The covalent attachment of cargo molecules (e.g., drugs and fluorophores) in β-position to a disulfide moiety through carbamate and carbonate bonds finds many applications in responsiverelease systems. Recently, we showed that the combination of this release process with polymer mechanochemistry-induced disulfide scission enabled the remote-controlled release of small molecule drugs and fluorophores from their inactive parent macromolecules using ultrasound. The nature of the linker bond largely governed the subsequent release kinetics, an aspect that has not been investigated so far. To compare the differences, we here employ disulfide-centered polymers releasing either hydroxyl- or amino-naphthalimides from their respective β-carbonate or -carbamate linkers by force-induced intramolecular 5-exo-trig cyclization. We present the synthesis, characterization, and cell imaging evaluation of three naphthalimides featuring colorimetric and green fluorescence turn-on upon release, allowing monitoring of the release process. We believe that the insights gained from these experiments would advance the tailoring of release rates for force-induced pharmacotherapy.

货物分子（例如，药物和荧光团）通过氨基甲酸酯和碳酸酯键在 β 位与二硫化物部分的共价连接在响应释放系统中得到了许多应用。最近，我们表明，这种释放过程与聚合物机械化学诱导的二硫键断裂相结合，可以使用超声波从其非活性母体大分子中远程控制释放小分子药物和荧光团。连接键的性质在很大程度上决定了随后的释放动力学，这是迄今为止尚未研究的方面。为了比较差异，我们在这里使用以二硫化物为中心的聚合物，通过力诱导的分子内 5 -exo-trig从它们各自的 β-碳酸酯或 -氨基甲酸酯接头中释放羟基-或氨基-萘二甲酰亚胺环化。我们介绍了三种萘酰亚胺的合成、表征和细胞成像评估，其特征是释放时会开启比色和绿色荧光，从而可以监测释放过程。我们相信，从这些实验中获得的见解将推动力诱导药物治疗释放速率的定制。