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Chemical Compound Review

Deltorphin     (3S)-3-aminocarbonyl-3- [[(2S)-2-[[(2S)-2...

Synonyms: Dermenkephalin, Deltorphin A, AC1MHYOS, CHEMBL20775, CHEBI:125539, ...
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Disease relevance of Deltorphin A


Psychiatry related information on Deltorphin A

  • The delta1-selective opioid receptor antagonist, 7-benzylidenenaltrexone (3.5 ng), and the delta2-selective opioid receptor antagonist, naltriben (19 ng), significantly antagonized the inhibitory effects of DPLPE (3 microg) and deltorphin (3 microg) on passive avoidance learning, respectively [5].
  • The increased locomotor activity and rearing were dose-related over the range of 0.13 to 3.8 nmol/rat for [D-Ala2]deltorphin II (DADELT II) and 1.04 to 20.8 nmol/rat for deltorphin [6].
  • In contrast, DPLPE (3 microg) or deltorphin (3 microg) did not markedly influence behavioral responses induced by electroshocks during training of passive avoidance learning [5].

High impact information on Deltorphin A


Chemical compound and disease context of Deltorphin A

  • To determine the role of delta-opioid receptors in the modulation of hypothalamic-pituitary-adrenal activity, we studied in normal subjects the effect of the highly selective delta-opioid receptor agonist deltorphin (DT) on the secretion of ACTH, cortisol, and arginine vasopressin in response to insulin-induced hypoglycemia [1].
  • 1. Following a 5 min in vitro exposure to morphine (1.3 x 10(-7) M), U-50,488H (2.5 x 10(-8) M) and deltorphin (1.6 x 10(-8)-6.5 x 10(-9) M), the rabbit isolated jejunum exhibited a precipitated contracture after the addition of naloxone (2.75 x 10(-7) M) [12].
  • To test this hypothesis, DOR-Ju.1 cells, derived from Jurkat cells stably transfected with a cDNA encoding the neuronal DOR, were stimulated with deltorphin or benzamide, 4-[[2,5-dimethyl-4-(2-propenyl)-1-piperazinyl](3-methoxyphenyl)methyl]N- ,[2S[(S*),2alpha,5beta]]-(9Cl) (SNC-80) prior to the addition of HIV-1 [4].

Biological context of Deltorphin A


Anatomical context of Deltorphin A

  • Stress-induced activation of sympathetic nervous system is attenuated by the delta-opioid receptor agonist deltorphin in healthy man [18].
  • Naltrindole 10(-12) M abolished the antiproliferative effect of 10(-7) M deltorphin on CD4+ T cells [19].
  • This effect was also observed when rabbit isolated jejunum was pretreated with deltorphin (a highly selective delta agonist) [20].
  • The responses to dermenkephalin in the hamster vas deferens were increased by addition of peptidase inhibitors; the maximum effect was obtained with 3 microM thiorphan [21].
  • To determine whether DORs expressed by T cells signal through the MAPKs, extracellular-regulated kinases (ERKs) 1 and 2, two delta opioid peptides, deltorphin and [D-Ala2,D-Leu5]-enkephalin (DADLE), were studied in Jurkat cells that had been stably transfected with DOR (DOR-Ju.1) [22].

Associations of Deltorphin A with other chemical compounds


Gene context of Deltorphin A

  • Recently we demonstrated the inhibitory action on Growth Hormone (GH) secretion of an opioid heptapeptide, deltorphin (DT), that is highly selective in binding delta-opioid receptors [28].
  • Overall, the data collected demonstrate that the putative prodermorphin product Tyr-D-Met-Phe-His-Leu-Met-Asp-NH2 named dermenkephalin, behaves as a potent delta opioid agonist exhibiting high affinity and high selectivity for the delta opioid receptor [29].
  • Substitution on the Phe3 aromatic ring in cyclic delta opioid receptor-selective dermorphin/deltorphin tetrapeptide analogues: electronic and lipophilic requirements for receptor affinity [30].
  • Deltorphin showed a biphasic effect: 10(-11) M enhanced IL-2 secretion, whereas higher concentrations (10(-9)-10(-7) M) were inhibitory.(ABSTRACT TRUNCATED AT 250 WORDS)[19]
  • Moreover, the delta-opioid receptor agonist, Deltorphin (1 microM), mimicked the effects as NPFF and also occluded NPFF's actions on synaptic currents [31].

Analytical, diagnostic and therapeutic context of Deltorphin A


  1. Effect of deltorphin on pituitary-adrenal response to insulin-induced hypoglycemia and ovine corticotropin-releasing hormone in healthy man. Degli Uberti, E.C., Salvadori, S., Trasforini, G., Margutti, A., Ambrosio, M.R., Rossi, R., Portaluppi, F., Pansini, R. J. Clin. Endocrinol. Metab. (1992) [Pubmed]
  2. Up-regulation and trafficking of delta opioid receptor in a model of chronic inflammation: implications for pain control. Cahill, C.M., Morinville, A., Hoffert, C., O'Donnell, D., Beaudet, A. Pain (2003) [Pubmed]
  3. Dexamethasone selective inhibition of acute opioid physical dependence in isolated tissues. Capasso, A., Di Giannuario, A., Loizzo, A., Pieretti, S., Sagratella, S., Sorrentino, L. J. Pharmacol. Exp. Ther. (1996) [Pubmed]
  4. Delta-opioid suppression of human immunodeficiency virus-1 expression in T cells (Jurkat). Sharp, B.M., Gekker, G., Li, M.D., Chao, C.C., Peterson, P.K. Biochem. Pharmacol. (1998) [Pubmed]
  5. Stimulation of delta1- and delta2-opioid receptors produces amnesia in mice. Ukai, M., Takada, A., Sasaki, Y., Kameyama, T. Eur. J. Pharmacol. (1997) [Pubmed]
  6. Behavioural effects of deltorphins in rats. Negri, L., Noviello, V., Angelucci, F. Eur. J. Pharmacol. (1991) [Pubmed]
  7. Deltorphin transport across the blood-brain barrier. Fiori, A., Cardelli, P., Negri, L., Savi, M.R., Strom, R., Erspamer, V. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  8. Posttranslational amino acid epimerization: enzyme-catalyzed isomerization of amino acid residues in peptide chains. Heck, S.D., Faraci, W.S., Kelbaugh, P.R., Saccomano, N.A., Thadeio, P.F., Volkmann, R.A. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  9. kappa -opioid receptor agonists modulate visceral nociception at a novel, peripheral site of action. Joshi, S.K., Su, X., Porreca, F., Gebhart, G.F. J. Neurosci. (2000) [Pubmed]
  10. Delta-opioid receptors expressed by Jurkat T cells enhance IL-2 secretion by increasing AP-1 complexes and activity of the NF-AT/AP-1-binding promoter element. Hedin, K.E., Bell, M.P., Kalli, K.R., Huntoon, C.J., Sharp, B.M., McKean, D.J. J. Immunol. (1997) [Pubmed]
  11. Binding and internalization of fluorescent opioid peptide conjugates in living cells. Arttamangkul, S., Alvarez-Maubecin, V., Thomas, G., Williams, J.T., Grandy, D.K. Mol. Pharmacol. (2000) [Pubmed]
  12. Manifestations of acute opiate withdrawal contracture in rabbit jejunum after mu-, kappa- and delta-receptor agonist exposure. Valeri, P., Morrone, L.A., Romanelli, L. Br. J. Pharmacol. (1992) [Pubmed]
  13. Synthesis and structure-activity relationships of deltorphin analogues. Salvadori, S., Marastoni, M., Balboni, G., Borea, P.A., Morari, M., Tomatis, R. J. Med. Chem. (1991) [Pubmed]
  14. 32P-labeled opioid peptides with high affinity for the delta-opioid receptor. Kieffer, B.L., Black, D., Hirth, C.G. Anal. Biochem. (1993) [Pubmed]
  15. Effect of delta-opioid receptor agonist deltorphin on circulating concentrations of luteinizing hormone and follicle stimulating hormone in healthy fertile women. Bondanelli, M., Ambrosio, M.R., Franceschetti, P., Guerrini, R., Valentini, A., degli Uberti, E.C. Hum. Reprod. (1998) [Pubmed]
  16. Delta opioid receptor-selective ligands: [D-Pen2,D-Pen5]enkephalin-dermenkephalin chimeric peptides. Cavagnero, S., Misicka, A., Knapp, R.J., Davis, P., Fang, L., Burks, T.F., Yamamura, H.I., Hruby, V.J. Life Sci. (1991) [Pubmed]
  17. Molecular dynamics conformations of deltorphin analogues advocate delta opioid binding site models. Bryant, S.D., Attila, M., Salvadori, S., Guerrini, R., Lazarus, L.H. Pept. Res. (1994) [Pubmed]
  18. Stress-induced activation of sympathetic nervous system is attenuated by the delta-opioid receptor agonist deltorphin in healthy man. degli Uberti, E.C., Ambrosio, M.R., Vergnani, L., Portaluppi, F., Bondanelli, M., Trasforini, G., Margutti, A., Salvadori, S. J. Clin. Endocrinol. Metab. (1993) [Pubmed]
  19. Antiproliferative effects of delta opioids on highly purified CD4+ and CD8+ murine T cells. Shahabi, N.A., Sharp, B.M. J. Pharmacol. Exp. Ther. (1995) [Pubmed]
  20. Further studies on the involvement of the arachidonic acid cascade in the acute dependence produced by mu, kappa and delta opioid agonists in isolated tissues. Capasso, A. Neuropharmacology (1999) [Pubmed]
  21. Opioid activity of dermenkephalin analogues in the guinea-pig myenteric plexus and the hamster vas deferens. Sagan, S., Corbett, A.D., Amiche, M., Delfour, A., Nicolas, P., Kosterlitz, H.W. Br. J. Pharmacol. (1991) [Pubmed]
  22. Delta opioid receptors expressed by stably transfected jurkat cells signal through the map kinase pathway in a ras-independent manner. Shahabi, N.A., Daaka, Y., McAllen, K., Sharp, B.M. J. Neuroimmunol. (1999) [Pubmed]
  23. Blockade of opioid receptors in rostral ventral medulla prevents antihyperalgesia produced by transcutaneous electrical nerve stimulation (TENS). Kalra, A., Urban, M.O., Sluka, K.A. J. Pharmacol. Exp. Ther. (2001) [Pubmed]
  24. Participation of delta opioid receptor subtypes in the stimulation of adenylyl cyclase activity in rat olfactory bulb. Olianas, M.C., Onali, P. J. Pharmacol. Exp. Ther. (1995) [Pubmed]
  25. Role of endogenous pro-enkephalin A-derived peptides in human T cell proliferation and monocyte IL-6 production. Kamphuis, S., Eriksson, F., Kavelaars, A., Zijlstra, J., van de Pol, M., Kuis, W., Heijnen, C.J. J. Neuroimmunol. (1998) [Pubmed]
  26. Folding trends in a flexible peptide: two-dimensional NMR study of deltorphin-I, a delta selective opioid heptapeptide. Duchesne, D., Naim, M., Nicolas, P., Baron, D. Biochem. Biophys. Res. Commun. (1993) [Pubmed]
  27. Topographical requirements for delta opioid ligands: common structural features of dermenkephalin and deltorphin. Misicka, A., Lipkowski, A.W., Horvath, R., Davis, P., Kramer, T.H., Yamamura, H.I., Hruby, V.J. Life Sci. (1992) [Pubmed]
  28. Differential effects of deltorphin on arginine and galanin-induced growth hormone secretion in healthy man. degli Uberti, E.C., Salvadori, S., Trasforini, G., Ambrosio, M.R., Margutti, A., Bondanelli, M., Rossi, R., Valentini, A. Regul. Pept. (1995) [Pubmed]
  29. Dermenkephalin (Tyr-D-Met-Phe-His-Leu-Met-Asp-NH2): a potent and fully specific agonist for the delta opioid receptor. Amiche, M., Sagan, S., Mor, A., Delfour, A., Nicolas, P. Mol. Pharmacol. (1989) [Pubmed]
  30. Substitution on the Phe3 aromatic ring in cyclic delta opioid receptor-selective dermorphin/deltorphin tetrapeptide analogues: electronic and lipophilic requirements for receptor affinity. Heyl, D.L., Mosberg, H.I. J. Med. Chem. (1992) [Pubmed]
  31. Synaptic actions of neuropeptide FF in the rat parabrachial nucleus: interactions with opioid receptors. Chen, X., Zidichouski, J.A., Harris, K.H., Jhamandas, J.H. J. Neurophysiol. (2000) [Pubmed]
  32. Identification of a D-alanine-containing polypeptide precursor for the peptide opioid, dermorphin. Mor, A., Delfour, A., Nicolas, P. J. Biol. Chem. (1991) [Pubmed]
  33. Synthesis and biological properties of beta-MePhe3 analogues of deltorphin I and dermenkephalin: influence of biased chi 1 Phe3 residues on peptide recognition for delta-opioid receptors. Misicka, A., Cavagnero, S., Horvath, R., Davis, P., Porreca, F., Yamamura, H.I., Hruby, V.J. J. Pept. Res. (1997) [Pubmed]
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