Modifications of the cyclic mu receptor selective tetrapeptide Tyr-c[D- Cys-Phe-D-Pen]NH2 (Et): Effects on opioid receptor binding and activation

Journal of Peptide Research

Volumn 55, Issue 3, 2000, Pages 255-261

  McFadyen, I J ^a   Ho, J C ^b   Mosberg, H I ^b   Traynor, John R ^a  

^a UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

^b UNIVERSITY OF MICHIGAN   (United States)

Author keywords

Conformational restriction; Cyclic peptides; Delta opioid receptor; Mu opioid receptor; Opioid peptides

Indexed keywords

4 [ALPHA (4 ALLYL 2,5 DIMETHYL 1 PIPERAZINYL) 3 HYDROXYBENZYL] N,N DIETHYLBENZAMIDE; DELTA OPIATE RECEPTOR; DELTA OPIATE RECEPTOR AGONIST; FENTANYL; MU OPIATE RECEPTOR; OPIATE PEPTIDE; TYROSINE;

AMINO ACID SUBSTITUTION; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BRAIN HOMOGENATE; CONTROLLED STUDY; GUINEA PIG; NONHUMAN; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN MODIFICATION; PROTEIN STRUCTURE; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION;

ANIMALS; BRAIN; ENKEPHALIN, ALA(2)-MEPHE(4)-GLY(5)-; ENKEPHALIN, D-PENICILLAMINE (2,5)-; GUANOSINE 5'-O-(3-THIOTRIPHOSPHATE); GUINEA PIGS; HYDROGEN BONDING; OLIGOPEPTIDES; PEPTIDES, CYCLIC; PROTEIN BINDING; RECEPTORS, OPIOID, DELTA; RECEPTORS, OPIOID, KAPPA; RECEPTORS, OPIOID, MU; TUMOR CELLS, CULTURED;

ANIMALIA; CAVIA PORCELLUS; SUS SCROFA;

EID: 0033993709     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.2000.00177.x     Document Type: Article

References (18)

1. 1. Mosberg, H.I., Hurst, R., Hruby, V.J. et al. (1983) Bis-penicillamine enkephalins possess highly improved specificity toward delta opioid receptors. Proc. Natl Acad. Sci. USA 80, 5871-5874.
2. 2. Mosberg, H.I., Omnaas, J.R., Medzihradsky, F. & Smith, C.B. (1988) Cyclic, disulfide-and dithioether-containing opioid tetrapeptides: development of a ligand with high delta opioid receptor selectivity and affinity. Life Sci. 43, 1013-1020.
3. 3. Wang, C., McFadyen, I.J., Traynor, J.R. & Mosberg, H.I. (1998) Design of a high affinity peptidomimetic opioid agonist from peptide pharmacophore models. Bioorg. Med. Chem. Lett. 8, 2685-2688.
4. 3 replacements in the cyclic delta receptor selective tetrapeptide Tyr-c[D-Cys-Phe-D-Pen]OH (JOM-13). J. Med. Chem. 37, 4384-4391.
5. 35S]thio) triphosphate binding to membranes from human neuroblastoma SH-SY5Y cells. Mol. Pharmacol. 47, 848-854.
6. 6. Heath, W.F., Tam, J.P. & Merrifield, R.B. (1986) Improved deprotection of cysteine-containing peptides in HF. Int. J. Peptide Protein Res. 28, 498.
7. 7. Mosberg, H.I., Omnaas, J.R. & Goldstein, A. (1987) Structural requirements for delta opioid receptor binding. Mol. Pharmacol. 31, 599-602.
8. 8. Mosberg, H.I. & Kroona, H. (1992) Incorporation of a novel conformationally restricted tyrosine analogue into a cyclic, delta-opioid receptor selective tetrapeptide (JOM-13) enhances delta receptor binding affinity and selectivity. J. Med. Chem. 35, 4498-4500.
9. 9. Mosberg, H.I., Lomize, A.L., Wang, C. et al. (1994) Development of a model for the delta opioid receptor pharmacophore. 1. Conformationally restricted Tyr1 replacements in the cyclic delta receptor selective tetrapeptide Tyr-c[D-Cys-Phe-D-Pen]OH (JOM-13). J. Med. Chem. 37, 4371-4383.
10. 10. Emmerson, P.J., Clark, M.J., Mansour, A., Akil, H., Woods, J.H. & Medzihradsky, F. (1996) Characterization of opioid agonist efficacy in a C6 glioma cell line expressing the mu opioid receptor. J. Pharmacol. Exp. Ther. 278, 1121-1127.
11. 11. Clark, M.J., Emmerson, P.J., Mansour, A. et al. (1997) Opioid efficacy in a C6 glioma cell line stably expressing the delta opioid receptor. J. Pharmacol. Exp. Ther. 283, 501-510.
12. 12. Clark, M.J., Carter, B.D. & Medzihradsky, F. (1988) Selectivity of ligand binding to opioid receptors in brain membranes from the rat, monkey and guinea pig. Eur. J. Pharmacol. 148, 343-351.
13. 13. Medzihradsky, F., Dahlstrom, P.J., Woods, J.H., Fischel, S.V. & Mitsos, S.E. (1984) Resolution in the receptor binding of putative mu and kappa opiates. Life Sci. 34, 2129-2138.
14. 14. Munson, P.J. & Rodbard, D. (1980) Ligand: a versatile computerized approach for characterization of ligand-binding systems. Anal. Biochem. 107, 220-239.
15. 50) of an enzymatic reaction. Biochem. Pharmacol. 22, 3099-3108.
16. 16. Pogozheva, I.D., Lomize, A.L. & Mosberg, H.I. (1998) Opioid receptor three-dimensional structures from distance geometry calculations with hydrogen bonding constraints. Biophys. J. 75, 612-634.
17. 17. Ho, J.C., Mousigian, C. & Mosberg, H.I. (1999) Elucidation of the conformational features within a series of tetrapeptides which determine the selective recognition of mu versus delta opioid receptors. In Peptides. Frontiers of Peptide Science. Proceedings of the 15th American Peptide Symposium (Tam, J.P. & Kaumaya, P.T.P., eds). Kluwer Academic Publishers, Dordrecht, The Netherlands, pp. 629-630.
18. 18. Mosberg, H.I., Dua, R.K., Pogozheva, I.D. & Lomize, A.L. (1996) Development of a model for the delta opioid receptor pharmacophore. 4. Residue 3 dehydrophenylalanine analogues of Tyr-c[D-Cys-Phe-D-Pen]OH (JOM-13) confirm required gauche orientation of aromatic side chain. Biopolymers 39, 287-296.