A novel 3-hydroxychromone fluorescent probe for hydrogen sulfide based on an excited-state intramolecular proton transfer mechanism
23 Jul 2018-New Journal of Chemistry (The Royal Society of Chemistry)-Vol. 42, Iss: 15, pp 12918-12923
TL;DR: The 3-hydroxychromone-based fluorescent probe A is based on a H2S-induced thiolysis reaction and an excited-state intramolecular proton transfer (ESIPT) process and shows high selectivity and sensitivity for the detection of H 2S over glutathione, cysteine and homocysteine.
Abstract: Hydrogen sulfide (H2S) is a signaling gasotransmitter that plays important roles in modulating the functions of different systems. We have designed and synthesized a 3-hydroxychromone-based fluorescent probe A for H2S detection. Probe A is based on a H2S-induced thiolysis reaction and an excited-state intramolecular proton transfer (ESIPT) process. The probe shows high selectivity and sensitivity for the detection of H2S over glutathione, cysteine and homocysteine. Moreover, this probe was successfully applied for imaging exogenous and endogenous H2S in living cells.
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TL;DR: The general approach for a reaction-based probe is to design and implement chemose-lective and biocompatible reactions, whereby a functional group on the probe molecule reacts with an analyte of inter-est with selectivity versus other biological molecules.
Abstract: Gasotransmitters and related reactive sulfur, oxygen, and nitrogen species such as nitric oxide (NO), hydrogen sul-fide (H2S), carbon monoxide (CO), hydrogen peroxide (H2O2) and downstream products like peroxynitrite (ONOO–), polysulfides (HSnH), hydroxyl radical (HO•), and azanone (nitroxyl, HNO) are produced under physiological condi-tions and impact cellular signaling and stress. Evolution-ary pressures have driven life to develop sophisticated mechanisms to control the formation and response to this complex reactive species interactome, making it a critical fulcrum that balances health and disease in human physiol-ogy. Driven by a need to understand and measure these types of reactive species, the last decade has witnessed ex-tensive research activity in developing reaction-based probes for optical detection and imaging of reactive sulfur, oxygen, and nitrogen species in living systems. – The cen-tral advantage of this approach is that it is compatible with living cells and animals, thereby enabling t...
90 citations
TL;DR: In this paper, a simple H2S selective fluorescent probe (L) has been designed and synthesized by two-step reactions using 4-diethylaminosalicylaldehyde and 1,4-dimethylpyridinium iodide as raw materials.
75 citations
TL;DR: A recent review of small-molecule fluorescent probes for H2S imaging was presented in this paper, focusing on researches conducted between January 2018 and June 2020, and their structures and biological applications were highlighted.
Abstract: Since attributed to the involvement in important physiological and pathological processes, hydrogen sulfide (H2S) is regarded as another gasotransmitter like nitric oxide (NO) and carbon monoxide (CO). Traditional H2S detection methods are limited by the fast volatility and catabolism of H2S and difficult to real-time detect H2S in biological systems. Hence, numerous small-molecule fluorescent probes have been developed. Besides high sensitivity, the selectivity, response capability and optical performance are improved by combining new response groups and extending the emission wavelength to near infrared (NIR) region. Moreover, probes tend to selectively locate in a specific organelle, which detect H2S more accurately and contribute to understand the physiological roles of H2S in diseases. In this review, recent developments of small-molecule fluorescent probes for H2S imaging were summarized, focusing on researches conducted between January 2018 and June 2020, and their structures and biological applications were highlighted.
58 citations
TL;DR: In this paper, the photophysical properties of 3-hydroxychromone (HC)-based derivatives (BFHC, BTHC, BSeHC, BDTHC and BDSeHC) were explored systematically using density functional theory and time-dependent DFT (TD-DFT) methods.
Abstract: The excited state intramolecular proton transfer (ESIPT) reaction and photophysical properties of a series of 3-hydroxychromone (HC)-based derivatives (BFHC, BTHC, BSeHC, BDFHC, BDTHC and BDSeHC) were explored systematically using density functional theory (DFT) and time-dependent DFT (TD-DFT) methods. The enhanced excited-state intramolecular hydrogen bonds of the studied molecules contributed to the ESIPT reaction according to hydrogen-bond parameters and infrared-vibration analyses. The various substituent groups induced regular multi-channel signal changes (wavelength and intensity) of the fluorescence spectra of molecules in enol and keto forms. The potential energy curves showed the energy barriers in the S1-state of the molecules followed the order BFHC < BTHC < BSeHC and BDFHC < BDTHC < BDSeHC. Combination of topology analyses of the bond critical point present in the molecules revealed that BFHC and BTHC would show an ultrafast ESIPT reaction, whereas the other molecules would have a slower ESIPT reaction. The weakened electron-withdrawing ability of an atom and longer substituent group would frustrate the ESIPT reaction of the studied molecules, thereby affecting their photophysical properties. These novel discoveries can extend the application of HC derivatives in ESIPT-based optical devices.
30 citations
TL;DR: The probe HZ-NBD, a near-infrared fluorescent probe based on SNAr reactions was exploited to achieve the sensitive and selective detection of H2S and glutathione (GSH) simultaneously in the same conditions and was successfully applied to bioimage H 2S and GSH in HepG2 cells and zebrafish.
29 citations
References
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TL;DR: It is shown that H2S is physiologically generated by cystathionine γ-lyase (CSE) and that genetic deletion of this enzyme in mice markedly reduces H 2S levels in the serum, heart, aorta, and other tissues.
Abstract: Studies of nitric oxide over the past two decades have highlighted the fundamental importance of gaseous signaling molecules in biology and medicine The physiological role of other gases such as carbon monoxide and hydrogen sulfide (H2S) is now receiving increasing attention Here we show that H2S is physiologically generated by cystathionine γ-lyase (CSE) and that genetic deletion of this enzyme in mice markedly reduces H2S levels in the serum, heart, aorta, and other tissues Mutant mice lacking CSE display pronounced hypertension and diminished endothelium-dependent vasorelaxation CSE is physiologically activated by calcium-calmodulin, which is a mechanism for H2S formation in response to vascular activation These findings provide direct evidence that H2S is a physiologic vasodilator and regulator of blood pressure
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TL;DR: It is shown that physiological concentrations of H2S selectively enhance NMDA receptor-mediated responses and facilitate the induction of hippocampal long-term potentiation, suggesting that endogenous H 2S functions as a neuromodulator in the brain.
Abstract: Hydrogen sulfide (H2S), which is well known as a toxic gas, is produced endogenously from L-cysteine in mammalian tissues. H2S is present at relatively high levels in the brain, suggesting that it has a physiological function. Two other gases, nitric oxide and carbon monoxide, are also endogenously produced and have been proposed as neuronal messengers in the brain. In this work we show the following: (1) an H2S-producing enzyme, cystathionine beta-synthase (CBS), is highly expressed in the hippocampus; (2) CBS inhibitors hydroxylamine and amino-oxyacetate suppress the production of brain H2S; and (3) a CBS activator, S-adenosyl-L-methionine, enhances H2S production, indicating that CBS contributes to the production of endogenous H2S. We also show that physiological concentrations of H2S selectively enhance NMDA receptor-mediated responses and facilitate the induction of hippocampal long-term potentiation. These observations suggest that endogenous H2S functions as a neuromodulator in the brain.
1,940 citations
TL;DR: The physiology and biochemistry of H2S is overviews, the effects of H 2S inhibitors or H2s donors in animal models of disease are summarized, the potential options for the therapeutic exploitation of H1S are outlined and they are outlined.
Abstract: Hydrogen sulphide (H2S) is increasingly being recognized as an important signalling molecule in the cardiovascular and nervous systems. The production of H2S from L-cysteine is catalysed primarily by two enzymes, cystathionine gamma-lyase and cystathionine beta-synthase. Evidence is accumulating to demonstrate that inhibitors of H2S production or therapeutic H2S donor compounds exert significant effects in various animal models of inflammation, reperfusion injury and circulatory shock. H2S can also induce a reversible state of hypothermia and suspended-animation-like state in rodents. This article overviews the physiology and biochemistry of H2S, summarizes the effects of H2S inhibitors or H2S donors in animal models of disease and outlines the potential options for the therapeutic exploitation of H2S.
1,639 citations
TL;DR: In this paper, the authors showed that mRNA for another H2S producing enzyme, cystathionine gamma-lyase, is expressed in the ileum, portal vein, and thoracic aorta.
1,144 citations
TL;DR: Pharmacological experiments using H₂S donors and genetic experiments using CSE knockout mice suggest important roles for this vasodilator gas in the regulation of blood vessel caliber, cardiac response to ischemia/reperfusion injury, and inflammation.
Abstract: Hydrogen sulfide (H₂S) is a gaseous mediator synthesized from cysteine by cystathionine γ lyase (CSE) and other naturally occurring enzymes. Pharmacological experiments using H₂S donors and genetic experiments using CSE knockout mice suggest important roles for this vasodilator gas in the regulation of blood vessel caliber, cardiac response to ischemia/reperfusion injury, and inflammation. That H₂S inhibits cytochrome c oxidase and reduces cell energy production has been known for many decades, but more recently, a number of additional pharmacological targets for this gas have been identified. H₂S activates K(ATP) and transient receptor potential (TRP) channels but usually inhibits big conductance Ca²(+)-sensitive K(+) (BK(Ca)) channels, T-type calcium channels, and M-type calcium channels. H₂S may inhibit or activate NF-κB nuclear translocation while affecting the activity of numerous kinases including p38 mitogen-activated protein kinase (p38 MAPK), extracellular signal-regulated kinase (ERK), and Akt. These disparate effects may be secondary to the well-known reducing activity of H₂S and/or its ability to promote sulfhydration of protein cysteine moieties within the cell.
1,129 citations