4.1 Review

Boron-Containing Coumarins (Review)

Related references

Note: Only part of the references are listed.
Article Biochemistry & Molecular Biology

Development of a New Methodology for Dearomative Borylation of Coumarins and Chromenes and Its Applications to Synthesize Boron-Containing Retinoids

Bhaskar C. Das et al.

Summary: A new and general copper (I) catalyzed dearomative borylation process for synthesizing boron-containing oxacycles is reported. Coumarins, chromones, and chromenes with functional groups such as esters, nitriles, carbonyls, and amides can be borylated using this method. The borylated oxacycles can serve as intermediates for generating a library of compounds, including potential boron-based retinoids with oxadiazole and anthocyanin motifs.

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Exploring Coumarin-Based Boron Emissive Complexes as Temperature Thermometers in Polymer-Supported Materials

Goncalo Pedro et al.

Summary: Three coumarin-based boron complexes (L1, L2 and L3) were successfully incorporated into polymeric matrixes for temperature probes, showing high fluorescence quantum yield in solution and positive solvatochromism. L1 exhibited a colour change and quenching in emission intensity in the presence of anions due to deprotonation. The dye@doped polymers of L1, L2 and L3 showed excellent fluorescent response and reversibility as temperature sensors.

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Article Chemistry, Organic

A coumarin-based fluorescent probe for sensitive monitoring H2O2 in water and living cells

Yuanyuan Li et al.

Summary: By introducing boronate esters as a recognition unit, a fluorescent probe (Probe 1) was developed for the qualitative and quantitative determination of hydrogen peroxide. The probe exhibited a change in absorbance and fluorescence emission spectra upon reaction with hydrogen peroxide, and it showed high sensitivity with a detection limit of 118.2 nM. The probe also demonstrated good stability and selectivity in the presence of various ions and was successfully used for imaging macrophage and colon cancer cells.

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Supramolecular chemistry of anionic boron clusters and its applications in biology

Jakub Cebula et al.

Summary: This article discusses the intertwining of supramolecular chemistry and biology, and the importance and potential of boron cluster chemistry in biological applications.

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Recent Advances in Hydrogen Peroxide Responsive Organoborons for Biological and Biomedical Applications

Eron Saxon et al.

Summary: This review discusses the importance of hydrogen peroxide in various disease conditions and the reactivity of organoborons with H2O2, providing a method for developing chemoselective molecules for biological and medical applications. Additionally, it highlights the design and application of boron-derived molecules for H2O2 detection, as well as the utility of boron moieties for masking reactive compounds.

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Water-soluble cationic boronate probe based on coumarin imidazolium scaffold: Synthesis, characterization, and application to cellular peroxynitrite detection

Aleksandra Grzelakowska et al.

Summary: A new water-soluble and cationic boronate probe (CI-Bz-BA) based on a coumarin-imidazolium scaffold for the fluorescent detection of ONOO- in cells was developed. The probe reacts stoichiometrically with ONOO- to form major phenolic product CI-OH and minor nitrated product CI-Bz-NO2, which were not formed by other oxidants tested. Detection of endogenously produced ONOO- was demonstrated using the probe in RAW 264.7 cells through fluorescence measurements and liquid chromatography/mass spectrometry analyses.

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Boronate-Based Fluorescent Probes as a Prominent Tool for H2O2 Sensing and Recognition

Ling Wang et al.

Summary: Fluorescent probes have been widely used as important tools for detecting H2O2 to reflect the physiological and pathological conditions of biological systems, with boronate ester and boronic acid groups serving as sensitive responsive parts in these probes. This review summarizes fluorescent probes based on boronate ester/boronic acid groups reported from 2012 to 2020, and classifies the fluorophores into six categories to elaborate the design strategy and systematic performance comprehensively.

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Deep-red/NIR emitting coumarin derivatives- Synthesis, photophysical properties, and biological applications

Suryapratap J. Sharma et al.

Summary: Dyes with a coumarin core are highly valuable for their ability to absorb and emit light in the deep-red to NIR region. They play essential roles in biology, DSSC, NLO materials, and LASER dyes. This review summarizes the photophysical features, synthetic methodologies, and applications of these dyes. The relevance of DFT and TD-DFT techniques in obtaining the desired photophysical characteristics of coumarin dyes before synthesis is also discussed.

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Coumarins derivatives and inflammation: Review of their effects on the inflammatory signaling pathways

Batoul Rostom et al.

Summary: Natural and synthetic coumarins have been studied as effective drugs with multiple pharmacological activities, particularly in anti-inflammatory potential. However, there has been no major breakthrough in the development of therapeutic anti-inflammatory agents using coumarins. This review summarizes the relevant studies conducted in the last two decades and presents evidence for the anti-inflammatory mechanisms of coumarins, specifically targeting Toll-like receptors, JAK/STAT pathway, inflammasomes, MAPK pathway, NF-kappa B pathway, and TGF-beta/SMAD pathway.

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Synthetic and natural coumarins as potent anticonvulsant agents: A review with structure-activity relationship

Rangappa S. Keri et al.

Summary: This review aims to summarize the most relevant studies since 1990 in the field of medicinal chemistry related to coumarin-based anticonvulsant agents. It provides a panoramic view and design suggestions for biologists and medicinal chemists. These findings contribute to the rational design of more effective and safer antiepileptic drugs.

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Carboranes as unique pharmacophores in antitumor medicinal chemistry

Yu Chen et al.

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New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their Click Chemistry Reactions for the Conjugation with closo-Dodecaborate Anion

Julia Laskova et al.

Summary: In this study, novel fluorescent coumarins modified with an azido-group on the side chain were synthesized and their photophysical properties and crystal structure characteristics were investigated. The possibilities of fluorescent labeling were demonstrated by testing the synthesized coumarins with a closo-dodecaborate derivative bearing a terminal alkynyl group. Fluorescent conjugates were formed through Cu-I catalyzed Huisgen 1,3-dipolar cycloaddition reaction. The antiproliferative activity and uptake of the compounds against various human cell lines were evaluated.

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Radiation-Chemical Transformations of 7-NH3-4-CH3-Coumarin Decahydro-closo-Decaborate as a Potential Inhibitor of Free Radicals

L. Goeva et al.

Summary: Compound (7-NH3-L)(2)[B10H10] was synthesized and characterized by elemental analysis, IR and UV spectroscopy. It was found that this compound has the potential to inhibit free radicals and contains a representative of biological active coumarins and boron cluster anions widely used in scientific and technological fields.

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Reaction of Chloroacetyl-Modified Peptides with Mercaptoundecahydrododecaborate (BSH) Is Accelerated by Basic Amino Acid Residues in the Peptide

Mizuki Kitamatsu et al.

Summary: This study assessed the reactivity between chloroacetyl-modified tripeptides with different amino acid residues and mercaptoundecahydrododecaborate. The results showed that the reactivity varied with the type and number of amino acid residues as well as the length of the alkyl linker. The electrostatic attraction between positively charged amino acid residues and negatively charged mercaptoundecahydrododecaborate was found to play a key role in the accelerated reaction.

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Dual-Ratiometric Fluorescent Probe for H2O2 and HClO in Living Cells and Zebrafish and Application in Alcoholic Liver Injury Monitoring

Peixin Niu et al.

Summary: This study presents a ratio-based fluorescent probe that can simultaneously distinguish HClO and H2O2. The probe exhibits high sensitivity and selectivity in aqueous media, and is applicable in a wide pH range. Imaging experiments in cells and zebrafish confirm the feasibility of using this probe, which can also be used for monitoring the variation of HClO and H2O2 levels in alcoholic liver injury.

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New boron-based coumarin fluorophores for bioimaging applications

Anita Marfavi et al.

Summary: The synthesis and characterisation of five new boron-based coumarin fluorophores were reported, showing significant bathochromic shifts compared to the parent compound and displaying distinct intra-cellular distributions in lung cancer cells. Boronic acid species were found to localise in the endoplasmic reticulum, while closo-1,2-carborane derivatives were found to localise within lipid droplets.

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Pharmacological perspectives and molecular mechanisms of coumarin derivatives against virus disease

Zhoupeng Li et al.

Summary: Virus infections are a major cause of morbidity and mortality worldwide, with a lack of available therapeutic agents for most viruses. Recent research has highlighted the potential role of coumarin derivatives as antiviral agents, making them important for the inhibition of various viruses.

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Summary: This study reports on the synthesis and characterization of a coumarin derivative containing an oxidant-sensitive boronate group as a fluorescent probe for the detection of peroxynitrite. The probe showed high stability and a fast response time, with the ability to detect peroxynitrite and hypochlorite in biological settings. HPLC-based identification of oxidant-specific products complements the fluorescence measurements for accurate detection of the oxidants.

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Neville Murphy et al.

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