Conjugation of chitosan nanoparticles with biogenic and synthetic polyamines: A delivery tool for antitumor polyamine analogues

•The conjugation of chitosan with biogenic and synthetic polyamines is studied.•Biogenic polyamines form more stable conjugates than synthetic polyamines.•As chitosan size increased more stable polyamine conjugates were formed.•The loading efficacy was increased as chitosan size increased.•Chitosan nanoparticles can deliver antitumor polyamine analogues.

We report the conjugation of chitosan nanoparticles with biogenic polyamines spermine (spm), spermidine (spmd) and synthetic polyamines 3,7,11,15-tetrazaheptadecane.4HCl (BE-333) in aqueous solution. Multiple spectroscopic methods, thermodynamic parameters and molecular modeling were used to analyse polyamine bindings to chitosan nanoparticles. Thermodynamic parameters ΔS, ΔH and ΔG showed that polyamines bind protein through H-bonding and hydrophobic contacts with biogenic polyamines form more stable conjugates than synthetic polyamines. As polymer size increases the stability of polyamine-chitosan conjugate increases. The loading efficacy was 40–50% for polyamine-chitosan conjugates. Modeling showed that polyamine-protein interaction is spontaneous and chitosan nanoparticles can be used for delivery of antitumor polyamine analogues.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide