Formation of reversible shell cross-linked micelles from the biodegradable amphiphilic diblock copolymer poly(L-cysteine)-block-poly(L-lactide)

Langmuir. 2008 Sep 16;24(18):10099-106. doi: 10.1021/la8013877. Epub 2008 Aug 13.

Abstract

A novel biodegradable diblock copolymer, poly(L-cysteine)-b-poly(L-lactide) (PLC-b-PLLA), was synthesized by ring-opening polymerization (ROP) of N-carboxyanhydride of beta-benzyloxycarbonyl-L-cysteine (ZLC-NCA) with amino-terminated poly(L-lactide) (NH 2-PLLA) as a macroinitiator in a convenient way. The diblock copolymer and its precursor were characterized by (1)H NMR, Fourier transform infrared (FT-IR), gel permeation chromatography (GPC), and X-ray photoelectron spectroscopy (XPS) measurements. The length of each block polymer could be tailored by molecular design and the ratios of feeding monomers. The cell adhesion and cell spread on the PZLC-b-PLLA and PLC-b-PLLA films were enhanced compared to those on pure PLA film. PLC-b-PLLA can self-assemble to form micelles in aqueous media. A pyrene probe is used to demonstrate the micelle formation of PLC-b-PLLA in aqueous solution. Due to the ease of disulfide exchange with thiols, the obtained micelles are reversible shell cross-linked (SCL) micelles. The morphology and size of the micelles are studied by dynamic light scattering (DLS) and environmental scanning electron microscopy (ESEM).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biocompatible Materials / chemistry*
  • Cell Adhesion
  • Cell Culture Techniques / instrumentation
  • Cell Line, Tumor
  • Cysteine / analogs & derivatives*
  • Cysteine / chemistry
  • Humans
  • Lactic Acid / chemistry*
  • Magnetic Resonance Spectroscopy
  • Micelles*
  • Molecular Weight
  • Peptides / chemistry
  • Polyesters
  • Polymers / chemistry*
  • Pyrenes / chemistry
  • Spectrometry, X-Ray Emission / methods
  • Spectroscopy, Fourier Transform Infrared
  • Surface Properties

Substances

  • Biocompatible Materials
  • Micelles
  • Peptides
  • Polyesters
  • Polymers
  • Pyrenes
  • poly(L-cysteine)-block-poly(L-lactide)
  • Lactic Acid
  • poly(lactide)
  • polycysteine
  • Cysteine