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Chemical Compound Review

Deprolorphin     2-[[(2S)-1-[(2S)-2-[[1-[(2S)- 2-amino-3-(4...

Synonyms: AC1L3UDG, AR-1J3501, LS-176947, C30H37N5O7, (D-Tyr(1))CM-5, ...
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Disease relevance of Tyr-pro-phe-pro-gly


Psychiatry related information on Tyr-pro-phe-pro-gly

  • The effects of systemic administration of bovine beta-casomorphin-5 (Tyr-Pro-Phe-Pro-Gly), a mu-opioid receptor agonist derived from milk beta-casein, on spontaneous alternation behavior in the Y-maze (spatial short-term memory) and step-down-type passive avoidance response (non-spatial long-term memory) were investigated in mice [2].

High impact information on Tyr-pro-phe-pro-gly


Biological context of Tyr-pro-phe-pro-gly

  • The gene sequence of a human beta-casomorphin-5, including plasmid insertion and fusion protein expression and cleavage instrumentary, has been synthesized by a manual phosphoramidite procedure and cloned in a bacterial system [7].
  • Intracerebroventricular administration of 166 nmoles of the exogenic opioid beta-casomorphin (5) produced a potent and reversible depression of the compound action potential evoked in dentate granule cells by stimulation of the medial perforant path, whereas the extracellularly recorded excitatory postsynaptic potential is left unchanged [8].

Anatomical context of Tyr-pro-phe-pro-gly

  • Deprolorphin (0.01-10 microM) causes a large enhancement of the population spike (PS) and appearance of additional spikes of CA1 pyramidal cells to Schaffer-commissural stimulation, which were partially antagonized by the opiate receptor antagonist naloxone [9].
  • The influence of beta-casomorphin-5 on the beta-adrenoceptor complex in guinea pig heart membranes was studied by means of binding studies, G-protein investigations and isolated heart preparations [10].
  • Substitution of D-Pro or D-pipecolic acid for L-Pro4 considerably increased the analgesic action and the potency on guinea-pig ileum of beta-casomorphin (5) as well as of casomorphin [4] amide [11].
  • The degradation of beta-casomorphin 1-5 (Tyr-Pro-Phe-Pro-Gly (beta CM]--an opiate-like acting pentapeptide--was investigated in brain stem and corpus striatum of male Wistar rats during the first 20 min after an intracerebroventricular (i.c.v.) application of 166 nmol [3H]Phe3-beta CM [12].


  1. Beta-casomorphin-5 stimulates neurite outgrowth in a mouse neuroblastoma cell line (Neuro-2a). Sakaguchi, M., Murayama, K., Yabe, K., Satoh, M., Takeuchi, M., Matsumura, E. Neurosci. Lett. (1998) [Pubmed]
  2. Effects of systemic administration of beta-casomorphin-5 on learning and memory in mice. Sakaguchi, M., Koseki, M., Wakamatsu, M., Matsumura, E. Eur. J. Pharmacol. (2006) [Pubmed]
  3. Cyclic beta-casomorphin analogues with mixed mu agonist/delta antagonist properties: synthesis, pharmacological characterization, and conformational aspects. Schmidt, R., Vogel, D., Mrestani-Klaus, C., Brandt, W., Neubert, K., Chung, N.N., Lemieux, C., Schiller, P.W. J. Med. Chem. (1994) [Pubmed]
  4. Tyr-c[D-Orn-Tyr(Bzl)-Pro-Gly]: a novel antiproliferative acting somatostatin receptor agonist with mu-opioid receptor-sensitizing properties. Stirnweiss, J., Hartrodt, B., Greksch, G., Stürzebecher, U., Böhmer, F.D., Neubert, K., Liebmann, C. Br. J. Pharmacol. (2003) [Pubmed]
  5. Rotational behaviour produced by intranigral injections of bovine and human beta-casomorphins in rats. Herrera-Marschitz, M., Terenius, L., Grehn, L., Ungerstedt, U. Psychopharmacology (Berl.) (1989) [Pubmed]
  6. Structure-activity relationships of cyclic beta-casomorphin-5 analogues. Schmidt, R., Neubert, K., Barth, A., Liebmann, C., Schnittler, M., Chung, N.N., Schiller, P.W. Peptides (1991) [Pubmed]
  7. Synthesis and cloning of a human beta-casomorphin-5 gene. Hoffmann, S., Günther, E., Kunze, G., Bärwolff, D., Teppke, M., Barth, A. Nucleic Acids Symp. Ser. (1987) [Pubmed]
  8. Effects of beta-casomorphin on dentate hippocampal field potentials in freely moving rats. Reymann, K.G., Chepkova, A.N., Schulzeck, K., Ott, T. Biomed. Biochim. Acta (1985) [Pubmed]
  9. Effects of deprolorphin, a casomorphin analog, on hippocampal CA1 field potentials in vitro. Reymann, K.G., Chepkova, A.N., Matthies, H. Peptides (1983) [Pubmed]
  10. Nonopioid effects of beta-casomorphin-5 in guinea pig heart: alterations to the beta-adrenoceptor-G-protein complex and inhibition of myocardial responses to isoproterenol. Liebmann, C., Mentz, P., Schnittler, M., Schrader, U., Neubert, K., Barth, A. Peptides (1991) [Pubmed]
  11. Derivatives of beta-casomorphins with high analgesic potency. Matthies, H., Stark, H., Hartrodt, B., Ruethrich, H.L., Spieler, H.T., Barth, A., Neubert, K. Peptides (1984) [Pubmed]
  12. Degradation of beta-casomorphin in the rat brain in vivo. Stark, H., Lössner, B., Matthies, H. Biomed. Biochim. Acta (1986) [Pubmed]
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