Poly(ether urethane)s incorporating long alkyl side-chains with terminal carboxyl groups as fatty acid mimics: synthesis, structural characterization and protein adsorption

Citation

Simonovsky, Felix I.; Wu, Yuguang; Golledge, Stephen L.; Ratner, Buddy D.; & Horbett, Thomas A. (2005). Poly(ether urethane)s incorporating long alkyl side-chains with terminal carboxyl groups as fatty acid mimics: synthesis, structural characterization and protein adsorption. J Biomater Sci Polym Ed, 16(12), 1463-1483.

Abstract

The object of this work was to produce polyurethanes with greater affinity for albumin (Alb) and improved hemocompatibility by introduction of carboxyl-terminated alkyl side-chains that better mimic fatty acids, in contrast to methyl terminated alkyl side-chains used previously. Synthesis of poly(ether urethane)s (PEUs) with long alkyl side-chains via a multi-step solution addition polymerization is described. The synthesis is based upon the polymerization of a diisocyanate pre-polymer with various chain extenders and reaction with Br-terminated compound in the final stage. The side-chains had terminal methyl or carboxylic groups, and were attached either directly to the polymer backbone or to an oligo(ethylene glycol) spacer. The bulk structure of the PEUs was confirmed by 1H-NMR and the surface polymer structure was characterized by ToF-SIMS. The influence of the incorporated C16-alkyl, C16-carboxyalkyl and oxyethylene-C16-carboxyalkyl side-chains attached to the polymer backbone on fibrinogen (Fg) and Alb adsorption from blood plasma, and Fg adsorption from buffer solutions and binary mixtures with Alb was measured. Incorporation of C16-alkyl or C16-carboxyalkyl side-chains into PEUs caused relatively small changes in Fg and Alb adsorption. PEUs with oxyethylene-C16-carboxyalkyl side-chains exhibited the lowest Fg adsorption and the highest Alb adsorption among all the tested polymers.

Keyword(s)

Adsorption
Animals
Biomimetics
Buffers
Cattle
Fatty Acids
Fibrinogen
Humans
Iodine Radioisotopes
Isocyanates
Nuclear Magnetic Resonance, Biomolecular
Polyurethanes
proteins
Serum Albumin
Solutions
Spectrometry, Mass, Electrospray Ionization

Reference Type

Journal Article

Secondary Title

J Biomater Sci Polym Ed

Author(s)

Simonovsky, Felix I.
Wu, Yuguang
Golledge, Stephen L.
Ratner, Buddy D.
Horbett, Thomas A.

Year Published

2005

Date Published

1104537600

Volume Number

16

Issue Number

12

Pages

1463-1483

DOI

Poly(ether urethane)s incorporating long alkyl side-chains with terminal carboxyl groups as fatty acid mimics