Synthesis and biological activity of a lysine-containing cyclic analog of (Leu/sup 5/)enkephalin

Journal Article · Mon Sep 01 00:00:00 EDT 1986 · Sov. J. Bioorg. Chem. (Engl. Transl.); (United States)

OSTI ID:5244063

Bobrova, I V; Abissova, N A; Rozental', G F; Nikiforovich, G V; Chipens, G I

A cyclic analog of enkephalin - cyclo(Lys-Tyr-Gly-Gly-Phe-Leu) -- and two corresponding linear hexapeptides containing a residue of the amino acid lysine at the beginning and the end of the molecule - Lys-Tyr-Gly-Gly-Phe-Leu and Tyr-Gly-Gly-Phe-Leu-Lys - have been synthesized by the classical methods of peptide chemistry. The addition of a lysine residue to the N-end of the enkephalin molecule or the cyclization of this hexapeptide decreased the action of the analogs on the central and peripheral opiate receptors. The addition of lysine through the epsilon-amino group to the C-end of the enkephalin molecule scarcely changed the interaction of the analog with the ..mu..-type of opiate receptor but lowered its affinity for the delta-type of receptor approximately 10-fold. All three analogs that were synthesized possessed an analgesic activity comparable in magnitude with the activity of (Leu/sup 5/)enkephalin determined by the tail pinch method on intracisternal administration to mice.

• Research Organization: Institute of Organic Synthesis, Riga (USSR)
• OSTI ID: 5244063
• Journal Information: Sov. J. Bioorg. Chem. (Engl. Transl.); (United States), Vol. 11:11; Other Information: Translated from Bioorganicheskaya Khim.; 11: No. 11, 1457-1467(Nov 1985)
• Country of Publication: United States
• Language: English

Related Subjects

59 BASIC BIOLOGICAL SCIENCES
LYSINE
BIOLOGICAL EFFECTS
BIOSYNTHESIS
NARCOTICS
RECEPTORS
NERVE CELLS
RADIORECEPTOR ASSAY
POLYPEPTIDES
BIOCHEMISTRY
DEHYDROCYCLIZATION
ENKEPHALINS
INHIBITION
LABELLING
MASS SPECTRA
MICE
TRITIUM COMPOUNDS
AMINO ACIDS
ANIMAL CELLS
ANIMALS
AUTONOMIC NERVOUS SYSTEM AGENTS
CARBOXYLIC ACIDS
CENTRAL NERVOUS SYSTEM DEPRESSANTS
CHEMICAL REACTIONS
CHEMISTRY
DRUGS
ENDORPHINS
ISOTOPE APPLICATIONS
LABELLED COMPOUNDS
MAMMALS
MEMBRANE PROTEINS
NEUROREGULATORS
ORGANIC ACIDS
ORGANIC COMPOUNDS
PEPTIDES
PROTEINS
RODENTS
SOMATIC CELLS
SPECTRA
SYNTHESIS
TRACER TECHNIQUES
VERTEBRATES
550201* - Biochemistry- Tracer Techniques