Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 14, Issue 28, Pages 6720-6728Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6ob00894a
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Funding
- National Natural Science Foundation of China [21205135]
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The regulation of copper homeostasis in lysosomes of living cells is closely related to various physiological and pathological processes. Thus, it is of urgent need to develop a fluorescent probe for selectively and sensitively monitoring the location and concentration of lysosomal Cu2+. Herein, a six-membered ring, thiosemicarbazide, was incorporated into a Si-rhodamine (SiR) scaffold for the first time, affording a SiRbased fluorescent probe SiRB-Cu. Through the effective Cu2+-triggered ring-opening process, the probe exhibits fast NIR chromogenic and fluorogenic responses to Cu2+ within 2 min as the result of formation of a highly fluorescent product SiR-NCS. Compared with a five-membered ring, the expanded ring retains great tolerance to H+, ensuring the superior sensitivity with a detection limit as low as 7.7 nM and 200-fold enhancement of relative fluorescence in the presence of 1.0 equiv. of Cu2+ in pH = 5.0 solution, the physiological pH of lysosome. Moreover, the thiosemicarbazide moiety acts not only as the chelating and reactive site, but also as an efficient lysosome-targeting group, leading to the proactive accumulation of the probe into lysosomes. Taking advantage of these distinct properties, SiRB-Cu provides a functional probe suitable for imaging exogenous and endogenous lysosomal Cu2+ with high imaging contrast and fidelity.
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