A guideline for design of photoinduced electron transfer-based viscosity probe with rigid fluorophore-quencher configuration

Gao, Yong; Qiu, Jianwen; Li, Meng; Xiong, Xinyi; Zhu, Hu

doi:10.1016/j.cej.2023.143100

Cited by 10 publications

(4 citation statements)

References 37 publications

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“…To date, the mechanism of action of PET-based probes has been extensively studied . For instance, de Silva and co-workers examined the mechanism of PET probes containing fluorophore-spaced configurations of bursting agents. − They postulated a hypothesis suggesting that the activation of PET (referred to as a-PET) occurs when the energy level of HOMO of the “bursting agent” (otherwise known as the donor) is greater than that of the fluorophore (Δ E = E HOMO,fluorophore – E HOMO,quencher < 0); similarly, when the “bursting agent” (also known as the acceptor) has a more stable LUMO than the fluorophore (Δ E = E LUMO,quencher – E LUMO,fluorophore < 0), PET can be activated (named d-PET).…”

Section: Resultsmentioning

confidence: 99%

Ratiometric Near-Infrared Fluorescent Probe Monitors Ferroptosis in HCC Cells by Imaging HClO in Mitochondria

Zhao,

Xu,

Wen

et al. 2024

Anal. Chem.

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Hypochlorous acid (HClO) is a typical endogenous ROS produced mainly in mitochondria, and it has strong oxidative properties. Abnormal HClO levels lead to mitochondrial dysfunction, strongly associated with various diseases. It has been shown that HClO shows traces of overexpression in cells of both ferroptosis and hepatocellular carcinoma (HCC). Therefore, visualization of HClO levels during ferroptosis of HCC is important to explore its physiological and pathological roles. So far, there has been no report on the visualization of HClO in ferroptosis of HCC. Thus, we present a ratiometric near-infrared (NIR) fluorescent probe Mito-Rh-S which visualized for the first time the fluctuation of HClO in mitochondria during ferroptosis of HCC. Mito-Rh-S has an ultrafast response rate (2 s) and large emission shift (115 nm). Mito-Rh-S was constructed based on the PET sensing mechanism and thus has a high signal-to-noise ratio. The cell experiments of Mito-Rh-S demonstrated that Fe 2+ -and erastin-induced ferroptosis in HepG2 cells resulted in elevated levels of mitochondrial HClO and that high concentration levels of Fe 2+ and erastin cause severe mitochondrial damage and oxidative stress and had the potential to kill HepG2 cells. By regulating the erastin concentration, erastin induction time, and treatment of the ferroptosis model, Mito-Rh-S can accurately detect the fluctuation of mitochondrial HClO levels during ferroptosis in HCC.

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Section: Resultsmentioning

confidence: 99%

Ratiometric Near-Infrared Fluorescent Probe Monitors Ferroptosis in HCC Cells by Imaging HClO in Mitochondria

Zhao,

Xu,

Wen

et al. 2024

Anal. Chem.

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“…Since traditional 9-position phenyl group-substituted rhodamine dyes have a small Stokes shift, which are adverse to imaging, our previous study proved that amine substituents can alter this defect and improve the signal-to-noise ratio. − Therefore, we used n -propylamine to replace the 9-position of the Si-rhodamine mother nucleus to improve Stokes shift. In addition, most of the viscosity-responsive probes , have lower fluorescence brightness, photostability, and nonspecific interactions, which create image distortion. On the other hand, their rotors are bulky or the molecular weights are relatively large, which makes the synthesis relatively complex.…”

Section: Resultsmentioning

confidence: 99%

Rational Design of Near-Infrared Fluorescent Probes for Accurately Tracking Lysosomal Viscosity with Allyl Snchoring Si-Rhodamine

Xiang

Zhou

et al. 2023

Chemical & Biomedical Imaging

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The abnormal microenvironment parameter, viscosity, is closely connected with various diffusion processes, signal transduction, molecule interactions, and various diseases. It is greatly significant to design viscosity-dependent near-infrared (NIR) small molecule fluorescence probes for visualizing biological processes or diagnosing diseases. Herein, through the stepwise modulating structure of the silicon−rhodamine fluorophore (SR), we report three viscosity probes with allyl or methyl group as rotors, named SR-T-Al, SR-S-Al, and SR-T-Me. Among them, SR-T-Al demonstrates better viscosity responsibility from 1.0 to 1410.4 cP of viscosity. Therefore, the probe of SR-T-Al is successfully applied to sensitively monitor lysosome microscopic viscosity changes of living cells induced by oxygen stress. What's more, based on its advantages in NIR emission (669 nm) and large Stokes shift (201 nm), we also use it to image variations of viscosity in an acute hepatitis mouse induced by carbon tetrachloride. Both time and concentration-dependent induction models display the great ability of SR-T-Al to detect viscosity alteration. All the experimental results indicated that this allyl-rotor-based NIR viscosity probe could provide a general platform to monitor abnormal physiological processes and diseases relating to viscosity.

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“…In a rare attempt to develop photoinduced electron transfer (PET)-based viscosity probes, a range of phenyl-rhodol compound featuring a fluorophore-quencher arrangement were formulated and synthesized by Yong Gao et al 57 In the present study, rhodol was employed as the stable fluorophore component, while a series of mono and disubstituted benzenes were incorporated as the movable quencher element. Through systematic alterations of the substituent groups on the phenyl rings, the connection between the switchable photoinduced electron transfer (PET) and the responsiveness of these derivatives to changes in viscosity was investigated.…”

Section: Examples Of Prominent Viscosity Probesmentioning

confidence: 99%

“…Gao et al fabricated a wide variety of phenyl-rhodol derivatives constituted of fluorophore-quencher combinations. 57 They connected a rhodol unit to a diverse range of phenyl rings comprising a range of substituents from a strongly electron-donating one like the methoxy group to a strongly electron-withdrawing one like the nitro group (Fig. 10).…”

Section: Examples Of Prominent Viscosity Probesmentioning

confidence: 99%

Mechanistic analysis of viscosity-sensitive fluorescent probes for applications in diabetes detection

Sreejaya,

M Pillai,

et al. 2024

J. Mater. Chem. B

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A guideline for design of photoinduced electron transfer-based viscosity probe with rigid fluorophore-quencher configuration

Cited by 10 publications

References 37 publications

Ratiometric Near-Infrared Fluorescent Probe Monitors Ferroptosis in HCC Cells by Imaging HClO in Mitochondria

Ratiometric Near-Infrared Fluorescent Probe Monitors Ferroptosis in HCC Cells by Imaging HClO in Mitochondria

Rational Design of Near-Infrared Fluorescent Probes for Accurately Tracking Lysosomal Viscosity with Allyl Snchoring Si-Rhodamine

Mechanistic analysis of viscosity-sensitive fluorescent probes for applications in diabetes detection

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