Synthesis and characterization of a novel tritiated KATP channel opener with a benzopyran structure

Br J Pharmacol. 2001 May;133(2):275-85. doi: 10.1038/sj.bjp.0704071.

Abstract

The synthesis of a tritiated benzopyran-type opener of the ATP-dependent K+ channel (KATP channel), [3H]-PKF217 - 744 (3S,4R)-N-[3,4-dihydro-2,2-dimethyl-3-hydroxy-6-(2-methyl-4-pyridinyl)-2H-1-benzopyran-4-yl]-3-[2,6-3H]pyridinecarboxamide with a specific activity of 50 Ci mmol(-1) is described. Binding of the ligand was studied in membranes from human embryonic kidney cells transfected with the sulphonylurea receptor isoforms, SUR2B and SUR2A, respectively. PKF217 - 744 was confirmed as being a KATP channel opener by its ability to open the Kir6.1/SUR2B channel, the recombinant form of the vascular KATP channel, and to inhibit binding of the pinacidil analogue, [3H]-P1075, to SUR2B (Ki=26 nM). The kinetics of [3H]-PKF217 - 744 binding to SUR2B was described by rate constants of association and dissociation of 6.9x10(6) M(-1) min(-1) and 0.09 min(-1), respectively. Binding of [3H]-PKF217 - 744 to SUR2B/2A was activated by MgATP (EC50 approximately 3 microM) and inhibited (SUR2B) or enhanced (SUR2A) by MGADP: Binding of [3H]-PKF217 - 744 to SUR2B was inhibited by representatives of the different structural classes of openers and sulphonylureas. Ki values were identical with those obtained using the opener [3H]-P1075 as the radioligand. Glibenclamide accelerated dissociation of the SUR2B-[3H]-PKF217 - 744 complex. The data show that the affinity of [3H]-PKF217 - 744 binding to SUR2B is approximately 6 times lower than that of [3H]-P1075. This is due to a surprisingly slow association rate of the benzopyran-type ligand, suggesting a complex mechanism of opener binding to SUR. The other pharmacological properties of the two opener radioligands are identical.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • ATP-Binding Cassette Transporters
  • Algorithms
  • Animals
  • Benzopyrans / chemistry
  • Benzopyrans / pharmacology*
  • Binding, Competitive / drug effects
  • Cell Line
  • Cell Membrane / metabolism
  • Humans
  • In Vitro Techniques
  • KATP Channels
  • Kinetics
  • Muscle, Smooth, Vascular / drug effects
  • Patch-Clamp Techniques
  • Portal Vein / drug effects
  • Potassium Channels / agonists*
  • Potassium Channels, Inwardly Rectifying*
  • Pyridines / pharmacology*
  • Radioligand Assay
  • Rats
  • Recombinant Proteins
  • Transfection

Substances

  • ATP-Binding Cassette Transporters
  • Benzopyrans
  • KATP Channels
  • N-(3,4-dihydro-2,2-dimethyl-3-hydroxy-6-(2-methyl-4-pyridinyl)-2H-1-benzopyran-4-yl)-3-(2,6-3H)pyridinecarboxamide
  • Potassium Channels
  • Potassium Channels, Inwardly Rectifying
  • Pyridines
  • Recombinant Proteins
  • uK-ATP-1 potassium channel