Citation: Bao-tong Ye, Zhi Cai, Jing Wu, Xin Lin, Jing-xiao Chen, Jing-hua Chen. Preparation of Sulfonated Galactose-based Glycopolymers and Interactions with Lectins[J]. Acta Polymerica Sinica, ;2018, (4): 490-498. doi: 10.11777/j.issn1000-3304.2017.17138 shu

Preparation of Sulfonated Galactose-based Glycopolymers and Interactions with Lectins

Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Pharmaceutical Sciences, Jiangnan University, Wuxi 214122

Corresponding author: Jing-xiao Chen, tomchenjx@jiangnan.edu.cn Jing-hua Chen, chenjinghua@jiangnan.edu.cn
Received Date: 22 May 2017
Revised Date: 27 June 2017

A series of sulfonated galactose-based glycopolymers with different chemical structures were synthesized through reversible addition-fragmentation chain transfer (RAFT) polymerization. Galactose modified hydroxyethyl methacrylate and sodium p-styrene sulfonate were used as monomers to construct homo-, block-, and random-glycopolymers. The chemical structures and molecular weights of the synthesized polymers were characterized through ¹H-NMR spectroscopy and GPC-MALLS analyses. Results showed that each glycopolymer possessed an average molecular weight of 1.5 x 10⁴ with narrow molecular weight distribution (PDI~1.1). The turbidimetry assay indicated that the interactions between the glycopolymers and peanut agglutinin (PNA), which were used as model lectin, were influenced by the structure of the glycopolymers. The introduction of the sulfonic group significantly improved the PNA-binding ability of the glycopolymers through the synergistic effect of specific recognition and electrostatic interactions. Importantly, this effect was adjustable by varying the amount and distribution of the sulfonic groups. Both block-and random-glycopolymers exhibited significantly enhanced PNA-binding behavior with increasing amount of sulfonic groups. Moreover, the binding ability peaked when the molar ratio of the sulfonic groups was 66.7%. By contrast, the random-type glycopolymer, namely, P(Gal₂₁-r-SS₄₁), exhibited the strongest PNA-binding ability, which increased by 2.7-fold compared with that of the homo-type glycopolymer PGal. The ELISA assay further revealed that the polymerization and random distribution of the sulfonic groups in the glycopolymer substantially enhanced the recognition between PNA and the galactose moiety. The inhibition rate of galactose (30 mmol/L) against the PNA binding of PGal, P(Gal₂₁-b-SS₄₃), and P(Gal₂₁-r-SS₄₁) were 80%, 57.3%, and 34.2%, respectively. However, the contents of the galactose moiety in these samples were 3.8, 2.1 and 2.0 mmol/L, respectively. Overall, the order of PNA-binding ability was:P(Gal-r-SS) > P(Gal-b-SS) > PGal > PSS. In addition, the viability of B16 cancer cells and COS7 normal cells was higher than 80% when the concentration of the glycopolymers was 256 mg/L, indicating a good biocompatibility of these polymers. Based on the analysis of glycopolymer-lectin interactions, P(Gal₂₁-r-SS₄₁) effectively inhibited the migration of B16 tumor cells and thus can be applied in clinical therapy for tumor metastasis.
- Galactose-based glycopolymer,
- Peanut agglutinin,
- Sulfonic group,
- Interactions,
- Tumor cell migration
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