Hybromet: a ligand for purifying opioid receptors

J Med Chem. 1985 Dec;28(12):1950-3. doi: 10.1021/jm00150a032.

Abstract

Condensation of the Grignard reagent derive from 2-[4-(allyloxy)phenyl]ethyl bromide (4b) with 7 alpha-acetyl-6,14-endo-ethenotetrahydrothebaine (5) furnished the (R) tertiary carbinol, 7, which upon methoxymercuration followed by treatment with the KBr gave the bromomercurio compound 10 (Hybromet). The corresponding N-cyclopropylmethyl analogue, 11, was prepared also. The bromomercurio compound, 1, and the mercaptobenzothiazole derivative, 3, gave allyl phenyl ether when treated with BAL at room temperature. Similar treatment of 10 with BAL gave 7 in high yield. Binding studies using rat brain homogenates indicated that 7, 13, and 14 have moderately high affinities for mu rather than delta binding sites. Although much weaker, 10 showed preferential mu binding also. These results along with the fact that 10 reacted smoothly with sulfhydryl groups suggest that Hybromet would be a suitable ligand for use in affinity chromatography.

Publication types

  • Comparative Study
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Binding Sites
  • Brain / metabolism
  • Chemical Phenomena
  • Chemistry
  • Chromatography, Affinity
  • Indicators and Reagents
  • Ligands
  • Naltrexone / metabolism
  • Organomercury Compounds / chemical synthesis
  • Organomercury Compounds / metabolism*
  • Rats
  • Receptors, Opioid / isolation & purification*
  • Receptors, Opioid / metabolism
  • Thebaine / analogs & derivatives*
  • Thebaine / chemical synthesis
  • Thebaine / metabolism

Substances

  • Indicators and Reagents
  • Ligands
  • Organomercury Compounds
  • Receptors, Opioid
  • Thebaine
  • Naltrexone
  • hybromet