IBMM (UMR5247), Univ Montpellier, CNRS, ENSCM, Montpellier, France.
IBMM (UMR5247), Univ Montpellier, CNRS, ENSCM, Montpellier, France; Laboratory of Applied Chemistry, Faculty of Science III, Lebanese University, P.O. Box 826, Tripoli, Lebanon.
J Colloid Interface Sci. 2018 Mar 15;514:468-478. doi: 10.1016/j.jcis.2017.12.057. Epub 2017 Dec 20.
The functionalization of poly(ethylene glycol)-poly(ε-caprolactone) (PEG-PCL) block copolymers with moieties allowing for core-crosslinking is expected to result in improved micellar stability and drug delivery properties.
PEG-(PCL) star block copolymers were functionalized with pendant benzylthioether (BTE) groups by applying an anionic post-polymerization modification technique followed by photoradical thiol-yne addition of benzyl mercaptan. The micellar properties of PEG-(PCL) and PEG-(PCL-BTE) were studied and compared in terms of critical micelle concentration (CMC), size, morphology, drug loading and release and in vitro cytotoxicity.
In comparison with unmodified PEG-(PCL) micelles, PEG-(PCL-BTE) micelles exhibited a 15-fold lower CMC, a 15-fold smaller size and a 50% higher drug loading and encapsulation efficiency thanks to the presence of pendant benzyl groups which provide the possibility for micellar core-crosslinking via supramolecular π-π stacking and additional hydrophobic interactions. Whereas the PEG-(PCL) micelles showed significant aggregation during in vitro cytotoxicity experiments, the PEG-(PCL-BTE) micelles showed no signs of aggregation and were capable of solubilizing high concentrations of curcumin, resulting in a significant decrease in MCF-7 cell viability after 48 h. Their ease of synthesis combined with promising results regarding drug delivery make the PEG-(PCL-BTE) micelles appealing for application in the field of encapsulation.
通过将允许核交联的部分官能化聚（乙二醇）-聚（ε-己内酯）（PEG-PCL）嵌段共聚物，可以预期得到改善的胶束稳定性和药物传递性能。
通过应用阴离子后聚合修饰技术，然后用光引发的苯硫醚自由基与苯硫醇加成，将 PEG-（PCL）星型嵌段共聚物官能化，得到带有侧链苄基硫醚（BTE）基团的 PEG-（PCL-BTE）。根据临界胶束浓度（CMC）、粒径、形态、载药量和释放以及体外细胞毒性，研究并比较了 PEG-（PCL）和 PEG-（PCL-BTE）的胶束性质。
与未修饰的 PEG-（PCL）胶束相比，由于存在侧链苄基基团，PEG-（PCL-BTE）胶束的 CMC 降低了 15 倍，粒径减小了 15 倍，载药量和包封效率提高了 50%，这是因为侧链苄基基团提供了通过超分子π-π堆积和额外的疏水相互作用进行胶束核交联的可能性。虽然 PEG-（PCL）胶束在体外细胞毒性实验中显示出明显的聚集，但 PEG-（PCL-BTE）胶束没有聚集的迹象，并且能够溶解高浓度的姜黄素，导致 MCF-7 细胞活力在 48 小时后显著降低。它们的合成简便性以及在药物传递方面的有前景的结果使 PEG-（PCL-BTE）胶束在封装领域具有吸引力。
