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首页> 外文期刊>Biochemical Pharmacology >Spin adduct formation from lipophilic EMPO-derived spin traps with various oxygen- and carbon-centered radicals.
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Spin adduct formation from lipophilic EMPO-derived spin traps with various oxygen- and carbon-centered radicals.

机译：从亲脂性EMPO衍生的自旋阱中形成具有多种氧和碳中心自由基的自旋加合物。

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摘要

Free radicals are involved in the onset of many diseases, therefore the availability of adequate spin traps is crucial to the identification and localization of free radical formation in biological systems. In recent studies several hydrophilic compounds of 2-ethoxycarbonyl-2-methyl-pyrroline-N-oxide (EMPO) have been found to form rather stable superoxide spin adducts with half-lives up to twenty minutes at physiological pH. This is a major improvement over DMPO (t(1/2)=ca. 45s), and even over DEPMPO (t(1/2)=ca. 14min), the best commercially available spin trap for the unambiguous detection of superoxide radicals. In order to allow the detection of superoxide and also other radicals in lipid environment a series of more lipophilic derivatives of EMPO was synthesized and their structure unambiguously characterized by (1)H and (13)C NMR spectroscopy. In this way, six different compounds with a n-butyl group in position 5 and either an ethoxy- (EBPO), propoxy- (PBPO), iso-propoxy- (iPBPO), butoxy- (BBPO),sec-butoxy- (sBBPO) or tert-butoxycarbonyl group (tBBPO) in position 5 of the pyrroline ring were obtained and fully analytically characterized (NMR, IR). The stability of the superoxide adducts of all investigated spin traps were comparable with EMPO (t(1/2)=ca. 8min), except for the two compounds bearing an additional methyl group in position 3 or 4 of the pyrroline ring, 5-butyl-5-ethoxycarbonyl-3-methyl-pyrroline-N-oxide (BEMPO-3) and 5-butyl-5-ethoxycarbonyl-4-methyl-pyrroline-N-oxide (BEMPO-4), of which the superoxide adducts were stable for more than 30min. Spin adducts of other carbon- and oxygen-centered radicals were also investigated.
机译：自由基与许多疾病的发作有关，因此是否有足够的自旋阱对于生物系统中自由基形成的鉴定和定位至关重要。在最近的研究中，已发现2-乙氧基羰基-2-甲基-吡咯啉-N-氧化物（EMPO）的几种亲水性化合物可形成相当稳定的超氧化物自旋加合物，在生理pH下的半衰期长达二十分钟。这是对DMPO（t（1/2）= ca.45s）甚至是DEPMPO（t（1/2）= ca.14min）的重大改进，后者是用于明确检测超氧化物自由基的最佳市售自旋阱。为了允许在脂质环境中检测超氧化物以及其他自由基，合成了一系列更多的EMPO亲脂性衍生物，并通过（1）H和（13）C NMR光谱清楚地表征了它们的结构。这样，六种不同的化合物在位置5上带有正丁基，并且具有乙氧基-（EBPO），丙氧基-（PBPO），异丙氧基-（iPBPO），丁氧基-（BBPO），仲丁氧基-（获得了吡咯啉环第5位的sBBPO）或叔丁氧羰基（tBBPO），并进行了完全分析表征（NMR，IR）。所有研究的自旋阱的超氧化物加合物的稳定性均与EMPO相当（t（1/2）=约8分钟），除了在吡咯啉环的3或4位带有5个甲基的化合物丁基-5-乙氧基羰基-3-甲基吡咯啉-N-氧化物（BEMPO-3）和5-丁基-5-乙氧基羰基-4-甲基吡咯啉-N-氧化物（BEMPO-4），其中超氧化物加合物为稳定超过30分钟。还研究了其他以碳和氧为中心的自由基的自旋加合物。

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