Synthesis of novel morphiceptin analogues modified in position 3 and their binding to mu-opioid receptors in experimental mammary adenocarcinoma

Bioorg Med Chem. 2003 Sep 1;11(18):3855-60. doi: 10.1016/s0968-0896(03)00448-6.

Abstract

Binding of the (125)I-labeled mu-opioid receptor selective ligands, morphiceptin (Tyr-Pro-Phe-Pro-NH(2)) and [D-Phe(3)]morphiceptin, to membranes isolated from experimental mouse mammary adenocarcinoma was examined in vitro using a cross-linking assay followed by a Western blot technique. The radioactive complex had a molecular weight of about 65 kDa and was detectable by anti-mu-opioid receptor antibody, indicating the presence of mu-opioid receptors in tumor membranes. A series of new morphiceptin analogues, modified at the pharmacophoric position 3, was synthesized in order to find the correlation between the lipophilicity, electronic and steric properties of the amino acid in this position and the in vitro affinity of new analogues for mu-opioid receptors on mouse brain and tumor membranes. In in vivo studies the uptake of (131)I-labeled analogues by experimental mammary adenocarcinoma was estimated. The highest affinity for mu-opioid receptors in both, in vitro and in vivo experiments was observed for [D-Phe(3)]morphiceptin and [D-ClPhe(3)]-morphiceptin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenocarcinoma / metabolism
  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor / drug effects
  • Endorphins / chemical synthesis*
  • Endorphins / chemistry
  • Endorphins / pharmacology
  • Iodine Radioisotopes
  • Ligands
  • Mammary Neoplasms, Experimental / metabolism
  • Membrane Proteins / metabolism
  • Mice
  • Molecular Weight
  • Protein Binding
  • Protein Conformation
  • Receptors, Opioid, mu / drug effects
  • Receptors, Opioid, mu / metabolism*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Endorphins
  • Iodine Radioisotopes
  • Ligands
  • Membrane Proteins
  • Receptors, Opioid, mu
  • morphiceptin