Glycopolymers Bearing Galactose and Betulin: Synthesis, Encapsulation, and Lectin Recognition

Abstract

Betulin is a natural triterpene compound with anticarcinogen and antiviral activities. It is conjugated with methacrylate and then copolymerized with a galactose-bearing comonomer by RAFT polymerization to yield both random and block copolymers. These glycopolymers are designed to possess similar molecular weights and monomer compositions for easy comparison. They self-assembled into micelles, as shown by dynamic light scattering (DLS) and transmission electron microscopy. The smaller micelles formed by the random copolymers facilitated the encapsulation of Nile Red and released more of this hydrophobic model compound (46% in 4 days versus 32% released from the block copolymers). These glycopolymers interacted with lectins, such as RCA, as studied by turbidity assay and DLS. The block copolymers formed larger aggregates and clustered faster than the random copolymers. The betulin-based glycopolymers may serve as biocompatible multifunctional biomaterials and carriers for use in targeted release of drugs.

Design of Thermoresponsive Elastin-Like Glycopolypeptides for Selective Lectin Binding and Sorting

“…This technique was also used by Ma et al to show the interactions between RCA 120 and glycopolymers bearing galactose and betulin. They also observed the increase in size of the aggregates with time upon the addition of the lectin, which was explained by a possible intermicellar cross-linking due to the two identical binding sites of the RCA 120 …”

Synthesis and Characterization of Methacrylate-Functionalized Betulin Derivatives as Antibacterial Comonomer for Dental Restorative Resins

“…M 1 Bet was synthesized by an esterification reaction (Scheme 1) following a literature procedure with modification. 36 Betulin (4.2 g, 9.6 mmol), DMAP (0.8 g), and dichloromethane (70 mL) were added to a 500 mL round-bottom flask, and the solution was stirred for 30 min. Subsequently, a mixture of methacrylic anhydride (1.5 mL, 10.0 mmol) and dichloromethane (18 mL) was added dropwise.…”

Multi-Arm Star-Shaped Glycopolymers with Precisely Controlled Core Size and Arm Length

“…7 Therefore, glycopolymers of different types and their interactions with lectins are now being widely explored for biological applications such as drug and gene delivery. [8][9][10][11][12] Branched glycopolymers, in particular, have shown successful drug encapsulation as well as stronger interactions with lectins. 13,14 For this reason, the synthesis of various brush and starshaped glycopolymers has been reported in the literature.…”