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Pyrene-Labeled and Quaternized Chitosan: Synthesis, Characterization, and Its Potential Application for Fluorescently
Kornkanya Pratumyot1,2, Pongsakorn Yuntasiri1,3, Phim-On Khunsuk4
1Organic Synthesis, Electrochemistry and Natural Product Research Unit, Department of Chemistry, Faculty of Science, King Mongkut's University of Technology Thonburi (KMUTT), Pracha Uthit Road, Bang Mod, Thung Khru, Bangkok 10140, Thailand.
Abstract:
A chitosan derivative (Pyr-CS-HTAP) having pyrene (Pyr) and N-[(2-hydroxyl-3-trimethylammonium)] propyl (HTAP) units conjugated at C6 and C2 positions, respectively, was synthesized and characterized. Dynamic light scattering and scanning electron microscopy revealed that Pyr-CS-HTAP self-assembled into spherical nanoparticles with a hydrodynamic diameter of 211 ± 5 nm and a ζ-potential of +49 mV. The successful binding of Pyr-CS-HTAP with nucleic acid was ascertained by fluorescence resonance energy-transfer analysis and gel electrophoresis. Pyr-CS-HTAP facilitated the cellular uptake of nucleic acid up to 99%. Co-localization analysis using fluorescence microscopy revealed the endosomal escape of the Pyr-CS-HTAP/nucleic acid complexes and the successful release of the nucleic acid cargoes from the polyplexes into the nucleus. It is strongly believed that Pyr-CS-HTAP can potentially be developed into a fluorescently trackable gene delivery system in the future.
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