Synthesis and photodynamic effect of new highly photostable decacationically armed [60]- and [70]fullerene decaiodide monoadducts to target pathogenic bacteria and cancer cells

Min Wang, Liyi Huang, Sulbha K. Sharma, Seaho Jeon, Sammaiah Thota, Felipe F. Sperandio, Suhasini Nayka, Julie Chang, Michael R. Hamblin, Long Y. Chiang

Research output: Contribution to journalArticlepeer-review

54 Citations (Scopus)

Abstract

Novel water-soluble decacationically armed C 60 and C 70 decaiodide monoadducts, C 60- and C 70[> M(C 3N 6 +C 3) 2], were synthesized, characterized, and applied as photosensitizers and potential nano-PDT agents against pathogenic bacteria and cancer cells. A high number of cationic charges per fullerene cage and H-bonding moieties were designed for rapid binding to the anionic residues displayed on the outer parts of bacterial cell walls. In the presence of a high number of electron-donating iodide anions as parts of quaternary ammonium salts in the arm region, we found that C 70[>M(C 3N 6 +C 3) 2] produced more HO than C 60[> M(C 3N 6 +C 3) 2], in addition to 1O 2. This finding offers an explanation of the preferential killing of Gram-positive and Gram-negative bacteria by C 60[>M(C 3N 6 +C 3) 2] and C 70[>M(C 3N 6 +C 3) 2], respectively. The hypothesis is that 1O 2 can diffuse more easily into porous cell walls of Gram-positive bacteria to reach sensitive sites, while the less permeable Gram-negative bacterial cell wall needs the more reactive HO to cause real damage.

Original languageEnglish
Pages (from-to)4274-4285
Number of pages12
JournalJournal of Medicinal Chemistry
Volume55
Issue number9
DOIs
Publication statusPublished - 10 May 2012
Externally publishedYes

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

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