A Synthetic Strategy for Multi-Functionalized Phospharhodamines via Catalytic P-Arylation
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN(2023)
摘要
The visualization of complex biological events in living cells is highly reliant on the development of sophisticated fluorescent probes with multiple functions. Herein, we report a general synthetic strategy for the synthesis of near-infrared-emissive phospharhodamines (PORs) bearing various types of aryl groups on their bridging phosphorus atoms. This versatile approach utilizes a Ni-catalyzed P-arylation that allows for the design of POR-based multi-functionalized fluorescent probes. We found that PORs substituted with an aminophenyl group exhibited pH-responsive fluorescence intensity, where photo-induced electron transfer occurs to quench the fluorescence. The combination of our new approach with conventional modification at the 9-position of the xanthene skeleton facilitates the development of multi-functionalized fluorescent probes. As one demonstration of this method, we synthesized a fluorescence probe that can selectively visualize the lysosomes that result from endosomal maturation.
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关键词
Catalytic arylation, NIR fluorophores, pH probes
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