title: Synthesis of decacationic [60]fullerene decaiodides giving photoinduced production of superoxide radicals and effective PDT-mediation on antimicrobial photoinactivation.
abstract: We report a novel class of highly water-soluble decacationic methano[60]fullerene decaiodides C60[>M(C3N6(+)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 O2(-)·-reactive bis(2,4-dinitrobenzenesulfonyl)tetrafluorofluorescein probe and correlated to the photoinduced electron-transfer event going from iodide anions to (3)C60*[>M(C3N6(+)C3)2] leading to C60(-)·[>M(C3N6(+)C3)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(C3N6(+)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.
authors.affiliation: Department of Chemistry, Institute of Nanoscience and Engineering Technology, University of Massachusetts, Lowell, MA 01854, USA.
authors.forename: Min
authors.initials: M
authors.lastname: Wang
authors.forename: Satyanarayana
authors.initials: S
authors.lastname: Maragani
authors.forename: Liyi
authors.initials: L
authors.lastname: Huang
authors.forename: Seaho
authors.initials: S
authors.lastname: Jeon
authors.forename: Taizoon
authors.initials: T
authors.lastname: Canteenwala
authors.forename: Michael R
authors.initials: MR
authors.lastname: Hamblin
authors.forename: Long Y
authors.initials: LY
authors.lastname: Chiang
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004926:Escherichia coli / Q000187:drug effects / Q000528:radiation effects; D037741:Fullerenes / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D008027:Light; D050296:Microbial Viability / Q000187:drug effects / Q000528:radiation effects; D008956:Models, Chemical; D015394:Molecular Structure; D010778:Photochemotherapy / Q000379:methods; D017319:Photosensitizing Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013050:Spectrometry, Fluorescence; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D017550:Spectroscopy, Fourier Transform Infrared; D013211:Staphylococcus aureus / Q000187:drug effects / Q000528:radiation effects; D013481:Superoxides / Q000737:chemistry* / Q000378:metabolism
chemical_list: D000890:Anti-Infective Agents; D037741:Fullerenes; D007454:Iodides; D017319:Photosensitizing Agents; D013481:Superoxides; C069837:fullerene C60