Innovative cationic fullerenes as broad-spectrum light-activated antimicrobials

Liyi Huang, Mitsuhiro Terakawa, Timur Zhiyentayev, Ying Ying Huang, Yohei Sawayama, Ashlee Jahnke, George P. Tegos, Tim Wharton, Michael R. Hamblin

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Abstract

Photodynamic inactivation is a rapidly developing antimicrobial technology that combines a nontoxic photoactivatable dye or photosensitizer in combination with harmless visible light of the correct wavelength to excite the dye to its reactive-triplet state that will then generate reactive oxygen species that are highly toxic to cells. Buckminsterfullerenes are closed-cage molecules entirely composed of sp2-hybridized carbon atoms, and although their main absorption is in the UV, they also absorb visible light and have a long-lived triplet state. When C60 fullerene is derivatized with cationic functional groups it forms molecules that are more water-soluble and can mediate photodynamic therapy efficiently upon illumination; moreover, cationic fullerenes can selectively bind to microbial cells. In this report we describe the synthesis and characterization of several new cationic fullerenes. Their relative effectiveness as broad-spectrum antimicrobial photosensitizers against gram-positive and gram-negative bacteria, and a fungal yeast was determined by quantitative structure-function relationships. From the Clinical Editor: Photodynamic inactivation (PDI) is a rapidly developing antimicrobial technology in which a non-toxic photoactivatable dye or photosensitizer is excited with harmless visible light to its reactive state, where it will generate highly toxic reactive oxygen species. Buckminsterfullerenes derivatized with cationic functional groups form molecules that are water-soluble and mediate PDI efficiently. These fullerenes can also selectively bind to microbial cells. Several new cationic fullerenes are presented in this paper, and their efficacy against Gram-positive, Gram-negative bacteria, and a fungal yeast is also demonstrated.

Original languageEnglish
Pages (from-to)442-452
Number of pages11
JournalNanomedicine: Nanotechnology, Biology, and Medicine
Volume6
Issue number3
DOIs
Publication statusPublished - 2010 Jun 1

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Keywords

  • Antimicrobial photoinactivation
  • Broad-spectrum antimicrobials
  • Functionalized fullerenes
  • Photodynamic therapy
  • Quantitative structure-function relationships

ASJC Scopus subject areas

  • Bioengineering
  • Medicine (miscellaneous)
  • Molecular Medicine
  • Biomedical Engineering
  • Materials Science(all)
  • Pharmaceutical Science

Cite this

Huang, L., Terakawa, M., Zhiyentayev, T., Huang, Y. Y., Sawayama, Y., Jahnke, A., Tegos, G. P., Wharton, T., & Hamblin, M. R. (2010). Innovative cationic fullerenes as broad-spectrum light-activated antimicrobials. Nanomedicine: Nanotechnology, Biology, and Medicine, 6(3), 442-452. https://doi.org/10.1016/j.nano.2009.10.005