A highly selective fluorescent probe based on Michael addition for fast detection of hydrogen sulfide

Gao, Baozhen; Cui, Lixia; Pan, Yong; Xue, Min-Jie; Zhu, Bin; Zhang, Guomei; Zhang, Caihong; Shuang, Shaomin; Dong, Chuan

doi:10.1016/j.saa.2016.09.051

Cited by 18 publications

(6 citation statements)

References 41 publications

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“…For instance, H 2 S-mediated azide to amine reduction leads to 1,6-elimination, which subsequently results in the release of the active scaffold while activating the ICT process . High nucleophilicity of H 2 S is mostly utilized to trigger nucleophilic aromatic substitution, disulfide bond cleavage, or Michael addition reactions. − Nitrobenzene rings, for example, generally tend to undergo nucleophilic aromatic substitution, leading to the release of active phototherapeutic agents, which possess altered photophysical properties due to the modulation of PeT and/or ICT processes. 7-Nitro-1,2,3-benzoxadiazole (NBD) is another well-known group that is cleaved upon nucleophilic attack of H 2 S .…”

Section: Introductionmentioning

confidence: 99%

Hydrogen Sulfide Responsive Phototherapy Agents: Design Strategies and Biological Applications

Dirak

Turan

Kölemen

2023

ACS Bio Med Chem Au

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Hydrogen sulfide (H2S) is one of the critical gasotransmitters, which play important roles in regular physiological processes, especially in vital signaling pathways. However, fluctuations in endogenous H2S concentration can be linked to serious health problems, such as neurodegenerative diseases, cancer, diabetes, inflammation, cardiovascular diseases, and hypertension. Thus, it has attracted a great deal of attention in therapeutic applications, specifically in the field of phototherapy. Photodynamic therapy (PDT) and photothermal therapy (PTT) are two subclasses of phototherapy, which utilize either reactive oxygen species (ROS) or local temperature increase upon irradiation of a photosensitizer (PS) to realize the therapeutic action. Phototherapies offer unique advantages compared to conventional methods; thus, they are highly promising and popular. One of the design principles followed in new generation PSs is to build activity-based PSs, which stay inactive before getting activated by disease-associated stimuli. These activatable PSs dramatically improve the selectivity and efficacy of the therapy. In this review, we summarize small molecule and nanomaterial-based PDT and PTT agents that are activated selectively by H2S to initiate their cytotoxic effect. We incorporate single mode PDT and PTT agents along with synergistic and/or multimodal photosensitizers that can combine more than one therapeutic approach. Additionally, H2S-responsive theranostic agents, which offer therapy and imaging at the same time, are highlighted. Design approaches, working principles, and biological applications for each example are discussed in detail.

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Section: Introductionmentioning

confidence: 99%

Hydrogen Sulfide Responsive Phototherapy Agents: Design Strategies and Biological Applications

Dirak

Turan

Kölemen

2023

ACS Bio Med Chem Au

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“…23 summarises the different fluorescent probes for measurement of sulfide. Measurement of sulfide in fluids 14,24–26 and living cells 13,27–29 has been usually performed using bulk sample making it unwieldy for clinical use. However, by miniaturizing the detection and measurement system, it would be possible to usher in point of care devices for gasotransmitters.…”

Section: Introductionmentioning

confidence: 99%

Rapid measurement of hydrogen sulphide in human blood plasma using a microfluidic method

Karunya

Jayaprakash

Gaikwad

et al. 2019

Sci Rep

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Hydrogen sulfide (H 2 S) is emerging as an important gasotransmitter in both physiological and pathological states. Rapid measurement of H 2 S remains a challenge. We report a microfluidic method for rapid measurement of sulphide in blood plasma using Dansyl-Azide, a fluorescence (FL) based probe. We have measured known quantities of externally added (exogenous) H 2 S to both buffer and human blood plasma. Surprisingly, a decrease in FL intensity with increase in exogenous sulphide concentration in plasma was observed which is attributed to the interaction between the proteins and sulphide present in plasma underpinning our observation. The effects of mixing and incubation time, pH, and dilution of plasma on the FL intensity is studied which revealed that the FL assay required a mixing time of 2 min, incubation time of 5 min, a pH of 7.1 and performing the test within 10 min of sampling; these together constitute the optimal parameters at room temperature. A linear correlation (with R 2 ≥ 0.95) and an excellent match was obtained when a comparison was done between the proposed microfluidic and conventional spectrofluorometric methods for known concentrations of H 2 S (range 0–100 µM). We have measured the baseline level of endogenous H 2 S in healthy volunteers which was found to lie in the range of 70 μM – 125 μM. The proposed microfluidic device with DNS-Az probe enables rapid and accurate estimation of a key gasotransmitter H 2 S in plasma in conditions closely mimicking real time clinical setting. The availability of this device as at the point of care, will help in understanding the role of H 2 S in health and disease.

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“…Zhang and Dong also expanded on this approach to prepare the naphthalimide-based probe 645, which showed an emission maximum at 550 nm in 50% MeCN in buffer, but biological compatibility was not reported. 667 4.4.4. Addition to Benzyl Electrophiles and Subsequent Ester Cleavage.…”

Section: Addition To Aldehydes and Subsequent Ester Cleavagementioning

confidence: 99%

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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A highly selective fluorescent probe based on Michael addition for fast detection of hydrogen sulfide

Cited by 18 publications

References 41 publications

Hydrogen Sulfide Responsive Phototherapy Agents: Design Strategies and Biological Applications

Hydrogen Sulfide Responsive Phototherapy Agents: Design Strategies and Biological Applications

Rapid measurement of hydrogen sulphide in human blood plasma using a microfluidic method

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

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