Comparative studies on the affinities of ATP derivatives for P2x-purinoceptors in rat urinary bladder

Br J Pharmacol. 1994 Aug;112(4):1151-9. doi: 10.1111/j.1476-5381.1994.tb13204.x.

Abstract

1. Radioligand binding assays have been used to determine the affinities of a series of ATP derivatives with modifications of the polyphosphate chain, adenine and ribose moieties of the ATP molecule for [H]-alpha,beta-methylene ATP ([3H]-alpha,beta-MeATP) binding sites in rat urinary bladder. 2. The replacement of the bridging oxygen in the triphosphate chain of ATP (pIC50 = 5.58) with a methylene or imido group markedly increased the affinity (691 fold in IC50 values for beta,gamma-imidoATP, 15 fold for beta,gamma-methylene ATP), and the replacement of an ionized oxygen on the gamma-phosphate with a sulphur (ATP gamma S) also led to increased affinity (5623 fold in IC50 values). 3. Modifications at N6, N1, and C-8 positions on the purine base usually reduced the affinity of ATP (a decrease of 2.8 fold in IC50 values for N6-methylATP and 8.9 fold for 8-bromo ATP), while the attachment of an alkylthio group to the C-2 position greatly increased the affinity for P2x-purinoceptors (from 3.5 to 98 fold increase in IC50 values). 4. Replacement of the 3'-hydroxyl group on the ribose with substituted amino or acylamino groups produced more potent P2x-purinoceptor agonists (an increase of 447 fold in IC50 values for 3'-deoxy-3'-benzylamino ATP and 28 fold for 3'-deoxy-3'-(4-hydroxyphenylpropionyl)amino ATP. 5. Diadenosine polyphosphates (Ap[n]A) were also shown to displace the [3H]-alpha,beta-MeATP binding. The rank order of potency was Ap6A > Ap5A > Ap4A >> Ap3A >> Ap2A. 6. Suramin, PPADS, and reactive blue 2 could competitively displace the binding of [3H]-alpha,beta-MeATP toP2X-purinoceptors, with pIC50 values of 6.26, 5.35, and 6.22, respectively.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine Triphosphate / analogs & derivatives
  • Adenosine Triphosphate / metabolism*
  • Animals
  • In Vitro Techniques
  • Male
  • Radioligand Assay
  • Rats
  • Rats, Wistar
  • Receptors, Purinergic P2 / metabolism*
  • Structure-Activity Relationship
  • Urinary Bladder / metabolism*

Substances

  • Receptors, Purinergic P2
  • Adenosine Triphosphate