Inclusion complexes of EMPO derivatives with 2,6-di-O-methyl-β- cyclodextrin: Synthesis, NMR and EPR investigations for enhanced superoxide detection

David Bardelang, Antal Rockenbauer, Hakim Karoui, Jean Pierre Finet, Inga Biskupska, Karol Banaszak, Paul Tordo

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

The free radical trapping properties of eight 5-alkoxycarbonyl-5-methyl-1- pyrroline N-oxide (EMPO) type nitrones and those of 5,5-dimethyl-1-pyrroline N-oxide (DMPO) were evaluated for trapping of superoxide anion radicals in the presence of 2,6-di-O-methyl-β-cyclodextrin (DM-β-CD). 1H-NMR titrations were performed to determine both stoichiometries and binding constants for the diamagnetic nitrone-DM-β-CD equilibria. EPR titrations were then performed and analyzed using a two-dimensional EPR simulation program affording 1: 1 and 1: 2 stoichiometries for the nitroxide spin adducts with DM-β-CD and the associated binding constants after spin trapping. The nitroxide spin adducts associate more strongly with DM-β-CD than the nitrones. The ability of the nitrones to trap superoxide, the enhancement of the EPR signal intensity and the supramolecular protection by DM-β-CD against sodium l-ascorbate reduction were evaluated.

Original languageEnglish
Pages (from-to)2874-2882
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume4
Issue number15
DOIs
Publication statusPublished - Jul 27 2006

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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