0000000000064498

AUTHOR

Benoît Roubinet

0000-0001-7075-0235

showing 3 related works from this author

A FRET-​based probe for fluorescence sensing of sulfide​/sulfite analytes, using a novel long-​wavelength water-​soluble 7-​hydroxycoumarin as report…

2015

International audience; A FRET-based fluorescent probe for the detection of sulfide and/or sulfite in aqueous buffer, was constructed by connecting the quencher moiety nitrobenzofurazan (7-nitro-1,2,3-benzoxadiazole, NBD) to a water-soluble 3-(2-benzimidazolyl)-7-hydroxycoumarin carboxylic acid through a piperazine linker. This probe exhibits good selectivity and high sensitivity for sulfite and sulfide over cysteine and other potential analytes. Furthermore, this is one of the few examples of fluorogenic coumarins whose solubility in water is maintained upon its conversion into reaction-based fluorescent probes.

FluorophoreSulfideCarboxylic acidInorganic chemistry[CHIM.THER]Chemical Sciences/Medicinal Chemistry010402 general chemistry01 natural sciencesBiochemistrychemistry.chemical_compoundSulfite[CHIM.ANAL]Chemical Sciences/Analytical chemistryDrug DiscoveryMoietychemistry.chemical_classification010405 organic chemistryChemistry[CHIM.ORGA]Chemical Sciences/Organic chemistryOrganic Chemistry[CHIM.CATA]Chemical Sciences/CatalysisFluorescenceCombinatorial chemistry0104 chemical sciences[CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistryFörster resonance energy transferLinker[CHIM.CHEM]Chemical Sciences/Cheminformatics
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New insights into the water-solubilization of thiol-sensitive fluorogenic probes based on long-wavelength 7-hydroxycoumarin scaffolds

2014

Abstract The synthesis and photophysical properties of novel water-soluble phenol-based fluorophores derived from 3-benzothiazolyl-7-hydroxycoumarin and emitting in the range 485–631 nm are described. Further conversion into thiol-sensitive fluorogenic probes through the chemical modification of their hydroxyl group was next investigated. Depending on the type of thiol-reactive quenching moiety used (2,4-dinitrobenzenesulfonyl ester, 2,4-dinitrophenyl ether or benzoquinone-type Michael acceptors) and the water-solubilizing group(s) pre-introduced into the coumarin core, dramatic differences in the thiol-induced fluorescence activation of these pro-fluorophores under physiological conditions…

chemistry.chemical_classificationQuenching (fluorescence)[CHIM.ORGA]Chemical Sciences/Organic chemistryProcess Chemistry and TechnologyGeneral Chemical EngineeringChemical modificationEther[CHIM.CATA]Chemical Sciences/Catalysis[CHIM.THER]Chemical Sciences/Medicinal ChemistryPhotochemistryCoumarinFluorescence[CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistrychemistry.chemical_compoundchemistry[CHIM.ANAL]Chemical Sciences/Analytical chemistryThiolPhenolMoietyComputingMilieux_MISCELLANEOUS[CHIM.CHEM]Chemical Sciences/CheminformaticsDyes and Pigments
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A Synthetic Route to 3-(Heteroaryl)-7-hydroxycoumarins Designed for Biosensing Applications

2014

A straightforward method to synthesize 3-(2-benzimidazolyl)-7-hydroxycoumarins, based on the condensation reaction of 7-acetoxy-3-formylcoumarin with various C- and/or N-substituted ortho-phenylenediamine derivatives is presented. This unusual approach proved particularly effective for introducing different hydrophilic groups (carboxylic or sulfonic acids or trimethylalkylammonium moieties) onto the heteroaryl scaffold, leading to cyan-green emitting coumarins that were both water-soluble and strongly fluorescent under physiological conditions. The further extension of this condensation reaction to bis(2-aminophenyl)diselenide enabled the first synthesis of 3-(2-benzoselenazolyl)-7-hydroxyc…

Protease010405 organic chemistryChemistrymedicine.medical_treatmentOrganic Chemistry010402 general chemistryCondensation reaction01 natural sciencesFluorescence0104 chemical sciencesDiselenidemedicineOrganic chemistryPhysical and Theoretical ChemistryBiosensorEuropean Journal of Organic Chemistry
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