Abstract

A series of 14 Beta-substituted morphine derivatives have been prepared. Among the 14 Beta-substituents which have been successfully incorporated into the morphine skeleton are the nitro, bromo, chloro, mercapto, acetamido, chloracetamido, bromacetamido, and p-azidocinnamylamido groups. The chloroacetamido and bromoacetamido compounds were prepared for use as chemical affinity labels for the morphine receptor. The p-azidocinnamyl-amide derivative was prepared as a potential photo-affinity label for the same receptor.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Institute on Drug Abuse (NIDA)
Type
Research Project (R01)
Project #
5R01DA001674-09
Application #
3206987
Study Section
(DABB)
Project Start
1977-06-01
Project End
1987-06-30
Budget Start
1985-07-01
Budget End
1986-06-30
Support Year
9
Fiscal Year
1985
Total Cost
Indirect Cost

  Institution

Name
Rensselaer Polytechnic Institute
Department
Type
Schools of Arts and Sciences
DUNS #
002430742
City
Troy
State
NY
Country
United States
Zip Code
12180

  Publications

Archer, S; Seyed-Mozaffari, A; Jiang, Q et al. (1994) 14 alpha,14' beta-[Dithiobis[(2-oxo-2,1-ethanediyl)imino]]bis (7,8-dihydromorphinone) and 14 alpha,14' beta-[dithiobis[(2-oxo-2,1- ethanediyl)imino]]bis[7,8-dihydro-N-(cyclopropylmethyl)normorphinone]: chemistry and opioid binding properties. J Med Chem 37:1578-85
Simon, E J; Fan, L Q; Hiller, J M et al. (1993) Photoaffinity ligands for the mu opioid receptor. Life Sci 53:1173-8
Sebastian, A; Bidlack, J M; Jiang, Q et al. (1993) 14 beta-[(p-nitrocinnamoyl)amino]morphinones, 14 beta-[(p-nitrocinnamoyl)amino]-7,8-dihydromorphinones, and their codeinone analogues: synthesis and receptor activity. J Med Chem 36:3154-60
Jiang, Q; Seyed-Mozaffari, A; Archer, S et al. (1993) Pharmacological study of 14 beta-(thioglycolamido)-7,8-dihydro-N(cyclopropylmethyl)-normor phinone (N-CPM-TAMO). J Pharmacol Exp Ther 264:1021-7
Bidlack, J M; Kaplan, R A; Subbramanian, R A et al. (1993) Affinity labeling of the mu opioid receptor in bovine striatal membranes with [3H]-14 beta-(bromoacetamido)-7,8-dihydromorphine. Biochemistry 32:6703-11
Jiang, Q; Seyed-Mozaffari, A; Archer, S et al. (1993) Antinociceptive evaluation of 14 beta-(bromoacetamido)-7,8-dihydro- N(cyclopropylmethyl)-normorphinone in mice. Eur J Pharmacol 240:201-6
Jiang, Q; Seyed-Mozaffari, A; Archer, S et al. (1992) Antinociceptive properties of two alkylating derivatives of morphinone: 14 beta-(thioglycolamido)-7,8-dihydromorphinone (TAMO) and 14 beta-(bromoacetamido)-7,8-dihydromorphinone (H2BAMO). J Pharmacol Exp Ther 262:526-31
Archer, S; Medzihradsky, F; Seyed-Mozaffari, A et al. (1992) Synthesis and characterization of 7-nitrobenzo-2-oxa-1,3-diazole (NBD)-labeled fluorescent opioids. Biochem Pharmacol 43:301-6
Archer, S; Bidlack, J; Mulholland, G K (1990) Opium alkaloids and affinity labels. NIDA Res Monogr 96:21-34
Bidlack, J M; Frey, D K; Kaplan, R A et al. (1990) Affinity labeling of mu opioid receptors by sulfhydryl alkylating derivatives of morphine and morphinone. Mol Pharmacol 37:50-9

Showing the most recent 10 out of 14 publications