Synthesis and biochemical applications of a solid cyclic nitrone spin trap: A relatively superior trap for detecting superoxide anions and glutathiyl radicals
Synthesis and biochemical applications of a solid cyclic nitrone spin trap: A relatively superior trap for detecting superoxide anions and glutathiyl radicals
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DOI：
10.1016/s0891-5849(01)00619-0
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发表时间：
2001-09-01
影响因子：
7.4
通讯作者：
Kalyanaraman, B
中科院分区：
文献类型：
--
作者：
Zhao, HT;Joseph, J;Kalyanaraman, B
首次合成了一种新型环状硝酮自旋陷阱，5-叔丁氧基羰基5-甲基-1-吡咯啉N-氧化物（BMPO），为纯白色固体。与现有的自旋陷阱相比，BMPO 在生物系统中硫基自由基、羟基自由基和超氧阴离子的检测和表征方面具有多种优势。相应的 BMPO 加合物表现出独特的特征电子自旋共振 (ESR) 光谱模式。与 5,5-二甲基-1-吡咯啉 N-氧化物 (DMPO) 衍生的超氧化物加合物不同，BMPO 超氧化物加合物不会非酶分解为 BMPO 羟基加合物。这一特性显然被认为是 BMPO 在其生物应用中的明显优势。此外，BMPO 谷胱甘肽加合物 (BMPO/*SG) 的 ESR 光谱与其羟基加合物的光谱不完全重叠。该光谱特征再次与 DMPO 明显不同，因为 DMPO 谷胱甘肽和羟基自由基加合物的 ESR 光谱线大部分重叠。最后，BMPO 衍生加合物的 ESR 谱在生物系统中表现出更高的信噪比。这些有利的化学和光谱特征使 BMPO 非常适合检测生化氧化和还原中的超氧阴离子、羟基和硫基自由基。 (C) 2001 爱思唯尔科学公司。
A novel cyclic nitrone spin trap, 5-tert-butoxycarbonyl 5-methyl-1-pyrroline N-oxide (BMPO) as a pure white solid has been synthesized for the first time. BMPO offers several advantages over the existing spin traps in the detection and characterization of thiyl radicals, hydroxyl radicals, and superoxide anions in biological systems. The corresponding BMPO adducts exhibit distinct and characteristic electron spin resonance (ESR) spectral patterns. Unlike the 5,5-dimethyl-1-pyrroline N-oxide (DMPO)-derived superoxide adduct, the BMPO superoxide adduct does not non-enzymatically decompose to the BMPO hydroxyl adduct. This feature is clearly perceived as a definite advantage of BMPO in its biological applications. In addition, the ESR spectrum of the BMPO glutathionyl adduct (BMPO/*SG) does not fully overlap with the spectrum of its hydroxyl adduct. This spectral feature is again distinctly different from that of DMPO because the ESR spectral lines of DMPO glutathionyl and hydroxyl radical adducts largely overlap. Finally, the ESR spectra of BMPO-derived adducts exhibit a much higher signal-to-noise ratio in biological systems. These favorable chemical and spectroscopic features make BMPO ideal for the detection of superoxide anions, hydroxyl and thiyl radicals in biochemical oxidation and reduction. (C) 2001 Elsevier Science Inc.