title: Synthesis and photodynamic effect of new highly photostable decacationically armed [60]- and [70]fullerene decaiodide monoadducts to target pathogenic bacteria and cancer cells.
abstract: Novel water-soluble decacationically armed C(60) and C(70) decaiodide monoadducts, C(60)- and C(70)[>M(C(3)N(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(3)N(6)(+)C(3))(2)] produced more HO(•) than C(60)[>M(C(3)N(6)(+)C(3))(2)], in addition to (1)O(2). This finding offers an explanation of the preferential killing of Gram-positive and Gram-negative bacteria by C(60)[>M(C(3)N(6)(+)C(3))(2)] and C(70)[>M(C(3)N(6)(+)C(3))(2)], respectively. The hypothesis is that (1)O(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.
authors.affiliation: Department of Chemistry, Institute of Nanoscience and Engineering Technology, University of Massachusetts, Lowell, Massachusetts 01854, USA.
authors.forename: Min
authors.initials: M
authors.lastname: Wang
authors.forename: Liyi
authors.initials: L
authors.lastname: Huang
authors.forename: Sulbha K
authors.initials: SK
authors.lastname: Sharma
authors.forename: Seaho
authors.initials: S
authors.lastname: Jeon
authors.forename: Sammaiah
authors.initials: S
authors.lastname: Thota
authors.forename: Felipe F
authors.initials: FF
authors.lastname: Sperandio
authors.forename: Suhasini
authors.initials: S
authors.lastname: Nayka
authors.forename: Julie
authors.initials: J
authors.lastname: Chang
authors.forename: Michael R
authors.initials: MR
authors.lastname: Hamblin
authors.forename: Long Y
authors.initials: LY
authors.lastname: Chiang
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects*; D004355:Drug Stability; D037741:Fullerenes / Q000737:chemistry / Q000494:pharmacology*; D006367:HeLa Cells; D006801:Humans; D007454:Iodides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D010778:Photochemotherapy / Q000379:methods*; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013056:Spectrophotometry, Ultraviolet
chemical_list: D000970:Antineoplastic Agents; D037741:Fullerenes; D007454:Iodides; D017319:Photosensitizing Agents; D000644:Quaternary Ammonium Compounds