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The Electrochemical Society, ECS Transactions, 27(53), p. 1-14, 2013

DOI: 10.1149/05327.0001ecst

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Synthesis of Decacationic C70 Bisadducts by Incorporating Covalently BoundElectron-Donors for Enhancement of Radical-Based Type-I PDT

Journal article published in 2013 by M. Wang, L. Huang, T. Dai, F. F. Sperandio, Y.-Y. Huang, M. Hamblin ORCID, L. Chiang
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

We designed, synthesized, and characterized two types of highly water-soluble C70 monoadduct, C70[>M(C3N6 +C3)2]-(I)10 (LC17), and bisadducts, C70[>M(C3N6 +C3)2][>M(C3N6C3)2] (LC18). Each of these compounds consist of a well-defined decacationic quaternary ammonium iodide moiety with ten positive charges per C70 for increasing water-solubility and the ability to target pathogenic bacterial cells. The structural modification enables them to act as broad-spectrum antibacterial nano-PDT drugs. We found that white light was more effective with LC17 while UVA light was more effective with LC18 to the antimicrobial effects against human pathogens, Gram-positive (Staphylococcus aureus) and Gram-negative species (Escherichia coli and Acinetobacter baumannii). Both compounds were effective in a mouse model of Gram-negative 3rd-degree burn infections. The observation led to our proposition that the attachment of an additional electron-donating deca(tertiary ethylenylamino)malonate arm to C70, giving a product of LC18, allowed the moiety to act as a potent electron source and increased the generation yield of hydroxyl radicals under UVA illumination. This demonstrated a new approach in enhancing HO·-induced radical-killing (Type-I photochemistry) of pathogenic bacteria.