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Issue 14, 2016
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Maltotriose-conjugation to a fluorinated chlorin derivative generating a PDT photosensitizer with improved water-solubility

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Abstract

Photoactive molecules with the frameworks of chlorin and/or porphyrin possessing four perfluorinated aromatic rings were conjugated with maltotriose (Mal3) via the nucleophilic aromatic substitution reaction and subsequent deprotection reaction of the oligosaccharide moieties. The resulting oligosaccharide-conjugated molecules are ultimately improved as compared to the previously reported monosaccharide-counterparts in terms of water-solubility. In particular, a water-soluble chlorin derivative surrounded by four Mal3 molecules showed an excellent biocompatibility, strong photoabsorption in the longer wavelength regions, and a very high photocytotoxicity. Thus, the present synthetic route combined with the use of an oligosaccharide was shown to be a straightforward strategy to develop a third generation photosensitizer for photodynamic therapy (PDT).

Graphical abstract: Maltotriose-conjugation to a fluorinated chlorin derivative generating a PDT photosensitizer with improved water-solubility

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Publication details

The article was received on 02 Feb 2016, accepted on 07 Mar 2016 and first published on 08 Mar 2016


Article type: Paper
DOI: 10.1039/C6OB00276E
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2016,14, 3608-3613
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    Maltotriose-conjugation to a fluorinated chlorin derivative generating a PDT photosensitizer with improved water-solubility

    A. Narumi, T. Tsuji, K. Shinohara, H. Yamazaki, M. Kikuchi, S. Kawaguchi, T. Mae, A. Ikeda, Y. Sakai, H. Kataoka, M. Inoue, A. Nomoto, J. Kikuchi and S. Yano, Org. Biomol. Chem., 2016, 14, 3608
    DOI: 10.1039/C6OB00276E

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