Synthesis and Photodynamic Effect of New Highly Photostable Decacationically Armed [60]- and [70]Fullerene Decaiodide Monoadducts To Target Pathogenic Bacteria and Cancer Cells

• Published in: Journal of medicinal chemistry Vol. 55; no. 9; pp. 4274 - 4285
• Main Authors: Wang, Min, Huang, Liyi, Sharma, Sulbha K, Jeon, Seaho, Thota, Sammaiah, Sperandio, Felipe F, Nayka, Suhasini, Chang, Julie, Hamblin, Michael R, Chiang, Long Y
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 10-05-2012
• Subjects: Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Bacteria - drug effects; Drug Stability; Fullerenes - chemistry; Fullerenes - pharmacology; HeLa Cells; Humans; Iodides - chemical synthesis; Iodides - chemistry; Iodides - pharmacology; Magnetic Resonance Spectroscopy; Photochemotherapy - methods; Photosensitizing Agents - chemical synthesis; Photosensitizing Agents - chemistry; Photosensitizing Agents - pharmacology; Quaternary Ammonium Compounds - chemical synthesis; Quaternary Ammonium Compounds - chemistry; Quaternary Ammonium Compounds - pharmacology; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Spectrophotometry, Ultraviolet
• ISSN: 0022-2623; 1520-4804
• DOI: 10.1021/jm3000664

Novel water-soluble decacationically armed C60 and C70 decaiodide monoadducts, C60- and C70[>M(C3N6 +C3)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 C70[>M(C3N6 +C3)2] produced more HO• than C60[>M(C3N6 +C3)2], in addition to 1O2. This finding offers an explanation of the preferential killing of Gram-positive and Gram-negative bacteria by C60[>M(C3N6 +C3)2] and C70[>M(C3N6 +C3)2], respectively. The hypothesis is that 1O2 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.