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 (1-((3-(dimethylamino)propyl)amino)anthracene-9,10-dione, 1). 1, as the guest molecule, was synthesized by the direct reaction of 1-nitroanthraquinone with N1,N1-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). 1H 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.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideResearch highlights▶ We prepared a novel anthraquinone derivate by the direct reaction of 1-nitroanthraquinone with N1, N1-dimethylpropane-1,3-diamine without catalyst. ▶ We designed and prepared a novel pH-reversible vesicles based on the “supramolecular amphiphilies” formed by cyclodextrin and anthraquinone derivate and the vesicles were fully characterized. ▶ The novel pH-reversible vesicles were successfully applied in the staining of the living cells.