title: Synthesis and characterization of positively charged pentacationic [60]fullerene monoadducts for antimicrobial photodynamic inactivation.
abstract: We designed and synthesized two analogous pentacationic [60]fullerenyl monoadducts, C₆₀(>ME₁N₆⁺C₃) (1) and C₆₀(>ME₃N₆⁺C₃) (2), with variation of the methoxyethyleneglycol length. Each of these derivatives bears a well-defined number of cationic charges aimed to enhance and control their ability to target pathogenic Gram-positive and Gram-negative bacterial cells for allowing photodynamic inactivation. The synthesis was achieved by the use of a common synthon of pentacationic N,N′,N,N,N,N-hexapropylhexa(aminoethyl)amine arm (C₃N₆⁺) having six attached propyl groups, instead of methyl or ethyl groups, to provide a well-balanced hydrophobicity-hydrophilicity character to pentacationic precursor intermediates and better compatibility with the highly hydrophobic C₆₀ cage moiety. We demonstrated two plausible synthetic routes for the preparation of 1 and 2 with the product characterization via various spectroscopic methods.
authors.affiliation: Department of Chemistry, Institute of Nanoscience and Engineering Technology, University of Massachusetts, Lowell, MA 01854, USA.
authors.forename: Sammaiah
authors.initials: S
authors.lastname: Thota
authors.forename: Min
authors.initials: M
authors.lastname: Wang
authors.forename: Seaho
authors.initials: S
authors.lastname: Jeon
authors.forename: Satyanarayana
authors.initials: S
authors.lastname: Maragani
authors.forename: Michael R
authors.initials: MR
authors.lastname: Hamblin
authors.forename: Long Y
authors.initials: LY
authors.lastname: Chiang
mesh_terms: D000900:Anti-Bacterial Agents / Q000032:analysis / Q000138:chemical synthesis*; D002412:Cations / Q000737:chemistry*; D037741:Fullerenes / Q000032:analysis / Q000737:chemistry*; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010778:Photochemotherapy; D017319:Photosensitizing Agents / Q000032:analysis / Q000138:chemical synthesis*; D017550:Spectroscopy, Fourier Transform Infrared; D055672:Static Electricity
chemical_list: D000900:Anti-Bacterial Agents; D002412:Cations; D037741:Fullerenes; D017319:Photosensitizing Agents