Design, synthesis, and evaluation of original carriers for targeting vascular endothelial growth factor receptor interactions

Pharm Res. 2005 Aug;22(8):1411-21. doi: 10.1007/s11095-005-5265-9. Epub 2005 Aug 3.

Abstract

Purpose: Angiogenesis is a key event in tumor growth and metastasis, chronic inflammatory disease, and cardiovascular disease. It is controlled by positive and negative regulators, which include vascular endothelial growth factor (VEGF) as the most active of these. VEGF/VEGF receptors are important targets not only for therapy but also for imaging. Based on the structural study of VEGF, we developed a novel cyclopeptide (cyclo-VEGI) that exhibits powerful antitumor properties. We herein report the design of novel molecules derived from cyclo-VEGI as potential targeting agents in cancer and other angiogenesis-related diseases.

Methods: We performed selective chemical modification of the most active VEGF-derived cyclopeptide (cyclo-VEGI). Original hydrophilic linkers were synthesized and coupled to cyclo-VEGI. These reactions provide nanocarriers for delivery. The inhibitory effect of the different compounds on VEGF binding was evaluated in competition assays with 125I-VEGF. A fluorescent cyclo-VEGI peptide was synthezised to assess direct binding and internalization of cyclo-VEGI.

Results: Chemical modifications of cyclo-VEGI do not diminish the biological activity of cyclo-VEGI as measured in competition assays; in fact, it is even increased. Moreover there is a strong cellular accumulation of the fluorescent-labeled cyclo-VEGI. Conjugates synthesized in this study may be useful leads to design delivery systems for targeting approaches in cancer and other angiogenesis-related diseases.

Conclusion: The modified cyclo-VEGIs may have a wide range of applications and represent a useful tool to develop delivery/carrier systems for therapeutic targeting or imaging.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Angiogenesis Inhibitors / chemical synthesis*
  • Angiogenesis Inhibitors / metabolism
  • Angiogenesis Inhibitors / pharmacology*
  • Animals
  • CHO Cells
  • Cricetinae
  • Drug Carriers / chemistry*
  • Drug Design
  • Endothelial Growth Factors / chemical synthesis*
  • Endothelial Growth Factors / metabolism
  • Endothelial Growth Factors / pharmacology*
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / metabolism
  • Peptides, Cyclic / pharmacology*
  • Protein Binding
  • Receptors, Vascular Endothelial Growth Factor / drug effects*
  • Receptors, Vascular Endothelial Growth Factor / metabolism
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

  • Angiogenesis Inhibitors
  • Drug Carriers
  • Endothelial Growth Factors
  • Indicators and Reagents
  • Peptides, Cyclic
  • cyclo-VEGI
  • Receptors, Vascular Endothelial Growth Factor