Synthesis and characterization of a practically better DEPMPO-type spin trap, 5-(2,2-dimethyl-1,3-propoxy cyclophosphoryl)-5-methyl-1-pyrroline N-oxide (CYPMPO)
Synthesis and characterization of a practically better DEPMPO-type spin trap, 5-(2,2-dimethyl-1,3-propoxy cyclophosphoryl)-5-methyl-1-pyrroline N-oxide (CYPMPO)
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DOI：
10.1080/10715760600883254
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发表时间：
2006-11-01
影响因子：
3.3
通讯作者：
Kotake, Yashige
中科院分区：
文献类型：
--
作者：
Kamibayashi, Masato;Oowada, Shigeru;Kotake, Yashige
评估了一种新型环状 DEPMPO 型硝酮 5-(2,2-二甲基-1,3-丙氧基环磷酰基)-5-甲基-1-吡咯啉 N-氧化物 (CYPMPO) 对羟基和超氧自由基的自旋捕获能力。 CYPMPO是无色结晶，易溶于水。在环境条件下，固体和稀释的水溶液至少 1 个月内都没有产生电子自旋共振 (ESR) 信号。 CYPMPO 可以在化学和生物系统中自旋捕获超氧化物和羟基自由基，并且 ESR 光谱很容易分配。在紫外线照射的过氧化氢溶液中产生的 CYPMPO 超氧化物加合物的半衰期约为 15 分钟，在次黄嘌呤 (HX)/黄嘌呤氧化酶 (XOD) 等生物系统中，超氧化物加合物的半衰期约为 50 分钟。在紫外线照射的过氧化氢溶液中，没有从超氧化物加合物转化为羟基加合物。虽然CYPMPO的整体自旋捕获能力与DEPMPO相似，但其高熔点、低吸湿性和长保质期对于实际应用非常有利。
5-(2,2-Dimethyl-1,3-propoxy cyclophosphoryl)-5-methyl-1-pyrroline N-oxide (CYPMPO), a new cyclic DEPMPO-type nitrone was evaluated for spin-trapping capabilities toward hydroxyl and superoxide radicals. CYPMPO is colorless crystalline and freely soluble in water. Both the solid and diluted aqueous solution did not develop electron spin resonance (ESR) signal for at least 1 month at ambient conditions. CYPMPO can spin-trap superoxide and hydroxyl radicals in both chemical and biological systems, and the ESR spectra are readily assignable. Half life for the superoxide adduct of CYPMPO produced in UV-illuminated hydrogen peroxide solution was approximately 15 min, and in biological systems such as hypoxanthine (HX)/xanthine oxidase (XOD) the half-life of the superoxide adduct was approximately 50 min. In UV-illuminated hydrogen peroxide solution, there was no conversion from the superoxide adduct to the hydroxyl adduct. Although overall spin-trapping capabilities of CYPMPO are similar to DEPMPO, its high melting point, low hygroscopic property, and the long shelf-life would be highly advantageous for the practical use.