Rational Design of Highly Selective Sialyllactose-Imprinted Nanogels.
Cecilia ContardiLiliia MavliutovaMassimo SerraDavide RubesRossella DoratiVistoli GiulioAlessio MacoranoBörje SellergrenErsilia De LorenziPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2024)
We describe a facile method to prepare water-compatible molecularly imprinted polymer nanogels (MIP NGs) as synthetic antibodies against target glycans. Three different phenylboronic acid (PBA) derivatives were explored as monomers for the synthesis of MIP NGs targeting either α2,6- or α2,3-sialyllactose, taken as oversimplified models of cancer-related sT and sTn antigens. Starting from commercially available 3-acrylamidophenylboronic acid, also its 2-substituted isomer and the 5-acrylamido-2-hydroxymethyl cyclic PBA monoester derivative were initially evaluated by NMR studies. Then, a small library of MIP NGs imprinted with the α2,6-linked template was synthesized and tested by mobility shift Affinity Capillary Electrophoresis (msACE), to rapidly assess an affinity ranking. Finally, the best monomer 2-acrylamido PBA was selected for the synthesis of polymers targeting both sialyllactoses. The resulting MIP NGs display an affinity constant≈10 6 M -1 and selectivity towards imprinted glycans. This general procedure could be applied to any non-modified carbohydrate template possessing a reducing end.
Keyphrases
- molecularly imprinted
- capillary electrophoresis
- solid phase extraction
- mass spectrometry
- liquid chromatography
- tandem mass spectrometry
- simultaneous determination
- cancer therapy
- high resolution
- magnetic resonance
- cell surface
- molecular docking
- minimally invasive
- gold nanoparticles
- solid state
- molecular dynamics simulations
- metal organic framework
- case control
- oxide nanoparticles
- structure activity relationship