Effect of Modification Manner on the Photodynamic Antitumor Activity of C60 Modified with Pullulan

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Abstract:

To design a novel cytospecific photosensitizer for photodynamic antitumor therapy, a fullerene (C60) was chemically modified with pullulan, a water-soluble polysaccharide with a high affinity for asialoglycoprotein receptors (ASGPRs). The effect of the molecular weight of pullulan and the modification manner to C60 on the photodynamic antitumor activity of C60 modified with pullulan was evaluated. In this study, two modification manners were selected. First, ethylene diamine was chemically introduced to the hydroxyl groups of pullulan with different molecular weights. Then, C60 was coupled to pullulan through the amino groups introduced (pendant type). Second, ethylene diamine was introduced to the terminal aldehyde groups of pullulan by a reductive amination reaction, and then the pullulan with the terminal amino groups was coupled to C60 (terminal type). Irrespective of the pullulan molecular and the modification manner, the C60–pullulan conjugates exhibited a similar ability to generate superoxide anions upon light irradiation. Comparing the C60–pullulan conjugates of pendant and terminal types, a high lectin affinity was observed for the latter conjugates. The conjugates showed a high affinity for HepG2 cells with ASGPRs and, consequently, a strong in vitro antitumor activity on the cells. It is concluded that the manner of pullulan modification is a key factor contributing to the photodynamic antitumor activity of modified C60.

Keywords: ANTITUMOR ACTIVITY; FULLERENE; HEPATOMA; PHOTODYNAMIC THERAPY; PULLULAN; TUMOR TARGETING

Document Type: Research Article

DOI: http://dx.doi.org/10.1163/092050610X535680

Affiliations: 1: Department of Biomaterials, Field of Tissue Engineering, Institute for Frontier Medical Sciences, Kyoto University, 53 Kawara-cho Shogoin, Sakyo-ku, Kyoto 606-8507, Japan 2: Department of Biomaterials, Field of Tissue Engineering, Institute for Frontier Medical Sciences, Kyoto University, 53 Kawara-cho Shogoin, Sakyo-ku, Kyoto 606-8507, Japan., Email: yasuhiko@frontier.kyoto-u.ac.jp

Publication date: January 1, 2011

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