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

Thota, Sammaiah; Wang, Min; Jeon, Seaho; Maragani, Satyanarayana; Hamblin, Michael R.; Chiang, Long Y.

doi:10.3390/molecules17055225

Open AccessArticle

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

by

Sammaiah Thota

¹,

Min Wang

¹,

Seaho Jeon

¹,

Satyanarayana Maragani

¹,

Michael R. Hamblin

^2,3,4,*

and

Long Y. Chiang

^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.

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

Submission 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

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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. https://doi.org/10.3390/molecules17055225

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. https://doi.org/10.3390/molecules17055225

Chicago/Turabian Style

Thota, Sammaiah, Min Wang, Seaho Jeon, Satyanarayana Maragani, Michael R. Hamblin, and Long Y. Chiang. 2012. "Synthesis and Characterization of Positively Charged Pentacationic [60]Fullerene Monoadducts for Antimicrobial Photodynamic Inactivation" Molecules 17, no. 5: 5225-5243. https://doi.org/10.3390/molecules17055225

APA Style

Thota, S., Wang, M., Jeon, S., Maragani, S., Hamblin, M. R., & Chiang, L. Y. (2012). Synthesis and Characterization of Positively Charged Pentacationic [60]Fullerene Monoadducts for Antimicrobial Photodynamic Inactivation. Molecules, 17(5), 5225-5243. https://doi.org/10.3390/molecules17055225

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

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