Screening of dicyanoisophorone-based probes for highly sensitive detection of viscosity changes in living cells and zebrafish

Kong, Fanming; Li, Ying; Xiao, Liquan; Wang, Xiaoxiu; Fu, Guanyu; Zhao, Qiuyue; Tang, Bo

doi:10.1039/d1cc03738b

Cited by 27 publications

(10 citation statements)

References 39 publications

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“…We first investigated the fluorescent properties of TIR-V lighted up by viscosity in a PBS-glycerol system. ,− As shown in Figure S1, TIR-V exhibited a distinct absorption peak at about 700 nm in PBS with a low viscosity (ε = 5 × 10 3 M –1 cm –1 ). As the viscosity of the solvent medium was increased, the maximum absorption peak of TIR-V blue-shifted to around 685 nm.…”

Section: Resultsmentioning

confidence: 99%

Precision Navigation of Venous Thrombosis Guided by Viscosity-Activatable Near-Infrared Fluorescence

Zhang

Wang

et al. 2023

Anal. Chem.

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Thrombus are blood clots formed by abnormal hemostasis in blood vessels and are closely associated with various diseases such as pulmonary embolism, myocardial infarction and stroke. Early diagnosis and treatment of thrombus is the key to reducing the high risk of thrombotic disease. Given that early thrombus is small in early size, free instability, wide regional distribution and fast formation, it is urgent to develop all-inclusive detection methods that combine high signal-to-noise ratio, in situ dynamic and rapid in-depth tissue imaging. Near-infrared (NIR) fluorescence imaging, with its excellent high spatiotemporal resolution and tissue penetration depth, is a powerful technique for direct visualization of thrombotic events in situ. Considering the fibrin highly expressed in the thrombus is a typical thrombotic target. Moreover, the viscosity of the thrombus is markedly higher than its surroundings. Therefore, we developed a fibrin-targeting and viscosity-activating thrombus NIR fluorescent probe (TIR-V) for high-resolution and high-sensitivity in situ lighten-up thrombus. TIR-V has the advantages of good thrombus targeting, significant "off−on" fluorescence specific response to viscosity, bright NIR fluorescence and good biocompatibility. The thrombus is clearly delineated by a high signal-to-noise ratio NIR fluorescence imaging, enabling imaging detection and precise navigation of thrombotic regions. This work demonstrates the potential of TIR-V as a bifunctional probe for definitive diagnostic imaging and direct navigation of thrombotic lesions in clinical applications.

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Section: Resultsmentioning

confidence: 99%

Precision Navigation of Venous Thrombosis Guided by Viscosity-Activatable Near-Infrared Fluorescence

Zhang

Wang

et al. 2023

Anal. Chem.

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“…In contrast, in high viscosity conditions, the rotation of the C–C single bond of the probe was inhibited, which restricted the probe to stay in a planar configuration, causing the probe ZL‐1 to return to the ground state via a radiation pathway. [ 29–31 ] The fluorescence intensity of the probe ZL‐1 increased markedly. Therefore, probe ZL‐1 could be used to measure viscosity variation.…”

Section: Resultsmentioning

confidence: 99%

A novel fluorescent probe with large Stokes shift for the detection of viscosity changes and its imaging in living cells

et al. 2022

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As an important cellular microenvironmental parameter, viscosity could reflect the status of living cells. Small molecular fluorescent probes are a vital tool to measure the change of viscosity in living cells. A novel fluorescence probe ZL-1 with a large Stokes shift (in methanol it reached to 153 nm and in glycerol it reached to 125 nm) and excellent sensitivity toward viscosity was developed. The sharp enhancement of the emission intensity for the probe ZL-1 from low viscous methanol to high viscous glycerol indicated that the probe ZL-1 could respond to the viscosity variations.Moreover, the probe ZL-1 has been successfully utilized to detect of the viscosity variations in living cells.

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“…Tang and fellows designed and synthesized a series of DCIbased molecular rotors with varying aromatic groups as electron donors for viscosity detection. 221 Among them, the selected probe DCO-5 (P142) displayed a large Stokes shift up to 185 nm (λ abs = 450 nm, λ em = 615 nm). In the presence of rotenone (mitochondrial complex I inhibitor), nystatin (an ionophore) and fetal bovine serum-free medium to induce starvation, both HepG2 and HeLa cells exhibited noticeable fluorescence enhancement, suggesting that DCO-5 (P142) was capable of sensing changes in intracellular viscosity stimulated by these drugs (Figure 41a).…”

Section: Other Applications Using Bodipy Derivatives For Viscosity De...mentioning

confidence: 99%

Design and Application of Fluorescent Probes to Detect Cellular Physical Microenvironments

Ma,

Sun,

Xia

et al. 2024

Chem. Rev.

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The microenvironment is indispensable for functionality of various biomacromolecules, subcellular compartments, living cells, and organisms. In particular, physical properties within the biological microenvironment could exert profound effects on both the cellular physiology and pathology, with parameters including the polarity, viscosity, pH, and other relevant factors. There is a significant demand to directly visualize and quantitatively measure the fluctuation in the cellular microenvironment with spatiotemporal resolution. To satisfy this need, analytical methods based on fluorescence probes offer great opportunities due to the facile, sensitive, and dynamic detection that these molecules could enable in varying biological settings from in vitro samples to live animal models. Herein, we focus on various types of small molecule fluorescent probes for the detection and measurement of physical parameters of the microenvironment, including pH, polarity, viscosity, mechanical force, temperature, and electron potential. For each parameter, we primarily describe the chemical mechanisms underlying how physical properties are correlated with changes of various fluorescent signals. This review provides both an overview and a perspective for the development of small molecule fluorescent probes to visualize the dynamic changes in the cellular environment, to expand the knowledge for biological process, and to enrich diagnostic tools for human diseases.

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Screening of dicyanoisophorone-based probes for highly sensitive detection of viscosity changes in living cells and zebrafish

Abstract: Herein, seven viscosity-sensitive probes were developed via simple structural modification of dicyanoisophorone (DCO)-derived dyes. Among the new dyes, DCO-5 significantly enhances (180-fold) the response signal in highly viscous aqueous media...

Cited by 27 publications

References 39 publications

Precision Navigation of Venous Thrombosis Guided by Viscosity-Activatable Near-Infrared Fluorescence

Precision Navigation of Venous Thrombosis Guided by Viscosity-Activatable Near-Infrared Fluorescence

A novel fluorescent probe with large Stokes shift for the detection of viscosity changes and its imaging in living cells

Design and Application of Fluorescent Probes to Detect Cellular Physical Microenvironments

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