Dai Shuhui, Tao Maliang, Zhong Yuan, Li Zixiong, Liang Jianshu, Chen Dongcheng, Liu Kai, Wei Binbin, Situ Bo, Gao Meng, Tang Ben Zhong
National Engineering Research Center for Tissue Restoration and Reconstruction, Key Laboratory of Biomedical Engineering of Guangdong Province, Key Laboratory of Biomedical Materials and Engineering of the Ministry of Education, Innovation Center for Tissue Restoration and Reconstruction, School of Materials Science and Engineering, South China University of Technology, Guangzhou, 510006, China.
Department of Laboratory Medicine, Nanfang Hospital, Southern Medical University, Guangzhou, 510515, China.
Adv Mater. 2023 Apr;35(15):e2209940. doi: 10.1002/adma.202209940. Epub 2023 Mar 4.
Red-to-near-infrared (NIR) fluorescent probes, with advantages such as high spatiotemporal resolution and in situ sensing abilities, are highly attractive for diagnosis of gastrointestinal diseases and targeted drug development. However, conventional red-to-NIR fluorophores with electron closed-shell structures require tedious synthetic procedures for preparation, and it is difficult to further decorate them with sensing groups. In this study, a series of easily prepared pyrroles with simple structures that can quickly be transformed into red-to-NIR emissive radical cations in acidic buffer solution and in vivo stomachs is developed. The in-situ-generated red-to-NIR emissive pyrrole radical cations in the stomach have excellent biocompatibility and stability and can be used not only for intravital gastrointestinal imaging with high spatiotemporal resolution, but also for dynamic monitoring of the gastric emptying process and assessment of anti-gastric-acid therapy. The acidity-induced generation of pyrrole radical cations is believed to provide a facile strategy for developing red-to-NIR fluorophores and studying gastrointestinal diseases.
红到近红外（NIR）荧光探针具有高时空分辨率和原位传感能力等优点，在胃肠道疾病诊断和靶向药物开发方面极具吸引力。然而，具有电子闭壳结构的传统红到近红外荧光团需要繁琐的合成步骤来制备，并且很难用传感基团对其进行进一步修饰。在本研究中，开发了一系列结构简单、易于制备的吡咯，它们在酸性缓冲溶液和体内胃部中能快速转化为红到近红外发射的自由基阳离子。胃中原位生成的红到近红外发射的吡咯自由基阳离子具有优异的生物相容性和稳定性，不仅可用于高时空分辨率的活体胃肠道成像，还可用于动态监测胃排空过程和评估抗酸治疗效果。酸度诱导的吡咯自由基阳离子生成被认为是开发红到近红外荧光团和研究胃肠道疾病的一种简便策略。
