Fluorescent probes based on nucleophilic aromatic substitution reactions for reactive sulfur and selenium species: Recent progress, applications, and design strategies

Liu, Yuning; Yu, Yanan; Zhao, Qingyu; Tang, Chaohua; Zhang, Huiyan; Qin, Yuchang; Feng, Xiaohui; Zhang, Junmin

doi:10.1016/j.ccr.2020.213601

Cited by 66 publications

(20 citation statements)

References 280 publications

(423 reference statements)

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“…The third step was to analyze the emission wavelengths. For a fluorogenic substrate, the analytical wavelength above 500 nm could avoid the background fluorescence during the assay process, 37,38 and two hits FP46, designated XLR, and FP84 met this criterion (Figure 2). Synthesis of the Fluorogenic Probes.…”

Section: ■ Results and Discussionmentioning

confidence: 97%

Discovery of a Broad-Spectrum Fluorogenic Agonist for Strigolactone Receptors through a Computational Approach

Wang

Pang

et al. 2021

J. Agric. Food Chem.

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Strigolactones (SLs) are plant hormones that play various roles in plant physiology, including provoking the germination of parasitic weeds Orobanche and Striga. A family of α/β-hydrolases have been proposed to be the SL receptor proteins. Effective assays for measuring the activity of SL receptors could promote the development of SL-related biology and chemistry. In this study, we developed a new approach called pharmacophore-linked probe virtual screening (PPVS). Its application yielded an effective "off−on" probe named Xilatone Red (XLR). This probe showed a broad spectrum and excellent sensitivity toward SL receptors, including ShD14 (Striga D14), for which the detection limit was determined to be in the micromolar range, outperforming that of the commercial fluorogenic agonist Yoshimulactone Green (YLG). Upon hydrolysis by SL receptors, XLR provided fluorogenic and colorimetric signaling responses. Furthermore, XLR could induce germination of Phelipanche aegyptiaca seeds and prevent Arabidopsis max4-1 branching defects at micromolar concentrations. Our molecular simulations revealed the essential factors in the molecular perception of XLR. We anticipate that this study can prompt the discovery of high-performance SL agonists/antagonists to combat parasitic weeds.

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Section: ■ Results and Discussionmentioning

confidence: 97%

Discovery of a Broad-Spectrum Fluorogenic Agonist for Strigolactone Receptors through a Computational Approach

Wang

Pang

et al. 2021

J. Agric. Food Chem.

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“…Noteworthily, there are a rich variety of endogenous mercapto biomolecules in creatures, like the representative biothiols (e.g., Cys, Hcy, and GSH), 83,84 which commonly act as effective Hg 2+ scavengers. 85,86 Actually, the sensing mechanism and luminescent traits play definitive roles in the bioapplications of the fluorescent chemoprobes for metal cations.…”

Section: Practical Application Studiesmentioning

confidence: 99%

An α-naphtholphthalein-derived colorimetric fluorescent chemoprobe for the portable and visualized monitoring of Hg²⁺by the hydrolysis mechanism

et al. 2022

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“…It has long been recognized that unmitigated production of reactive species is closely associated with a variety of diseases and disorders. Oxidants represent both the origin and aftermath of biomolecule damage and studies focused on the detection of reactive species, or markers of protein oxidation, have been extensively reviewed [65][66][67][68] . Using sulfur chemical biology approaches, scientists can now mine the dynamic cysteine redoxome for OxiPTMs that "drive" the pathological state.…”

Section: Size Of Redoxomementioning

confidence: 99%

Defining and refining the cysteine redoxome with sulfur chemical biology

Carroll

2022

Preprint

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Posttranslational changes in the redox state of cysteine residues can rapidly and reversibly alter protein function, modulating biological processes and drug pharmacology. Recent innovations in organosulfur chemistry, small-molecule tools, and computational methods for proteomic analysis have dramatically improved selectivity, cellular application, and site-specific quantitation of the cysteine redoxome. In this perspective, we start with a brief overview of cysteine sulfur chemistry and factors affecting thiol reactivity, followed by a critical discussion of similarities and differences between reactive and redox-sensitive cysteine residues. Next, we address mechanisms of post-translational cysteine oxidation and methods to quantify redoxome site-stoichiometry to prioritize follow-up study. Finally, we highlight recent chemoproteomic studies of the cysteine redoxome that offer new insights into the regulation of physiological processes and provide a framework for development of novel redox-based targeted therapeutic strategies.

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Fluorescent probes based on nucleophilic aromatic substitution reactions for reactive sulfur and selenium species: Recent progress, applications, and design strategies

Abstract: Graphical abstract

Cited by 66 publications

References 280 publications

Discovery of a Broad-Spectrum Fluorogenic Agonist for Strigolactone Receptors through a Computational Approach

Discovery of a Broad-Spectrum Fluorogenic Agonist for Strigolactone Receptors through a Computational Approach

An α-naphtholphthalein-derived colorimetric fluorescent chemoprobe for the portable and visualized monitoring of Hg²⁺by the hydrolysis mechanism

Defining and refining the cysteine redoxome with sulfur chemical biology

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Fluorescent probes based on nucleophilic aromatic substitution reactions for reactive sulfur and selenium species: Recent progress, applications, and design strategies

Abstract: Graphical abstract

Cited by 66 publications

References 280 publications

Discovery of a Broad-Spectrum Fluorogenic Agonist for Strigolactone Receptors through a Computational Approach

Discovery of a Broad-Spectrum Fluorogenic Agonist for Strigolactone Receptors through a Computational Approach

An α-naphtholphthalein-derived colorimetric fluorescent chemoprobe for the portable and visualized monitoring of Hg2+by the hydrolysis mechanism

Defining and refining the cysteine redoxome with sulfur chemical biology

Contact Info

Product

Resources

About

An α-naphtholphthalein-derived colorimetric fluorescent chemoprobe for the portable and visualized monitoring of Hg²⁺by the hydrolysis mechanism