Synthesis and Characterization of Positively Charged Pentacationic [60]Fullerene Monoadducts for Antimicrobial Photodynamic Inactivation
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Thota-2012-Synthesis and charac.pdf
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Author(s)
Thota, Sammaiah
Wang, Min
Jeon, Seaho
Maragani, Satyanarayana
Hamblin, Michael R.
Chiang, Long Y.
Date Issued
May 2012
Journal
Molecules
Publisher
MDPI AG
Citation
Thota, Sammaiah, Min Wang, Seaho Jeon, Satyanarayana Maragani, Michael R. Hamblin, and Long Y. Chiang. “Synthesis and Characterization of Positively Charged Pentacationic [60]Fullerene Monoadducts for Antimicrobial Photodynamic Inactivation.” Molecules 17, no. 12 (May 7, 2012): 5225–5243.
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Final published version
Abstract
We designed and synthesized two analogous pentacationic [60]fullerenyl monoadducts, C[subscript 60](>ME[subscript 1]N[subscript 6]+C[subscript 3]) (1) and C[subscript 60](>ME[subscript 3]N[subscript 6]+C[subscript 3]) (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 (C[subscript 3]N[subscript 6]+) 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 C[subscript 60] cage moiety. We demonstrated two plausible synthetic routes for the preparation of 1 and 2 with the product characterization via various spectroscopic methods.
MIT Department
Harvard University--MIT Division of Health Sciences and Technology
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DOI of Published Version
https://doi.org/10.3390/molecules17055225
