Departamento de Química y Edafología, Facultad de Ciencias, Universidad de Navarra, 31080, Pamplona, Spain.
J Phys Chem B. 2010 Aug 19;114(32):10541-9. doi: 10.1021/jp103546u.
The chemiluminescence (CL) yield of two isoluminol derivatives, N-(4-aminobutyl)-N-ethylisoluminol (ABEI) and N-(6-aminohexyl)-N-ethylisoluminol (AHEI), is remarkably increased in the presence of natural cyclodextrins (CDs). The most notable effect is produced by the addition of gamma-CD that produces enhancements up to 15-fold in the light emission of both compounds. Although proton nuclear magnetic resonance ((1)H NMR) measurements prove the encapsulation of these luminescent reagents in the CDs, with more stable associations by decreasing the width of the CD cavity, the improvement in the light emission of ABEI and AHEI is mainly due to the topology of the complexes. Evaluation of the rotating frame Overhauser effect spectroscopy (ROESY) spectra cross-peaks combined with semirigid-docking simulations has been used to gather information about the spatial conformation of the guest molecules into the CDs. These calculations have shown that a deeper inclusion in the CD cavity of the heterocyclic moiety of the luminescent molecules is directly related with a higher enhancement in the CL. The augment of the CL by natural CDs is of interest for increasing the detection limit in biochemical assays or liquid chromatography, for example, in which the CL of these compounds serves to quantify other molecular species that may take part, direct or indirectly, in the luminescent reaction.
两种异鲁米诺衍生物，N-(4-氨基丁基)-N-乙基异鲁米诺（ABEI）和 N-(6-氨基己基)-N-乙基异鲁米诺（AHEI）的化学发光（CL）产率在天然环糊精（CDs）的存在下显著增加。最显著的效果是添加γ-CD 产生的，这两种化合物的发光增强了 15 倍。尽管质子核磁共振（1H NMR）测量证明这些发光试剂被包封在 CDs 中，但通过减小 CD 腔的宽度，形成更稳定的结合，ABEI 和 AHEI 的发光增强主要归因于配合物的拓扑结构。评估旋转框架奥弗豪瑟效应光谱（ROESY）谱交叉峰结合半刚性对接模拟，用于收集有关客体分子在 CDs 中空间构象的信息。这些计算表明，发光分子的杂环部分在 CD 腔中的更深包埋与更高的 CL 增强直接相关。天然 CDs 对 CL 的增强对于提高生物化学分析或液相色谱中的检测限很有意义，例如，这些化合物的 CL 用于定量可能直接或间接参与发光反应的其他分子物种。
