Synthesis and in vitro evaluation of a novel iodinated resiniferatoxin derivative that is an agonist at the human vanilloid VR1 receptor

Bioorg Med Chem Lett. 2002 Apr 22;12(8):1189-92. doi: 10.1016/s0960-894x(02)00127-0.

Abstract

Using a 'directed' iodination procedure, novel iodo-resiniferatoxin congeners were synthesized from 4-acetoxy-3-methoxyphenylacetic acid and resiniferinol- 9,13,14-ortho-phenylacetate (ROPA). The 2-iodo-4-hydroxy-5-methoxyphenylacetic acid ester of resiniferinol 5 displayed high affinity binding (K(i)=0.71 nM) for the human vanilloid VR1 receptor and functioned as a partial agonist.

MeSH terms

  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Diterpenes / pharmacology*
  • Drug Evaluation, Preclinical
  • Humans
  • In Vitro Techniques
  • Iodine / chemistry*
  • Receptors, Drug / agonists*

Substances

  • Diterpenes
  • Receptors, Drug
  • Iodine
  • resiniferatoxin