Synthesis and characterization of functionalized triblock polymer: The prepared polymer is cholesteryl terminated and chain‐extended PCL

Abstract

The functionalized triblock polymer for the preparation of self-assembly biomaterials, Chol-(CL) n -Chol, was synthesized through ring-opening polymerization of ecaprolactone (e-CL) following by chain-extension reaction. The chemical structure of functionalized triblock polymer was confirmed by Fourier transform infrared and 1 H-NMR. The molecular weight of the functionalized polymer increased with decreasing feed ratio of the initiator cholesterol (Chol) to the monomer e-CL. Liquid crystalline properties and the self-assembly behavior of the functionalized polymer were validated by Wide angle X-ray diffraction, differential scanning calorimetry, and polarizing light microscope. The results showed that Chol-(CL) n -Chol ( n 40) exhibited liquid crystallinity in particular temperature ranges because of the incorporation of the cholesteryl moiety. In addition, the functionalized triblock polymer can be homogeneously blended with high molecular weight poly(e-caprolactone) (PCL), which offers the possibility to modify the properties of biomaterials based on PCL. Mixing a small amount of a Chol-(CL) n -Chol functionalized polymer with PCL, or coating a thin layer of the functionalized polymer on the surface of a PCL-based implant may modify cell response.

Synthesis of Terpene-Based Polymers

“…Drug-release properties were evaluated in vitro, and the incorporation of Chol moiety in the Chol-PCL conjugate was found to improve cell proliferation. Additionally, PCL with a Chol moiety at both ends has been synthesized by coupling two monofunctional Chol-PCL conjugates to one hexamethylene diisocyanate [145]. This bifunctional conjugate has proven to be miscible with high MW PCL and thus is expected to be useful for the modification of PCL-based biomaterials.…”

New amphiphilic polycarbonates with side functionalized cholesteryl groups as biomesogenic units: synthesis, structure and liquid crystal behavior

“…3,[23][24][25][26][27][28][29] Stupp and coworkers rst reported the synthesis of cholesterol end functionalized oligo(L-lactic acid). 3,23 Later, Cheng 24,25 and Yang 26 et al also reported cholesteryl end-capped aliphatic polycarbonates and dicholesteryl end functionalized block poly(3-caprolactone), respectively, as biodegradable polymers. These study results have shown that the cholesterol-functionalized biodegradable polycarbonate block copolymers can play an important role in encapsulation of complex hydrophobic therapeutics for drug application.…”

Synthesis and Self-Assembled Behavior of pH-Responsive Chiral Liquid Crystal Amphiphilic Copolymers Based on Diosgenyl-Functionalized Aliphatic Polycarbonate

“…Stupp et al [ 28 ] first reported the synthesis of cholesterol end functionalized oligo(L-lactic acid) and its interaction with cells. Subsequently, Guo [ 29 ] and Cheng et al [ 30 ] reported cholesteryl end-capped aliphatic polycarbonates and dicholesteryl end functionalized triblock poly(ε-caprolactone), respectively, as biodegradable polymers. Recently, the cholesteryl-functional polymers have been applied in the field of nanomedicine, such as drugs or nucleic acids delivery, complex hydrophobic therapeutics, etc.…”