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Spin trapping experiments with ethyl-substituted EMPO derivatives (EEMPO)

Free radicals in biological systems play a major role in the onset of many diseases, e.g. oxygen-centered radicals such as hydroxyl or superoxide radicals. In order to identify and localize these radicals a series of four novel spin traps have been developed and their structure fully characterized by [1H]- and [13C]-NMR spectroscopy as well as mass spectrometry. The novel compounds can be described as ethyl-substituted EMPO derivatives, namely 5-ethoxycarbonyl-3-ethyl-5-methyl-pyrroline N-oxide (3,5-EEMPO), 5-ethoxycarbonyl-4-ethyl-5-methyl-pyrroline N-oxide (4,5-EEMPO), 5-ethoxycarbonyl-5-ethyl-3-methyl-pyrroline N-oxide (5,3-EEMPO) and 5-ethoxycarbonyl-5-ethyl-4-methyl-pyrroline N-oxide (5,4-EEMPO). Their spin trapping behaviour towards a series of different oxygen- and carbon-centered radicals is described. All compounds were obtained in two different stereochemical forms (cis and trans), but only 3,5-EEMPO and 5,3-EEMPO could be separated into the different diastereomers using conventional chromatographic procedures. The cis- and trans-forms exhibited considerably different spectral parameters and stabilities of the respective superoxide adducts (ranging from about 12 to 35 min). In addition, spin adducts obtained from different carbon-centered radicals derived from methanol, ethanol, formic acid and linoleic acid hydroperoxide have also been characterized.

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Correspondence to Klaus Stolze.

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Open Access This article is published under license to BioMed Central Ltd. This is an Open Access article is distributed under the terms of the Creative Commons Attribution 2.0 International License (, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Stolze, K., Rohr-Udilova, N., Rosenau, T. et al. Spin trapping experiments with ethyl-substituted EMPO derivatives (EEMPO). BMC Pharmacol 7 (Suppl 2), A52 (2007).

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