Hydrogen sulfide‐activatable fluorescence turn‐on azide‐containing naphthalimide derivative

Yoo, Song Yi; Gopala, Lavanya; Kang, Chulhun; Lee, Min Hee

doi:10.1002/bkcs.12611

Cited by 9 publications

(9 citation statements)

References 17 publications

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“…Expanding to aromatic-functionalized motifs, Kang and Lee prepared a naphthalimide-hydrazone 14 , which displayed a fluorescence turn-on response to H 2 S in 40% DMSO in buffer and good selectivity for H 2 S over biologically relevant metals, ROS, and RSS . Similarly, Sahoo reported 15 that responded to H 2 S with a 5-fold fluorescence turn-on at 524 nm with good selectivity for H 2 S over various RNS, ROS, and thiols .…”

Section: H2s Fluorescent Probes: Reduction Of Oxidized Nitrogen Motifsmentioning

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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Section: H2s Fluorescent Probes: Reduction Of Oxidized Nitrogen Motifsmentioning

confidence: 99%

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

Fosnacht,

Pluth

2024

Chem. Rev.

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“…Recently, Lee's team further functionalized an azide‐containing naphthalimide with biotin to fabricate the biocompatible probe 25 (Figure 12). [ 70 ] Probe 25 has fluorescent peak at 545 nm and can be utilized to perform the in vivo real‐time analysis of H 2 S. It showed good selectivity for H 2 S independent of the presence of other biological reductants or under biological relevant pH effects. In the presence of various H 2 S inducers and inhibitors, the functionalized probe often provides effective fluorescence response.…”

Section: Naphthalimide Fluorescent Probes To Detect Small Molecules A...mentioning

confidence: 99%

Research Progress on Naphthalimide Fluorescent Probes

Xu,

Xiao,

Liu

et al. 2023

Advanced Sensor Research

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Naphthalimide derivatives are attracting increasing attention as fluorescent probes due to their excellent modifiability and photophysical properties. Their large, rigid coplanar structures and conjugated systems enable easy generation of fluorescence. The imide units and bromonaphthalene functionality offer facile and concise modification pathways in preparing amenable probes for different metal cations, anions, small molecules, and organelles. Therefore, naphthalimide probes have great potential for application in research fields, such as analytical chemistry, cell biology, and clinical diagnosis.

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“…In mammals, H 2 S is mainly generated with cysteine (Cys) or homocysteine (Hcy) degradation through the action of three main enzymes, cystathionine β-synthase (CBS), cystathionine γ-lyase (CSE) and 3-mercaptopyruvate sulphurtransferase (3-MST) [12]. Overexpression of H 2 S is related to various diseases like diabetes [13], tumors [14], liver cirrhosis [15,16], asthma [17], and myocardial damage [18]. That explains the increasing attention devoted to H 2 S detection and determination in living systems [16].…”

Section: Introductionmentioning

confidence: 99%

Sensitive Detection of Various Forms of Hydrogen Sulfide via Highly Selective Naphthalimide-Based Fluorescent Probe

Słowiński,

Świerczyńska,

Romański

et al. 2023

Molecules

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Hydrogen sulfide (H2S) is an important gasotransmitter, but only a few methods are available for real-time detection. Fluorescent probes are attractive tools for biological applications because of their high sensitivity, convenience, rapid implementation, noninvasive monitoring capability, and simplicity in fluorescent imaging of living cells and tissues. Herein, we report on a pro-fluorescent probe, NAP-Py-N3 based on naphthalimide derivative, which was found to show high selectivity toward H2S over various other analytes, including biothiols, making it feasible to detect H2S. After reaction with H2S, this probe showed rapid and significant turn-on green fluorescent enhancement at 553 nm (about 54-fold, k2 = 9.62 M−1s−1), high sensitivity (LOD: 15.5 nM), significant Stokes shift (118 nm), and it was found that the fluorescence quantum yield of fluorescence product can reach 0.36. Moreover, the probe has also been successfully applied to detect the gaseous H2S and to confirm the presence of H2S released from modern organic donors, which in recent years have been commonly used to investigate the role of H2S in biological systems. All the results indicate that this probe is excellent and highly valuable.

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Hydrogen sulfide‐activatable fluorescence turn‐on azide‐containing naphthalimide derivative

Cited by 9 publications

References 17 publications

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

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

Research Progress on Naphthalimide Fluorescent Probes

Sensitive Detection of Various Forms of Hydrogen Sulfide via Highly Selective Naphthalimide-Based Fluorescent Probe

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