Synthesis of decacationic [60]fullerene decaiodides giving photoinduced production of superoxide radicals and effective PDT-mediation on antimicrobial photoinactivation

Min Wang, Satyanarayana Maragani, Liyi Huang, Seaho Jeon, Taizoon Canteenwala, Michael R. Hamblin, Long Y. Chiang

Research output: Contribution to journalArticlepeer-review

40 Citations (Scopus)

Abstract

We report a novel class of highly water-soluble decacationic methano[60]fullerene decaiodides C60[>M(C3N 6+C3)2]-(I-) 10 [1-(I-)10] capable of co-producing singlet oxygen (Type-II) and highly reactive hydroxyl radicals, formed from superoxide radicals in Type-I photosensitizing reactions, upon illumination at both UVA and white light wavelengths. The O2-·-production efficiency of 1-(I-)10 was confirmed by using an O 2-·-reactive bis(2,4-dinitrobenzenesulfonyl) tetrafluorofluorescein probe and correlated to the photoinduced electron-transfer event going from iodide anions to 3C 60*[>M(C3N6+C 3)2] leading to C60 -·[>M(C3N6+C 3)2]. Incorporation of a defined number (ten) of quaternary ammonium cationic charges per C60 in 1 was aimed to enhance its ability to target pathogenic Gram-positive and Gram-negative bacterial cells. We used the well-characterized malonato[60]fullerene diester monoadduct C60[>M(t-Bu)2] as the starting fullerene derivative to provide a better synthetic route to C60[>M(C 3N6+C3)2] via transesterification reaction under trifluoroacetic acid catalyzed conditions. These compounds may be used as effective photosensitizers and nano-PDT drugs for photoinactivation of pathogens.

Original languageEnglish
Pages (from-to)170-184
Number of pages15
JournalEuropean Journal of Medicinal Chemistry
Volume63
DOIs
Publication statusPublished - 2013
Externally publishedYes

Keywords

  • Antimicrobial photodynamic therapy
  • Decacationic C monoadducts
  • Di(N,N′,N,N,N,N-hexapropyl-hexa(aminoethyl)amido) malonate arm
  • Photoinduced radicals
  • Photosensitizer
  • Transesterification

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

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