A new
versatile cyclic polymer platform for the design of advanced
cyclic materials was prepared by combining ring-expansion metathesis
polymerization (REMP) and click chemistry. Cyclic poly(norbornenyl
azlactone) backbones were synthesized over an unprecedented length
range with number-average degree of polymerization (DP
n
) ranging from 25 to 1000. The cyclic
topology was thoroughly characterized using 1H NMR, size
exclusion chromatography (SEC) with multiangle light scattering (MALS)
and viscometer detection. Postpolymerization modification (PPM) of
these scaffolds was carried out with amino-terminated mannoses using
the click aminolysis of the azlactone moiety to prepare a library
of multivalent cyclic glycopolymers. The binding inhibition of the
resulting cyclic glycopolymers was assessed against a panel of model
and biologically relevant lectins (Bc2L-A, FimH, langerin, DC-SIGN,
and ConA). The cyclic carbohydrate-functionalized polynorbornenes
exhibited high lectin-binding inhibitory potency in the biochip assay,
surpassing their monovalent analogues by several orders of magnitude
and competing strongly with their linear polymer analogues in terms
of IC50 values. Interestingly, the cyclic polymers also
prevented the adhesion of Adherent-Invasive Escherichia
coli implied in Crohn’s disease, to intestinal
cells.