Development of a unique reversible fluorescent probe for tracking endogenous sulfur dioxide and formaldehyde fluctuation <i>in vivo</i>

Ma, Yanyan; Gao, Wenjie; Zhu, Linlin; Zhao, Yuping; Lin, Weiying

doi:10.1039/c9cc04411f

Cited by 50 publications

(28 citation statements)

References 37 publications

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“…The marked emission changes (reduction and enhancement in the red and green channel, respectively) are in agreement with the isomerization of Ly-NT-SP to the merocyanine form Ly-NT-MR and subsequent reaction with lysosome SO 2 . For the control experiment, FA (formaldehyde), which is known as an inhibitor of bisulfite, was used for SO 2 imaging during heat shock …”

Section: Resultsmentioning

confidence: 99%

Heat Stroke in Cell Tissues Related to Sulfur Dioxide Level Is Precisely Monitored by Light-Controlled Fluorescent Probes

et al. 2020

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Heat stroke (HS) can cause serious organism damage or even death. Early understanding of the mechanism of heat cytotoxicity can prevent or treat heat stroke related diseases. In this work, probe Ly-NT-SP was synthesized, characterized, and used for sulfur dioxide (SO2) detection in lysosomes. PBS solutions of probe Ly-NT-SP at pH 5.0 present a marked broad emission band in the green zone (535 nm). After UV irradiation, the spiropyran group in Ly-NT-SP isomerizes to the merocyanine form (Ly-NT-MR), which presented a weak red-shifted emission at 630 nm. In addition, photocontrolled isomerization of Ly-NT-SP to Ly-NT-MR generated a CC–CN+ fragment able to react, through a Michael addition, with SO2 to yield a highly emissive adduct with a marked fluorescence in the green channel (535 nm). In vitro studies showed a remarkable selectivity of photoactivated Ly-NT-MR to SO2 with a limit of detection as low as 4.7 μM. MTT viability assays demonstrated that the Ly-NT-SP is nontoxic to HeLa cells and can be used to detect SO2 in lysosomes. Taking advantage of this, the sensor is successfully applied to image increasing SO2 values in lysosomes during heat shock for the first time. Moreover, we also confirmed that the increased SO2 can protect the small intestine against damage induced by heat shock through regulating oxidative stress in cells and mice.

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Section: Resultsmentioning

confidence: 99%

Heat Stroke in Cell Tissues Related to Sulfur Dioxide Level Is Precisely Monitored by Light-Controlled Fluorescent Probes

et al. 2020

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“…In recent years, studies have shown that the concentration and metabolic abnormalities of active sulfur-containing molecules are closely related to a variety of diseases. − For example, biothiol and hydrogen sulfide are closely related to cardiovascular diseases. The endogenous sulfur dioxide concentration is closely related to the occurrence and development of cancer. − Studying their metabolic pathways is conducive to effective intervention to prevent the occurrence and development of related major diseases.…”

Section: Introductionmentioning

confidence: 99%

A New Strategy: Distinguishable Multi-substance Detection, Multiple Pathway Tracing Based on a New Site Constructed by the Reaction Process and Its Tumor Targeting

et al. 2020

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In recent years, it has become a trend to employ organic molecular fluorescent probes with multireaction sites for the distinguishable detection and biological imaging of similar substances. However, the introduction of multireaction sites brought great challenges to organic synthesis, and at the same time, often destroyed the conjugated structure of the molecules, leading to an unsatisfactory fluorescence emission wavelength not conducive to practical application. As the eternal theme of life, metabolism goes on all the time. Metabolism is a series of ordered chemical reactions that occurs in the organism to maintain life. Chemical reactions in metabolism can be summarized as metabolic pathways. Simultaneous monitoring of different metabolic pathways of the same substance poses a lofty challenge to the probe. Here, we developed a new strategy: to construct new sites through the preliminary reactions between probes and some targets, which can be used to further distinguish among targets or detect their metabolites, so as to realize the simultaneous visualization tracer of multiple metabolic pathways. By intravenous injection, it revealed that the probe containing benzopyrylium ion can target tumors efficiently, and thiols are highly expressed in tumors compared to other tissues (heart, lung, kidney, liver, etc.). The consumption of thiols by the probe could not prevent tumor growth, suggesting that the tumor cure was not correlated with thiol concentration. The construction of new sites in the reaction process is a novel idea in the pursuit of multiple reaction sites, which will provide more effective tools for solving practical problems.

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“…To explore the interconnected biological roles between SO 2 and FA, Lin et al creatively developed the first reversible probe 98 for sensing SO 2 and FA based on the Michael addition reaction and the reaction between nucleophilic bisulfite with electrophilic FA. 119 As shown in Fig. 19, the carbazolebenzopyrylium p-conjugated system was interfered by SO 2 via the Michael addition, resulting in a hypsochromic shift of fluorescence emission (from 645 nm to 540 nm).…”

Section: Miscellaneous Approachesmentioning

confidence: 95%

Reaction-based fluorescent and chemiluminescent probes for formaldehyde detection and imaging

Huang

Liu

et al. 2022

Chem. Commun.

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Development of a unique reversible fluorescent probe for tracking endogenous sulfur dioxide and formaldehyde fluctuation in vivo

Abstract: A FRET-based reversible fluorescent probe for sensing SO2 and FA was designed. The probe was first used for imaging endogenous SO2 and FA in vitro and in vivo. Moreover, we first found that the interaction of SO2 and FA can reduce the cytotoxicity.

Cited by 50 publications

References 37 publications

Heat Stroke in Cell Tissues Related to Sulfur Dioxide Level Is Precisely Monitored by Light-Controlled Fluorescent Probes

Heat Stroke in Cell Tissues Related to Sulfur Dioxide Level Is Precisely Monitored by Light-Controlled Fluorescent Probes

A New Strategy: Distinguishable Multi-substance Detection, Multiple Pathway Tracing Based on a New Site Constructed by the Reaction Process and Its Tumor Targeting

Reaction-based fluorescent and chemiluminescent probes for formaldehyde detection and imaging

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