Incorporating monomers into sequence-defined synthetic macromolecules endows them to mimic nature which results in key residues being anchored in the molecular recognition pattern.
Two amphiphilic block copolymers using hydrophobic poly(ε-caprolactone) (PCL) and hydrophilic poly(ethylene glycol) (PEG) were successfully synthesized. One of them is an (A-b-B) 4 type star polymer [(PCL-b-PEG) 4 ] and the other one is a Y-shaped PEG-(PCL) 2 . A star-shaped polymer (PCL-b-PEG) 4 was prepared by ring-opening polymerization (ROP) of ε-caprolactone continued by click reaction of (PCL-azide) 4 and PEG-alkyne. The synthesis of Y-shaped PEG-(PCL) 2 block copolymer was carried out via Diels-Alder click reaction of a furan protected maleimide end-functionalized PEG (PEG-MI) with an anthracene end-functionalized PCL following the ROP of ε-caprolactone. The characterization of micelles is carried out using both materials in aqueous media as drug delivery vehicles, which showed satisfying results and enhanced the cytotoxic effect of the
OPEN ACCESSPolymers 2014, 6 215 anti-cancer drug vinorelbine (VLB). However, micelles consisted of Y-shaped unimers were found to be more convenient for delivery of hydrophobic drugs such as VLB because they formed in lower concentration, carrying a higher amount of drugs and owing a monomodal distribution. We concluded that the free tails of hydrophobic chains in Y-shaped block copolymer facilitate the assembly of amphiphilic material in water to form micelles.
The successful postfunctionalization of multiarm star polystyrene (PS) with pentafluorophenyl and allyl moieties at the periphery is demonstrated employing modular thiol‐para‐fluoro and photoinduced radical thiol‐ene double “click” reactions, respectively. α‐Fluoro and α‐allyl functionalized PS (α‐fluoro‐PS and α‐allyl‐PS) are in situ prepared by atom transfer radical polymerization of styrene and their mixture is used as macroinitiator in a crosslinking reaction with divinyl benzene (DVB) yielding (fluoro‐PS)m–polyDVB–(allyl‐PS)m multiarm star polymer. It is found that the multiarm star polymer includes nearly identical number of arms possessing pentafluorophenyl and allyl moieties at the periphery. The obtained multiarm star polymer is then reacted with 1‐propanethiol through thiol‐para‐fluoro “click” reaction to give (propyl‐PS)m–polyDVB–(allyl‐PS)m multiarm star polymer, which is subsequently reacted with N‐acetyl‐l‐cysteine methyl ester via radical thiol‐ene “click” reaction in order to give well‐defined heterofunctionalized (propyl‐PS)m–polyDVB–(cysteine‐PS)m multiarm star polymer, with higher molecular weight and narrow molecular weight distribution. Multiarm star polymers are characterized by using viscotek triple detection gel permeation chromatography, 1H, and 19F NMR.
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