A fluorogenic H2S donor activated by reactive oxygen species for real-time monitoring in cells and in vivo

Li, Li; Zhang, Ziqian

doi:10.1016/j.saa.2021.120243

“…Fluorogenic H 2 S donors with direct H 2 S-releasing scaffolds, such as trisulfides and activated thioethers, or indirect COS/H 2 S-releasing scaffolds, such as thioesters, thiocarbamates, thiocarbonates, and sulfenyl thiocarbonates, have been reported previously (Figure 1a). [20,[23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38] Indirect COS/ H 2 S donors function by the intermediate release of COS, which is rapidly converted to H 2 S in cellular environments by the enzyme carbonic anhydrase (CA). These COS/H 2 S 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

Angewandte Chemie

0

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Hydrogen sulfide (H2S) 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 imaging H2S release in live rats via subcutaneous injection of the donor loaded into an alginate gel, which to the best of our knowledge is the first in vivo tracking of H2S release from a fluorogenic donor in non‐transparent organisms.

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“…1a). [18][19][20][21] In 2020, for the first time, we designed and reported single analyte-responsive (biothiol) coumarin-based turn-on fluorogenic probes as H 2 S donors with lysosomal selectivity. 22 However, the utilized fluorophore absorbed light in the UV range with high energy blue emission.…”

Section: Introductionmentioning

confidence: 99%

Thioredoxin reductase-triggered fluorogenic donor of hydrogen sulfide: a model study with a symmetrical organopolysulfide probe with turn-on near-infrared fluorescent emission

Bhabak

¹

,

Mahato

²

,

Bhattacherjee

³

et al. 2022

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

Fosnacht,

Dorogin,

Jefferis

et al. 2024

Angew Chem Int Ed

2

0

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Hydrogen sulfide (H2S) 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 imaging H2S release in live rats via subcutaneous injection of the donor loaded into an alginate gel, which to the best of our knowledge is the first in vivo tracking of H2S release from a fluorogenic donor in non‐transparent organisms.

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A fluorogenic H2S donor activated by reactive oxygen species for real-time monitoring in cells and in vivo

Cited by 9 publications

References 37 publications

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

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

Thioredoxin reductase-triggered fluorogenic donor of hydrogen sulfide: a model study with a symmetrical organopolysulfide probe with turn-on near-infrared fluorescent emission

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

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A fluorogenic H2S donor activated by reactive oxygen species for real-time monitoring in cells and in vivo

Cited by 9 publications

References 37 publications

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

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

Thioredoxin reductase-triggered fluorogenic donor of hydrogen sulfide: a model study with a symmetrical organopolysulfide probe with turn-on near-infrared fluorescent emission

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

Contact Info

Product

Resources

About

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

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

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