Nuclease-resistant nucleic acid ligands to vascular permeability factor/vascular endothelial growth factor

Chem Biol. 1995 Oct;2(10):683-95. doi: 10.1016/1074-5521(95)90032-2.

Abstract

Background: Vascular permeability factor/vascular endothelial growth factor (VPF/VEGF) is a potent inducer of new blood vessel growth (angiogenesis) that contributes to the pathology of many angiogenesis-associated disease states such as psoriasis, rheumatoid arthritis and cancer. Few molecular entities capable of binding to VPF/VEGF with high affinity and specificity have been described to date.

Results: Nuclease-resistant 2'-amino-2'-deoxypyrimidine nucleotide RNA (2'-aminopyrimidine RNA) ligands that bind to VPF/VEGF with high affinity have been identified by iterative rounds of affinity-selection/amplification from two independent random libraries. The sequence information that confers high affinity binding to VPF/VEGF is contained in a contiguous stretch of 24 nucleotides, 5'-CCCUGAUGGUAGACGCCGGGGUG-3' (2'-aminopyrimidine nucleotides are designated with italic letters). Of the 14 ribopurines in this minimal ligand, 10 can be substituted with the corresponding 2'-O-methylpurine nucleotides without a reduction in binding affinity to VPF/VEGF. In fact, the 2'-O-methyl substitution at permissive positions leads to a approximately 17-fold improvement in the binding affinity to VPF/VEGF. The higher affinity results from the reduction in the dissociation rate constant of the 2'-O-methyl-substituted RNA ligand from the protein compared to the unsubstituted ligand. The 2'-O-methyl-substituted minimal ligand, which folds into a bulged hairpin motif, is also more thermally stable than the unsubstituted ligand. Nuclease resistance of the ligand is further improved by the 2'-O-methyl substitutions and the addition of short phosphorothioate caps to the 3'- and 5'-ends.

Conclusions: We have used the SELEX (systematic evolution of ligands by exponential enrichment) process in conjunction with post-SELEX modifications to define a highly nuclease-resistant oligonucleotide that binds to VPF/VEGF with high affinity and specificity.

MeSH terms

  • Animals
  • Base Sequence
  • Chemical Phenomena
  • Chemistry, Physical
  • Endothelial Growth Factors / chemistry*
  • Endothelial Growth Factors / urine
  • Humans
  • Ligands
  • Lymphokines / chemistry*
  • Lymphokines / urine
  • Molecular Sequence Data
  • Nuclear Magnetic Resonance, Biomolecular
  • Nucleic Acids / chemistry*
  • Nucleic Acids / urine
  • Oligonucleotides / chemical synthesis
  • Oligonucleotides / chemistry
  • Peptide Library
  • Purines / chemistry
  • Rats
  • Recombinant Proteins / chemistry
  • Ribonucleases / chemistry*
  • Ribonucleases / urine
  • Vascular Endothelial Growth Factor A
  • Vascular Endothelial Growth Factors

Substances

  • Endothelial Growth Factors
  • Ligands
  • Lymphokines
  • Nucleic Acids
  • Oligonucleotides
  • Peptide Library
  • Purines
  • Recombinant Proteins
  • Vascular Endothelial Growth Factor A
  • Vascular Endothelial Growth Factors
  • Ribonucleases