A coassembly strategy for a supramolecular vector/ drug was proposed with a biocompatible ternary dodecyl-bi(thirdgeneration polyglycerol (PG) dendrons) (C 12 -(G3) 2 ) amphiphile, dodecyl sulfobetaine (SB3-12) surfactant, and poorly water-soluble drug rutin. C 12 -(G3) 2 and rutin will mutually enhance their pH response by protonation and deprotonation of dendritic PG and rutin's ionization as the pH changes from the acidic gastric lumen to the weakly alkaline intestine. SB3-12 may increase the payload and bring about sustained release for rutin by intermolecular interactions. Self-assembling behaviors of C 12 -(G3) 2 , SB3-12, sodium dodecyl sulfate (SDS), and dodecyl trimethylammonium bromide (DTAB) and their hybrids with rutin were characterized by UV−vis spectroscopy, a fluorescence probe, and 1 H NMR. UV−vis and 1 H NMR were used to identify the position and orientation of rutin in the vectors. The functions of the vector/drug were confirmed by measuring the solubility and in vitro release of rutin. The ternary coassembling vector/drug easily imparted functions of pH-responsive and sustained release without complex synthetic processes. The nanocaves framed by PG dendrons in the micelles provide pH-responsive compartments for rutin and SB3-12 in the supramolecular vector/drug anchors that accommodate rutin by weak interactions. The finely matched supramolecular vector/drug coassemblies exhibit the pH-responsive function for a potential application in the treatment of inflammatory bowel disease.
Owing to the unique geometric structure of dendritic amphiphiles with voluminous dendrons, their micelles can harbor a large void space, which provides a new research focus and approach for micellar functionalization. In this work, we used the void space to construct a UV responsive micelle system of the mixed dendritic amphiphile (C12-(G3)2) and cationic azobenzene surfactant (C4AzoTAB). The synthesized C12-(G3)2 that possesses double third generation polyglycerol (PG) dendrons and a single alkyl chain is expected to highlight the large void space within the inside of the micelles. Thus, the aims of this work are to achieve the isomerization of C4AzoTAB in situ and to deeply understand the intermolecular interaction in the mixed micelles. The effect of the large void room with a wall decorated with the ether oxygen atoms on the isomerization of C4AzoTAB was studied by isomerization kinetics, conductivity measurements, isothermal titration calorimetry (ITC), and 1H NMR and 2D NOESY spectroscopies. The isomerization behavior of C4AzoTAB in C12-(G3)2 micelles was presented in terms of its kinetic constant, counterionic association, interaction enthalpy, and position and orientation of C4AzoTAB. The results of NMR and conductivity show that the quaternary ammonium group of C4AzoTAB situates on the surface of the mixed micelles with C12-(G3)2 both before and after UV-irradiation, while the position of azobenzene group in C12-(G3)2 micelles depends on its conformation. The C12-(G3)2 micelles can inhibit the UV response of the trans-isomer and activate the thermal relaxation of the cis-isomer, which has a potential application in the field of light-controlled smart nanocarriers.
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