title: Synthesis of quinoline dicarboxylic esters as biocompatible fluorescent tags.
abstract: A series of dicarboxylic quinoline derivatives bearing electron-releasing or -withdrawing substituents have been synthesized using mono- or/and biphasic methodologies. By controlling the regioselectivity of addition into our electrophilic intermediate, we also characterized by which mechanism the Doebner-Miller cyclization step occurred. As anticipated, electron-releasing substituents induce a red shift of the low-energy absorption allowing excitation in the visible region. In addition, by playing on the strength and position of the electron-releasing substituents, chromophore having interesting fluorescent properties such as large Stoke shifts, good fluorescent quantum yields, emission in the visible green-yellow region and reasonable two-photon absorption in the NIR region have been obtained. These small-size fluorophores, which can be made water-soluble and have been shown to be non-toxic, can be hetero- and/or polyfunctionalized and thus represent promising key units for fluorescence-based physiological experiments with low background interactions.
authors.affiliation: Université Paris Descartes, Sorbonne Paris Cité, Centre National de la Recherche Scientifique, UMR 8601, F-75006 Paris, France.
authors.forename: Younes
authors.initials: Y
authors.lastname: Laras
authors.forename: Vincent
authors.initials: V
authors.lastname: Hugues
authors.forename: Yogesh
authors.initials: Y
authors.lastname: Chandrasekaran
authors.forename: Mireille
authors.initials: M
authors.lastname: Blanchard-Desce
authors.forename: Francine C
authors.initials: FC
authors.lastname: Acher
authors.forename: Nicolas
authors.initials: N
authors.lastname: Pietrancosta
mesh_terms: D000042:Absorption; D003998:Dicarboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D004583:Electrons; D004952:Esters; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013050:Spectrometry, Fluorescence
chemical_list: D003998:Dicarboxylic Acids; D004952:Esters; D005456:Fluorescent Dyes; D011804:Quinolines