Very stable superoxide radical adducts of 5-ethoxycarbonyl- 3,5-dimethyl-pyrrolineN-oxide (3,5-EDPO) and its derivatives


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Abstract

Oxygen radicals are involved in the onset of many diseases. Adequate spin traps are required for identification and localisation of free radical formation in biological systems. Superoxide spin adducts with half-lives up to 20 min at physiological pH have recently been reported to be formed from derivatives of the spin trap 5-ethoxycarbonyl-5-methyl-1-pyrroline N-oxide (EMPO). This is a major improvement over DMPO (t1/2 ca. 45 s), and even DEPMPO (t1/2 ca. 14 min). In this study, an additional methyl group was introduced into position 3 or 4 of the pyrroline ring which greatly increases the stability of the respective superoxide spin adducts. In addition, the ethoxy group of EMPO was exchanged by either a propoxy- or an iso-propoxy group in order to test the influence of increasing lipophilic properties of the investigated spin traps. The structure of all compounds was confirmed by 1H and 13C-NMR with full signal assignment. In comparison with EMPO (t1/2 ca. 8 min) or DEPMPO (t1/2 ca. 14 min), the superoxide adducts of all novel spin traps were considerably higher (t1/2 ca. 12–55 min). In addition, various other spin adducts obtained from oxygen-centered as well as carbon-centered radicals (e.g. derived from methanol or linoleic acid hydroperoxide) were also detected.

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