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A novel AIE-active imidazolium macrocyclic ratiometric fluorescence sensor for pyrophosphate anion.

ABSTRACT: An imidazolium bridged macrocyclophane was synthesized as a ratiometric fluorescence sensor with aggregation-induced emission (AIE) characteristic to detect pyrophosphate anion with high selectivity among various anions. In the presence of zinc ion, macrocyclophane can form aggregates through complexation with pyrophosphate anion and emit ratiometric fluorescence, resulting from an enhancement in its aggregate-state emission and a reduction in its monomer emission. This AIE-active macrocycle showed great potential as a ratiometric fluorescence receptor.

SUBMITTER: Xiong JB

PROVIDER: S-EPMC8981699 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature

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A novel AIE-active imidazolium macrocyclic ratiometric fluorescence sensor for pyrophosphate anion.

Xiong Jia-Bin JB Ban Ding-Ding DD Zhou Yong-Juan YJ Li Jin-Zhan JZ Chen Si-Ru SR Liu Guo-Qun GQ Tian Jing-Jing JJ Mi Li-Wei LW Li Dong-Mi DM

RSC advances 20220201 11

An imidazolium bridged macrocyclophane was synthesized as a ratiometric fluorescence sensor with aggregation-induced emission (AIE) characteristic to detect pyrophosphate anion with high selectivity among various anions. In the presence of zinc ion, macrocyclophane can form aggregates through complexation with pyrophosphate anion and emit ratiometric fluorescence, resulting from an enhancement in its aggregate-state emission and a reduction in its monomer emission. This AIE-active macrocycle sho ...[more]

PMID: 35424634

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Project description:Chemical structures bearing a combination of aggregation-induced emission enhancement (AIEE) and intramolecular charge transfer (ICT) properties attracted the attention of many researchers. Recently, there is an increasing demand to pose tunable AIEE and ICT fluorophores that could present their conformation changes-related emission colors by adjusting the medium polarity. In this study, we designed and synthesized a series of 4-alkoxyphenyl-substituted 1,8-naphthalic anhydride derivatives NAxC using the Suzuki coupling reaction to construct donor-acceptor (D-A)-type fluorophores with alkoxyl substituents of varying carbon chain lengths (x = 1, 2, 4, 6, 12 in NAxC). To explain the observation that molecules with longer carbon chains revealed unusual fluorescence enhancement in water, we study the optical properties and evaluate their locally excited (LE) and ICT states by solvent effects combined with Lippert-Mataga plots. Then, we explored the self-assembly abilities of these molecules in water-organic (W/O) mixed solutions and observed the morphology of its nanostructure using a fluorescence microscope and SEM. The results show that NAxC, x = 4, 6, 12 show different degrees of self-assembly behaviors and corresponding aggregation-induced emission enhancement (AIEE) progresses. At the same time, different nanostructures and corresponding spectral changes can be obtained by adjusting the water ratio in the mixed solution. That is, NAxC compounds present different transitions between LE, ICT and AIEE based on the polarity, water ratio and time changes. We designed NAxC as the structure-activity relationship (SAR) of the surfactant to demonstrate that AIEE comes from the formation of micelle-like nanoaggregates, which causes a restriction of the transfer from the LE state to the ICT state, and micelle formation results in a blue-shift in emission and enhances the intensity in the aggregate state. Among them, NA12C is most likely to form micelles and the most obvious fluorescence enhancement, which will switch over time due to the nano-aggregation transition.

Project description:Potassium is the most abundant intracellular metal in the body, playing vital roles in regulating intracellular fluid volume, nutrient transport, and cell-to-cell communication through nerve and muscle contraction. On the other hand, aberrant alterations in K+ homeostasis contribute to a diverse array of diseases spanning cardiovascular and neurological disorders to diabetes to kidney disease to cancer. There is an unmet need for studies of K+ physiology and pathology owing to the large differences in intracellular versus extracellular K+ concentrations ([K+]intra = 150 mM, [K+]extra = 3-5 mM). With a relative dearth of methods to reliably measure dynamic changes in intracellular K+ in biological specimens that meet the dual challenges of low affinity and high selectivity for K+, particularly over Na+, currently available fluorescent K+ sensors are largely optimized with high-affinity receptors that are more amenable for extracellular K+ detection. We report the design, synthesis, and biological evaluation of Ratiometric Potassium Sensor 1 (RPS-1), a dual-fluorophore sensor that enables ratiometric fluorescence imaging of intracellular potassium in living systems. RPS-1 links a potassium-responsive fluorescent sensor fragment (PS525) with a low-affinity, high-selectivity crown ether receptor for K+ to a potassium-insensitive reference fluorophore (Coumarin 343) as an internal calibration standard through ester bonds. Upon intracellular delivery, esterase-directed cleavage splits these two dyes into separate fragments to enable ratiometric detection of K+. RPS-1 responds to K+ in aqueous buffer with high selectivity over competing metal ions and is sensitive to potassium ions at steady-state intracellular levels and can respond to decreases or increases from that basal set point. Moreover, RPS-1 was applied for comparative screening of K+ pools across a panel of different cancer cell lines, revealing elevations in basal intracellular K+ in metastatic breast cancer cell lines vs. normal breast cells. This work provides a unique chemical tool for the study of intracellular potassium dynamics and a starting point for the design of other ratiometric fluorescent sensors based on two-fluorophore approaches that do not rely on FRET or related energy transfer designs.

Dataset Information

A novel AIE-active imidazolium macrocyclic ratiometric fluorescence sensor for pyrophosphate anion.

Publications

A novel AIE-active imidazolium macrocyclic ratiometric fluorescence sensor for pyrophosphate anion.

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