Fluoropolymer based on a polyaspartamide containing 1,2,4-oxadiazole units: a potential artificial oxygen (O2) carrier

Macromol Biosci. 2007 Jun 7;7(6):836-45. doi: 10.1002/mabi.200600266.

Abstract

In this preliminary work we have prepared a fluorinated polymer capable of solubilizing an appreciable amount of O(2) and, at the same time, maintaining a higher water solubility than perfluoroalkanes investigated as injectable O(2) carriers. In particular, we describe the synthesis and characterization of a new macromolecular conjugate obtained by derivatization of alpha,beta-poly(N-2-hydroxyethyl)-DL-aspartamide (PHEA) with 5-pentafluorophenyl-3-perfluoroheptyl-1,2,4-oxadiazole, called PHEA-F. This new water soluble fluoropolymer was prepared in high yield using a simple procedure. It was characterized by FT-IR and UV-vis spectrophotometry, (19)F-NMR and SEC measurements. O(2) solubility studies on PHEA-F aqueous solutions were carried out at 25 degrees C and 37 degrees C at atmospheric pressure and showed that PHEA-F conjugate, despite its low degree of derivatization in fluorine containing groups (2.60 mol-%), is capable of dissolving 13-15% more O(2) than non-fluorinated PHEA. Moreover, O(2) release in simulated physiological conditions is faster for PHEA-F than for PHEA. The biocompatibility of this conjugate has been evaluated by performing an in vitro viability assay on human chronic myelogenous leukaemia cells (K-562) chosen as a model cell line and in vitro haemolysis experiments on human RBCs. All these properties suggest the potential use of PHEA-F as an artificial O(2) carrier.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fluorocarbon Polymers / chemistry*
  • Macromolecular Substances / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oxygen / chemistry*
  • Peptides / chemical synthesis*
  • Spectrophotometry, Ultraviolet
  • Spectroscopy, Fourier Transform Infrared
  • Temperature

Substances

  • Fluorocarbon Polymers
  • Macromolecular Substances
  • Peptides
  • alpha,beta-poly((2-hydroxyethyl)-aspartamide)
  • Oxygen