Publication: Synthesis and fluorescence properties of n-substituted 1-cyanobenz[ F ]isoindole chitosan polymers and nanoparticles for live cell imaging
2
Issued Date
2014-08-11
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ISSN
15264602
15257797
15257797
Other identifier(s)
2-s2.0-84905822755
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Mahidol University
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SCOPUS
Bibliographic Citation
Biomacromolecules. Vol.15, No.8 (2014), 2879-2888
Suggested Citation
Pattarapond Gonil, Warayuth Sajomsang, Uracha Rungsardthong Ruktanonchai, Preeyawis Na Ubol, Alongkot Treetong, Praneet Opanasopit, Satit Puttipipatkhachorn Synthesis and fluorescence properties of n-substituted 1-cyanobenz[ F ]isoindole chitosan polymers and nanoparticles for live cell imaging. Biomacromolecules. Vol.15, No.8 (2014), 2879-2888. doi:10.1021/bm5004459 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/33561
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Title
Synthesis and fluorescence properties of n-substituted 1-cyanobenz[ F ]isoindole chitosan polymers and nanoparticles for live cell imaging
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.