Design of OFF/ON fluorescent thiol probes based on coumarin fluorophore

Sun, Wei; Li, Jing; Li, Wenhua; Su, Lijuan; Du, Lüpei; Li, Minyong

doi:10.1007/s11426-012-4601-2

Cited by 9 publications

(3 citation statements)

References 24 publications

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“…The DNBS group was further utilized as a fluorescence quencher in the π-extended coumarin-based probes 345 – 350 (Figure ). − The addition of biothiols to these probes resulted in a dramatically enhanced fluorescence intensity, which was very similar to the previously described compounds.…”

Section: Fluorescent Chemosensors Based On Coumarin Platform For Biol...supporting

confidence: 77%

Coumarin-Based Small-Molecule Fluorescent Chemosensors

et al. 2019

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Coumarins are a very large family of compounds containing the unique 2H-chromen-2-one motif, as it is known according to IUPAC nomenclature. Coumarin derivatives are widely found in nature, especially in plants and are constituents of several essential oils. Up to now, thousands of coumarin derivatives have been isolated from nature or produced by chemists. More recently, the coumarin platform has been widely adopted in the design of small-molecule fluorescent chemosensors because of its excellent biocompatibility, strong and stable fluorescence emission, and good structural flexibility. This scaffold has found wide applications in the development of fluorescent chemosensors in the fields of molecular recognition, molecular imaging, bioorganic chemistry, analytical chemistry, materials chemistry, as well as in the biology and medical science communities. This review focuses on the important progress of coumarin-based small-molecule fluorescent chemosensors during the period of 2012− 2018. This comprehensive and critical review may facilitate the development of more powerful fluorescent chemosensors for broad and exciting applications in the future.

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Section: Fluorescent Chemosensors Based On Coumarin Platform For Biol...supporting

confidence: 77%

Coumarin-Based Small-Molecule Fluorescent Chemosensors

et al. 2019

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“…Today, we realize that chemistry can advance a molecular understanding of biology, and the harnessing of biology can advance chemical knowledge as well [1][2][3][4]. Chemicals are widely used as probes to investigate biological functions [5][6][7].…”

Section: Prefacementioning

confidence: 99%

Preface

Hagler

2013

Sci. China Chem.

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“…7-Hydroxy-2 H -chromen-2-one (also known as 7-hydroxycoumarin, COH , or umbelliferone) is widely used as a fluorophore in sensors and probes due to the relatively simple methods of masking its hydroxyl group and a high water solubility (621 mg L −1 [ 4 ]). Umbelliferone was chosen as a scaffold to construct a wide variety of probes, by listing only several example, e.g., for the detection of anions [ 1 , 5 , 6 ], formaldehyde [ 7 ], hydrogen sulfide [ 8 , 9 , 10 ], biothiols [ 11 , 12 ], enzymes [ 13 , 14 ], Ser/Thr protein phosphatases [ 15 ], sulfane sulfurs [ 16 ], peroxynitrite [ 17 ], and hydrogen peroxide [ 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

Novel Boronate Probe Based on 3-Benzothiazol-2-yl-7-hydroxy-chromen-2-one for the Detection of Peroxynitrite and Hypochlorite

et al. 2021

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Derivatives of coumarin, containing oxidant-sensitive boronate group, were recently developed for fluorescent detection of inflammatory oxidants. Here, we report the synthesis and the characterization of 3-(2-benzothiazolyl)-7-coumarin boronic acid pinacol ester (BC-BE) as a fluorescent probe for the detection of peroxynitrite (ONOO–), with high stability and a fast response time. The BC-BE probe hydrolyzes in phosphate buffer to 3-(2-benzothiazolyl)-7-coumarin boronic acid (BC-BA) which is stable in the solution even after a prolonged incubation time (24 h). BC-BA is slowly oxidized by H2O2 to form the phenolic product, 3-benzothiazol-2-yl-7-hydroxy-chromen-2-one (BC-OH). On the other hand, the BC-BA probe reacts rapidly with ONOO−. The ability of the BC-BA probe to detect ONOO– was measured using both authentic ONOO– and the system co-generating steady-state fluxes of O2•– and •NO. BC-BA is oxidized by ONOO– to BC-OH. However, in this reaction 3-benzothiazol-2-yl-chromen-2-one (BC-H) is formed in the minor pathway, as a peroxynitrite-specific product. BC-OH is also formed in the reaction of BC-BA with HOCl, and subsequent reaction of BC-OH with HOCl leads to the formation of a chlorinated phenolic product, which could be used as a specific product for HOCl. We conclude that BC-BA shows potential as an improved fluorescent probe for the detection of peroxynitrite and hypochlorite in biological settings. Complementation of the fluorescence measurements by HPLC-based identification of oxidant-specific products will help to identify the oxidants detected.

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Design of OFF/ON fluorescent thiol probes based on coumarin fluorophore

Cited by 9 publications

References 24 publications

Coumarin-Based Small-Molecule Fluorescent Chemosensors

Coumarin-Based Small-Molecule Fluorescent Chemosensors

Preface

Novel Boronate Probe Based on 3-Benzothiazol-2-yl-7-hydroxy-chromen-2-one for the Detection of Peroxynitrite and Hypochlorite

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