclodextrins: Syntheses, thermokinetics of self-inclusion and application to superoxide spin-trapping

David Bardelang, Laurence Charles, Jean Pierre Finet, Laszlo Jicsinszky, Hakim Karoui, Sylvain R.A. Marque, Valérie Monnier, Antal Rockenbauer, Roseline Rosas, Paul Tordo

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

α-Phenyl-ZV-Zerr-butylnitrone (PBN) derivatives bound to β-cyclodextrin derivatives have been synthesized. Inclusion of the PBN group into the β-cyclodextrin moiety is host- and temperature-dependent. In the case of the nitrone linked to permethylated cyclodextrin (Me3CD-PBN), the thermokinetic parameters are in favour of a slow chemical exchange between a tight and a loose complex. In contrast. 2,6-di-O-Me-β-cyclodextrin-grafted PBN (Me2CD-PBN) exists either in a fast exchange or as a strongly self-associated complex. The covalent cyclodextrin - PBN compounds have been used to trap carbon and oxygen-centred free radicals. The self-associated forms of the β-CD-spin-traps are compatible with effective spin-trapping, affording spin-adducts with enhanced EPR signal intensities relative to noncovalent CD-nitrone systems or the nitrone alone. This kind of cyclodextrin-bound nitrone is the first type of covalent supramolecular spin-trap and should open new possibilities for the study of biological free radicals in vivo.

Original languageEnglish
Pages (from-to)9344-9354
Number of pages11
JournalChemistry - A European Journal
Volume13
Issue number33
DOIs
Publication statusPublished - Jan 1 2007

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Keywords

  • Cyclodextrins
  • EPR spectroscopy
  • Spin trapping
  • Superoxide
  • Supramolecular chemistry

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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