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Chemical Compound Review

Delt-I     (3S)-3-[[1-[[(1S)-1- (aminocarbonylmethylca...

Synonyms: Deltorphin I, AC1L3XGS, LS-172539, C37H52N8O10, (D-Ala2)Deltorphin I, ...
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Disease relevance of Deltorphin C

  • Endogenous human delta-opioid receptors (hDOR) are differentially regulated in terms of desensitization by peptide ([d-Pen2,5]enkephalin (DPDPE) and Deltorphin I) and alkaloid (etorphine) agonists in the neuroblastoma cell line SK-N-BE (Allouche, S., Roussel, M., Marie, N., and Jauzac, P. (1999) Eur. J. Pharmacol. 371, 235-240) [1].

High impact information on Deltorphin C

  • Agonist withdrawal results in a greater recycling process correlated with a stronger hDOR resensitization after etorphine treatment compared with DPDPE or Deltorphin I, as shown in binding, immunocytochemical, and functional experiments [1].
  • This Con A-induced expression of PEA mRNA is modulated by the delta opioid receptor agonist, deltorphin I, in a biphasic, dose-dependent manner [2].
  • The NPFF analog [D-Tyr1, (NMe)Phe3]NPFF (1DMe) did not modify the binding parameters of the mu- and delta-specific agonists [D-Ala2,N-Me-Phe4,Gly5-ol]-enkephalin and deltorphin-I, respectively [3].
  • Molecular dynamics conformation analyses suggested that Aib residues caused distinct changes in deltorphin C secondary structure when substituted for D-Ala2, Asp4, and simultaneously D-Ala2 and Phe3 but not when substituted for Phe3 [4].
  • The autoradiographic distribution of specific binding sites for the 125I-labeled dermorphin and deltorphin-I analogues in rat brain is in complete agreement with previously reported localizations of mu- and delta-opioid receptors [5].

Biological context of Deltorphin C

  • [125I]FK33-824 and [125I][D.Ala2] deltorphin-I exhibited similar diffusion kinetics after i.c.v. injection and bound specifically to sites characterized pharmacologically as mu and delta receptors respectively [6].
  • Binding to delta and mu opioid receptors by deltorphin I/II analogues modified at the Phe3 and Asp4/Glu4 side chains: a report of 32 new analogues and a QSAR study [7].
  • With the goal of development of structure-activity relationships for deltorphins and comparison with that of the cyclic tetrapeptides, ten analogs of deltorphin I were synthesized in which Phe3 was replaced with specific aromatic and nonaromatic amino acids with varying physicochemical properties [8].

Anatomical context of Deltorphin C


Associations of Deltorphin C with other chemical compounds


Gene context of Deltorphin C

  • [(R or S)Atc3]deltorphin C also exhibited the highest biological selectivity (GPI/MVD) (= 3,522), which was 3-fold greater than that observed for deltorphin C [16].
  • However, several notable exceptions were recognized: peptides containing the constrained, bicyclic structures Aic3 and (R or S) Atc3 enhanced delta affinity, but only the latter increased delta selectivity 4-fold (= 2475) relative to deltorphin C (= 661); at the other extreme, delta affinity of N alpha MePh3 fell 900-fold [16].
  • Phe3-substituted analogues of deltorphin C. Spatial conformation and topography of the aromatic ring in peptide recognition by delta opioid receptors [16].
  • At 10 microM [Phe1psi(CH2-NH)Gly2]NC(1-13)NH2 does not modify either the inhibitory effect of deltorphin I (the selective delta opioid receptor agonist) in the mouse vas deferens or that of dermorphine (the selective mu opioid receptor agonist) in the guinea-pig ileum [17].
  • The biological potency of peptoids was compared with that of dermorphin in GPI preparations and with that of deltorphin I in MVD preparations [18].

Analytical, diagnostic and therapeutic context of Deltorphin C

  • Since the motor stimulant response to intra-accumbens microinjection of the delta-opioid agonist, [D-penicillamine2,5]-enkephalin, was not augmented in a previous study, we tested the behavioral response to a new endogenous delta-opioid agonist, [D-Ala2] deltorphin I [19].
  • Monoclonal and polyclonal antibodies were used to examine the cellular and ultrastructural distributions of deltorphin I and dermaseptin B in the serous glands by immunofluoresence confocal microscopy and immunogold-electron microscopy [11].


  1. Differential sorting of human delta-opioid receptors after internalization by peptide and alkaloid agonists. Marie, N., Lecoq, I., Jauzac, P., Allouche, S. J. Biol. Chem. (2003) [Pubmed]
  2. Met-enkephalin-containing peptides encoded by proenkephalin A mRNA expressed in activated murine thymocytes inhibit thymocyte proliferation. Linner, K.M., Quist, H.E., Sharp, B.M. J. Immunol. (1995) [Pubmed]
  3. Neuropeptide FF (NPFF) analogs functionally antagonize opioid activities in NPFF2 receptor-transfected SH-SY5Y neuroblastoma cells. Mollereau, C., Mazarguil, H., Zajac, J.M., Roumy, M. Mol. Pharmacol. (2005) [Pubmed]
  4. Helix-inducing alpha-aminoisobutyric acid in opioid mimetic deltorphin C analogues. Bryant, S.D., Guerrini, R., Salvadori, S., Bianchi, C., Tomatis, R., Attila, M., Lazarus, L.H. J. Med. Chem. (1997) [Pubmed]
  5. Preparation and binding properties of radioiodinated analogues of dermorphin and deltorphin with high specificity for the mu- and delta-opioid receptors. Gaudriault, G., Zsürger, N., Vincent, J.P. J. Neurochem. (1997) [Pubmed]
  6. Binding in vivo of selective mu and delta opioid agonists: localization by autoradiography. Mokhtari, M., Tafani, J.A., Zajac, J.M. Neuropeptides (1993) [Pubmed]
  7. Binding to delta and mu opioid receptors by deltorphin I/II analogues modified at the Phe3 and Asp4/Glu4 side chains: a report of 32 new analogues and a QSAR study. Schullery, S.E., Mohammedshah, T., Makhlouf, H., Marks, E.L., Wilenkin, B.S., Escobar, S., Mousigian, C., Heyl, D.L. Bioorg. Med. Chem. (1997) [Pubmed]
  8. Substitution of aromatic and nonaromatic amino acids for the Phe3 residue in the delta-selective opioid peptide deltorphin I: effects on binding affinity and selectivity. Heyl, D.L., Schmitter, S.J., Bouzit, H., Johnson, T.W., Hepp, A.M., Kurtz, K.R., Mousigian, C. Int. J. Pept. Protein Res. (1994) [Pubmed]
  9. Activity of mu- and delta-opioid agonists in vas deferens from mice deficient in MOR gene. Maldonado, R., Severini, C., Matthes, H.W., Kieffer, B.L., Melchiorri, P., Negri, L. Br. J. Pharmacol. (2001) [Pubmed]
  10. Transient expression of [D-Ala2] deltorphin I-like immunoreactivity in prenatal rat small intestine. Matsui, J., Fujimiya, M., Matsui, S., Amakata, Y., Renda, T., Kimura, H., Maeda, T. J. Histochem. Cytochem. (1994) [Pubmed]
  11. Post-translational amino acid racemization in the frog skin peptide deltorphin I in the secretion granules of cutaneous serous glands. Auvynet, C., Seddiki, N., Dunia, I., Nicolas, P., Amiche, M., Lacombe, C. Eur. J. Cell Biol. (2006) [Pubmed]
  12. Antinociceptive effects of isoleucine derivatives of deltorphin I and deltorphin II in rat spinal cord: a search for selectivity of delta receptor subtypes. Labuz, D., Toth, G., Machelska, H., Przewlocka, B., Borsodi, A., Przewłocki, R. Neuropeptides (1998) [Pubmed]
  13. Fate of (D-Ala2)-deltorphin-I-like immunoreactive neurons in 6-hydroxydopamine lesioned rat brain. Casini, A., Pinna, A., Tooyama, I., Kimura, H., Di Chiara, G., Renda, T.G. European journal of histochemistry : EJH. (2004) [Pubmed]
  14. 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]
  15. Structure-activity relationships of dermorphin analogues containing N-substituted amino acids in the 2-position of the peptide sequence. Schmidt, R., Kálmán, A., Chung, N.N., Lemieux, C., Horváth, C., Schiller, P.W. Int. J. Pept. Protein Res. (1995) [Pubmed]
  16. Phe3-substituted analogues of deltorphin C. Spatial conformation and topography of the aromatic ring in peptide recognition by delta opioid receptors. Salvadori, S., Bryant, S.D., Bianchi, C., Balboni, G., Scaranari, V., Attila, M., Lazarus, L.H. J. Med. Chem. (1993) [Pubmed]
  17. A new selective antagonist of the nociceptin receptor. Guerrini, R., Calo, G., Rizzi, A., Bigoni, R., Bianchi, C., Salvadori, S., Regoli, D. Br. J. Pharmacol. (1998) [Pubmed]
  18. Synthesis, conformation and biological activity of dermorphin and deltorphin I analogues containing N-alkylglycine in place of residues in position 1, 3, 5 and 6. Biondi, L., Giannini, E., Filira, F., Gobbo, M., Marastoni, M., Negri, L., Scolaro, B., Tomatisc, R., Rocchi, R. J. Pept. Sci. (2003) [Pubmed]
  19. Dopamine depletion augments endogenous opioid-induced locomotion in the nucleus accumbens using both mu 1 and delta opioid receptors. Churchill, L., Roques, B.P., Kalivas, P.W. Psychopharmacology (Berl.) (1995) [Pubmed]
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