Synthesis and biological activity of N-terminal-truncated derivatives of human epidermal growth factor (h-EGF)

Peptides. 1995;16(2):205-10. doi: 10.1016/0196-9781(94)00181-2.

Abstract

To investigate the contribution of the N-terminal sequence of h-EGF to its biological activity and the formation of three intramolecular disulfide bonds by oxidative refolding via air oxidation, five derivatives of h-EGF with a single N-terminal amino acid deletion were synthesized by solid-phase synthesis. The homogeneity of the synthetic peptides was confirmed by analytical reversed-phase HPLC, amino acid analysis, and FAB-MS. The pairing of the three disulfide bridges in synthetic peptides was determined by thermolytic digestion. All N-truncated derivatives of h-FGF formed the correct intramolecular three disulfide linkages during oxidative refolding and had equipotent activity in both EGF receptor binding on A-431 epidermoid carcinoma cells and mitogenesis on NIH-3T3 fibroblast cells, compared with authentic h-EGF. The results suggested that the five residues from N-terminal sequence of h-EGF have no effect on the formation of the correct disulfide linkages in h-EGF and do not exert a significant influence on its biological activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 3T3 Cells
  • Amino Acid Sequence
  • Animals
  • Binding, Competitive
  • Carcinoma, Squamous Cell
  • Cell Division / drug effects
  • Chromatography, High Pressure Liquid
  • Cysteine
  • Dose-Response Relationship, Drug
  • Epidermal Growth Factor / chemical synthesis*
  • Epidermal Growth Factor / chemistry
  • Epidermal Growth Factor / pharmacology*
  • ErbB Receptors / metabolism*
  • Humans
  • Indicators and Reagents
  • Kinetics
  • Mice
  • Molecular Sequence Data
  • Peptide Fragments / chemical synthesis*
  • Peptide Fragments / chemistry
  • Peptide Fragments / pharmacology*
  • Protein Conformation
  • Protein Folding
  • Tumor Cells, Cultured

Substances

  • Indicators and Reagents
  • Peptide Fragments
  • Epidermal Growth Factor
  • ErbB Receptors
  • Cysteine