title: New 3-(heteroaryl)-2-iminocoumarin-based borate complexes: synthesis, photophysical properties, and rational functionalization for biosensing/biolabeling applications.
abstract: 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.
authors: Normandie Université, COBRA UMR 6014 & FR 3035, UNIV Rouen; INSA Rouen; CNRS, IRCOF, 1, Rue Tesnières, 76821 Mont-Saint-Aignan cedex (France), Fax: (+33) 2-35-52-29-71 http://ircof.crihan.fr.
authors: Benoît
authors: B
authors: Roubinet
authors: Normandie Université, COBRA UMR 6014 & FR 3035, UNIV Rouen; INSA Rouen; CNRS, IRCOF, 1, Rue Tesnières, 76821 Mont-Saint-Aignan cedex (France), Fax: (+33) 2-35-52-29-71 http://ircof.crihan.fr.
authors: Cédrik
authors: C
authors: Massif
authors: ICMUB, UMR 6302, CNRS, Univ. Bourgogne Franche-Comté, 9, Avenue Alain Savary, 21000 Dijon (France), Fax: (+33) 3-80-39-61-17 http://www.icmub.fr.
authors: Mathieu
authors: M
authors: Moreau
authors: CheMatech, 9, Avenue Alain Savary, 21000 Dijon (France) http://www.chematech-mdt.com.
authors: Frédéric
authors: F
authors: Boschetti
authors: COMBO-ICPEES, ECPM, UMR 7515, CNRS/Université de Strasbourg, 25, Rue Becquerel, 67087 Strasbourg cedex (France) http://icpees.unistra.fr.
authors: Gilles
authors: G
authors: Ulrich
authors: LCOSA-ICPEES, ECPM, UMR 7515, CNRS/Université de Strasbourg, 25, Rue Becquerel, 67087 Strasbourg cedex (France) http://icpees.unistra.fr.
authors: Raymond
authors: R
authors: Ziessel
authors: Normandie Université, COBRA UMR 6014 & FR 3035, UNIV Rouen; INSA Rouen; CNRS, IRCOF, 1, Rue Tesnières, 76821 Mont-Saint-Aignan cedex (France), Fax: (+33) 2-35-52-29-71 http://ircof.crihan.fr.
authors: Pierre-Yves
authors: PY
authors: Renard
authors: ICMUB, UMR 6302, CNRS, Univ. Bourgogne Franche-Comté, 9, Avenue Alain Savary, 21000 Dijon (France), Fax: (+33) 3-80-39-61-17 http://www.icmub.fr. anthony.romieu@u-bourgogne.fr.|Institut Universitaire de France, 103, Boulevard Saint-Michel, 75005 Paris (France). anthony.romieu@u-bourgogne.fr.
authors: Anthony
authors: A
authors: Romieu
mesh_terms: D049933:Aminocoumarins / Q000138:chemical synthesis* / Q000737:chemistry*; D001881:Borates / Q000138:chemical synthesis* / Q000737:chemistry; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D008024:Ligands; D047028:Macrocyclic Compounds / Q000737:chemistry*; D015394:Molecular Structure; D012710:Serum Albumin, Bovine / Q000737:chemistry*
chemical_list: C000607308:7-hydroxy-boron(III)iminocoumarin; D049933:Aminocoumarins; D001881:Borates; D001896:Boron Compounds; D003374:Coumarins; D005456:Fluorescent Dyes; D008024:Ligands; D047028:Macrocyclic Compounds; D012710:Serum Albumin, Bovine
keywords: boron; coumarin dyes; dyes; fluorescence; macrocyclic ligands