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Decacationic [70]fullerenyl-light harvesting chromophore conjugates for efficient photokilling of infectious bacteria (Conference Presentation)
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Paper Abstract

We report a novel class of highly water-soluble decacationic methano[60]fullerene 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 malonato[60]fullerene 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.

Paper Details

Date Published: 14 March 2018
Proc. SPIE 10479, Light-Based Diagnosis and Treatment of Infectious Diseases, 104790Y (14 March 2018); doi: 10.1117/12.2289070
Show Author Affiliations
Min Wang, Univ. of Massachusetts Lowell (United States)
Ying-Ying Huang, Wellman Ctr. for Photomedicine, Massachusetts General Hospital (United States)
Liyi Huang, Wellman Ctr. for Photomedicine (United States)
Tianhong Dai, Wellman Ctr. for Photomedicine (United States)
Michael R. Hamblin, Wellman Ctr. for Photomedicine (United States)
Long Chiang, Univ. of Massachusetts Lowell (United States)

Published in SPIE Proceedings Vol. 10479:
Light-Based Diagnosis and Treatment of Infectious Diseases
Tianhong Dai, Editor(s)

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