Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Tripeptides – e.g. – tripeptide thyroliberin – etc.
Patent
1994-11-30
1998-07-14
Lukton, David
Chemistry: natural resins or derivatives; peptides or proteins;
Peptides of 3 to 100 amino acid residues
Tripeptides, e.g., tripeptide thyroliberin , etc.
514 18, 514 19, A61K 3806
Patent
active
057805890
ABSTRACT:
Novel opioidmimetic dipeptides, tripeptides and cyclic peptides exhibit enhanced affinity and selectivity for .delta. opioid receptors. The peptides are represented by the formulas L/D-Dmt-L-/D-Tic-R', L/D-Dmt-L-/D-Tic-R-R' and cyclic (L/D-Dmt-L/D-Tic) wherein Dmt is 2',6',-dimethyl-L/D-tyrosine Tic is L-/D-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, R is a natural or unusual aliphatic amino residue and R' is a functional group at the carboxyl terminus of the peptide. Pharmacological and therapeutic and compositions are also provided.
REFERENCES:
patent: 5455230 (1995-10-01), Schiller
Barnett S. Pitzele, et al., (1994) "Enkephalin Analogs as Systemically Active Antinociceptive Agents: O-and N-Alkylated Derivatives of the Dipeptide Amide L-2,6-Dimethyltryosyl-N-(3-phenylpropyl)-D-alaninamdie" J. Med. Chem. 37, 888-896.
P. Amodeo et al., (1995) "Confirmation analysis of potent and very selective .delta.opiod dipeptide antagonists" FEBS Letters 377:363-367.
S. Salvadori et al.(1995) ".delta.Opioidmimetic Antagonists: Prototypes for Designing a New Generation of Ultraselective Opoid Peptides" Molecular Medicine 1076-1551/95 678-689.
M.R. Ciajolo, et al. "Solution and solid-state structure of the diketopiperazine of tyrosyl-tetrahydroisoquinoline-3-caboxylic acid" International Journal of Peptide & Protein Research 1995, 46, 134-138.
Lazarus, L.H., et al., (1994) "Frog Skin Opioid Peptides: A Case for Environmental Mimicry" Environmental Health Perspectives, vol. 102, pp. 648-654.
Lazarus, L.H. And Attila, M., (1993) "The Toad, Ugly and Venomous. Wears Yet A Precious Jewel in His Skin" Progress in Neurobiology , vol. 41, pp. 473-507.
Temussi, P.A., et al., (1994) "Selective Opiod Dipeptides" Biochem. and Biophys. Res. Comm., vol. 198, pp. 933-939.
Lazarus, L.H., et al., (1992) "Stereospecificity of Amino Acid Side Chains in Deltorphin Defines Bindings to Opioid Receptors" J. Med. Chem., vol. 35 pp. 1222-1227.
Lazarus, L.H., et al., (1989) "Dermorphin Gene Sequence Peptide with High Affinity and Selectivity for .delta.-Opioid Receptors" J. Biol. Chem., vol. 264 pp. 3047-3050.
Salvadori, S., et al., (1993) "Phe.sup.3 -Substituted Analogues of Deltorphin C. Spatial Conformation and Topography of the Aromatic Ring in Peptide Recognition by .delta.Opioid Receptors" J. Med. Chem., 36 pp. 3748-3756.
Hammond, D.L. et al., "Antinociception Produced By Oral, Subcutaneous Or Intrathecal Administration of SC-39566, An Opioid Dipeptide Arylalkylamide, In The Rodent.sup.1 ", J. Pharmacol. Exper. Ther 268:607-615.
Schiller, P.W. et al., (1991) Conformationally Restricted Deltorphin Analogues.dagger., .dagger-dbl. J. Med. Chem. 35:3965-3961.
Portoghese, P.S. (1989) "Bivalent Ligands And The Message--Address Concept In The Design Of Selective Opioid Receptor Antagonists" Trend's Phar. Sci.10:230-235.
Deeks, T. et al., (1983) "Synthesis and Analgesic Properties of Two Leucine-Enkephalin Analogues Containing a Conformationally Restrained N-Terminal Tyrosine Residue" J. Med. Chem. 26:762-765.
Hruby V.J. et al. (1989) "Recent Developments in the Design of Receptor Specific Opioid Peptides." Med. Res. Rev. 9,343-401. Pseudopeptide .delta. Opioid Receptor Antagonist With Extraordinary .delta.Selectivity. J. Med. Chem. 36, 3182-3187.
Chandrakumar N.S., et al. (1992) "Preparation And Opioid Activity Of Analogues Of The Analgesic Dipeptide 2,6-Dimethyl-L-tyrosyl-N-(3-phenylpropyl)-D-alaninamide." J. Med. Chem. 35, 223-233.
Chandrakumar N.S., et al. (1992) "Analogs Of The .delta. Opioid Receptor 5-D-penicillamine!enkephalin:2',6'-dimethyltrosine and Gly.sup.3 -Phe.sup.4 Amide Bond Isostere Substitutions." J. Med. Chem. 35, 2928-2938.
Mosberg H.I., et al. (1992) Incorporation Of A Novel Conformationally Restricted Tyrosine Analog Into a Cyclic, .delta. Opioid Receptor Selective Tetrapeptide (JOM-13) Enhances .delta. Receptor Binding Affinity And Selectivity. J. Med. Chem. 35, 4498-4500.
Lazarus L.H., et al. (1991) "Opioid Receptor Selectivity Reversal In Deltorphin Tetrapeptide Analogues." Biochem. Biophys. Res. Commun. 178, 110-115.
Marastoni M., et al. (1991) "On the Degradation Of Deltorphin Peptides By Plasma And Brain Homogenates." Farmaco 46, 1273-1279.
Temussi P.A., et al. (1994) "Selective Opioidi Peptides." Biochem. Biophys. Res. Commun. 198, 933-939.
Schiller, Proc. 13th Amer Pept Symp (1994) pp. 483-486.
Lazarus Lawrence H.
Salvadori Severo
Temussi Piero Andrea
Lukton David
The United States of America as represented by the Department of
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