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Nucleoside imidodiphosphates synthesis and biological activities.

J Tomasz1, M M Vaghefi, P C Ratsep

  • 1Department of Chemistry, Brigham Young University, Provo, UT 84602.

Nucleic Acids Research
|September 12, 1988
PubMed
Summary

Researchers synthesized novel imidodiphosphate analogues of nucleoside 5'-diphosphates for the first time. These compounds show potent inhibition of ecto-5'-nucleotidase and phosphoribosyl pyrophosphate (PPRP) synthetase, offering new therapeutic potential.

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Nucleosides, nucleotides & nucleic acids·2001

Area of Science:

  • Medicinal Chemistry
  • Biochemistry
  • Organic Synthesis

Background:

  • Nucleoside 5'-diphosphates are crucial biological molecules.
  • Imidodiphosphate analogues can serve as enzyme inhibitors.
  • Developing novel nucleoside analogues is important for drug discovery.

Purpose of the Study:

  • To synthesize novel imidodiphosphate analogues of natural nucleoside 5'-diphosphates.
  • To evaluate the inhibitory potential of these analogues against key enzymes.
  • To explore their potential as therapeutic agents.

Main Methods:

  • Synthesis of adenosine 5'-imidodiphosphate (4a), guanosine 5'-imidodiphosphate (4b), 2'-deoxyadenosine 5'-imidodiphosphate (4c), and 2'-deoxy-guanosine 5'-imidodiphosphate (4d) using nucleosides and trichloro[(dichlorophosphoryl)imido] phosphorane.

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  • Characterization of synthesized compounds and by-products.
  • Enzyme inhibition assays for ecto-5'-nucleotidase, phosphoribosyl pyrophosphate (PPRP) synthetase, and IMP dehydrogenase.

    • Main Results:

    • Successful synthesis of four nucleoside 5'-imidodiphosphate analogues (4a-d) and ribavirin imidodiphosphate (4e).
    • Compounds 4b, 4c, and 4d demonstrated potent inhibition of ecto-5'-nucleotidase.
    • Compound 4b was the most potent inhibitor of PPRP synthetase, outperforming ADP and GDP.
    • Compound 4e showed strong inhibition of IMP dehydrogenase, while 4a-d were weak inhibitors of this enzyme.

    Conclusions:

    • The study presents the first synthesis of key nucleoside 5'-imidodiphosphate analogues.
    • These novel compounds exhibit significant inhibitory activity against ecto-5'-nucleotidase and PPRP synthetase.
    • The findings highlight the potential of these imidodiphosphate analogues as valuable tools in biochemical research and as lead compounds for drug development.