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Open Access

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

  • Klaus Stolze1Email author,
  • Nataliya Rohr-Udilova2,
  • Thomas Rosenau3,
  • Andreas Hofinger3 and
  • Hans Nohl1
BMC Pharmacology20077(Suppl 2):A52

https://doi.org/10.1186/1471-2210-7-S2-A52

Published: 14 November 2007

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.

Authors’ Affiliations

(1)
Molecular Pharmacology and Toxicology Unit, Department of Natural Science, University of Veterinary Medicine
(2)
Division of Gastroenterology and Hepatology, Clinic of Internal Medicine III, Medical University of Vienna
(3)
Department of Chemistry, University of Natural Resources and Applied Life Sciences (BOKU)

Copyright

© Stolze et al; licensee BioMed Central Ltd. 2007

This article is published under license to BioMed Central Ltd.

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