Highly Selective Binding and Inhibition of Pyr-His-Pro-NH2 (TRH) Function using a Polypyridinyl Macrocyclic Receptor with an Amphiphilic Cavity

Chemistry. 2020 Aug 3;26(43):9466-9470. doi: 10.1002/chem.202000888. Epub 2020 Jul 8.

Abstract

Macrocycle, cyclo[4] [(1,3-(4,6)-dimethylbezene)[4](2,6-(3,5)-dimethylpyridine (B4P4), shows highly selective binding affinity with protirelin (Pyr-His-Pro-NH2 ; TRH) among the tested 26 drug or drug adductive substrates. The stable complexation in a 1:1 manner was fully characterized in solution, gas phase, and solid state study. Furthermore, B4P4 acts as an efficient TRH inhibitor even at [macrocycle]:[drug] <1:300, both in membrane transport and cellar incubation. The current work provides an unprecedented strategy for macrocycles to be efficiently used in drug target therapy.

Keywords: adductive dosage; drug inhibition; host-guest systems; macrocyclic receptors; molecular recognition.

MeSH terms

  • Dipeptides / chemistry*
  • Dipeptides / metabolism
  • Pyridines / chemistry*
  • Thyrotropin-Releasing Hormone / chemistry
  • Thyrotropin-Releasing Hormone / metabolism
  • Thyrotropin-Releasing Hormone / pharmacology*

Substances

  • Dipeptides
  • Pyridines
  • histidylproline
  • Thyrotropin-Releasing Hormone