首页|Julolidinyl aza-BODIPYs as NIR-Ⅱ fluorophores for the bioimaging of nanocarriers

Julolidinyl aza-BODIPYs as NIR-Ⅱ fluorophores for the bioimaging of nanocarriers

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The aggregation-caused quenching(ACQ)rationale has been employed to improve the fluorescence imaging accuracy of nanocarriers by precluding free probe-derived interferences.However,its usefulness is undermined by limited penetration and low spatiotemporal resolution of NIR-Ⅰ(700-900 nm)bioimaging owing to absorption and diffraction by biological tissues and tissue-derived autofluorescence.This study aimed to develop ACQ-based NIR-Ⅱ(1000-1700 nm)probes to further improve the imaging resolution and accuracy.The strategy employed is to install highly planar and electron-rich julolidine into the 3,5-position of aza-BODIPY based on the larger substituent effects.The newly developed probes displayed remarkable photophysical properties,with intense absorption centered at approximately 850 nm and bright emission in the 950-1300 nm region.Compared with the NIR-Ⅰ counterpart P2,the NIR-Ⅱ probes demonstrated superior water sensitivity and quenching stability.ACQ1 and ACQ6 exhibited more promising ACQ effects with absolute fluorescence quenching at water fractions above 40％and higher quenching stability with less than 2.0％fluorescence reillumination in plasma after 24 h of incubation.Theoretical calculations verified that molecular planarity is more important than hydrophobicity for ACQ properties.Additionally,in vivo and ex vivo reillumination studies revealed less than 2.5％signal interference from prequenched ACQ1,in contrast to 15％for P2.

3,5-JulolidinylAza-BODIPYNanocarriersNear-infrared ⅡFluorescence imagingAggregation-caused quenchingPolymeric micellesPolymeric nanoparticles

Chang Liu、Yifan Cai、Zichen Zhang、Yi Lu、Quangang Zhu、Haisheng He、Zhongjian Chen、Weili Zhao、Wei Wu

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Shanghai Skin Disease Hospital,Tongji University School of Medicine,Shanghai 200443,China

Key Laboratory of Smart Drug Delivery of MOE,School of Pharmacy,Fudan University,Shanghai 201203,China

Department of MediChinal Chemistry,School of Pharmacy,Fudan University,Shanghai 201203,China

National Natural Science Foundation of ChinaNational Natural Science Foundation of ChinaScience and Technology Commission of Shanghai Municipality,China

822738678203010721430760800

2024

10.1016/j.apsb.2024.04.002

药学学报(英文版)

药学学报(英文版)

CSTPCD
ISSN：
年,卷(期)：2024.14(7)