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Cell Membrane-Specific Fluorescent Probe Featuring Dual and Aggregation-Induced Emissions.

ABSTRACT: A cell membrane-specific fluorescent probe was prepared by conjugating a coumarin dye with a tetraphenylethene (TPE) derivative through an α,β-unsaturated ketone connection. The probe has two absorptions: one from the TPE moiety at 300 nm and a second one due to the coumarin moiety at 458.5 nm. The probe fluoresces at 470 nm in tetrahydrofuran (THF) solution. The probe exhibits a useful aggregation-induced emission (AIE) property. A gradual increase in the water content of a THF solution causes a significant decrease and 12 nm red shift in the fluorescence peak at 470 nm, giving rise to a new strong fluorescence peak at 591 nm at a 95% water content. The probe is hydrophobic with an AIE property and binds to cell membranes, resulting in 591 nm fluorescence upon implantation into cells. The probe possesses a long retention time despite the lack of a long, cell membrane-anchored hydrophobic alkyl chain, which is typical for traditional membrane-specific probes. Our probe also displays low cytotoxicity and excellent photostability.

SUBMITTER: Zhang Y

PROVIDER: S-EPMC7347209 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:Carbon monoxide (CO) acts as an important gasotransmitter in delivering intramolecular and intermolecular signals to regulate a variety of physiological processes. This lipid-soluble gas can freely pass through the cell membrane and then diffuse to adjacent cells acting as a messenger. Although many fluorescent probes have been reported to detect intracellular CO, it is still a challenge to visualize the release behavior of endogenous CO. The main obstacle is the lack of a probe that can anchor onto the cell membrane while having the ability to image CO in real time. In this work, by grafting a polar head onto a long and linear hydrophobic Nile Red molecule, a cell membrane-anchored fluorophore ANR was developed. This design strategy of a cell membrane-anchored probe is simpler than the traditional one of using a long hydrophobic alkyl chain as a membrane-anchoring group, and endows the probe with better water solubility. ANR could rapidly bind to the cell membrane (within 1 min) and displayed a long retention time. ANR was then converted to a CO-responsive fluorescent probe (ANRP) by complexation with palladium based on a metal palladium-catalyzed reaction. ANRP exhibited a fast response to CO with a 25-fold fluorescence enhancement in vitro. The detection limit was calculated to be 0.23 μM, indicating that ANRP is sensitive enough to image endogenous CO. Notably, ANRP showed excellent cell membrane-anchoring ability. With ANRP, the release of CO from HepG2 cells under LPS- and heme-stimulated conditions was visualized and the cell self-protection effect during a drug-induced hepatotoxicity process was also studied. Moreover, ANRP was successfully applied to the detection of intracellular CO in several cell lines and tissues, and the results demonstrated that the liver is the main organ for CO production, and that cancer cells release more CO from their cells than normal cells. ANRP is the first membrane-anchored CO fluorescent probe that has the ability to reveal the relationship between CO release and diseases. It also has prospects for the studying of intercellular signaling functions of CO.

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Cell Membrane-Specific Fluorescent Probe Featuring Dual and Aggregation-Induced Emissions.

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