Orally active adenosine A(1) receptor agonists with antinociceptive effects in mice

J Med Chem. 2012 Jul 26;55(14):6467-77. doi: 10.1021/jm3004834. Epub 2012 Jul 16.

Abstract

Adenosine A(1) receptor (A(1)AR) agonists have antinociceptive effects in multiple preclinical models of acute and chronic pain. Although numerous A(1)AR agonists have been developed, clinical applications of these agents have been hampered by their cardiovascular side effects. Herein we report a series of novel A(1)AR agonists, some of which are structurally related to adenosine 5'-monophosphate (5'-AMP), a naturally occurring nucleotide that itself activates A(1)AR. These novel compounds potently activate A(1)AR in several orthogonal in vitro assays and are subtype selective for A(1)AR over A(2A)AR, A(2B)AR, and A(3)AR. Among them, UNC32A (3a) is orally active and has dose-dependent antinociceptive effects in wild-type mice. The antinociceptive effects of 3a were completely abolished in A(1)AR knockout mice, revealing a strict dependence on A(1)AR for activity. The apparent lack of cardiovascular side effects when administered orally and high affinity (K(i) of 36 nM for the human A(1)AR) make this compound potentially suitable as a therapeutic.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Adenosine A1 Receptor Agonists / administration & dosage*
  • Adenosine A1 Receptor Agonists / chemistry
  • Adenosine A1 Receptor Agonists / metabolism
  • Adenosine A1 Receptor Agonists / pharmacology*
  • Adenosine Monophosphate / administration & dosage*
  • Adenosine Monophosphate / chemistry
  • Adenosine Monophosphate / metabolism
  • Adenosine Monophosphate / pharmacology*
  • Administration, Oral
  • Analgesics / administration & dosage*
  • Analgesics / chemistry
  • Analgesics / metabolism
  • Analgesics / pharmacology*
  • Animals
  • Behavior, Animal / drug effects
  • HEK293 Cells
  • Humans
  • Male
  • Mice
  • Nociception / drug effects
  • Receptor, Adenosine A1 / metabolism*
  • Substrate Specificity
  • Temperature

Substances

  • Adenosine A1 Receptor Agonists
  • Analgesics
  • Receptor, Adenosine A1
  • Adenosine Monophosphate