Group for Organic Photochemistry, Institute for Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-University Düsseldorf, Düsseldorf, Germany.
Photochem Photobiol. 2010 Nov-Dec;86(6):1247-54. doi: 10.1111/j.1751-1097.2010.00803.x. Epub 2010 Sep 29.
Earlier we reported on the synthesis of α,4-dicarboxy-2-nitrobenyzl caged compounds (Schaper, K. et al. [2002] Eur. J. Org. Chem., 1037-1046). These compounds have the advantage of an increased hydrophilicity compared with the well-established α-carboxy-2-nitrobenzyl caged compounds; however, the release of the active compound becomes slower due to the introduction of the additional carboxy group. Based upon theoretical calculations we predicted that the release would become faster when the additional carboxy group is moved to the 5-position. Here we describe the synthesis and the photochemical and biological characterization of an α,5-dicarboxy-2-nitrobenyzl caged compound. The high hydrophilicity of the new caging group is maintained due to the fact that the additional carboxy moiety is preserved, while the release of the active species from the new derivative is even faster than for the reference, an α-CNB caged compound.
我们之前报道过α,4-二羧酸-2-硝基苄基笼状化合物的合成（Schaper, K. 等人，[2002] Eur. J. Org. Chem.，1037-1046）。与成熟的α-羧酸-2-硝基苄基笼状化合物相比，这些化合物具有更高的亲水性；然而，由于引入了额外的羧基，活性化合物的释放变得更慢。基于理论计算，我们预测当额外的羧基被移动到 5 位时，释放速度会更快。在这里，我们描述了一种α,5-二羧酸-2-硝基苄基笼状化合物的合成以及光化学和生物学特性。由于额外的羧基部分得以保留，新的笼状基团保持了较高的亲水性，而新衍生物中活性物质的释放速度甚至比参考物质，即α-CNB 笼状化合物更快。
