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1. Fluorescent Photoswitchable Diarylethenes for Biolabeling and Single-Molecule Localization Microscopies with Optical Superresolution

Author

Masahiro Irie, Heydar Shojaei, Michael Weber, Mariano L. Bossi, Mark Bates, Vladimir N. Belov, Benoît Roubinet, and Stefan W. Hell

Subjects
Single molecule localization, chemistry.chemical_classification, Aqueous solution, Chemistry, Carboxylic acid, Nanotechnology, 02 engineering and technology, General Chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, Ring (chemistry), Photochemistry, 01 natural sciences, Biochemistry, Fluorescence, Superresolution, Catalysis, 0104 chemical sciences, Colloid and Surface Chemistry, Microscopy, 0210 nano-technology, Conjugate
Abstract

A modular assembly of water-soluble diarylethenes (DAEs), applicable as biomarkers for optical nanoscopy, is reported. Reversibly photoswitchable 1,2-bis(2-alkyl-6-phenyl-1-benzothiophene-1,1-dioxide-3-yl)perfluorocyclopentenes possessing a fluorescent "closed" form were decorated with one or two methoxy group(s) attached to the para-position(s) of phenyl ring(s) and two, four, or eight carboxylic acid groups. Antibody conjugates of these DAEs feature low aggregation, efficient photoswitching in aqueous buffers, specific staining of cellular structures, and photophysical properties (high emission efficiencies and low cycloreversion quantum yields) enabling their application in superresolution microscopy. Images of tubulin, vimentin, and nuclear pore complexes are presented. The superresolution images can also be acquired by using solely 488 nm light without additional photoactivation with UV light. These DAEs exhibit reversible photoswitching without requiring any additives to the imaging media and open new paths toward the modular design of fluorescent dyes for bioimaging with optical superresolution.

Published
2017

2. Reinvestigation of the Synthesis of 'Covalent-Assembly' Type Probes for Fluoride Ion Detection. Identification of Novel 7-(Diethylamino)coumarins with Aggregation-Induced Emission Properties

Author

Benoît Roubinet, Pierre-Yves Renard, Anthony Romieu, Valentin Quesneau, Institut de Chimie Moléculaire de l'Université de Bourgogne [Dijon] (ICMUB), Centre National de la Recherche Scientifique (CNRS)-Université de Bourgogne (UB)-Institut de Chimie du CNRS (INC), Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), and Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Chemistry, Organic Chemistry, Substituent, 02 engineering and technology, Tetraphenylethylene, Alkylation, 021001 nanoscience & nanotechnology, 010402 general chemistry, 01 natural sciences, Biochemistry, Combinatorial chemistry, Fluorescence, 0104 chemical sciences, Adduct, chemistry.chemical_compound, Salicylaldehyde, Covalent bond, Drug Discovery, Moiety, 0210 nano-technology, Fluoride
Abstract

International audience; An unprecedented C-3 functionalization of 4-(diethylamino)salicylaldehyde through a Friedel-Crafts type alkylation reaction has been discovered during the synthesis of “covalent-assembly”-based fluorescent probes for detection of fluoride ions. The resulting Friedel-Crafts adduct was successfully used for the preparation of two novel 8-substituted 7-(diethylamino)coumarin dyes. The photophysical study of these fluorophores has enabled us to highlight their remarkable aggregation-induced emission (AIE) properties characterized by a yellow-orange emission of aggregates in water. Therefore, 4-(tert-butyldimethylsilyloxy)benzyl substituent was identified as a novel AIE-active moiety which could be seen as a possible alternative to popular tetraphenylethylene (TPE).

Published
2019

3. Carboxylated Photoswitchable Diarylethenes for Biolabeling and Super‐Resolution RESOLFT Microscopy

Author

Stefan W. Hell, Masahiro Irie, Shamil Nizamov, Philipp Alt, Vladimir N. Belov, Mariano L. Bossi, Benoît Roubinet, Heydar Shojaei, Marcel Leutenegger, and Sebastian Schnorrenberg

Subjects
RESOLFT, photochromic dyes, 010402 general chemistry, Photochemistry, 01 natural sciences, Catalysis, law.invention, Optical microscope, law, Microscopy, Specific staining, optical microscopy, water solubility, Aqueous solution, 010405 organic chemistry, Chemistry, Communication, Resolution (electron density), Optical Microscopy | Very Important Paper, General Chemistry, Fluorescence, Superresolution, Communications, 0104 chemical sciences, diarylethenes, fluorescence
Abstract

Reversibly photoswitchable 1,2‐bis(2‐ethyl‐6‐phenyl‐1‐benzothiophene‐1,1‐dioxide‐3‐yl)perfluorocyclopentenes (EBT) having fluorescent “closed” forms were decorated with four or eight carboxylic groups and attached to antibodies. Low aggregation, efficient photoswitching in aqueous buffers, specific staining of cellular structures, and good photophysical properties were demonstrated. Alternating light pulses of UV and blue light induce numerous reversible photochemical transformations between two stables states with distinct structures. Using relatively low light intensities, EBTs were applied in biology‐related super‐resolution microscopy based on the reversible saturable (switchable) optical linear fluorescence transitions (RESOLFT) and demonstrated optical resolution of 75 nm.

Published
2016

4. New insights into the water-solubilization of thiol-sensitive fluorogenic probes based on long-wavelength 7-hydroxycoumarin scaffolds

Author

Pierre-Yves Renard, Benoît Roubinet, Anthony Romieu, Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), and Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
chemistry.chemical_classification, Quenching (fluorescence), [CHIM.ORGA]Chemical Sciences/Organic chemistry, Process Chemistry and Technology, General Chemical Engineering, Chemical modification, Ether, [CHIM.CATA]Chemical Sciences/Catalysis, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Photochemistry, Coumarin, Fluorescence, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, chemistry.chemical_compound, chemistry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Thiol, Phenol, Moiety, ComputingMilieux_MISCELLANEOUS, [CHIM.CHEM]Chemical Sciences/Cheminformatics
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 were observed. Results for this comparative study provide valuable informations for the selection of the most suitable structural features for designing 7-hydroxycoumarin-based long-wavelength fluorescent probes for thiol bioimaging.

Published
2014

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

Author

Benoît Roubinet, Anthony Romieu, Emilie Petit, Pierre-Yves Renard, Laetitia Bailly, Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), and Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Fluorophore, Sulfide, Carboxylic acid, Inorganic chemistry, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 010402 general chemistry, 01 natural sciences, Biochemistry, chemistry.chemical_compound, Sulfite, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Drug Discovery, Moiety, chemistry.chemical_classification, 010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, [CHIM.CATA]Chemical Sciences/Catalysis, Fluorescence, Combinatorial chemistry, 0104 chemical sciences, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, Förster resonance energy transfer, Linker, [CHIM.CHEM]Chemical Sciences/Cheminformatics
Abstract

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.

Published
2015

6. New 3-(Heteroaryl)-2-iminocoumarin-based Borate Complexes: Synthesis, Photophysical Properties, and Rational Functionalization for Biosensing/Biolabeling Applications

Author

Pierre-Yves Renard, Anthony Romieu, Benoît Roubinet, Frédéric Boschetti, Mathieu Moreau, Gilles Ulrich, Raymond Ziessel, Cédrik Massif, Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement - UMR 8516 (LASIRE), Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Centrale Lille Institut (CLIL), CheMatech - Macrocycle Design Technologies, Institut de chimie et procédés pour l'énergie, l'environnement et la santé (ICPEES), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Organique Fine (IRCOF), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Rouen Normandie (UNIROUEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), and Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Aminocoumarins, Boron Compounds, Macrocyclic Compounds, Carboxylic acid, Substituent, Ligands, 010402 general chemistry, 01 natural sciences, Catalysis, Fluorescence, chemistry.chemical_compound, Macrocyclic ligands, Coumarins, Borates, Organic chemistry, Molecule, Moiety, [CHIM]Chemical Sciences, Dyes, Fluorescent Dyes, Boron, chemistry.chemical_classification, Molecular Structure, 010405 organic chemistry, Coumarin dyes, Organic Chemistry, Chemical modification, Serum Albumin, Bovine, General Chemistry, Combinatorial chemistry, 0104 chemical sciences, chemistry, Amine gas treating, Biosensor
Abstract

International audience; Members of a series of boron difluoride complexes with 3‐(heteroaryl)‐2‐iminocoumarin ligands bearing both a phenolic hydroxyl group (acting as a fluorogenic center) and an N‐aryl substituent (acting as a stabilizing moiety) have been synthesized in good yields by applying a straightforward two‐step method. These novel fluorogenic dyes belong to the family of “Boricos” (D. Frath et al., Chem. Commun.­ 2013, 49, 4908–4910) and are the first examples of phenol‐based fluorophores of which the photophysical properties in the green‐yellow spectral range are dramatically improved by N,N‐chelation of a boron atom. Modulation of their fluorescence properties through reversible chemical modification of their phenol moieties has been demonstrated by the preparation of the corresponding 2,4‐dinitrophenyl (DNP) ethers, which led to a dramatic “OFF‐ON” fluorescence response upon reaction with thiols. Additionally, to expand the scope of these “7‐hydroxy‐Borico” derivatives, particularly in biolabeling, amine or carboxylic acid functionalities amenable to (bio)conjugation have been introduced within their scaffold. Their utility has been demonstrated in the preparation of fluorescent bovine serum albumin (BSA) conjugates and “Borico”‐DOTA‐like scaffolds in an effort to design novel monomolecular multimodal fluorescence‐ radioisotope imaging agents.

Published
2015

7. Back Cover: Carboxylated Photoswitchable Diarylethenes for Biolabeling and Super-Resolution RESOLFT Microscopy (Angew. Chem. Int. Ed. 49/2016)

Author

Marcel Leutenegger, Heydar Shojaei, Philipp Alt, Benoît Roubinet, Sebastian Schnorrenberg, Shamil Nizamov, Vladimir N. Belov, Masahiro Irie, Stefan W. Hell, and Mariano L. Bossi

Subjects
Materials science, Optical microscope, law, RESOLFT, Microscopy, Cover (algebra), General Chemistry, Photochemistry, Superresolution, Fluorescence, Catalysis, law.invention
Published
2016

8. A Synthetic Route to 3-(Heteroaryl)-7-hydroxycoumarins Designed for Biosensing Applications

Author

Arnaud Chevalier, Benoît Roubinet, Pierre-Yves Renard, and Anthony Romieu

Subjects
Protease, 010405 organic chemistry, Chemistry, medicine.medical_treatment, Organic Chemistry, 010402 general chemistry, Condensation reaction, 01 natural sciences, Fluorescence, 0104 chemical sciences, Diselenide, medicine, Organic chemistry, Physical and Theoretical Chemistry, Biosensor
Abstract

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-hydroxycoumarin. The potential utility of these new 7-hydroxycoumarins was demonstrated through the synthesis and spectroscopic and analyte-responsive behavior of fluorogenic probes suitable for sensing biologically relevant thiols and urokinase, a protease that plays a key role in cancer invasion and metastasis.

Published
2014

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