Coumarin as a structural component of substrates and probes for serine and cysteine proteases

Breidenbach, Julian; Bartz, Ulrike; Gütschow, Michael

doi:10.1016/j.bbapap.2020.140445

Cited by 21 publications

(20 citation statements)

References 126 publications

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“…Fluorescence can be provided by means of a fluorescent low-molecular weight probe possessing sufficient affinity for the target protein. A widely used class of fluorophores, 7-aminocoumarins, are characterized by chemical and enzymatic stability, a small molecular size and large Stokes shifts (Breidenbach et al, 2020). Rigidization of the amino group due to cyclization resulted in increased quantum yields and restored fluorescence in aqueous media.…”

Section: Resultsmentioning

confidence: 99%

Development of Fluorescent and Biotin Probes Targeting NLRP3

et al. 2021

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Extracellular signals drive the nucleation of the NLRP3 inflammasome which leads to the release of cytokines and causes inflammatory events. Hence, the inflammasome has gained enormous momentum in biomedical basic research. The detailed mechanisms of inflammasome generation and regulation remain to be elucidated. Our study was directed toward the design, convergent synthesis, and initial biochemical evaluation of activity-based probes addressing NLRP3. For this purpose, probes were assembled from a CRID3/MCC950-related NLRP3-binding unit, a linker portion and a coumarin 343 fluorophore or biotin. The affinity of our probes to NLRP3 was demonstrated through SPR measurements and their cellular activity was confirmed by reduction of the interleukin 1β release from stimulated bone marrow-derived macrophages. The initial characterizations of NLRP3-targeting probes highlighted the coumarin probe 2 as a suitable tool compound for the cellular and biochemical analysis of the NLRP3 inflammasome.

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Section: Resultsmentioning

confidence: 99%

Development of Fluorescent and Biotin Probes Targeting NLRP3

et al. 2021

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“…In addition to the interest of coumarins as a versatile scaffold in drug design, the important role that this scaffold plays as fluorescent probes to detect metals, enzymes, and biomaterials, among others, should be highlighted [ 56 , 57 , 58 , 59 ]. These fluorescent probes have a great imaging potential for the diagnosis of several pathologies.…”

Section: Discussionmentioning

confidence: 99%

Trending Topics on Coumarin and Its Derivatives in 2020

et al. 2021

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Coumarins are naturally occurring molecules with a versatile range of activities. Their structural and physicochemical characteristics make them a privileged scaffold in medicinal chemistry and chemical biology. Many research articles and reviews compile information on this important family of compounds. In this overview, the most recent research papers and reviews from 2020 are organized and analyzed, and a discussion on these data is included. Multiple electronic databases were scanned, including SciFinder, Mendeley, and PubMed, the latter being the main source of information. Particular attention was paid to the potential of coumarins as an important scaffold in drug design, as well as fluorescent probes for decaging of prodrugs, metal detection, and diagnostic purposes. Herein we do an analysis of the trending topics related to coumarin and its derivatives in the broad field of drug discovery.

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“…Coumarins, thus, appear suitable as nuclear receptor ligands. Furthermore, it is not limited to ligands that target nuclear receptors, coumarins were reported to have an established structure for introducing fluorescence into tool compounds for the biochemical studies [ 53 ]. This was because studies on the effects of the positions of substituents and the properties of functional groups (electron-withdrawing or electron-donating) on the fluorescent properties of coumarin were widely studied for decades [ 54 ].…”

Section: Discussionmentioning

confidence: 99%

Synthesis of a Coumarin-Based PPARγ Fluorescence Probe for Competitive Binding Assay

Yoshikawa¹,

Ishida²,

Ohashi³

et al. 2021

IJMS

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Peroxisome proliferator-activated receptor γ (PPARγ) is a molecular target of metabolic syndrome and inflammatory disease. PPARγ is an important nuclear receptor and numerous PPARγ ligands were developed to date; thus, efficient assay methods are important. Here, we investigated the incorporation of 7-diethylamino coumarin into the PPARγ agonist rosiglitazone and used the compound in a binding assay for PPARγ. PPARγ-ligand-incorporated 7-methoxycoumarin, 1, showed weak fluorescence intensity in a previous report. We synthesized PPARγ-ligand-incorporating coumarin, 2, in this report, and it enhanced the fluorescence intensity. The PPARγ ligand 2 maintained the rosiglitazone activity. The obtained partial agonist 6 appeared to act through a novel mechanism. The fluorescence intensity of 2 and 6 increased by binding to the ligand binding domain (LBD) of PPARγ and the affinity of reported PPARγ ligands were evaluated using the probe.

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Coumarin as a structural component of substrates and probes for serine and cysteine proteases

Cited by 21 publications

References 126 publications

Development of Fluorescent and Biotin Probes Targeting NLRP3

Development of Fluorescent and Biotin Probes Targeting NLRP3

Trending Topics on Coumarin and Its Derivatives in 2020

Synthesis of a Coumarin-Based PPARγ Fluorescence Probe for Competitive Binding Assay

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