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

Journal Article · Mon Sep 01 04:00:00 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), Journal Name: Sov. J. Bioorg. Chem. (Engl. Transl.); (United States) Vol. 11:11; ISSN SJBCD
• Country of Publication: United States
• Language: English

Related Subjects

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