Identification and characterisation of SB-366791, a potent and selective vanilloid receptor (VR1/TRPV1) antagonist

Neuropharmacology. 2004 Jan;46(1):133-49. doi: 10.1016/s0028-3908(03)00305-8.

Abstract

Vanilloid receptor-1 (TRPV1) is a non-selective cation channel, predominantly expressed by peripheral sensory neurones, which is known to play a key role in the detection of noxious painful stimuli, such as capsaicin, acid and heat. To date, a number of antagonists have been used to study the physiological role of TRPV1; however, antagonists such as capsazepine are somewhat compromised by non-selective actions at other receptors and apparent modality-specific properties. SB-366791 is a novel, potent, and selective, cinnamide TRPV1 antagonist isolated via high-throughput screening of a large chemical library. In a FLIPR-based Ca(2+)-assay, SB-366791 produced a concentration-dependent inhibition of the response to capsaicin with an apparent pK(b) of 7.74 +/- 0.08. Schild analysis indicated a competitive mechanism of action with a pA2 of 7.71. In electrophysiological experiments, SB-366791 was demonstrated to be an effective antagonist of hTRPV1 when activated by different modalities, such as capsaicin, acid or noxious heat (50 degrees C). Unlike capsazepine, SB-366791 was also an effective antagonist vs. the acid-mediated activation of rTRPV1. With the aim of defining a useful tool compound, we also profiled SB-366791 in a wide range of selectivity assays. SB-366791 had a good selectivity profile exhibiting little or no effect in a panel of 47 binding assays (containing a wide range of G-protein-coupled receptors and ion channels) and a number of electrophysiological assays including hippocampal synaptic transmission and action potential firing of locus coeruleus or dorsal raphe neurones. Furthermore, unlike capsazepine, SB-366791 had no effect on either the hyperpolarisation-activated current (I(h)) or Voltage-gated Ca(2+)-channels (VGCC) in cultured rodent sensory neurones. In summary, SB-366791 is a new TRPV1 antagonist with high potency and an improved selectivity profile with respect to other commonly used TRPV1 antagonists. SB-366791 may therefore prove to be a useful tool to further study the biology of TRPV1.

Publication types

  • Comparative Study

MeSH terms

  • 8-Hydroxy-2-(di-n-propylamino)tetralin / pharmacology
  • Acids / pharmacology
  • Anilides / chemistry
  • Anilides / pharmacology*
  • Aniline Compounds / metabolism
  • Animals
  • Calcium / metabolism
  • Capsaicin / analogs & derivatives*
  • Capsaicin / pharmacology
  • Carrier Proteins / pharmacology
  • Cell Line
  • Cinnamates / chemistry
  • Cinnamates / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Interactions
  • Embryo, Mammalian
  • Excitatory Amino Acid Agonists / pharmacology
  • Excitatory Postsynaptic Potentials / drug effects
  • Hot Temperature
  • Humans
  • Intracellular Signaling Peptides and Proteins*
  • Kidney
  • Membrane Potentials / drug effects*
  • N-Methylaspartate / pharmacology
  • Neuropeptides / pharmacology
  • Norepinephrine / pharmacology
  • Orexins
  • Patch-Clamp Techniques / methods
  • Protein Binding / drug effects
  • Radioligand Assay / methods
  • Rats
  • Receptors, Drug / antagonists & inhibitors*
  • Receptors, Drug / chemistry
  • Serotonin Receptor Agonists / pharmacology
  • Xanthenes / metabolism
  • alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid / pharmacology

Substances

  • Acids
  • Anilides
  • Aniline Compounds
  • Carrier Proteins
  • Cinnamates
  • Excitatory Amino Acid Agonists
  • Intracellular Signaling Peptides and Proteins
  • N-(3-methoxyphenyl)-4-chlorocinnamanilide
  • Neuropeptides
  • Orexins
  • Receptors, Drug
  • Serotonin Receptor Agonists
  • Xanthenes
  • Fluo-3
  • N-Methylaspartate
  • alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid
  • 8-Hydroxy-2-(di-n-propylamino)tetralin
  • capsazepine
  • Capsaicin
  • Calcium
  • Norepinephrine