Red AIE-Active Fluorescent Probes with Tunable Organelle-Specific Targeting

作者：Alam, Parvej; He, Wei; Leung, Nelson L. C.; Ma, Chao; Kwok, Ryan T. K.; Lam, Jacky W. Y.; Sung, Herman H. Y.; Williams, Ian D.; Wong, Kam Sing; Tang, Ben Zhong^*

来源：Advanced Functional Materials, 2020, 30(10): 1909268.

DOI：10.1002/adfm.201909268

• aggregation-induced emission
• bioimaging
• endoplasmic reticulum
• zwitterionic

Cell staining is a fascinating research area where monitoring and visualizing different cell organelles can be done using fluorescence techniques. However, the design and synthesis of organelle-targeting fluorophores is still a challenge for several specific organelles. Herein, a platform for synthesizing efficient red-emitting aggregation-induced emission luminogens (AIEgens) with donor-acceptor characteristics is reported. The core molecule can be easily functionalized in order to modulate organelle targeting. The three synthesized AIEgens exhibit quantum yields of up to 39.3% and two-photon absorption cross-section values of up to 162 GM. The two zwitterionic AIEgens, CDPP-3SO(3) and CDPP-4SO(3,) with the sulfonate function group, are successfully utilized for specific one-photon and two-photon imaging of the endoplasmic reticulum (ER) in live human cells. Substituting the zwitterionic nature with a singly positive charge group, one-photon and two-photon imaging of CDPP-BzBr shows mitochondrial specificity, indicating the importance of the zwitterionic group for ER-targeting. Owing to the good in vitro photostability, cell viability, and high efficiency, these red dyes serve as a good potential candidate for specific organelle targeting, as well as illustrate how such a platform can easily aid in the study of structure-property relationships for designing such probes.

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