메뉴 건너뛰기




Volumn 378, Issue 1, 1997, Pages 19-29

Opioid diketopiperazines: Synthesis and activity of a prototypic class of opioid antagonists

Author keywords

Antagonist; Diketopiperazine; Opioid peptides; Peptide synthesis

Indexed keywords

AROMATIC COMPOUND; CARBOXYLIC ACID DERIVATIVE; HYDROXYL GROUP; METHYL GROUP; OPIATE; OPIATE ANTAGONIST; OPIATE PEPTIDE; PIPERAZINEDIONE; SIGMA OPIATE RECEPTOR; TETRAHYDROISOQUINOLINE DERIVATIVE; TYROSINE DERIVATIVE;

EID: 0031045077     PISSN: 14316730     EISSN: None     Source Type: Journal    
DOI: 10.1515/bchm.1997.378.1.19     Document Type: Article
Times cited : (38)

References (86)
  • 1
    • 0028953392 scopus 로고
    • New and known diketopiperazines from the Caribbean sponge, Calyx cf. podatypa
    • Adamczeski, M., Reed, A.R., and Crews, P. (1995). New and known diketopiperazines from the Caribbean sponge, Calyx cf. podatypa. J. Nat. Products 58, 201-208.
    • (1995) J. Nat. Products , vol.58 , pp. 201-208
    • Adamczeski, M.1    Reed, A.R.2    Crews, P.3
  • 2
    • 0009644628 scopus 로고
    • Some quantitative uses of drug antagonists
    • Arunlakshansa, O., and Schild, H.O. (1959). Some quantitative uses of drug antagonists. Br. J. Pharmacol. 14, 48-58.
    • (1959) Br. J. Pharmacol. , vol.14 , pp. 48-58
    • Arunlakshansa, O.1    Schild, H.O.2
  • 3
    • 0027373981 scopus 로고
    • Synthesis and receptor binding analysis of dermorphin hepta-, hexa- and pentapeptide analogues
    • Attila, M., Salvadori, S., Balboni, G., Bryant, S.D., and Lazarus, L.H. (1993). Synthesis and receptor binding analysis of dermorphin hepta-, hexa-and pentapeptide analogues. Int. J. Peptide Prot. Res. 42, 550-559.
    • (1993) Int. J. Peptide Prot. Res. , vol.42 , pp. 550-559
    • Attila, M.1    Salvadori, S.2    Balboni, G.3    Bryant, S.D.4    Lazarus, L.H.5
  • 4
    • 0027263188 scopus 로고
    • Radioactive iodinated cyclo(His-Pro) crosses the blood brain barrier and reverses ethanol-induced narcosis
    • Banks, W.A., Kastin, A.J., Akerstromy, and Jaspan, J.B. (1993). Radioactive iodinated cyclo(His-Pro) crosses the blood brain barrier and reverses ethanol-induced narcosis. Amer. J. Physiol. 264, E 723-E 729.
    • (1993) Amer. J. Physiol. , vol.264
    • Banks, W.A.1    Kastin, A.J.2    Akerstromy3    Jaspan, J.B.4
  • 6
    • 0030040907 scopus 로고    scopus 로고
    • The conserved aspartate residue in the third putative transmembrane domain of the δ-opioid receptor is not the anionic counterpart for cationic opiate binding but is a constituent of the receptor binding site
    • Befort, K., Tabbara, L., Bausch, S., Chavkin, C., Evans, C., and Kieffer, B. (1996a). The conserved aspartate residue in the third putative transmembrane domain of the δ-opioid receptor is not the anionic counterpart for cationic opiate binding but is a constituent of the receptor binding site. Mol. Pharmacol. 49, 216-223.
    • (1996) Mol. Pharmacol. , vol.49 , pp. 216-223
    • Befort, K.1    Tabbara, L.2    Bausch, S.3    Chavkin, C.4    Evans, C.5    Kieffer, B.6
  • 7
    • 0029937609 scopus 로고    scopus 로고
    • Role of aromatic transmembrane residues of the δ-opioid receptor in ligand recognition
    • Befort, K., Tabbara, L., Kling, D., Maigret, B., and Kieffer, B. (1996b). Role of aromatic transmembrane residues of the δ-opioid receptor in ligand recognition. J. Biol. Chem. 271, 10161-10168.
    • (1996) J. Biol. Chem. , vol.271 , pp. 10161-10168
    • Befort, K.1    Tabbara, L.2    Kling, D.3    Maigret, B.4    Kieffer, B.5
  • 8
    • 0019185831 scopus 로고
    • The effects of thyrotropin releasing hormone and histidyl-proline diketopiperazine on delta-9-tetrahydrocannabinol-induced hypothermia
    • Bhargava, H.N. (1980). The effects of thyrotropin releasing hormone and histidyl-proline diketopiperazine on delta-9-tetrahydrocannabinol-induced hypothermia. Life Sci. 26, 845-850.
    • (1980) Life Sci. , vol.26 , pp. 845-850
    • Bhargava, H.N.1
  • 9
    • 0027772479 scopus 로고
    • A new consistent model explaining structure (conformation)-activity relationship of opiates with μ-selectivity
    • Brandt, W., Barth, A., and Höltje, H.-D. (1993). A new consistent model explaining structure (conformation)-activity relationship of opiates with μ-selectivity. Drug Design Disc. 10, 257-283.
    • (1993) Drug Design Disc. , vol.10 , pp. 257-283
    • Brandt, W.1    Barth, A.2    Höltje, H.-D.3
  • 11
    • 0030060840 scopus 로고    scopus 로고
    • Design and synthesis of 1-aminocycloalkane-1-carboxylic acid-substituted deltorphin analogues: Unique δ and μ opioid activity in modified peptides
    • Breveglieri, A., Guerrini, R., Salvadori, S., Bianchi, C., Bryant, S.D., Attila, M., and Lazarus, L.H. (1996). Design and synthesis of 1-aminocycloalkane-1-carboxylic acid-substituted deltorphin analogues: unique δ and μ opioid activity in modified peptides. J. Med. Chem. 39, 773-780.
    • (1996) J. Med. Chem. , vol.39 , pp. 773-780
    • Breveglieri, A.1    Guerrini, R.2    Salvadori, S.3    Bianchi, C.4    Bryant, S.D.5    Attila, M.6    Lazarus, L.H.7
  • 12
    • 0028476063 scopus 로고
    • Molecular dynamics conformations of deltorphin analogues advocate δ opioid binding site models
    • Bryant, S.D., Attila, M., Salvadori, S., Guerrini, R., and Lazarus, L.H. (1994). Molecular dynamics conformations of deltorphin analogues advocate δ opioid binding site models. Peptide Res. 7, 175-184.
    • (1994) Peptide Res. , vol.7 , pp. 175-184
    • Bryant, S.D.1    Attila, M.2    Salvadori, S.3    Guerrini, R.4    Lazarus, L.H.5
  • 13
    • 0342663901 scopus 로고    scopus 로고
    • Dmt-Tic-OH, a highly selective and potent δ opioidmimetic receptor antagonist after systemic administration in the mouse
    • Capasso, A., Guerrini, R., Balboni, G., Sorrentino, L., Temussi, P.A., Lazarus, L.H., Bryant, S.D., and Salvadori, S. (1996). Dmt-Tic-OH, a highly selective and potent δ opioidmimetic receptor antagonist after systemic administration in the mouse. Life Sci. 59, PL 93-PL 98.
    • (1996) Life Sci. , vol.59
    • Capasso, A.1    Guerrini, R.2    Balboni, G.3    Sorrentino, L.4    Temussi, P.A.5    Lazarus, L.H.6    Bryant, S.D.7    Salvadori, S.8
  • 14
    • 0029065783 scopus 로고
    • Acid catalysis in the formation of dioxo-piperazines from peptides containing tetrahydroisoquinoline-3-carboxylic acid at position 2
    • Capasso, S., Sica, F., Mazzarella, L., Balboni, G., Guerrini, R., and Salvadori, S. (1995). Acid catalysis in the formation of dioxo-piperazines from peptides containing tetrahydroisoquinoline-3-carboxylic acid at position 2. Int. J. Pept. Prot. Res. 45, 567-573.
    • (1995) Int. J. Pept. Prot. Res. , vol.45 , pp. 567-573
    • Capasso, S.1    Sica, F.2    Mazzarella, L.3    Balboni, G.4    Guerrini, R.5    Salvadori, S.6
  • 16
    • 0026602250 scopus 로고
    • Preparation and opioid activity of analogues of the analgesic dipeptide2,6-dimethyl-L-tyrosyl-N-(3-phenylpropyl)-D-alanin-amide
    • Chandrakumar, N.S., Yonan, P.K., Stapelfeld, A., Savage, M., Rorbacher, E., Contreras, P.C., and Hammond, D. (1992). Preparation and opioid activity of analogues of the analgesic dipeptide2,6-dimethyl-L-tyrosyl-N-(3-phenylpropyl)-D-alanin-amide. J. Med. Chem. 35, 223-233.
    • (1992) J. Med. Chem. , vol.35 , pp. 223-233
    • Chandrakumar, N.S.1    Yonan, P.K.2    Stapelfeld, A.3    Savage, M.4    Rorbacher, E.5    Contreras, P.C.6    Hammond, D.7
  • 17
    • 0028308020 scopus 로고
    • Molecular cloning, tissue distribution and chromosomal localization of a novel member of the opioid receptor gene family
    • Chen, Y., Fan, Y., Mestek, A., Tian, M., Kozak, C.A., and Yu, L. (1994). Molecular cloning, tissue distribution and chromosomal localization of a novel member of the opioid receptor gene family. FEBS Lett. 347, 279-283.
    • (1994) FEBS Lett. , vol.347 , pp. 279-283
    • Chen, Y.1    Fan, Y.2    Mestek, A.3    Tian, M.4    Kozak, C.A.5    Yu, L.6
  • 19
    • 0014785883 scopus 로고
    • Carnosine and related substances in animal tissues
    • Crush, K.G. (1970). Carnosine and related substances in animal tissues. Comp. Biochem. Physiol. 34, 3-30.
    • (1970) Comp. Biochem. Physiol. , vol.34 , pp. 3-30
    • Crush, K.G.1
  • 20
    • 1842310464 scopus 로고
    • Occurrence of carnosine in skin of certain leptodactylid frogs
    • Daly, J.W., and Heatwole, H. (1966). Occurrence of carnosine in skin of certain leptodactylid frogs. Experientia 22, 764-765.
    • (1966) Experientia , vol.22 , pp. 764-765
    • Daly, J.W.1    Heatwole, H.2
  • 21
    • 0030043489 scopus 로고    scopus 로고
    • Cation-π interactions in chemistry and biology: A new view of benzene, Phe, Tyr, and Trp
    • Dougherty, D.A. (1996). Cation-π interactions in chemistry and biology: a new view of benzene, Phe, Tyr, and Trp. Science 271, 163-168.
    • (1996) Science , vol.271 , pp. 163-168
    • Dougherty, D.A.1
  • 24
    • 0027275029 scopus 로고
    • Primary structures and expression from cDNAs of rat opioid receptor δ- and μ-subtypes
    • Fukuda, K., Kato, S., Mori, K., Nishi, M., and Takeshima, H. (1993). Primary structures and expression from cDNAs of rat opioid receptor δ-and μ-subtypes. FEBS Lett. 327, 311-314.
    • (1993) FEBS Lett. , vol.327 , pp. 311-314
    • Fukuda, K.1    Kato, S.2    Mori, K.3    Nishi, M.4    Takeshima, H.5
  • 25
    • 0029131679 scopus 로고
    • Identification of the amino acid residues involved in selective agonist binding in the first extracellular loop of the δ- and μ-opioid receptors
    • Fukuda, K., Terasko, K., Kato, S., and Mori, K. (1995). Identification of the amino acid residues involved in selective agonist binding in the first extracellular loop of the δ-and μ-opioid receptors. FEBS Lett. 373, 171-181.
    • (1995) FEBS Lett. , vol.373 , pp. 171-181
    • Fukuda, K.1    Terasko, K.2    Kato, S.3    Mori, K.4
  • 26
    • 0017318380 scopus 로고
    • Attempted synthesis of 2-methylalanyl-L-prolyl-L-tryptophan. An unexpected result
    • Gerig, J.T., and McLeod, R.S. (1976). Attempted synthesis of 2-methylalanyl-L-prolyl-L-tryptophan. An unexpected result. J. Org. Chem. 41, 1653-1655.
    • (1976) J. Org. Chem. , vol.41 , pp. 1653-1655
    • Gerig, J.T.1    McLeod, R.S.2
  • 29
    • 0026612763 scopus 로고
    • 3 aromatic ring in cyclic δ opioid receptor-selective dermorphin/ deltorphin tetrapeptide analogues: Electronic and lipophilic requirements for receptor affinity
    • 3 aromatic ring in cyclic δ opioid receptor-selective dermorphin/ deltorphin tetrapeptide analogues: electronic and lipophilic requirements for receptor affinity. J. Med. Chem. 35, 1535-1541.
    • (1992) J. Med. Chem. , vol.35 , pp. 1535-1541
    • Heyl, D.L.1    Mosberg, H.I.2
  • 33
    • 0024334804 scopus 로고
    • Recent developments in the design of receptor specific opioid peptides
    • Hruby, V.J., and Gehrig, C. (1989). Recent developments in the design of receptor specific opioid peptides. Med. Res. Rev. 9, 343-401.
    • (1989) Med. Res. Rev. , vol.9 , pp. 343-401
    • Hruby, V.J.1    Gehrig, C.2
  • 34
    • 0027476992 scopus 로고
    • Intraventricular administration of histidyl-proline-diketopiperazine [cyclo(His-Pro)] suppresses prolactin secretion and synthesis: A possible role of cyclo(His-Pro) as dopamine uptake blocker in rat hypothalamus
    • Jikihara, H., Ikegami, H., Koike, K., Wada, K., Morishige, I., Kurachi, H., Hirota, K., Miyake, A., and Tanizawa, O. (1993). Intraventricular administration of histidyl-proline-diketopiperazine [cyclo(His-Pro)] suppresses prolactin secretion and synthesis: a possible role of cyclo(His-Pro) as dopamine uptake blocker in rat hypothalamus. Endocrinol. 132, 953-958.
    • (1993) Endocrinol. , vol.132 , pp. 953-958
    • Jikihara, H.1    Ikegami, H.2    Koike, K.3    Wada, K.4    Morishige, I.5    Kurachi, H.6    Hirota, K.7    Miyake, A.8    Tanizawa, O.9
  • 35
    • 0027182054 scopus 로고
    • Effects of two diketopiperazines, cyclo(His-Pro) and cyclo(Asp-Pro), on striatal dopamine: A microdialysis study
    • Kaakkola, S., and Wurtman, R.J. (1993). Effects of two diketopiperazines, cyclo(His-Pro) and cyclo(Asp-Pro), on striatal dopamine: a microdialysis study. Brain Res. Bull. 32, 667-672.
    • (1993) Brain Res. Bull. , vol.32 , pp. 667-672
    • Kaakkola, S.1    Wurtman, R.J.2
  • 36
    • 0027052952 scopus 로고
    • The δ-opioid receptor: Isolation of a cDNa by expression cloning and pharmacological characterization
    • Kieffer, B.L., Befort, K., Gaveriaux-Ruff, C., and Hirth, G.C. (1992). The δ-opioid receptor: isolation of a cDNA by expression cloning and pharmacological characterization. Proc. Natl. Acad. Sci. 89, 12048-12052.
    • (1992) Proc. Natl. Acad. Sci. , vol.89 , pp. 12048-12052
    • Kieffer, B.L.1    Befort, K.2    Gaveriaux-Ruff, C.3    Hirth, G.C.4
  • 37
    • 0027444691 scopus 로고
    • A single reside, aspartic acid 95, in the δ opioid receptor specifies selective high affinity agonist binding
    • Kong, H., Raynor, K., Yasuda, K., Moe, S.T., Portoghese, P.S., Bell, G.I., and Reisine, T. (1993). A single reside, aspartic acid 95, in the δ opioid receptor specifies selective high affinity agonist binding. J. Biol. Chem. 266, 23055-23055.
    • (1993) J. Biol. Chem. , vol.266 , pp. 23055-23055
    • Kong, H.1    Raynor, K.2    Yasuda, K.3    Moe, S.T.4    Portoghese, P.S.5    Bell, G.I.6    Reisine, T.7
  • 38
    • 0014298035 scopus 로고
    • Kinetic parameters of narcotic agonists and antagonists, with particular reference to N-allylnoroxymorphone (naloxone)
    • Kosterlitz, H.W., and Watt, A.J. (1968). Kinetic parameters of narcotic agonists and antagonists, with particular reference to N-allylnoroxymorphone (naloxone). Br. J. Pharmacol. Chemother. 33, 266-276.
    • (1968) Br. J. Pharmacol. Chemother. , vol.33 , pp. 266-276
    • Kosterlitz, H.W.1    Watt, A.J.2
  • 40
    • 0025283903 scopus 로고
    • Demorphin interaction with rat opioid receptors: Involvement of hydrophobic sites in the binding domain
    • Lazarus, L.H., Wilson, W.E., Guglietta, A., and de Castiglione, R. (1990). Demorphin interaction with rat opioid receptors: involvement of hydrophobic sites in the binding domain. Mol. Pharmacol. 37, 886-892.
    • (1990) Mol. Pharmacol. , vol.37 , pp. 886-892
    • Lazarus, L.H.1    Wilson, W.E.2    Guglietta, A.3    De Castiglione, R.4
  • 42
    • 0026654499 scopus 로고
    • Stereospecificity of amino acid side chains in deltorphin defines binding to opioid receptors
    • Lazarus, L.H., Salvadori, S., Balboni, G., Tomatis, R., and Wilson, W.E. (1992). Stereospecificity of amino acid side chains in deltorphin defines binding to opioid receptors. J. Med. Chem. 35, 1222-1227.
    • (1992) J. Med. Chem. , vol.35 , pp. 1222-1227
    • Lazarus, L.H.1    Salvadori, S.2    Balboni, G.3    Tomatis, R.4    Wilson, W.E.5
  • 43
    • 0027511496 scopus 로고
    • Interaction of deltorphin with opioid receptors: Molecular determinants for affinity and selectivity
    • Lazarus, L.H., Salvadori, S., Attila, M., Grieco, P., Bundy, D.M., Wilson, W.E., and Tomatis, R. (1993). Interaction of deltorphin with opioid receptors: molecular determinants for affinity and selectivity. Peptides 14, 21-28.
    • (1993) Peptides , vol.14 , pp. 21-28
    • Lazarus, L.H.1    Salvadori, S.2    Attila, M.3    Grieco, P.4    Bundy, D.M.5    Wilson, W.E.6    Tomatis, R.7
  • 44
    • 0030065629 scopus 로고    scopus 로고
    • Opioid infidelity: Novel opioid peptides with dual high affinity for δ- and μ-receptors
    • Lazarus, L.H., Bryant, S.D., Salvadori, S., Attila, M., and Jones, L.S. (1996). Opioid infidelity: novel opioid peptides with dual high affinity for δ-and μ-receptors. Trends Neurosci. 19, 31-35.
    • (1996) Trends Neurosci. , vol.19 , pp. 31-35
    • Lazarus, L.H.1    Bryant, S.D.2    Salvadori, S.3    Attila, M.4    Jones, L.S.5
  • 46
    • 0021351257 scopus 로고
    • Carnosine, homocarnosine and anserine in vertebrate retinas
    • Margolis, F.L., and Grillo, M. (1984). Carnosine, homocarnosine and anserine in vertebrate retinas. Neurochem. Int. 6, 207-209.
    • (1984) Neurochem. Int. , vol.6 , pp. 207-209
    • Margolis, F.L.1    Grillo, M.2
  • 47
    • 0027532576 scopus 로고
    • Spontaneous degradation via diketopiperazine formation of peptides containing a tetrahydroisoquinoline-3-carboxylic acid residue in the 2-position of the peptide sequence
    • Marsden, B.J., Nguyen, T.M.-D., and Schiller, P.W. (1993). Spontaneous degradation via diketopiperazine formation of peptides containing a tetrahydroisoquinoline-3-carboxylic acid residue in the 2-position of the peptide sequence. Int. J. Pept. Prot. Res. 41, 313-316.
    • (1993) Int. J. Pept. Prot. Res. , vol.41 , pp. 313-316
    • Marsden, B.J.1    Nguyen, T.M.-D.2    Schiller, P.W.3
  • 48
    • 0000871688 scopus 로고
    • A novel peptide cleavage reaction
    • Mazur, R.H., and Schlatter, J.M. (1963). A novel peptide cleavage reaction. J. Org. Chem. 28, 1025-1029.
    • (1963) J. Org. Chem. , vol.28 , pp. 1025-1029
    • Mazur, R.H.1    Schlatter, J.M.2
  • 49
    • 0027310803 scopus 로고
    • Formation of pyroglutamylglutamine (or asparagine) diketopiperazine in 'non-classical' conditions: A side reaction in peptide synthesis
    • Mazurov, A., Andronati, S.A., Korotenko, T.I., Gorbatyuk, V.Y., and Shapiro, Y.E. (1993). Formation of pyroglutamylglutamine (or asparagine) diketopiperazine in 'non-classical' conditions: a side reaction in peptide synthesis. Int. J. Pept. Prot. Res. 42, 14-19.
    • (1993) Int. J. Pept. Prot. Res. , vol.42 , pp. 14-19
    • Mazurov, A.1    Andronati, S.A.2    Korotenko, T.I.3    Gorbatyuk, V.Y.4    Shapiro, Y.E.5
  • 50
    • 0028866118 scopus 로고
    • On the role of extracellular loops of opioid receptors in conferring ligand selectivity
    • Metzger, T.G., and Ferguson, D.M. (1995). On the role of extracellular loops of opioid receptors in conferring ligand selectivity. FEBS Lett. 375, 1-4.
    • (1995) FEBS Lett. , vol.375 , pp. 1-4
    • Metzger, T.G.1    Ferguson, D.M.2
  • 51
    • 0029120292 scopus 로고
    • The synthesis and opioid receptor binding affinities of analogues of dermorphin and its N-terminal tetrapeptide fragment with dibasic acids in position 2
    • Misicka, A., Lipkowski, A.W., Slaninova, J., Davis, P., Yamamura, H.I., Porecca, R, and Hruby, V.J. (1995). The synthesis and opioid receptor binding affinities of analogues of dermorphin and its N-terminal tetrapeptide fragment with dibasic acids in position 2. Life Sci. 57, 1633-1640.
    • (1995) Life Sci. , vol.57 , pp. 1633-1640
    • Misicka, A.1    Lipkowski, A.W.2    Slaninova, J.3    Davis, P.4    Yamamura, H.I.5    Porecca, R.6    Hruby, V.J.7
  • 54
    • 0019501918 scopus 로고
    • Synthesis of thyrotropin releasing hormone analogues with selective central nervous system effects
    • Nutt, R.F., Hally, F.W., Homick, C., Hirshman, R., and Veber, D.F. (1981). Synthesis of thyrotropin releasing hormone analogues with selective central nervous system effects. J. Med. Chem 24, 692-698.
    • (1981) J. Med. Chem , vol.24 , pp. 692-698
    • Nutt, R.F.1    Hally, F.W.2    Homick, C.3    Hirshman, R.4    Veber, D.F.5
  • 55
    • 0028151089 scopus 로고
    • Glutamate and carnosine in the vestibular system of the frog
    • Panzanelli, P., Valli, P., Cantino, D., and Fasolo, A. (1994). Glutamate and carnosine in the vestibular system of the frog. Brain Res. 662, 293-296.
    • (1994) Brain Res. , vol.662 , pp. 293-296
    • Panzanelli, P.1    Valli, P.2    Cantino, D.3    Fasolo, A.4
  • 56
    • 0028201818 scopus 로고
    • Enkephalin analogs as systemically active antinociceptive agents: O- and N-alkylated derivatives of the dipeptide amide L-2,6-dimethyltyrosyl-N-(3-phenylpropyl)-D-alaninamide
    • Pitzele, B.S., Hamilton, R.W., Kudla, K.D., Tsymbalov, S., Stapelfeld, A., Savage, M.A., Clare, M., Hammond, D.L., and Hansen, D.W., Jr. (1994). Enkephalin analogs as systemically active antinociceptive agents: O-and N-alkylated derivatives of the dipeptide amide L-2,6-dimethyltyrosyl-N-(3-phenylpropyl)-D-alaninamide. J. Med. Chem. 37, 888-896.
    • (1994) J. Med. Chem. , vol.37 , pp. 888-896
    • Pitzele, B.S.1    Hamilton, R.W.2    Kudla, K.D.3    Tsymbalov, S.4    Stapelfeld, A.5    Savage, M.A.6    Clare, M.7    Hammond, D.L.8    Hansen Jr., D.W.9
  • 57
    • 0026472964 scopus 로고
    • Expression of carnosine-like immunoreactivity during retinal development in the clawed frog (Xenopus laevis)
    • Pognetto, M.S., Panzanelli, R, Fasolo, A., and Cantino, D. (1992). Expression of carnosine-like immunoreactivity during retinal development in the clawed frog (Xenopus laevis). Develop. Brain Res. 70, 134-138.
    • (1992) Develop. Brain Res. , vol.70 , pp. 134-138
    • Pognetto, M.S.1    Panzanelli, R.2    Fasolo, A.3    Cantino, D.4
  • 58
    • 0025895073 scopus 로고
    • Role of spacer and address components in peptidomimetic δ opioid receptor antagonists related to naltrindole
    • Porthogese, P.S., Nagase, H., MaloneyHuss, K.E., Lin, C.-E., and Takemori, A.E. (1991). Role of spacer and address components in peptidomimetic δ opioid receptor antagonists related to naltrindole. J. Med. Chem. 34, 1715-1720.
    • (1991) J. Med. Chem. , vol.34 , pp. 1715-1720
    • Porthogese, P.S.1    Nagase, H.2    Maloneyhuss, K.E.3    Lin, C.-E.4    Takemori, A.E.5
  • 59
    • 0017153641 scopus 로고
    • Demonstration of pyroglutamylpeptidase and amides activities toward thyrotropin-releasing hormone in hamster hypothalamus extracts
    • Prasad, C., and Peterkofsky, A. (1976). Demonstration of pyroglutamylpeptidase and amides activities toward thyrotropin-releasing hormone in hamster hypothalamus extracts. J. Biol. Chem. 251, 3229-3234.
    • (1976) J. Biol. Chem. , vol.251 , pp. 3229-3234
    • Prasad, C.1    Peterkofsky, A.2
  • 60
    • 0021245922 scopus 로고
    • Distribution and characterization of cyclo (His-Pro)-like immunoreactivity in anuran (frog) skins
    • Prasad, C., Edwards, R.M., Pegues, J., Mori, M., Wilber, J.F., Thomas, R.A., and Pierson, W. (1984). Distribution and characterization of cyclo (His-Pro)-like immunoreactivity in anuran (frog) skins. Peptides 5, 133-136.
    • (1984) Peptides , vol.5 , pp. 133-136
    • Prasad, C.1    Edwards, R.M.2    Pegues, J.3    Mori, M.4    Wilber, J.F.5    Thomas, R.A.6    Pierson, W.7
  • 61
    • 0027504774 scopus 로고
    • Novel, δ-opioid receptor-selective peptide antagonists: Demonstration of a possible opioid interaction in the absence of a protonated nitrogen and attempts to locate the protonated nitrogen site
    • Rónai, A.Z., Botyánski, J., Magyar, A., Borsodi, A., Benyhe, S., and Medzihradszky, K. (1993). Novel, δ-opioid receptor-selective peptide antagonists: demonstration of a possible opioid interaction in the absence of a protonated nitrogen and attempts to locate the protonated nitrogen site. Arch. Int. Pharmacodyn. 323, 114-125.
    • (1993) Arch. Int. Pharmacodyn. , vol.323 , pp. 114-125
    • Rónai, A.Z.1    Botyánski, J.2    Magyar, A.3    Borsodi, A.4    Benyhe, S.5    Medzihradszky, K.6
  • 63
    • 0023700023 scopus 로고
    • Biogenic amines and active peptides in the skin of fifty-two African amphibian species other than bufonids
    • Roseghini, M., Falconieri Erspamer, G., and Severini, C. (1988). Biogenic amines and active peptides in the skin of fifty-two African amphibian species other than bufonids. Comp. Biochem. Physiol. 91C, 281-286.
    • (1988) Comp. Biochem. Physiol. , vol.91 C , pp. 281-286
    • Roseghini, M.1    Falconieri Erspamer, G.2    Severini, C.3
  • 65
    • 0027008611 scopus 로고
    • Para-substituted Phe3 deltorphin analogues: Enhanced selectivity of halogenated derivatives for δ opioid receptor sites
    • Salvadori, S., Bianchi, C., Lazarus, L.H., Scaranari, V., Attila, M., and Tomatis, R. (1992). Para-substituted Phe3 deltorphin analogues: enhanced selectivity of halogenated derivatives for δ opioid receptor sites. J. Med. Chem. 35, 4651-4657.
    • (1992) J. Med. Chem. , vol.35 , pp. 4651-4657
    • Salvadori, S.1    Bianchi, C.2    Lazarus, L.H.3    Scaranari, V.4    Attila, M.5    Tomatis, R.6
  • 66
    • 0027330241 scopus 로고
    • 3-Substituted analogues of deltorphin C. Spatial conformation and topography of the aromatic ring in peptide recognition by δ opioid receptors
    • 3-Substituted analogues of deltorphin C. Spatial conformation and topography of the aromatic ring in peptide recognition by δ opioid receptors. J. Med. Chem. 36, 3748-3756.
    • (1993) J. Med. Chem. , vol.36 , pp. 3748-3756
    • Salvadori, S.1    Bryant, S.D.2    Bianchi, C.3    Balboni, G.4    Attila, M.5    Lazarus, L.H.6
  • 68
    • 0029834584 scopus 로고    scopus 로고
    • Opioid binding profile of morphiceptin, Tyr-MIF-1 and dynorphin-related peptides in rat brain membranes
    • Sartania, N., Benyhe, S., Magyar, A., Rónai, A.Z., Medzihradszky, K., and Borsodi, A. (1996). Opioid binding profile of morphiceptin, Tyr-MIF-1 and dynorphin-related peptides in rat brain membranes. Neuropeptides 30, 225-230.
    • (1996) Neuropeptides , vol.30 , pp. 225-230
    • Sartania, N.1    Benyhe, S.2    Magyar, A.3    Rónai, A.Z.4    Medzihradszky, K.5    Borsodi, A.6
  • 69
    • 0025110284 scopus 로고
    • 2]deltorphin I analogs with extraordinary delta receptor activity
    • J.M. van Ree, A.H. Mulder, V.M. Wiegant, and T.B. van Wimersma Greidanus, ed. (Amsterdam, The Netherlands: Excerpta Medica)
    • 2]deltorphin I analogs with extraordinary delta receptor activity. In: New Leads in Opioid Research, Vol. 914, J.M. van Ree, A.H. Mulder, V.M. Wiegant, and T.B. van Wimersma Greidanus, ed. (Amsterdam, The Netherlands: Excerpta Medica), pp. 288-290.
    • (1990) New Leads in Opioid Research , vol.914 , pp. 288-290
    • Schiller, P.W.1    Nguyen, T.M.-D.2    Weltrowska, G.3    Lemieux, C.4    Chung, N.N.5
  • 70
    • 0025987566 scopus 로고
    • Conformational restriction of the phenylalanine residue in a cyclic opioid peptide analogue: Effects of receptor selectivity and stereospecificity
    • Schiller, P.W., Weltrowska, G., Nguyen, T.M.-D., Lemieux, C., Chung, N.N., Marsden, B.J., and Wilkes, B.C. (1991). Conformational restriction of the phenylalanine residue in a cyclic opioid peptide analogue: effects of receptor selectivity and stereospecificity. J. Med. Chem. 34, 3125-3132.
    • (1991) J. Med. Chem. , vol.34 , pp. 3125-3132
    • Schiller, P.W.1    Weltrowska, G.2    Nguyen, T.M.-D.3    Lemieux, C.4    Chung, N.N.5    Marsden, B.J.6    Wilkes, B.C.7
  • 71
    • 0027049066 scopus 로고
    • Differential stereochemical requirements of μ vs. δ opioid receptors for ligand binding and signal transduction: Development of a class of potent and highly δ-selective peptide antagonists
    • Schiller, P.W., Nguyen, T.M.-D., Weltrowska, G., Wilkes, B.C., Marsden, B.J., Lemieux, C., and Chung, N.N. (1992a). Differential stereochemical requirements of μ vs. δ opioid receptors for ligand binding and signal transduction: development of a class of potent and highly δ-selective peptide antagonists. Proc. Natl. Acad. Sci. 89, 11871-11875.
    • (1992) Proc. Natl. Acad. Sci. , vol.89 , pp. 11871-11875
    • Schiller, P.W.1    Nguyen, T.M.-D.2    Weltrowska, G.3    Wilkes, B.C.4    Marsden, B.J.5    Lemieux, C.6    Chung, N.N.7
  • 73
    • 0027489176 scopus 로고
    • TIPP[ψ]: A highly potent and stable pseudopeptide δ opioid receptor antagonist with extraordinary δ selectivity
    • Schiller, P.W., Weltrowska, G., Nguyen, T.M.-D., Wilkes, B.C., Chung, N.N., and Lemieux, C. (1993). TIPP[ψ]: a highly potent and stable pseudopeptide δ opioid receptor antagonist with extraordinary δ selectivity. J. Med. Chem. 36, 3182-3187.
    • (1993) J. Med. Chem. , vol.36 , pp. 3182-3187
    • Schiller, P.W.1    Weltrowska, G.2    Nguyen, T.M.-D.3    Wilkes, B.C.4    Chung, N.N.5    Lemieux, C.6
  • 74
    • 0027973809 scopus 로고
    • Role of endogenous cyclo(His-Pro) in cold-induced hypothermia in the desert rat (Mostomys natalensis)
    • Shukla, R., Rahmani, N.H., Mizuma, H., Srimal, R.C., and Prasad, C. (1994). Role of endogenous cyclo(His-Pro) in cold-induced hypothermia in the desert rat (Mostomys natalensis). Peptides 15, 1471-1479.
    • (1994) Peptides , vol.15 , pp. 1471-1479
    • Shukla, R.1    Rahmani, N.H.2    Mizuma, H.3    Srimal, R.C.4    Prasad, C.5
  • 75
    • 0028327150 scopus 로고
    • Selective loss of δ opioid analgesia and binding by antisense oligodeoxynucleotides to a δ opioid receptor
    • Standifer, K.M., Chien, C.-C., Wahlestedt, C., Brown, G.P., and Pasternak, G.W. (1994). Selective loss of δ opioid analgesia and binding by antisense oligodeoxynucleotides to a δ opioid receptor. Neuron 12, 805-815.
    • (1994) Neuron , vol.12 , pp. 805-815
    • Standifer, K.M.1    Chien, C.-C.2    Wahlestedt, C.3    Brown, G.P.4    Pasternak, G.W.5
  • 77
    • 0026281331 scopus 로고
    • Diketopiperazine-mediated peptide formation in aqueous solution. II. Catalytic effect of phosphate
    • Takaoka, O., Yamagata, Y., and Inomata, K. (1991). Diketopiperazine-mediated peptide formation in aqueous solution. II. Catalytic effect of phosphate. Origins Life Evol. Biosphere 21, 113-118.
    • (1991) Origins Life Evol. Biosphere , vol.21 , pp. 113-118
    • Takaoka, O.1    Yamagata, Y.2    Inomata, K.3
  • 81
    • 10144241052 scopus 로고    scopus 로고
    • Involvement of Trp-284, Val-296, and Val-297 of the human δ-opioid receptor in binding of δ-selective ligands
    • Valiquette, M., Vu, H.K., Yue, S.Y., Wahlestedt, C., and Walker, P. (1996). Involvement of Trp-284, Val-296, and Val-297 of the human δ-opioid receptor in binding of δ-selective ligands. J. Biol. Chem. 271, 18789-18796.
    • (1996) J. Biol. Chem. , vol.271 , pp. 18789-18796
    • Valiquette, M.1    Vu, H.K.2    Yue, S.Y.3    Wahlestedt, C.4    Walker, P.5
  • 82
    • 0002910471 scopus 로고
    • Identification and quantification of diketopiperazines by liquid chromatography-mass spectrometry, using a moving belt interface
    • van der Greef, J., Tas, A.C., Nijssen, L.M., and Jetten, J. (1987). Identification and quantification of diketopiperazines by liquid chromatography-mass spectrometry, using a moving belt interface. J. Chromatog. 394, 77-88.
    • (1987) J. Chromatog. , vol.394 , pp. 77-88
    • Van Der Greef, J.1    Tas, A.C.2    Nijssen, L.M.3    Jetten, J.4
  • 84
    • 0019788374 scopus 로고
    • Minimum structure opioids - Dipeptide and tripeptide analogs of the enkephalins
    • Vavrek, R.J., Hsi, L.-H., York, E.J., Hall, M.E., and Stewart, J.M. (1981). Minimum structure opioids - dipeptide and tripeptide analogs of the enkephalins. Peptides 2, 303-308.
    • (1981) Peptides , vol.2 , pp. 303-308
    • Vavrek, R.J.1    Hsi, L.-H.2    York, E.J.3    Hall, M.E.4    Stewart, J.M.5
  • 85
    • 0016539299 scopus 로고
    • Amino acid composition and sequence of urinary peptides containing hydroxyproline
    • Wagner, F.W., Kapleau, B.R., and Shepherd, S.L. (1975). Amino acid composition and sequence of urinary peptides containing hydroxyproline. Biochem. Med. 13, 343-352.
    • (1975) Biochem. Med. , vol.13 , pp. 343-352
    • Wagner, F.W.1    Kapleau, B.R.2    Shepherd, S.L.3
  • 86
    • 0346423387 scopus 로고
    • Prolyl-leucyl-glycinamide, cyclo(leucylglycine), and derivatives block development of physical dependence on morphine in mice
    • Walter, R., Ritzmann, R.F., Bhargava, H.N., and Flexner, L.B. (1979). Prolyl-leucyl-glycinamide, cyclo(leucylglycine), and derivatives block development of physical dependence on morphine in mice. Proc. Natl. Acad. Sci. USA 76, 518-520.
    • (1979) Proc. Natl. Acad. Sci. USA , vol.76 , pp. 518-520
    • Walter, R.1    Ritzmann, R.F.2    Bhargava, H.N.3    Flexner, L.B.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.