A Simple Long-wavelength Fluorescent Probe for Simultaneous Discrimination of Cysteine/Homocysteine and Glutathione/Hydrogen Sulfide with Two Separated Fluorescence Emission Channels by Single Wavelength Excitation

Zhu, Hanchuang; Liu, Caiyun; Zhang, Hanming; Jia, Pan; Li, Zilu; Zhang, Xue; Yu, Yanyan; Sheng, Wenlong; Zhu, Baocun

doi:10.2116/analsci.19p214

Cited by 10 publications

(5 citation statements)

References 61 publications

(42 reference statements)

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“…Probe 557 was further used to image the time-dependent generation of H 2 S from H 2 S donor ADT-OH in A549 cells. Probe 558 was reported independently by Cao and Ye as well as by Liu and Sheng to discriminate between H 2 S, Cys, and GSH. , This probe was shown to provide different fluorescent responses depending on the analyte with an H 2 S response at 652 nm, which was also demonstrated in MCF-7 and Raw 264.7 cells.…”

Section: Electrophilic H2s Probesmentioning

confidence: 94%

Activity-Based Fluorescent Probes for Hydrogen Sulfide and Related Reactive Sulfur Species

Fosnacht,

Pluth

2024

Chem. Rev.

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Hydrogen sulfide (H 2 S) is not only a well-established toxic gas but also an important small molecule bioregulator in all kingdoms of life. In contemporary biology, H 2 S is often classified as a "gasotransmitter," meaning that it is an endogenously produced membrane permeable gas that carries out essential cellular processes. Fluorescent probes for H 2 S and related reactive sulfur species (RSS) detection provide an important cornerstone for investigating the multifaceted roles of these important small molecules in complex biological systems. A now common approach to develop such tools is to develop "activitybased probes" that couple a specific H 2 S-mediated chemical reaction to a fluorescent output. This Review covers the different types of such probes and also highlights the chemical mechanisms by which each probe type is activated by specific RSS. Common examples include reduction of oxidized nitrogen motifs, disulfide exchange, electrophilic reactions, metal precipitation, and metal coordination. In addition, we also outline complementary activity-based probes for imaging reductant-labile and sulfane sulfur species, including persulfides and polysulfides. For probes highlighted in this Review, we focus on small molecule systems with demonstrated compatibility in cellular systems or related applications. Building from breadth of reported activity-based strategies and application, we also highlight key unmet challenges and future opportunities for advancing activity-based probes for H 2 S and related RSS.

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Section: Electrophilic H2s Probesmentioning

confidence: 94%

Activity-Based Fluorescent Probes for Hydrogen Sulfide and Related Reactive Sulfur Species

Fosnacht,

Pluth

2024

Chem. Rev.

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“…Small fluorescent probes are effective methods for detecting biothiols at the cellular/subcellular levels due to features such as good selectivity, high sensitivity, and high temporal and spatial resolutions, especially noninvasiveness. − Yoon and co-workers have reported a series of fluorescent probes that could distinguish GSH from other reactive sulfur species, − facilitating the research of GSH-related physiological functions. Great efforts have been paid in distinguishing biothiols − and reactive sulfur species − through fluorescent methods. Among these probes, only few of them that can simultaneously discriminate Cys and Hcy are reported to date.…”

Section: Introductionmentioning

confidence: 99%

Red and Near-Infrared Fluorescent Probe for Distinguishing Cysteine and Homocysteine through Single-Wavelength Excitation with Distinctly Dual Emissions

Guo

Chen

et al. 2022

Anal. Chem.

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Small-molecule biothiols, including cysteine (Cys), homocysteine (Hcy), and glutathione (GSH), participate in various pathological and physiological processes. It is still a challenge to simultaneously distinguish Cys and Hcy because of their similar structures and reactivities, as well as the interference from the high intramolecular concentration of GSH. Herein, a novel fluorescent probe, CySI, based on cyanine and thioester was developed to differentiate Cys and Hcy through a singlewavelength excitation and two distinctly separated emission channels. The probe exhibited a turn-on fluorescence response to Cys at both 625 nm (the red channel) and 740 nm (the nearinfrared channel) but only showed fluorescence turn-on to Hcy at 740 nm (the near-infrared channel) and no fluorescent response to GSH. With the aid of built-in self-calibration of single excitation and dual emissions, simultaneous discriminative determinations of Cys and Hcy were realized through red and near-infrared channels. CySI exhibited excellent selectivity toward Cys and Hcy with a fast response. This probe was further exploited to visualize exogenous Cys and Hcy in cells through dual emission channels under one excitation. Moreover, it could efficiently target mitochondria and was applied to monitor the endogenous Cys fluctuations independently in mitochondria through the red emission channel.

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“…Hydrogen sulfide (H 2 S), L-cysteine (L-Cys), homocysteine (Hcy), and glutathione (GSH) are the most common small molecular biological thiols [ 1 ]. They are closely related and have essential distinct biological and pharmacological roles in many processes [ 2 ].…”

Section: Introductionmentioning

confidence: 99%

HPLC Study of Product Formed in the Reaction of NBD-Derived Fluorescent Probe with Hydrogen Sulfide, Cysteine, N-acetylcysteine, and Glutathione

Świerczyńska

Romański

2022

Molecules

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Hydrogen sulfide (H2S) and its bioderivatives analogs, such as L-cysteine (L-Cys) and glutathione (GSH), are ubiquitous biological thiols in the physiological and pathological processes of living systems. Their aberrant concentration levels are associated with many diseases. Although several NBD-based fluorescence probes have been developed to detect biological thiols, the HPLC-detection of H₂S, GSH, L-Cys, and N-acetylcysteine-specific products has not been described. Herein, a novel NBD-derived pro-coumarin probe has been synthesized and used to develop a new strategy for the triple mode detection of H₂S and such thiols as GSH, L-Cys, and NAC. Hydrogen sulfide and those biothiols at physiological pH release fluorescent coumarin from the probe and cause a significant fluorescence enhancement at 473 nm. The appropriate NBD-derived product for H₂S, L-Cys, GSH, and NAC has a different color and retention time that allows distinguishing these biological thiols meaning the probe has a great possibility in the biological application. Fluorescent imaging combined with colorimetric and HPLC detection of H₂S/biothiol-specific product(s) brings a potential tool for confirming the presence of biological thiols and determining concentrations in various aqueous biological samples.

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A Simple Long-wavelength Fluorescent Probe for Simultaneous Discrimination of Cysteine/Homocysteine and Glutathione/Hydrogen Sulfide with Two Separated Fluorescence Emission Channels by Single Wavelength Excitation

Cited by 10 publications

References 61 publications

Activity-Based Fluorescent Probes for Hydrogen Sulfide and Related Reactive Sulfur Species

Activity-Based Fluorescent Probes for Hydrogen Sulfide and Related Reactive Sulfur Species

Red and Near-Infrared Fluorescent Probe for Distinguishing Cysteine and Homocysteine through Single-Wavelength Excitation with Distinctly Dual Emissions

HPLC Study of Product Formed in the Reaction of NBD-Derived Fluorescent Probe with Hydrogen Sulfide, Cysteine, N-acetylcysteine, and Glutathione

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