title: Conjugates of Benzoxazole and GFP Chromophore with Aggregation-Induced Enhanced Emission: Influence of the Chain Length on the Formation of Particles and on the Dye Uptake by Living Cells.
abstract: Six conjugates of benzoxazole and green fluorescent protein chromophore that differ by the length of their alkyl chain (from C1 to C16) are investigated. They exhibit rigidofluorochromism and clear aggregation-induced emission enhancement (AIEE) behavior with emission in the orange-red that is specific to the solid state. A preparation method based on solvent exchange is used to prepare particles. The self-association properties of these molecules depend on the length of the alkyl chain. Microfibers, platelets, and rounded microparticles are successively obtained by increasing the chain length. The same method is used to prepare nanoparticles (NPs) that are fully characterized. In particular, homogeneous populations of stable NPs measuring around 70 nm are obtained with the analogs whose chains contain four to eight carbon atoms. The behavior with respect to living cells is also influenced by the nature of the compounds. Only the dyes with intermediate hydrophobicity are efficiently uptaken by both normal and tumor cells, and fluorescence only originates from dispersed dye molecules. There is no evidence for incorporation of NPs into cells. This work shows that small variations of the chemical structure must be taken into account for making the best use of AIEE compounds in view of precise applications.
authors.affiliation: SPCMIB, UMR5068, CNRS-Université Paul Sabatier-Toulouse III, 118 route de Narbonne, F31062, Toulouse, France.
authors.forename: Chantal
authors.initials: C
authors.lastname: Carayon
authors.affiliation: ITAV, USR 3505, CNRS-Université de Toulouse, F31106, Toulouse, France.
authors.forename: Abdelhamid
authors.initials: A
authors.lastname: Ghodbane
authors.affiliation: Equipe de Biophysique Cellulaire, IPBS-CNRS UMR 5089, 205 route de Narbonne, BP 64182, F31077, Toulouse Cedex, France.
authors.forename: Laure
authors.initials: L
authors.lastname: Gibot
authors.affiliation: ITAV, USR 3505, CNRS-Université de Toulouse, F31106, Toulouse, France.
authors.forename: Rémy
authors.initials: R
authors.lastname: Dumur
authors.affiliation: SPCMIB, UMR5068, CNRS-Université Paul Sabatier-Toulouse III, 118 route de Narbonne, F31062, Toulouse, France.
authors.forename: Jinhui
authors.initials: J
authors.lastname: Wang
authors.affiliation: Service Commun RX, Institut de Chimie de Toulouse, ICT- FR2599, Université Paul Sabatier, F31062, Toulouse Cedex 9, France.
authors.forename: Nathalie
authors.initials: N
authors.lastname: Saffon
authors.affiliation: Equipe de Biophysique Cellulaire, IPBS-CNRS UMR 5089, 205 route de Narbonne, BP 64182, F31077, Toulouse Cedex, France.
authors.forename: Marie-Pierre
authors.initials: MP
authors.lastname: Rols
authors.affiliation: School of Chemistry and Biochemistry, Georgia Institute of Technology, 901 Atlantic Drive, Atlanta, GA, 30332-0400, USA.|Olis Inc., 130 Conway Dr, Bogart, GA, 30622, USA.
authors.forename: Kyril M
authors.initials: KM
authors.lastname: Solntsev
authors.affiliation: SPCMIB, UMR5068, CNRS-Université Paul Sabatier-Toulouse III, 118 route de Narbonne, F31062, Toulouse, France.
authors.forename: Suzanne
authors.initials: S
authors.lastname: Fery-Forgues
mesh_terms: D001583:Benzoxazoles / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry; D049452:Green Fluorescent Proteins / Q000737:chemistry*; D064347:Microscopy, Electrochemical, Scanning; D053758:Nanoparticles / Q000737:chemistry* / Q000648:ultrastructure
chemical_list: D001583:Benzoxazoles; D005456:Fluorescent Dyes; D049452:Green Fluorescent Proteins
keywords: aggregation-induced emission; confocal microscopy; crystals; dye uptake; nanoparticles