We report a novel class of highly water-soluble decacationic methanofullerene decaiodides C60[>M(C3N6+C3)2]-(I−)10 [1-(I−)10] capable of co-producing singlet oxygen (Type-II) and highly reactive hydroxyl radicals, formed from superoxide radicals in Type-I photosensitizing reactions, upon illumination at both UVA and white light wavelengths. The O2‒·-production efficiency of 1-(I−)10 was confirmed by using a O2‒·-reactive bis(2,4-dinitrobenzenesulfonyl)tetrafluorofluorescein probe and correlated to the photoinduced electron-transfer event going from iodide anions to 3C60*[>M(C3N6+C3)2] leading to C60‒·[>M(C3N6+C3)2]. Incorporation of a defined number (ten) of quaternary ammonium cationic charges per C60 in 1 was aimed to enhance its ability to target pathogenic Gram-positive and Gram-negative bacterial cells. We used the well-characterized malonatofullerene diester monoadduct C60[>M(t-Bu)2] as the starting fullerene derivative to provide a better synthetic route to C60[>M(C3N6+C3)2] via transesterification reaction under trifluoroacetic acid catalyzed conditions. These compounds may be used as effective photosensitizers and nano-PDT drugs for photoinactivation of pathogens.
Min Wang, Ying-Ying Huang, Liyi Huang, Tianhong Dai, Michael R. Hamblin, and Long Chiang, "Decacationic fullerenyl-light harvesting chromophore conjugates for efficient photokilling of infectious bacteria (Conference Presentation)," Proc. SPIE 10479, Light-Based Diagnosis and Treatment of Infectious Diseases, 104790Y (Presented at SPIE BiOS: January 31, 2018; Published: 14 March 2018); https://doi.org/10.1117/12.2289070.5751486314001.
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