β-Cyclodextrin-conjugated amino poly(glycerol methacrylate)s for efficient insulin delivery

Abstract

A series of cationic polymers based on b-cyclodextrin (b-CD)-conjugated amino poly(glycerol methacrylate)s (PGOHMAs) was synthesized for potential insulin delivery by forming polyelectrolyte complexes (PECs). Both linear and star-shaped poly(glycidyl methacrylate)s were functionalized with mono(6-(diethylenetriamine)-6-deoxy)-b-CD and diethylenetriamine to obtain CD-DETA-PGOHMAs and DETA-PGOHMAs, respectively. The resulting polymers were characterized by 1 H NMR, FT-IR, elemental analysis, and TGA, and then used to prepare PECs with insulin. The association efficiency and loading capacity of CD-DETA-PGOHMAs were higher than those of DETA-PGOHMAs. The release of insulin depended on the introduction of b-CDs, the backbone architecture of the polymers, as well as the pH.The competitive binding release study indicted that insulin could be released rapidly when 1-aminoadamantane hydrochloride (ADA) was used as a competitive binding guest molecule. The in vitro cytotoxicity study revealed that CD-series polymers have much lower toxicity than the D-series. The CD-DETA-PGOHMA/insulin complexes, with lower cytotoxicity and proper release rate, showed great potential for insulin controlled release.

Post-polymerization modification reactions of poly(glycidyl methacrylate)s

“…The amine functionalisation strategy has been heavily used in the preparation of amphiphilic copolymers, star polymers, and gra copolymers that have found applications mainly in the arena of polyplexes formation and gene delivery. [63][64][65][66][67] In some cases, the tertiary amines were further quaternised through the use of an alkyl halide to give access to side-chain cationic polymers. 68,69 In most cases so far, atom transfer radical polymerization (ATRP) was used for the preparation of the PGMA scaffold.…”

Synthesis of cationic star polymers by simplified electrochemically mediated ATRP

“…This method has been applied to hydrophobic (meth) acrylates [14,15,[19][20][21][22][23][24][25][26], and hydrophilic (meth)acrylates and (meth)acrylamides [14, 16-18, 25, 27-31] for the synthesis of well-defined polymeric architec-tures. Star-shaped cationic polymers, consisting of multiple arms linked to a central β-cyclodextrin (β-CD) core, have recently attracted much attention, because of their dense branched architecture with moderate flexibility, tunable properties like solubility, chemically crosslinked structure, temperature or pH sensitivity, which could be manipulated by the parameters such as the block composition, MW, and arm number [32][33][34][35][36][37][38][39][40][41][42][43][44]. Amphiphilic star copolymers composed of poly(2-dimethylaminoethyl methacrylate)-block-poly(n-butyl acrylate) (PDMAEMA-b-PBA) arms covalently linked to a β-CD core are especially interesting, because they can be used in biomedical applications, including drug delivery and tissue engineering.…”

Readily Functionalizable and Stabilizable Polymeric Particles with Controlled Size and Morphology by Electrospray

“…7b ). Peaks at 849 and 908 cm −1 are characteristic epoxide bands 40 that are clearly present in the spectrum of the unmodified P(S- r -GMA) particles. These peaks clearly disappear upon functionalization, indicating that the epoxides become fully opened during the reaction.…”