Photoaffinity labeling of A1-adenosine receptors

J Biol Chem. 1985 Nov 25;260(27):14659-64.

Abstract

The ligand-binding subunit of the A1-adenosine receptor has been identified by photoaffinity labeling. A photolabile derivative of R-N6-phenylisopropyladenosine, R-2-azido-N6-p-hydroxyphenylisopropyladenosine (R-AHPIA), has been synthesized as a covalent specific ligand for A1-adenosine receptors. In adenylate cyclase studies with membranes of rat fat cells and human platelets, R-AHPIA has adenosine receptor agonist activity with a more than 60-fold selectivity for the A1-subtype. It competes for [3H]N6-phenylisopropyladenosine binding to A1-receptors of rat brain membranes with a Ki value of 1.6 nM. After UV irradiation, R-AHPIA binds irreversibly to the receptor, as indicated by a loss of [3H]N6-phenylisopropyladenosine binding after extensive washing; the Ki value for this photoinactivation is 1.3 nM. The p-hydroxyphenyl substituent of R-AHPIA can be directly radioiodinated to give a photoaffinity label of high specific radioactivity (125I-AHPIA). This compound has a KD value of about 1.5 nM as assessed from saturation and kinetic experiments. Adenosine analogues compete for 125I-AHPIA binding to rat brain membranes with an order of potency characteristic for A1-adenosine receptors. Dissociation curves following UV irradiation at equilibrium demonstrate 30-40% irreversible specific binding. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis indicates that the probe is photoincorporated into a single peptide of Mr = 35,000. Labeling of this peptide can be blocked specifically and stereoselectively by adenosine receptor agonists and antagonists in a manner which is typical for the A1-subtype. The results indicate that 125I-AHPIA identifies the ligand-binding subunit of the A1-adenosine receptor, which is a peptide with Mr = 35,000.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / metabolism*
  • Adenylyl Cyclases / metabolism
  • Adipose Tissue / metabolism
  • Affinity Labels / pharmacology*
  • Animals
  • Azides / pharmacology*
  • Blood Platelets / metabolism
  • Brain / metabolism
  • Cell Membrane / metabolism
  • Humans
  • Iodine Radioisotopes
  • Kinetics
  • Phenylisopropyladenosine / analogs & derivatives*
  • Phenylisopropyladenosine / pharmacology
  • Rats
  • Receptors, Cell Surface / drug effects
  • Receptors, Cell Surface / metabolism*
  • Receptors, Purinergic

Substances

  • Affinity Labels
  • Azides
  • Iodine Radioisotopes
  • Receptors, Cell Surface
  • Receptors, Purinergic
  • Phenylisopropyladenosine
  • 2-azido-N(6)-4-hydroxyphenylisopropyladenosine
  • Adenylyl Cyclases
  • Adenosine