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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,*
Received: 31 March 2012; in revised form: 22 April 2012 / Accepted: 28 April 2012 / Published: 7 May 2012
(This article belongs to the Special Issue Fullerene Chemistry)
Download PDF [476 KB, uploaded 18 June 2014]
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

Thota S, Wang M, Jeon S, Maragani S, Hamblin MR, Chiang LY. Synthesis and Characterization of Positively Charged Pentacationic [60]Fullerene Monoadducts for Antimicrobial Photodynamic Inactivation. Molecules. 2012; 17(5):5225-5243.

Chicago/Turabian Style

Thota, Sammaiah; Wang, Min; Jeon, Seaho; Maragani, Satyanarayana; Hamblin, Michael R.; Chiang, Long Y. 2012. "Synthesis and Characterization of Positively Charged Pentacationic [60]Fullerene Monoadducts for Antimicrobial Photodynamic Inactivation." Molecules 17, no. 5: 5225-5243.


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