Polynucleotide analogues. Copolymers of vinyl bases with acrylic acid, methylacrylic acid, acrylamide, and 1-vinylpyrrolidone

J Med Chem. 1977 Oct;20(10):1283-7. doi: 10.1021/jm00220a011.

Abstract

Preliminary studies are reported on the synthesis and testing of substituted vinyl polymers that are designed to have sequence specific affinity for polyribonucleic acids. Copolymers of 1-vinyluracil with acrylic acid, 2-methylacrylic acid, or 1-vinyl-2-pyrrolidone were prepared by gamma-irradiation to give the respective polymers 1,3, and 4. Similarly, 9-vinyladenine yielded copolymeric products 5 and 6 with acrylic acid or 2-methylacrylic acid. Radical initiated polymerization of 9-vinyladenine with acrylamide yielded copolymer 7. The products were characterized by elemental analysis and ultraviolet, infrared, and nuclear magnetic resonance spectroscopy. No hypochromicity could be detected on mixing polymers 1-4 with poly(adenylic acid). The acrylic acid copolymer 2 containing a high ratio of vinyluracil was a potent inhibitor of poly(adenylic acid) coded polylysine synthesis in an in vitro system. Polymers 6 and 7, containing a high proportion of vinyladenine, inhibited poly(uridylic acid) coded poly(phenylalanine) synthesis.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acrylamides / chemical synthesis*
  • Acrylamides / pharmacology
  • Acrylates / chemical synthesis*
  • Acrylates / pharmacology
  • Escherichia coli / drug effects
  • Escherichia coli / metabolism
  • Escherichia coli / ultrastructure
  • Lysine / metabolism
  • Methacrylates / chemical synthesis*
  • Methacrylates / pharmacology
  • Methods
  • Peptide Biosynthesis
  • Phenylalanine / metabolism
  • Poly A / metabolism
  • Poly U / metabolism
  • Polynucleotides / chemical synthesis*
  • Polynucleotides / pharmacology
  • Povidone / analogs & derivatives*
  • Povidone / chemical synthesis
  • Povidone / pharmacology
  • Ribosomes / drug effects
  • Ribosomes / metabolism
  • Vinyl Compounds / chemical synthesis*
  • Vinyl Compounds / pharmacology

Substances

  • Acrylamides
  • Acrylates
  • Methacrylates
  • Polynucleotides
  • Vinyl Compounds
  • Poly A
  • Poly U
  • Phenylalanine
  • Povidone
  • Lysine