Synthesis and characterization of novel polyurethane cationomers with dipeptide sequences and alkylammonium groups

• Published in: Journal of biomaterials science. Polymer ed. Vol. 15; no. 6; pp. 781 - 795
• Main Authors: Buruiana, Emil C., Buruiana, Tinca
• Format: Journal Article
• Language: English
• Published: England Taylor & Francis Group 01.01.2004
• Subjects: ALKYLAMMONIUM; Anticoagulants - pharmacology; Biocompatible Materials - chemistry; Calorimetry, Differential Scanning; Carbon - chemistry; Cations; DIPEPTIDE; ELASTOMERIC FILMS; Glutamic Acid - chemistry; Heparin - chemistry; Magnetic Resonance Spectroscopy; Models, Chemical; Peptides - chemistry; POLYCATION/HEPARIN COMPLEX; Polymers - chemistry; Polyurethanes - chemistry; PU-CATIONOMER; Quaternary Ammonium Compounds - chemistry; Spectrophotometry; Spectrophotometry, Infrared; Temperature; Time Factors
• ISSN: 0920-5063; 1568-5624
• DOI: 10.1163/156856204774196162

A synthetic approach to polyurethane cationomers containing S-pyroglutamyl-S-glutamic acid dipeptide (S-PyGlu-S-Glu) and alkylammonium groups is presented. Two segmented polycations, based on polycaprolactone diol, isophorone diisocyanate and dipeptide together with N-methyldiethanolamine, subsequently quaternized with dodecylbromide, were synthesized and characterized by IR spectroscopy, GPC, DSC and reduced viscosity measurements. Such polycations exhibited excellent film forming properties and their soft elastomeric nature provides adequate physical properties. Optical rotation varying from +10 (monomer) to -15 (polycation) could be associated with a configuration pertubation through the asymmetric carbon atoms of glutamic residues. Susceptibility of the cationic surface to heparinization and then to blood-polymer interaction suggested an anticoagulant activity of the heparinized polymeric films.