High affinity binding of the peptide agonist TIP-39 to the parathyroid hormone 2 (PTH2) receptor requires the hydroxyl group of Tyr-318 on transmembrane helix 5

Biochem Pharmacol. 2017 Mar 1:127:71-81. doi: 10.1016/j.bcp.2016.12.013. Epub 2016 Dec 22.

Abstract

TIP39 ("tuberoinfundibular peptide of 39 residues") acts via the parathyroid hormone 2 receptor, PTH2, a Family B G protein-coupled receptor (GPCR). Despite the importance of GPCRs in human physiology and pharmacotherapy, little is known about the molecular details of the TIP39-PTH2 interaction. To address this, we utilised the different pharmacological profiles of TIP39 and PTH(1-34) at PTH2 and its related receptor PTH1: TIP39 being an agonist at the former but an antagonist at the latter, while PTH(1-34) activates both. A total of 23 site-directed mutations of PTH2, in which residues were substituted to the equivalent in PTH1, were made and pharmacologically screened for agonist activity. Follow-up mutations were analysed by radioligand binding and cAMP assays. A model of the TIP39-PTH2 complex was built and analysed using molecular dynamics. Only Tyr318-Ile displayed reduced TIP39 potency, despite having increased PTH(1-34) potency, and further mutagenesis and analysis at this site demonstrated that this was due to reduced TIP39 affinity at Tyr318-Ile (pIC50=6.01±0.03) compared with wild type (pIC50=7.81±0.03). The hydroxyl group of the Tyr-318's side chain was shown to be important for TIP39 binding, with the Tyr318-Phe mutant displaying 13-fold lower affinity and 35-fold lower potency compared with wild type. TIP39 truncated by up to 5 residues at the N-terminus was still sensitive to the mutations at Tyr-318, suggesting that it interacts with a region within TIP39(6-39). Molecular modelling and molecular dynamics simulations suggest that the selectivity is based on an interaction between the Tyr-318 hydroxyl group with the carboxylate side chain of Asp-7 of the peptide.

Keywords: Agonist; GPCR; PTH; Parathyroid hormone; Receptor; TIP39.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • HEK293 Cells
  • Humans
  • Models, Molecular
  • Mutation
  • Neuropeptides / chemistry
  • Neuropeptides / genetics
  • Neuropeptides / pharmacology*
  • Protein Structure, Secondary
  • Radioligand Assay
  • Receptor, Parathyroid Hormone, Type 1 / chemistry
  • Receptor, Parathyroid Hormone, Type 1 / metabolism
  • Receptor, Parathyroid Hormone, Type 2 / agonists
  • Receptor, Parathyroid Hormone, Type 2 / chemistry
  • Receptor, Parathyroid Hormone, Type 2 / metabolism*
  • Tyrosine / chemistry
  • Tyrosine / genetics

Substances

  • Neuropeptides
  • Receptor, Parathyroid Hormone, Type 1
  • Receptor, Parathyroid Hormone, Type 2
  • tuberoinfundibular peptide 39
  • Tyrosine