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  • Title: Alpha-phenyl-N-tert-butylnitrone-type derivatives bound to beta-cyclodextrins: syntheses, thermokinetics of self-inclusion and application to superoxide spin-trapping.
    Author: Bardelang D, Charles L, Finet JP, Jicsinszky L, Karoui H, Marque SR, Monnier V, Rockenbauer A, Rosas R, Tordo P.
    Journal: Chemistry; 2007; 13(33):9344-54. PubMed ID: 17729216.
    Abstract:
    alpha-Phenyl-N-tert-butylnitrone (PBN) derivatives bound to beta-cyclodextrin derivatives have been synthesized. Inclusion of the PBN group into the beta-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-beta-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 beta-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.
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