PhotoChemLab, Department of Drug Sciences, University of Catania, 95125, Catania, Italy.
Department of Science and Drug Technology, University of Torino, Via Pietro Giuria 9, 10125, Torino, Italy.
Chemistry. 2020 Oct 27;26(60):13627-13633. doi: 10.1002/chem.202001538. Epub 2020 Sep 28.
A novel molecular hybrid has been designed and synthesized in which acridine orange (AO) is covalently linked to an N-nitrosoaniline derivative through an alkyl spacer. Photoexcitation of the AO antenna with the highly biocompatible green light results in intense fluorescence emission and triggers NO detachment from the N-nitroso appendage via an intramolecular electron transfer. The presence of the AO moiety encourages the binding with DNA through both external and partially intercalative fashions, depending on the DNA:molecular hybrid molar ratio. Importantly, this dual-mode binding interaction with the biopolymer does not preclude the NO photoreleasing performances of the molecular hybrid, permitting NO to be photogenerated nearby DNA with an efficiency similar to that of the free molecule. These properties make the presented compound an intriguing candidate for fundamental and potential applicative research studies where NO delivery in the DNA proximity precisely regulated by harmless green light is required.
一种新型的分子杂化物被设计和合成，其中吖啶橙（AO）通过烷基间隔物共价连接到 N-亚硝基苯胺衍生物上。用高度生物相容性的绿光激发 AO 天线会导致强烈的荧光发射，并通过分子内电子转移从 N-亚硝基附属物上触发 NO 的脱离。AO 部分的存在通过外部和部分嵌入方式鼓励与 DNA 的结合，具体取决于 DNA：分子杂化物的摩尔比。重要的是，这种与生物聚合物的双重结合相互作用不排除分子杂化物的 NO 光释放性能，允许 NO 在 DNA 附近以类似于游离分子的效率进行光生成。这些特性使得所提出的化合物成为基础和潜在应用研究的有趣候选物，其中需要通过无害的绿光精确调节 DNA 附近的 NO 输送。
