Insight into the structure-properties relationship of hydrophobic
hyaluronan derivatives
Marek VIDO1,2
, Martina HERMANNOVÁ2
, Petr TÁBORSKÝ1
1
Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 753/5, 625 00
Brno, Czech Republic
2
Contipro a.s., Dolní Dobrouč 401, 561 02 Dolní Dobrouč, Czech Republic
Email of presenting author: marekvido95@gmail.com
Hyaluronan (HA) is a polymeric biomolecule affiliated to glycosaminoglycans. It is promising
macromolecule for many cosmetic and biomedical applications thanks to its biocompatibility
and non-toxicity. Derivatives of HA with hydrophobic functional groups are often synthetized
to prolong the resistance to natural degradation or to fabricate amphiphilic molecules with
desired properties that can bind active compounds.[1] For complete characterization of novel
derivatives not only essential parameters are needed, such as a degree of substitution (DS),
molar mass distribution and polydispersity, but also distribution of substituents along the
molecule chain[2] is indispensable for proper assessment of structure-property relationship of
these polymers, due to the fact that HA derivatives with the same DS can differ in their
properties.
A comprehensive two-dimensional liquid chromatography method for separation of
oligosaccharides derived by enzymatic digestion from polymeric HA derivatives was
developed and a detail investigation of enzymatic degradation by three possible
hyaluronidases[3] was executed.
Finally, the developed method provided more insight into understanding very important
structure-property relationship. Group of samples that showed good correlation of swelling with
their DS was analyzed and compared with other samples that showed high deviation from a
dependence of swelling ratio on DS. Results enabled us to find structurally irregular patterns in
distribution of substituents for these deviant samples and thus explain the differences in their
properties in comparison with other samples.
References
[1] A. Fallacara, E. Baldini, S. Manfredini, S. Vertuani, Hyaluronic Acid in the Third
Millennium, Polymers. 10 (2018) 701. https://doi.org/10.3390/polym10070701.
[2] P. Mischnick, Analysis of the Substituent Distribution in Cellulose Ethers - Recent
Contributions, in: T. Rosenau, A. Potthast, J. Hell (Eds.), Cellulose Science and
Technology, John Wiley & Sons, Inc., Hoboken, NJ, USA, 2018: pp. 143–173.
https://doi.org/10.1002/9781119217619.ch7.
[3] R. Stern, G. Kogan, M.J. Jedrzejas, L. Šoltés, The many ways to cleave hyaluronan,
Biotechnology Advances. 25 (2007) 537–557.
https://doi.org/10.1016/j.biotechadv.2007.07.001.