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Molecules 2012, 17(5), 5225-5243; doi:10.3390/molecules17055225
Article

Synthesis and Characterization of Positively Charged Pentacationic [60]Fullerene Monoadducts for Antimicrobial Photodynamic Inactivation

1, 1, 1, 1, 2,3,4,*  and 1,5,*
1 Department of Chemistry, Institute of Nanoscience and Engineering Technology, University of Massachusetts, Lowell, MA 01854, USA 2 Wellman Center for Photomedicine, Massachusetts General Hospital, Boston, MA 02114, USA 3 Department of Dermatology, Harvard Medical School, Boston, MA 02115, USA 4 Harvard-MIT Division of Health Sciences and Technology, Cambridge, MA 02139, USA 5 Department of Laboratory Medicine and Pathobiology, University of Toronto, Toronto, ON M5S 1A8, Canada
* Authors to whom correspondence should be addressed.
Received: 31 March 2012 / Revised: 22 April 2012 / Accepted: 28 April 2012 / Published: 7 May 2012
(This article belongs to the Special Issue Fullerene Chemistry)
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Abstract

We designed and synthesized two analogous pentacationic [60]fullerenyl monoadducts, C60(>ME1N6+C3) (1) and C60(>ME3N6+C3) (2), with variation of the methoxyethyleneglycol length. Each of these derivatives bears a well-defined number of cationic charges aimed to enhance and control their ability to target pathogenic Gram-positive and Gram-negative bacterial cells for allowing photodynamic inactivation. The synthesis was achieved by the use of a common synthon of pentacationic N,N′,N,N,N,N-hexapropyl-hexa(aminoethyl)amine arm (C3N6+) having six attached propyl groups, instead of methyl or ethyl groups, to provide a well-balanced hydrophobicity–hydrophilicity character to pentacationic precursor intermediates and better compatibility with the highly hydrophobic C60 cage moiety. We demonstrated two plausible synthetic routes for the preparation of 1 and 2 with the product characterization via various spectroscopic methods.
Keywords: pentacationic C60 monoadducts; decacationic C60 monoadduct; N,N′,N,N,N,N-hexapropyl-hexa(aminoethyl)amine; photosensitizer pentacationic C60 monoadducts; decacationic C60 monoadduct; N,N′,N,N,N,N-hexapropyl-hexa(aminoethyl)amine; photosensitizer
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Thota, S.; Wang, M.; Jeon, S.; Maragani, S.; Hamblin, M.R.; Chiang, L.Y. Synthesis and Characterization of Positively Charged Pentacationic [60]Fullerene Monoadducts for Antimicrobial Photodynamic Inactivation. Molecules 2012, 17, 5225-5243.

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