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Full Color Tunable Aggregation-Induced Emission Luminogen for Bioimaging Based on an Indolizine Molecular Framework
Bioconjugate Chemistry ( IF 4.7 ) Pub Date : 2020-09-28 , DOI: 10.1021/acs.bioconjchem.0c00467
Sang-Kee Choi 1 , Jungi Rho 1 , Sang Eun Yoon 1 , Jin-Hong Seok 1 , Hyungi Kim 1 , Junsik Min 1 , Woojin Yoon 2 , Sanghee Lee 3 , Hoseop Yun 2 , O-Pil Kwon 1 , Jong H Kim 1 , Wook Kim 1 , Eunha Kim 1
Affiliation  

By taking advantage of a unique mechanism of aggregation-induced emission (AIE) phenomena, AIE luminogens (AIEgens) have been provided as a solution to overcome the limitations of conventional fluorophores bearing the feature of aggregation-caused quenching (ACQ) phenomena. Especially, AIEgens paved the way to develop fluorogenic probes ideal for fluorescent imaging in live cell conditions. Despite the high demand for discovery of new AIEgens, it is still challenging to find a versatile molecular platform to generate diverse AIEgens. Herein, we report a new colorful molecular framework, Kaleidolizine (KIz), as a molecular platform for AIEgen generation. The KIz system allows systematic tuning of the emission wavelength from 455 to 564 nm via perturbation of the electron density of substituents on the indolizine core. Increasing the water fraction of the KIz solution in the THF/water mixture induces the fluorescence intensity increase up to 120-fold. Crystal structure analysis, computational calculations, and solvatochromism studies suggest that a synergistic effect between the intramolecular charge transfer and restriction of intramolecular rotation acts as the AIE mechanism in the KIz system. Conjugation of the triphenylphosphonium moiety to KIz allows successful development of triphenylphosphonium (TPP)-KIz for real-time bioimaging of innate mitochondria in live cells, thereby revealing the potential of KIz as a versatile molecular platform to generate fluorogenic probes based on AIE phenomena. We do believe the KIz system could serve as a new, reliable, and generally applicable molecular platform to develop various AIEgens having desired photophysical properties along with an excellent signal-to-noise ratio and with experimental convenience especially for fluorogenic live cell imaging.

中文翻译:

基于吲哚嗪分子框架的全色可调谐聚集诱导的发光成像生物成像。

通过利用聚集诱导发射(AIE)现象的独特机制,提供了AIE发光剂(AIEgens)作为解决方案,以克服具有聚集引起猝灭(ACQ)现象特征的常规荧光团的局限性。尤其是,AIEgens为开发适合在活细胞条件下进行荧光成像的荧光探针铺平了道路。尽管对发现新的AIEgens的需求很高,但是寻找一种通用的分子平台来产生多种AIEgens仍然是一项挑战。在这里,我们报告了一种新的多彩分子框架,Kaleidolizine(KIz),作为生成AIEgen的分子平台。KIz系统可以通过干扰吲哚嗪核心上取代基的电子密度来系统地调节455至564 nm的发射波长。增加THF /水混合物中KIz溶液的水含量会导致荧光强度增加多达120倍。晶体结构分析,计算计算和溶剂变色研究表明,分子内电荷转移与分子内旋转限制之间的协同效应是KIz系统中的AIE机制。三苯基phosph部分与KIz的缀合允许成功开发出三苯基((TPP)-KIz用于实时活细胞中先天线粒体的生物成像,从而揭示了KIz作为基于AIE现象生成荧光探针的多功能分子平台的潜力。我们相信KIz系统可以充当一种新的,可靠的,
更新日期:2020-11-18
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