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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
Author(s) -
Carayon Chantal,
Ghodbane Abdelhamid,
Gibot Laure,
Dumur Rémy,
Wang Jinhui,
Saffon Nathalie,
Rols MariePierre,
Solntsev Kyril M.,
FeryForgues Suzanne
Publication year - 2016
Publication title -
small
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 3.785
H-Index - 236
eISSN - 1613-6829
pISSN - 1613-6810
DOI - 10.1002/smll.201602799
Subject(s) - chromophore , alkyl , benzoxazole , fluorescence , molecule , nanoparticle , photochemistry , green fluorescent protein , chemistry , small molecule , biophysics , materials science , nanotechnology , organic chemistry , biochemistry , physics , quantum mechanics , biology , gene
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.