A Photo-Crosslinkable Biotin Derivative of the Phosphoantigen (E)-4-Hydroxy-3-Methylbut-2-Enyl Diphosphate (HMBPP) Activates Vγ9Vδ2 T Cells and Binds to the HMBPP Site of BTN3A1

Chemistry. 2017 Sep 4;23(49):11945-11954. doi: 10.1002/chem.201702650. Epub 2017 Aug 10.

Abstract

Vγ9Vδ2 T cells play an important role in the cross talk of the innate and adaptive immune system. For their activation by phosphoantigens (PAgs), both cell surface receptors, the eponymous Vγ9Vδ2 T cell antigen receptors (Vγ9Vδ2 TCRs) on Vγ9Vδ2 T cells and butyrophilin 3A1 (BTN3A1) on the phosphoantigen-"presenting" cell, are mandatory. To find yet undetected but further contributing proteins, a biotinylated, photo-crosslinkable benzophenone probe BioBP-HMBPP (2) was synthesized from a known allyl alcohol in nine steps and overall 16 % yield. 2 is based on the picomolar PAg (E)-4-hydroxy-3-methylbut-2-enyl diphosphate (HMBPP, 1). Laser irradiation of 2 at 308 nm initiated the photo-crosslinking reaction with proteins. When the B30.2 domain of BTN3A1, which contains a positively charged PAg-binding pocket, was exposed to increasing amounts of HMBPP (1), labeling by BioBP-HMBPP (2) was reduced significantly. Because BSA labeling was not impaired, 2 clearly binds to the same site as natural ligand 1. Thus, BioBP-HMBPP (2) is a suitable tool to identify co-ligands or receptors involved in PAg-mediated T cell activation.

Keywords: B30.2 domain; BTN3A1; HMBPP; phosphoantigen; photoaffinity label.

MeSH terms

  • Animals
  • Antigens / immunology
  • Antigens / metabolism
  • Antigens, CD / chemistry
  • Antigens, CD / metabolism*
  • Antigens, Differentiation, T-Lymphocyte / metabolism
  • Biotin / analogs & derivatives*
  • Biotin / chemical synthesis
  • Biotinylation / radiation effects
  • Butyrophilins / chemistry
  • Butyrophilins / metabolism*
  • Cattle
  • Cell Line
  • Cell Proliferation / drug effects
  • Humans
  • Lasers
  • Lectins, C-Type / metabolism
  • Lymphocyte Activation / drug effects
  • Organophosphorus Compounds / chemical synthesis
  • Organophosphorus Compounds / chemistry*
  • Organophosphorus Compounds / pharmacology
  • Protein Binding
  • Serum Albumin, Bovine / chemistry
  • Serum Albumin, Bovine / metabolism
  • Spectrophotometry
  • T-Lymphocytes / cytology
  • T-Lymphocytes / metabolism
  • Up-Regulation / drug effects

Substances

  • (E)-4-hydroxy-3-methylbut-2-enyl diphosphate
  • Antigens
  • Antigens, CD
  • Antigens, Differentiation, T-Lymphocyte
  • BTN3A1 protein, human
  • BioBP-HMBPP
  • Butyrophilins
  • CD69 antigen
  • Lectins, C-Type
  • Organophosphorus Compounds
  • Serum Albumin, Bovine
  • Biotin