Hybromet: a ligand for purifying opioid receptors
| Autor: | Ahmad Seyed-Mozaffari, R. Suzanne Zukin, Sydney Archer, Peter Osei-Gyimah, Eric J. Simon, Rhoda Maneckjee, Theresa L. Gioannini, Josephine Michael |
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| Rok vydání: | 1985 |
| Předmět: |
Chemical Phenomena
Organomercury Compounds Stereochemistry Ether Ligands Chromatography Affinity Thebaine chemistry.chemical_compound Polycyclic compound Affinity chromatography Bromide Drug Discovery Animals Binding site chemistry.chemical_classification Binding Sites Brain Ligand (biochemistry) Naltrexone Rats Chemistry chemistry Receptors Opioid Molecular Medicine Indicators and Reagents Mercaptobenzothiazole Derivative (chemistry) |
| Zdroj: | Journal of Medicinal Chemistry. 28:1950-1953 |
| ISSN: | 1520-4804 0022-2623 |
| DOI: | 10.1021/jm00150a032 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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