Glycopolymers with LacNAc branching discriminate between galectins

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Glycopolymers with LacNAc branching discriminate between galectins

Pavla Bojarová 1,3 , Marina Tavares 2 , Petr Chytil 2 , Lieselotte Sedláková 1,3 , Markéta Bláhová 2 , Lucie Petrásková 1 , Tomáš Etrych 2 , Vladimír Křen 1

1 Institute of Microbiology, Czech Academy of Sciences, Vídeňská 1083, CZ-14220 Praha 4, Czech Republic, 2 Institute of Macromolecular Chemistry, Czech Academy of Sciences, Heyrovského nám. 2 , CZ-16206 Praha 6, Czech Republic, 3 Faculty of Biomedical Engineering, Czech Technical University in Prague, Sítná sq. 3105 , CZ-27201 Kladno, Czech Republic

LacNAc (Galβ4GlcNAc) is a typical carbohydrate ligand of galectins - human lectins regulating, e.g., intercellular communication, adhesion and signaling [1]. Human galectins participate in a number of pathologies including cancerogenesis, metastatic formation, inflammation or fibrosis. Therefore, they are prospective targets for therapeutical applications where selectivity for one particular galectin is highly desirable.

In the present study we synthesized a series of N-(2-hydroxypropyl)methacrylamide (HPMA) copolymers decorated with LacNAc epitope in various concentrations and architectures. The functionalized LacNAc disaccharide was prepared by enzymatic synthesis catalyzed by β-galactosidase from Bacillus circulans [2]. In a structure-affinity relationship study we compare the difference in affinity between LacNAc distributed statistically on the polymer backbone or nested on bi- and trivalent phenyl branches. The affinity of prepared glycopolymers to galectins was determined in ELISA-type assay. We conclude that the manner of the LacNAc presentation on the HPMA copolymer brings a clear discrimination between galectins, reaching affinity in nanomolar range. The prepared selective glycopolymers are attractive for in vivo use due to their good water solubility and lack of toxicity and immunogenicity [3].

Figure 1. HPMA copolymers decorated with LacNAc epitope on phenyl branches.

Laaf, D.; Bojarová, P.; Elling, L.; Křen, V. Trends Biotechnol. 2018, in press.

Bojarová, P.; Křen, V. Chimia 2011, 65, 65-70.

Ulbrich, K.; Šubr, V. Adv. Drug Deliv. Rev. 2010, 62, 150-166.

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