Development of highly sensitive indole and luminol chemiluminescence reagent

我们合成了多种双吲哚基马来酰亚胺(BIM)衍生物，并研究了它们的荧光(FL)和化学发光(CL)性质。我们发现BIM衍生物具有大的斯托克斯位移(200 Nm)，FL发射最大波长大于500 nm，几个FL发射和持续的化学发光(10分钟)。通过LC-ESI-MS测定化学发光反应产物，探讨了BIM可能的化学发光机理。结果表明，BIM衍生物是通过马来酰亚胺部分2，3-位上C=C键的二氧杂环己烷发射的。本研究采用计算化学的方法对实验结果进行理论分析。根据我们的实验和计算，C=C键的电子结构和马来酰亚胺部分2，3-位的C=C键的氧化是产生这些FL和CL性质的关键。这项研究为双吲哚马来酰亚胺选择性和灵敏发光分析的发展提供了重要事实。

We synthesized various bisindolylmaleimide (BIM) derivatives, and evaluated their fluorescence (FL) and chemiluminescence (CL) properties. We found BIM derivatives with large Stokes' shifts (200 nm), FL emission maxima wavelengths longer than 500 nm, several FL emissions and a lasting CL (10 min). The possible CL mechanism of BIM was studied by determinating of products after CL reactions using LC-ESI-MS. The results indicated that BIM derivatives emitted via dioxetane of C=C bond at the 2,3-position in maleimide moiety. In this study, computational chemistry was used for theoretical analysis of experimental results. The C=C bond electronic structure and oxidation of C=C bond at the 2,3-position of the maleimide moiety are crucial for producing these FL and CL properties based on our experiment and calculations. This study gives significant facts for development of selective and sensitive luminescence assays with bisindolylmaleimides.