Background and Objectives: Manifestations of intermolecular interaction based on hydrogen bonding in hyaluronic acid IR spectra and in multicomponent mixtures of hyaluronic acid with nitrogen-containing amino acids, which are part of mucin of the mucous membrane of the bladder and protein carrier microgels, have been studied using experimental and theoretical IR spectroscopy. Materials and Methods: Comparison of measured and calculated hyaluronic acid IR spectra in harmonic approximation is performed. Calculations of molecular complexes structure and their corresponding IR spectra were carried out, followed by an analysis of the parameters of the hydrogen bonds formed. Results: Estimates of hyaluronic acid complexation with amino acids strength, which are part of protein microgels used in targeted therapy, and in target cells proteins were given. Conclusion: It has been found that the presence of an additional protein structure significantly increases the hyaluronic acid interaction with mucous membrane mucin protein due to intermolecular complexation based on polar basic amino acids.