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 Φf decreasing as DS and molecular weight were increased. At similar DS values, CBI-CS exhibited 26 times higher Φf 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 0.1-1000 μg/mL, while an increased cytotoxicity level was evident in CBI-CS/TPP nanoparticles at concentrations greater than 100 μg/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.
journal_name
Biomacromoleculesjournal_title
Biomacromoleculesauthors
Gonil P,Sajomsang W,Ruktanonchai UR,Na Ubol P,Treetong A,Opanasopit P,Puttipipatkhachorn Sdoi
10.1021/bm5004459subject
Has Abstractpub_date
2014-08-11 00:00:00pages
2879-88issue
8eissn
1525-7797issn
1526-4602journal_volume
15pub_type
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