Preparation of boronate‐functionalized surface molecularly imprinted polymer microspheres with polydopamine coating for specific recognition and separation of glycoside template

Abstract

A facile strategy based on the boronate affinity and polydopamine coating was proposed for the preparation of surface molecularly imprinted polymer microspheres using naringin as the glycoside template. The poly(methacrylic acid-co-methyl methacrylate-co-ethyleneglycol dimethacrylate) microspheres were firstly synthesized as inner cores by suspension polymerization method, and then functionalized with 3-aminophenylboronic acid. The imprinted shell layer was obtained by selfpolymerization of dopamine on the surface of boronic acid-functionalized polymer microspheres after reversible immobilization of naringin. The resultant surface molecularly imprinted microspheres showed good imprinting efficiency and recognition specificity toward the template molecule in aqueous environment. The isothermal and kinetic adsorption behaviors of the polymers were investigated. The results showed that the covalent surface imprinted microspheres possessed homogeneous recognition sites, strong adsorption affinity, and rapid rebinding kinetics. In addition, the surface imprinted microspheres were utilized as the sorbents of solid phase extraction to successfully separate and enrich naringin from Citri Grandis extract, and the recovery of naringin in eluting solution reached 84.4%.

Structurally Constrained MUC1‐Tn Mimetic Antigen as Template for Molecularly Imprinted Polymers (MIPs): A Promising Tool for Cancer Diagnostics

“…To the best of our knowledge, there are very few examples of glycans and glycoconjugates used as templates for catecholamine-based molecular imprinting in the literature, and only referred to the use of PDA. [37][38][39] Such paucity of experimental studies, despite the large literature on polydopamine, somehow suggested to test the more hydrophilic polynorepinephrine for sugar imprinting. [22][23][24] Accordingly, our preliminary studies employed mimetic and natural Tn antigens (1 and 2 respectively, see Figure 1) as templates for MIPs, and Tn_mime [37]BSA as a model of multivalent glycoprotein.…”

“…The soundness of 1 to mimic the TnThr determinant, prompted us to synthesize 1 ‐imprinted polymers. To the best of our knowledge, there are very few examples of glycans and glycoconjugates used as templates for catecholamine‐based molecular imprinting in the literature, and only referred to the use of PDA [37–39] . Such paucity of experimental studies, despite the large literature on polydopamine, somehow suggested to test the more hydrophilic polynorepinephrine for sugar imprinting [22–24] .…”

Preparation and Application of Molecularly Imprinted Polymers for Flavonoids: Review and Perspective

“…Naringin and hesperidin are both flavanones. Successful preparation of MIPs of naringin [ 54 , 55 ] and hesperidin [ 56 ] has been reported. To selectively separate naringin from Citri Grandis, Pan et al [ 55 ] prepared MIP microspheres using surface imprinting, the IF of the MIP microspheres was 2.89.…”

“…Successful preparation of MIPs of naringin [ 54 , 55 ] and hesperidin [ 56 ] has been reported. To selectively separate naringin from Citri Grandis, Pan et al [ 55 ] prepared MIP microspheres using surface imprinting, the IF of the MIP microspheres was 2.89. Using the MIPs as molecular recognition elements, a fluorescent magnetic MIP sensor towards naringin was successfully constructed [ 54 ].…”

Recent advances and applications of molecularly imprinted polymers in solid‐phase extraction for real sample analysis

“…In addition, the MIP‐grafted or coated silica spheres were also reported for pretreatment of pharmaceutical samples [143–148]. As an example, Zhu et al.…”