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Tetraphenylporphyrin Tethered Chitosan Based Carriers for Photochemical Transfection

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† Faculty of Pharmaceutical Sciences, School of Health Sciences, University of Iceland, Hofsvallagata 53, IS-107 Reykjavík, Iceland
‡ PCI Biotech AS, N-1366 Lysaker, Norway
§ Oslo University Hospital, The Norwegian Radium Hospital, Institute for Cancer Research, Department of Radiation Biology, N-0310 Oslo, Norway
∥ Department of Physics, Science Institute, University of Iceland, Dunhagi 3, IS-107 Reykjavik, Iceland
⊥ Department of Chemistry, Science Institute, University of Iceland, Dunhagi 3, IS-107 Reykjavik, Iceland
*Phone: +354-8228301. Fax: +354-5254071. E-mail: [email protected]
Cite this: J. Med. Chem. 2013, 56, 3, 807–819
Publication Date (Web):January 3, 2013
https://doi.org/10.1021/jm301270r
Copyright © 2013 American Chemical Society
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    Abstract

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    Water-soluble amphiphilic chitosan nanocarriers tethered with the photosensitizer meso-tetraphenylporphyrin were synthesized in a seven-step procedure, starting from 3,6-di-O-tert-butyldimethylsilyl-chitosan and 5-(p-aminophenyl)-10,15,20-triphenylporphyrin. The lipophilic photosensitizer could be introduced in a quantitative and reproducible reaction to give either 0.1 or 0.25 degrees of substitution per glucosamine monomer. Fluorescence and NMR investigations revealed the dynamic structures of the carriers, which formed nanoparticles in aqueous solution with a core of π-stacked photosensitizers. These carriers can then unfold in the lipophilic environment, and the photosensitizer moiety can thus be inserted into the cell membrane. The efficacy of the carriers for photochemical internalization (PCI) mediated gene delivery was evaluated in vitro using the HCT116/LUC human colon carcinoma cell line. The efficacy of transfection was comparable to what could be achieved by the reference compound and current clinical candidate TPCS2a.

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    General experimental methods and the copies of 1H, 13C NMR, HRMS, and fluorescence spectra of key compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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