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

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• 作者：Min Wang ; Liyi Huang ; Sulbha K Sharma ; Seaho Jeon ; Sammaiah Thota ; Felipe F. Sperandio ; Suhasini Nayka ; Julie Chang ; Michael R. Hamblin ; Long Y. Chiang
• 刊名：Journal of Medicinal Chemistry
• 出版年：2012
• 出版时间：May 10, 2012
• 年：2012
• 卷：55
• 期：9
• 页码：4274-4285
• 全文大小：513K
• 年卷期：v.55,no.9(May 10, 2012)
• ISSN：1520-4804

文摘

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^{鈥?/sup> 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鈥?/sup> to cause real damage.}