Construction of β-cyclodextrin-based supramolecular hyperbranched polymers self-assemblies using AB2-type macromonomer and their application in the drug delivery field

Carbohydr Polym. 2019 Jun 1:213:411-418. doi: 10.1016/j.carbpol.2019.03.017. Epub 2019 Mar 6.

Abstract

Despite some efforts have been made in the research of supramolecular hyperbranched polymers (SHPs) self-assemblies, the study which has not been consideration to date is the influence of incoming stimuli-responsive polymer chain on their self-assembly property undergo outer stimuli. The introduction of stimuli-responsive segments which could maintain their hydrophilic property are expected to affect the self-assembly behaviour of SHPs and expand their further biomedical application. In this paper, AB2-type macromolecular monomer, LA-(CD-PDMA)2, which consisted one lithocholic acid (LA) and two β-cyclodextrin terminated poly(2-(dimethylamino)ethyl methacrylate) segments (CD-PDMA) was synthesized. LA-(CD-PDMA)2 based SHP were obtained based on the host-guest inclusion interactions of CD/LA moietes and with PDMA as pH-responsive hydrophilic chains. As a control to study the influence of incoming PDMA chains, both LA-(CD-PDMA)2 based SHPs-1 and LA-CD2 based SHPs-2 self-assemblies were comparatively investiged through 2D 1H NMR ROESY, transmission electron microscopy (TEM) and dynamic light scattering (DLS). The results suggested that except for the higher drug loading efficiency LA-(CD-PDMA)2 based SHPs-1 pocessing, the release rates of SHPs-1 increased notably at pH 5.0 than that of pH 7.4 due to the repulsion and stretch of protonated PDMA chains while the release rates of SHPs-2 showed no obvious difference. Finally, basic cell experiments demonstrated that the SHPs based self-assemblies can be internalized into cancer cells, indicating their potential application in the drug delivery field.

Keywords: Drug delivery; Host-guest interactions; Self-assembly behavior; Supramolecular hyperbranched polymer; β-Cyclodextrin.

MeSH terms

  • Cell Survival / drug effects
  • Doxorubicin / chemistry
  • Doxorubicin / pharmacology*
  • Drug Carriers / chemical synthesis
  • Drug Carriers / chemistry
  • Drug Carriers / pharmacology
  • Drug Delivery Systems*
  • Humans
  • Hydrogen-Ion Concentration
  • Hydrophobic and Hydrophilic Interactions
  • Lithocholic Acid / chemistry
  • Lithocholic Acid / pharmacology
  • MCF-7 Cells
  • Macromolecular Substances / chemical synthesis
  • Macromolecular Substances / chemistry
  • Macromolecular Substances / pharmacology
  • Molecular Conformation
  • Optical Imaging
  • Polymers / chemical synthesis
  • Polymers / chemistry
  • Polymers / pharmacology*
  • beta-Cyclodextrins / chemistry
  • beta-Cyclodextrins / pharmacology*

Substances

  • Drug Carriers
  • Macromolecular Substances
  • Polymers
  • beta-Cyclodextrins
  • Lithocholic Acid
  • Doxorubicin