Egyed Alexandra, Németh Krisztina, Molnár Tibor Á, Kállay Mihály, Kele Péter, Bojtár Márton
Chemical Biology Research Group, Institute of Organic Chemistry, Research Centre for Natural Sciences, Magyar tudósok krt. 2., H-1117 Budapest, Hungary.
Hevesy György PhD School of Chemistry, Eötvös Loránd University, Pázmány Péter sétány 1/a., H-1117 Budapest, Hungary.
J Am Chem Soc. 2023 Feb 8;145(7):4026-34. doi: 10.1021/jacs.2c11499.
Herein, we present high-yielding, concise access to a set of xanthenium-derived, water-soluble, low-molecular-weight photocages allowing light-controlled cargo release in the green to red region. Very importantly, these new photocages allow installation of various payloads through ester, carbamate, or carbonate linkages even at the last stage of the synthesis. Payloads were uncaged with high efficiency upon green, orange, or red light irradiation, leading to the release of carboxylic acids, phenols, and amines. The near-ideal properties of a carboxanthenium derivative were further evaluated in the context of light-controlled drug release using a camptothecin-derived chemotherapeutic drug, SN38. Notably, the caged drug showed orders of magnitude lower efficiency , which was reinstated after red light irradiation. The presented photocages offer properties that facilitate the translation of photoactivated chemotherapy toward clinical applications.
在此，我们展示了一种高产、简洁的方法来获得一组基于呫吨的水溶性低分子量光笼，这些光笼能够在绿色到红色区域实现光控的货物释放。非常重要的是，这些新型光笼即使在合成的最后阶段也能通过酯键、氨基甲酸酯键或碳酸酯键连接安装各种负载。在绿色、橙色或红色光照射下，负载能够高效地脱笼，从而释放出羧酸、酚类和胺类。使用喜树碱衍生的化疗药物SN38，在光控药物释放的背景下进一步评估了羧基呫吨衍生物的近乎理想的性质。值得注意的是，笼形药物显示出低几个数量级的效率，在红光照射后恢复。所展示的光笼具有一些特性，有助于光激活化疗向临床应用的转化。
