pH-reversible vesicles based on the "supramolecular amphiphilies" formed by cyclodextrin and anthraquinone derivate

Aggregates assembled by "supramolecular amphiphilies" are more promising in developing responsive materials. First pH-reversible vesicles based on "supramolecular amphiphilies" were prepared from the supramolecular inclusion of cyclodextrins (CDs) and anthraquinone derivate (14(3-(dimethylamino)propyl)amino)anthracene-9,10-dione. 1). 1, as the guest molecule, was synthesized by the direct reaction of 1-nitroanthraquinone with N-1,N-1-dimethylpropane-1,3-diamine. The vesicles were characterized in detail by transmission electron microscopy (TEM), scanning electron microscopy (SEM), dynamic light scattering (DLS), and epi fluorescence microscope (EFM). H-1 NMR, 2D NMR ROESY, UV-vis spectrum, and FT-IR were further employed to study the formation mechanism of the vesicles. The vesicles' responsive property, especially the pH-responsive property was tested. We also tried to use the vesicle system as a new kind of fluorescence staining material for living cells and mouse prostate carcinoma cells (RM-1) were found to be stained effectively by the vesicles. Our research may provide new references in exploiting novel intelligence materials and biomaterials. (C) 2010 Elsevier B.V. All rights reserved.