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Your search keyword '"Jean-Alexandre Richard"' showing total 2 results
Start Over Author "Jean-Alexandre Richard" Journal organic & biomolecular chemistry
2 results on '"Jean-Alexandre Richard"'

1. Divergent synthesis of 5′,7′-difluorinated dihydroxanthene-hemicyanine fused near-infrared fluorophores

Author

Gu Lingyue, Shasha Zheng, Jean-Alexandre Richard, Denis Jacquemin, Rajavel Srinivasan, Michelle Jui Hsien Ong, Anthony Romieu, Institute of Chemical and Engineering Sciences (ICES) (ICES), Agency for science, technology and research [Singapore] (A*STAR), Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), 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), Institut Universitaire de France (IUF), and Ministère de l'Education nationale, de l’Enseignement supérieur et de la Recherche (M.E.N.E.S.R.)

Subjects
chemistry.chemical_classification, 010405 organic chemistry, Organic Chemistry, Near-infrared spectroscopy, chemistry.chemical_element, 010402 general chemistry, 01 natural sciences, Biochemistry, Combinatorial chemistry, Sulfur, Aldehyde, 0104 chemical sciences, Nucleophile, chemistry, Nucleophilic aromatic substitution, Yield (chemistry), [CHIM]Chemical Sciences, Physical and Theoretical Chemistry, Divergent synthesis
Abstract

International audience; We describe an expedient access to a 5', 6', 7'-trifluoro dihydroxanthene-hemicyanine fused scaffold in 2 steps and 54% overall yield from the corresponding salicylic aldehyde. A 6'-regioselective nucleophilic aromatic substitution (SNAr) reaction with a wide range of nitrogen, sulfur or selenium nucleophiles then gives access to 16 near-infrared (NIR) fluorophores emitting in the 710-750 nm range. We also report the experimental and theoretical photophysical investigations of these unique optical agents that include the first series of 6'-heavy atom substituted dihydroxanthenes, extending the pool of polyfluorinated markers for biomedical and material applications.

Published
2019
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2. A comparative study of the self-immolation of para-aminobenzylalcohol and hemithioaminal-based linkers in the context of protease-sensitive fluorogenic probes

Author

Jean-Alexandre Richard, Pierre-Yves Renard, Anthony Romieu, Pauline Noack, Yves Meyer, Bruno Delest, 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
Signal response, Protease, Molecular Structure, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Chemistry, medicine.medical_treatment, Organic Chemistry, Glyoxylates, Context (language use), Prodrug, 010402 general chemistry, 01 natural sciences, Biochemistry, Combinatorial chemistry, 0104 chemical sciences, Cascade reaction, Benzaldehydes, medicine, Physical and Theoretical Chemistry, Linker, Benzyl Alcohols, Fluorescent Dyes, Peptide Hydrolases
Abstract

International audience; This study focuses on the disassembly-behavior of self-immolative pro-fluorescent linkers under physiological conditions and through an enzyme-initiated domino reaction. The targeted linkers are based on para-aminobenzylalcohol (PABA) or hemithioaminal derivatives of para-carboxybenzaldehyde or glyoxilic acid. We found that a fine tuning of the kinetic properties could be obtained through the modulation of the linker structure, giving either a fast signal response or free-adaptable systems suitable for the design of protease-sensitive fluorogenic probes or prodrug systems.

Published
2010
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