Glutathione nanosphere: Self-assembly of conformation-regulated trigonal-glutathiones in water

Kazunori Matsuura, Keisuke Fujino, Takeshi Teramoto, Kazuya Murasato, Nobuo Kimizuka

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    20 Citations (Scopus)


    A novel trigonal conjugate of glutathiones with a 1,3,5-tris(aminomethyl)- 2,4,6-triethylbenzene core was synthesized and its self-assembling behavior was investigated in water. Three glutathione units were regulated to orient on the same side of the benzene ring, through steric repulsions between ethyl groups attached on the benzene core. Concentration dependence of 1HNMR chemical shifts in D2O revealed formation of molecular assemblies with two affinity constants (Ka = 4.75 × 102 and 6.76 × 104M-1), which reflect stepwise assembly directed by electrostatic interactions, hydrophobic interactions, and hydrogen bonding. In scanning electron microscopy, hard spherical assemblies with the size of 310 ± 50 nm were observed at high concentration (10 mM), whereas slightly disordered spherical assemblies were obtained at lower concentrations. The spherical assemblies self-assembled from the conformationregulated trigonal glutathiones showed regular morphology and enhanced rigidity compared to those formed from conformationally non-regulated trigonal glutathiones.

    Original languageEnglish
    Pages (from-to)880-886
    Number of pages7
    JournalBulletin of the Chemical Society of Japan
    Issue number8
    Publication statusPublished - 2010

    All Science Journal Classification (ASJC) codes

    • General Chemistry


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