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Title: Synthesis and fluorescence properties of n-substituted 1-cyanobenz[ F ]isoindole chitosan polymers and nanoparticles for live cell imaging
Authors: Pattarapond Gonil
Warayuth Sajomsang
Uracha Rungsardthong Ruktanonchai
Preeyawis Na Ubol
Alongkot Treetong
Praneet Opanasopit
Satit Puttipipatkhachorn
Thailand National Science and Technology Development Agency
Silpakorn University
Mahidol University
Keywords: Chemical Engineering;Materials Science;Medicine
Issue Date: 11-Aug-2014
Citation: Biomacromolecules. Vol.15, No.8 (2014), 2879-2888
Abstract: Highly fluorescent N-substituted 1-cyanobenz[f]isoindole chitosans (CBI-CSs) with various degrees of N-substitution (DS) were synthesized by reacting chitosan (CS) with naphthalene-2,3-dicarboxaldehyde (NDA) in the presence of cyanide under mild acidic conditions. Introduction of 1-cyanobenz[f]isoindole moieties into the CS backbone resulted in lowering of polymer thermal stability and crystallinity. The fluorescence quantum yield (φf) of CBI-CS was found to be DS- and molecular-weight- dependent, with f decreasing as DS and molecular weight were increased. At similar DS values, CBI-CS exhibited 26 times higherf in comparison with fluorescein isothiocyanate-substituted chitosan (FITC-CS). CBI-CS/TPP nanoparticles were fabricated using an ionotropic gelation method in which pentasodium triphosphate (TPP) acted as a cross-linking agent. CS and CBI-CS exhibited low cytotoxicity to normal skin fibroblast cells over a concentration range of 0.1-1000μg/mL, while an increased cytotoxicity level was evident in CBI-CS/TPP nanoparticles at concentrations greater than 100μg/mL. In contrast with CBI-CS polymers, the CBI-CS/TPP nanoparticles exhibited lower fluorescence; however, confocal microscopy results showed that living normal skin fibroblast cells became fluorescent on nanoparticle uptake. These results suggest that CBI-CS and fabricated nanoparticles thereof may be promising fluorescence probes for live cell imaging. © 2014 American Chemical Society.
ISSN: 15264602
Appears in Collections:Scopus 2011-2015

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