Visible light-driven photogeneration of hydrogen sulfide

Yi, Seung Yeon; Moon, Yu Kyung; Kim, Sinheui; Kim, Sonam; Kim, Jin Ju; You, Youngmin

doi:10.1039/c7cc06990a

Cited by 27 publications

(17 citation statements)

References 34 publications

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“…The group of You used a hybrid approach to develop Pluronic F-127-based vesicles containing a photosensitizer that generates singlet oxygen upon irradiation with visible light. 1357 Two such photosensitizers were tested, as shown in Scheme 80 : Pt II octaethylporphine 379 (Φ r = 0.30) and [Ir III bis(2-(3-methoxyphenyl)pyridinate)(1,10-phenanthroline)]PF 6 380 (Φ Δ = 0.41). The singlet oxygen generated by these complexes upon irradiation (λ irr = 500–550 nm for 379 and 380–500 nm for 380 ) reacts with 1,3-diphenylisobenzothiophene 381 to form an endoperoxide, which then undergoes thermal decomposition to release H 2 S (Φ r = ∼2× 10 –3 ).…”

Section: Photorelease Of Gasotransmittersmentioning

confidence: 99%

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

et al. 2020

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Photoactivatable (alternatively, photoremovable, photoreleasable, or photocleavable) protecting groups (PPGs), also known as caged or photocaged compounds, are used to enable non-invasive spatiotemporal photochemical control over the release of species of interest. Recent years have seen the development of PPGs activatable by biologically and chemically benign visible and near-infrared (NIR) light. These long-wavelength-absorbing moieties expand the applicability of this powerful method and its accessibility to non-specialist users. This review comprehensively covers organic and transition metal-containing photoactivatable compounds (complexes) that absorb in the visible- and NIR-range to release various leaving groups and gasotransmitters (carbon monoxide, nitric oxide, and hydrogen sulfide). The text also covers visible- and NIR-light-induced photosensitized release using molecular sensitizers, quantum dots, and upconversion and second-harmonic nanoparticles, as well as release via photodynamic (photooxygenation by singlet oxygen) and photothermal effects. Release from photoactivatable polymers, micelles, vesicles, and photoswitches, along with the related emerging field of photopharmacology, is discussed at the end of the review.

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Section: Photorelease Of Gasotransmittersmentioning

confidence: 99%

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

et al. 2020

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“…38 Efforts to move photoactivation wavelengths to more biologically useful regions of the visible spectrum have resulted in several systems that can be triggered with visible and near-infrared light. 21–23 Except in one case, 22 these systems require upconverting nanoparticles to mediate the low-energy photoactivation process. 21–23 Because red light effectively penetrates biological tissue and is nontoxic, the development ofsmall-molecule red light-activated H 2 S-releasing agents would be particularly valuable for both studying the biological roles of H 2 S and leveraging the therapeutic effects of this gasotransmitter.…”

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confidence: 99%

Characterization and Biological Activity of a Hydrogen Sulfide-Releasing Red Light-Activated Ruthenium(II) Complex

et al. 2018

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Hydrogen sulfide (HS) is a biological gasotransmitter that has been employed for the treatment of ischemia-reperfusion injury. Despite its therapeutic value, the implementation of this gaseous molecule for this purpose has required HS-releasing prodrugs for effective intracellular delivery. The majority of these prodrugs, however, spontaneously release HS via uncontrolled hydrolysis. Here, we describe a Ru(II)-based HS-releasing agent that can be activated selectively by red light irradiation. This compound operates in living cells, increasing intracellular HS concentration only upon irradiation with red light. Furthermore, the red light irradiation of this compound protects H9c2 cardiomyoblasts from an in vitro model of ischemia-reperfusion injury. These results validate the use of red light-activated HS-releasing agents as valuable tools for studying the biology and therapeutic utility of this gasotransmitter.

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“…Although these complexes are more practical for the delivery of H 2 S than its direct administration as a gas, their rapid release profiles do not mimic endogenous H 2 S production and often elicit toxic side effects [13] . To circumvent these challenges, several groups have developed synthetic compounds that release H 2 S upon activation by external stimuli such as light, [14–21] pH, [22, 23] and reactive oxygen species [24, 25] . These compounds allow localized and controllable delivery of H 2 S in complex biological systems, making them promising therapeutic candidates.…”

Section: Figurementioning

confidence: 99%

A Dinuclear Persulfide‐Bridged Ruthenium Compound is a Hypoxia‐Selective Hydrogen Sulfide (H₂S) Donor

Woods

Wilson

2020

Angew Chem Int Ed

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Hydrogen sulfide (H 2 S) is a gaseous molecule that has received attention for its role in biological processes and therapeutic potential in diseases, such as ischemic reperfusion injury. Despite its clinical relevance, delivery of H 2 S to biological systems is hampered by its toxicity at high concentrations. Herein, we report the first metal-based H 2 S donor that delivers this gas selectively to hypoxic cells. We further show that H 2 S release from this compound protects H9c2 rat cardiomyoblasts from an in vitro model of ischemic reperfusion injury. These results validate the utility of redox-activated metal complexes as hypoxia-selective H 2 S-releasing agents for use as tools to study the role of this gaseous molecule in complex biological systems.

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Visible light-driven photogeneration of hydrogen sulfide

Abstract: The combined use of a singlet oxygen photosensitizer and 1,3-diarylisobenzothiophene enables efficient generation of hydrogen sulfide under visible light illumination.

Cited by 27 publications

References 34 publications

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

Characterization and Biological Activity of a Hydrogen Sulfide-Releasing Red Light-Activated Ruthenium(II) Complex

A Dinuclear Persulfide‐Bridged Ruthenium Compound is a Hypoxia‐Selective Hydrogen Sulfide (H₂S) Donor

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Visible light-driven photogeneration of hydrogen sulfide

Abstract: The combined use of a singlet oxygen photosensitizer and 1,3-diarylisobenzothiophene enables efficient generation of hydrogen sulfide under visible light illumination.

Cited by 27 publications

References 34 publications

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

Characterization and Biological Activity of a Hydrogen Sulfide-Releasing Red Light-Activated Ruthenium(II) Complex

A Dinuclear Persulfide‐Bridged Ruthenium Compound is a Hypoxia‐Selective Hydrogen Sulfide (H2S) Donor

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Product

Resources

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A Dinuclear Persulfide‐Bridged Ruthenium Compound is a Hypoxia‐Selective Hydrogen Sulfide (H₂S) Donor