Küllmer Florian, Gregor Lucas, Arndt Hans-Dieter
Institute for Organic Chemistry and Macromolecular Chemistry, Friedrich-Schiller-University, Humboldtstr. 10, 07743 Jena, Germany.
Org Biomol Chem. 2022 May 26;20(20):4204-4214. doi: 10.1039/d2ob00214k.
Suitable designed photoswitches based on azobenzenes are essential structural features for photopharmacological compounds. Optimized azobenzenes are important for serving as building blocks in "azo extension" strategies, and for designing photodrugs with tailored properties. Herein we present the synthesis and characterization of a variety of asymmetric azobenzenes by addressing selected structural features of the diazene core, such as polarity, steric demand, and electronic properties. Systematic exploration led to photoswitches with a relaxation half-life of seconds, minutes, hours, or days. Furthermore, the influence of different substitution patterns on the photophysical properties was charted. For analysis of all switches, robust characterization as well as examination under near-to physiological conditions was established, in order to assist with photoswitch choice for specific biological applications.
基于偶氮苯的合适设计的光开关是光药理学化合物的基本结构特征。优化的偶氮苯对于作为“偶氮扩展”策略中的构建块以及设计具有定制性质的光药物非常重要。在此，我们通过研究重氮烯核心的选定结构特征，如极性、空间需求和电子性质，展示了多种不对称偶氮苯的合成与表征。系统的探索导致了具有秒、分钟、小时或天的弛豫半衰期的光开关。此外，还绘制了不同取代模式对光物理性质的影响。为了分析所有开关，建立了强大的表征方法以及在接近生理条件下的检测，以帮助为特定生物应用选择光开关。
