D-4'-thioadenosine derivatives as highly potent and selective agonists at the human A3 adenosine receptor

Nucleosides Nucleotides Nucleic Acids. 2005;24(5-7):607-9. doi: 10.1081/NCN-200061827.

Abstract

4'-Thionucleoside derivatives as potent and selective A3 adenosaine receptor agonists were synthesized, starting from D-gulono-gamma-lactone via D-thioribosyl acetate as a key intermediate, among which the 2-chloro-N6-methyladenosine-5-methyluronamide showed the most potent and selective binding affinity (Ki = 0.28 +/- 0.09 nM) at the human A3 adenosine receptor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemistry
  • Adenosine / analogs & derivatives*
  • Adenosine / chemistry
  • Adenosine A3 Receptor Agonists*
  • Animals
  • Furans / chemistry
  • Gluconates / chemistry
  • Humans
  • Kinetics
  • Lactones / chemistry
  • Ligands
  • Models, Chemical
  • Nucleosides / chemistry
  • Oxygen / chemistry
  • Protein Binding
  • Rats
  • Receptor, Adenosine A3 / chemistry*
  • Thionucleosides / chemistry*

Substances

  • 2-chloro-N(6)-methyladenosine-5'-methyluronamide
  • Acetates
  • Adenosine A3 Receptor Agonists
  • Furans
  • Gluconates
  • Lactones
  • Ligands
  • Nucleosides
  • Receptor, Adenosine A3
  • Thionucleosides
  • 4'-thioadenosine
  • Adenosine
  • Oxygen