Chitosan-g-oligo(e-caprolactone) polymeric micelles as drug nanocarriers: Synthesis, characterization and rifampicin encapsulation

QUINTANA S; GLISONI RJ; MOLINA SOLER MA; CALDERÓN M; SOSNIK A

Chiang Mai

Congreso; MACRO; 2014

2014 IUPAC World Polymer Congress or MACRO 2014 and the Chemical Society of Thailand (CST)

In this study, we report on the grafting of -caprolactone onto low molecular weight chitosan via microwave-assisted ring-opening polymerization reactions, in the presence of methanesulfonic acid as solvent and catalyst. The reaction was completed within 10 min and the monomer conversion was above 90%. The grafting of oligo(CL) blocks was confirmed by ATR/FT-IR, 1H- and 13C-NMR, WAXD and thermal analysis. The molecular weight of the copolymers was determined by GPC and MALDI-ToF mass spectrometry. Micelles were obtained by the solvent diffusion/evaporation method and characterized by DLS (size, size distribution and zeta-potential) and TEM and AFM (morphology). Finally, the cytocompatibility and cell uptake were assessed in a lung epithelia carcinoma cell line (A549 cells). The encapsulation of rifampicin led to a modest solubility increase, though data indicated a better performance than other nanocarriers previously investigated. At the same time, since chitosan-g-oligo(E-caprolactone) are expected to conserve unique properties of chitosan such as muco-adhesiveness and capacity to transiently open tight cell junctions, more prolonged residence times of the micelles in the intestinal mucosa and greater drug bioavailability are envisioned. Acknowledgements: The authors thank the support of CONICET and the European Union's - Seventh Framework Programme under grant agreement #612675-MC-NANOTAR.