Photodynamic Activity of Fullerene Derivatives Solubilized in Water by Natural‐Product‐Based Solubilizing Agents

Abstract

Water-soluble fullerenes prepared by using solubilizing agents based on natural products are promising photosensitizers for photodynamic therapy. Cyclodextrin, β-1,3-glucan, lysozyme, and liposomes can stably solubilize not only C and C , but also some C derivatives in water. To improve the solubilities of fullerenes, specific methods have been developed for each solubilizing agent. Water-soluble C and C exhibit photoinduced cytotoxicity under near-ultraviolet irradiation, but not at wavelengths over 600 nm, which are the appropriate wavelengths for photodynamic therapy. However, dyad complexes of solubilized C derivatives combined with light-harvesting antenna molecules improve the photoinduced cytotoxicities at wavelengths over 600 nm. Furthermore, controlling the fullerene and antenna molecule positions within the solubilizing agents affects the performance of the photosensitizer.

A Molecular Dynamics Study of a Photodynamic Sensitizer for Cancer Cells: Inclusion Complexes of γ-Cyclodextrins with C70

“…Moreover, the inclusion complexes are not tight and particularly rigid: rather, the CDs are quite mobile around the main axis of C 70 , while their average planes undergo also a tilting motion about the same axis. This observation can be relevant to enhance the interaction and the release of C 70 close to liposomes or cell membranes [12], unlike what happens with C 60 as experimentally found in [3]. Figure 8 summarizes these results and replaces the sketch reported in Figure 1 by drawing the correct arrangements of the CDs in the two complexes as obtained in the present work.…”

A Bio‐Conjugated Fullerene as a Subcellular‐Targeted and Multifaceted Phototheranostic Agent

“…This work fully elaborates the capabilities of fullerene@protein complexes as image‐guided PDT agents. As such complexes are highly adaptable, future work could aim at their functionalization both with tumor‐targeting tags to improve the cancer cell selectivity and promote the cellular uptake of the photosensitizing agent, [ 76 ] and with light‐harvesting molecular antennae [ 45,77–79 ] to improve both therapeutic efficiency and treatment depth in PDT.…”

“…One means of effectively dispersing fullerenes in aqueous media, while preventing modification of their molecular structures, is through the use of supramolecular solubilizing agents. [ 45–47 ] Proteins and peptides can be used as biocompatible hosts for fullerenes, allowing the dispersion of fullerenes as single molecules in physiological environments to prevent aggregation phenomena. [ 48–53 ] In particular, lysozyme binds and disperses C 60 in water, and the resulting C 60 @lysozyme complex is still photoactive, generating significant quantities of ROS upon visible light irradiation, while remaining biocompatible in dark conditions.…”

Self-Assembling Peptides and Carbon Nanomaterials Join Forces for Innovative Biomedical Applications

“…Fullerenes are hollow, spherically shaped structures with a very interesting affinity for electrons and their transport that renders them attractive for applications in energy and photocatalysis [ 142 ], as well as photodynamic therapy [ 143 ]. In medicine, fullerenes have been widely studied as antioxidants [ 144 , 145 ], antimicrobials [ 146 ], and vehicles for drug delivery [ 147 , 148 ].…”