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Pyrene-Labeled and Quaternized Chitosan: Synthesis, Characterization, and Its Potential Application for Fluorescently Trackable Nucleic Acid Delivery into Cells.

Kornkanya PratumyotPongsakorn YuntasiriPhim-On KhunsukTinnakorn PhuangkaewChutamath SittplangkoonThitiporn PattarakankulTanapat PalagaSuda KiatkamjornwongVoravee P Hoven
Published in: Biomacromolecules (2023)
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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