A cysteine-triggered fluorogenic donor base on native chemical ligation for tracking H<sub>2</sub>S delivery <i>in vivo</i>

Li, Li; Lin, Zhenmei; Cheng, Yuxiang; Tang, Yaoping; Zhang, Ziqian

doi:10.1039/d1an01809d

Cited by 7 publications

(8 citation statements)

References 38 publications

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“…1,8-Naphthalimide has been widely applied in the development of H 2 S donors and possesses a self-reporting capability for hydrogen H 2 S. The Zhang group successfully synthesized HSD560, a H 2 S donor that is activated in the presence of Cys. 46 HSD560 is composed of the classic fluorescent group 1,8-naphthalimide and benzothioate (the source of H 2 S). In an enriched Cys environment, HSD560 undergoes a nonenzymatic native chemical ligation (NCL) reaction when the benzothioate moiety is exposed, releasing H 2 S and NapOH.…”

Section: 8-naphthalimidementioning

confidence: 99%

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Visible Tracking of Small Molecules of Gases with Fluorescent Donors

Yu,

Xu,

et al. 2024

Chemical & Biomedical Imaging

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Biological gasotransmitters (small molecules of gases) play important roles in signal transduction mechanisms and disease treatments. Although a large number of smallmolecule donors have been developed, visualizing the release of small molecules remains challenging. Owing to their unique optical properties, fluorophores have been widely applied in cellular imaging and tracking. Researchers have used various fluorophores to develop smallmolecule donors with fluorescent activity for visualizing the release of small molecules and their related therapies. These include fluorophores and their derivatives such as borondipyrromethene (BODIPY), coumarin, 1,8-naphthalimide, hemicyanine, porphyrin, rhodamine, and fluorescein. In this review, we summarize the design concepts of functional fluorescent small-molecule donors in terms of different types of fluorophores. Then, we discuss how these donors release small molecules, and the imaging modalities and biomedical applications facilitated by their fluorescent properties. With the systematic discussion of these publications, we hope to provide useful references for the development of more practical, advanced fluorescent small-molecule donors in the future.

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Section: 8-naphthalimidementioning

confidence: 99%

Section: Bodipymentioning

confidence: 99%

Visible Tracking of Small Molecules of Gases with Fluorescent Donors

Yu,

Xu,

et al. 2024

Chemical & Biomedical Imaging

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“…Fluorogenic H2S donors with direct H2S-releasing scaffolds, such as trisulfides and activated thioethers, or indirect COS/H2Sreleasing scaffolds, such as thioesters, thiocarbamates, thiocarbonates, and sulfenyl thiocarbonates, have been reported previously (Figure 1a). [19,[22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] Indirect COS/H2S donors function by the intermediate release of COS, which is rapidly converted to H2S in cellular environments by the enzyme carbonic anhydrase (CA). These COS/H2S donor scaffolds enable easy modification via addition of an alcohol or amine-modified fluorescent dye.…”

Section: Introductionmentioning

confidence: 99%

An Expanded Palette of Fluorescent COS/H2S-Releasing Donors for H2S Delivery, Detection, and In Vivo Application

Fosnacht,

Dorogin,

Jefferis

et al. 2024

Preprint

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Hydrogen sulfide is an important reactive sulfur species that is involved in many biological functions, and H2S imbalances have been indicated as a potential biomarker for various diseases. Different H2S donors have been developed to deliver H2S directly to biological systems, but few reports include donors with optical responses that allow for tracking of H2S release. Moreover, donor systems that use the same chemistry to deliver H2S across a palette of fluorescent responses remain lacking. Here we report five thiol-activated fluorescence turn-on COS/H2S donors that utilize blue, yellow, orange, red, and near infrared-emitting dyes functionalized with an H2S-releasing sulfenyl thiocarbonate scaffold. Upon treatment with thiols, each donor provides a fluorescence turn-on response (3–310-fold) and high H2S release efficiencies (>60%). Using combined electrode and fluorescence experiments, we directly correlate the measured H2S release with the fluorescence response. All donors are biocompatible and release H2S in live cell environments. In addition, we demonstrate that the NIR donor allows for H2S release tracking after subcutaneous injection in live rats, which to the best of our knowledge is the first in vivo tracking of fluorogenic H2S release in non-transparent organisms.

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“…Optical probes have been a powerful tool for monitoring and imaging anions, cations, enzymes, and biomolecules in vitro / vivo because of their easy operation, high sensitivity, good selectivity, and noninvasive detection ( Chen et al, 2018a ; Hou et al, 2020 ; Li et al, 2020 ; Park et al, 2020 ; Yang et al, 2020 ; Cui et al, 2021 ; Du et al, 2021 ). At present, a huge amount of fluorescent probes have been developed for the investigation of Cys, Hcy, and GSH in living cells based on cyclization with aldehyde, Michael addition, cleavage of sulfonamide, disulfide, selenium–nitrogen, and sulfonate ester ( Chen et al, 2018b ; Chen et al, 2020 ; Yue et al, 2020 ; Chen et al, 2021a ; Li et al, 2021a ; Zhang et al, 2021a ; Zheng et al, 2021 ; Chen et al, 2022 ). However, owing to the similar structures and reactivities of GSH and Cys/Hcy, simultaneous selective detection of Cys/Hcy and GSH is still a great challenge.…”

Section: Introductionmentioning

confidence: 99%

Simultaneous Discrimination of Cys/Hcy and GSH With Simple Fluorescent Probe Under a Single-Wavelength Excitation and its Application in Living Cells, Tumor Tissues, and Zebrafish

Yan

Liu

et al. 2022

Front. Chem.

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Owing to the important physiological sits of biothiols (Cys, Hcy, and GSH), developing accurate detection methods capable of qualitative and quantitative analysis of biothiols in living systems is needed for understanding the biological profile of biothiols. In this work, we have designed and synthesized a 4′-hydroxy-[1,1′-biphenyl]-4-carbonitrile modified with NBD group-based fluorescent probe, BPN-NBD, for sensitive detection of Cys/Hcy and GSH by dual emission signals via a single-wavelength excitation. BPN-NBD exhibited an obvious blue fluorescence (λmaxem = 475 nm) upon the treatment with GSH and reacted with Cys/Hcy to give a mixed blue-green fluorescence (λmaxem = 475 and 545 nm). Meanwhile, BPN-NDB performed sufficient selectivity, rapid detection (150 s), high sensitivity (0.011 µM for Cys, 0.015 µM for Hcy, and 0.003 µM for GSH) and could work via a single-wavelength excitation to analytes and had the ability to image Cys/Hcy from GSH in living MCF-7 cells, tumor tissues, and zebrafish by exhibiting different fluorescence signals. Overall, this work provided a powerful tool for thiols visualization in biological and medical applications.

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A cysteine-triggered fluorogenic donor base on native chemical ligation for tracking H₂S delivery in vivo

Abstract: A fluorogenic hydrogen sulfide (H2S) donor is a fundamental molecular tool used as an exogenous source in biological studies and therapies.

Cited by 7 publications

References 38 publications

Visible Tracking of Small Molecules of Gases with Fluorescent Donors

Visible Tracking of Small Molecules of Gases with Fluorescent Donors

An Expanded Palette of Fluorescent COS/H2S-Releasing Donors for H2S Delivery, Detection, and In Vivo Application

Simultaneous Discrimination of Cys/Hcy and GSH With Simple Fluorescent Probe Under a Single-Wavelength Excitation and its Application in Living Cells, Tumor Tissues, and Zebrafish

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A cysteine-triggered fluorogenic donor base on native chemical ligation for tracking H2S delivery in vivo

Abstract: A fluorogenic hydrogen sulfide (H2S) donor is a fundamental molecular tool used as an exogenous source in biological studies and therapies.

Cited by 7 publications

References 38 publications

Visible Tracking of Small Molecules of Gases with Fluorescent Donors

Visible Tracking of Small Molecules of Gases with Fluorescent Donors

An Expanded Palette of Fluorescent COS/H2S-Releasing Donors for H2S Delivery, Detection, and In Vivo Application

Simultaneous Discrimination of Cys/Hcy and GSH With Simple Fluorescent Probe Under a Single-Wavelength Excitation and its Application in Living Cells, Tumor Tissues, and Zebrafish

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A cysteine-triggered fluorogenic donor base on native chemical ligation for tracking H₂S delivery in vivo