Non-covalent nano-adducts of co-poly(ester amide) and poly(ethylene glycol): preparation, characterization and model drug-release studies

J Biomater Sci Polym Ed. 2007;18(6):673-85. doi: 10.1163/156856207781034106.

Abstract

Biodegradable, biocompatible poly(ester amide)s (co-PEAs), composed of amino acids, fatty diols and carboxylic acids, have been synthesized. To improve the performance of co-PEAs in Federal Drug Administration-approved solvents such as water and ethanol, these polymers were complexed with poly(ethylene glycol) (PEG) of 10 kDa molecular mass have been prepared by solution blending. The non-covalent adducts were purified by precipitation into hexanes. Co-PEAs are soluble in organic solvents but are insoluble in water and ethanol; however, the co-PEA/PEG (0.8:1, w/w) adducts are soluble in ethanol and slightly soluble in water. 2D-NOESY NMR spectroscopy suggests that the non-covalent adducts are held together by multiple non-covalent interactions between the -CH2- groups of the two polymers (co-PEA and PEG). Differential scanning calorimetry studies indicate that the two polymers are interacting in the non-covalent adducts; the thermal properties of the adducts are different from those of the pure polymers. The solid-state adduct structures have been determined by atomic force microscopy (AFM). By one sample preparation method, nanoscale pancake-like structures were observed with an average diameter of 260 nm and an average height of 16 nm. Films of co-PEAs and (co-PEA)/PEG adducts containing Rhodamine B Base (RhBB), a model hydrophobic drug, were prepared. From the adduct/RhBB film containing 3% RhBB, 20% of the total RhBB was released within the first 2 h. Film and adduct composition may be varied to obtain different release profiles. The studies reported here demonstrate that non-covalent conjugation is a relatively easy and effective approach in developing new materials for application as biomaterials.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amides / chemical synthesis
  • Amides / chemistry*
  • Biocompatible Materials / chemical synthesis
  • Biocompatible Materials / chemistry*
  • Buffers
  • Calorimetry, Differential Scanning
  • Drug Delivery Systems*
  • Ethanol / chemistry
  • Fluorescent Dyes
  • Hydrogen-Ion Concentration
  • Hydrophobic and Hydrophilic Interactions
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Microscopy, Atomic Force
  • Molecular Structure
  • Molecular Weight
  • Phosphates / chemistry
  • Polyesters / chemical synthesis
  • Polyesters / chemistry*
  • Polyethylene Glycols / chemistry*
  • Rhodamines
  • Solubility
  • Temperature
  • Water / chemistry

Substances

  • Amides
  • Biocompatible Materials
  • Buffers
  • Fluorescent Dyes
  • Phosphates
  • Polyesters
  • Rhodamines
  • Water
  • Ethanol
  • Polyethylene Glycols
  • rhodamine B