Development and validation of opioid ligand-receptor interaction models: The structural basis of mu vs. delta selectivity

Journal of Peptide Research

Volumn 60, Issue 6, 2002, Pages 329-335

  Mosberg, Henry I ^a   Fowler, C B ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

Docking; GPCR; Opioid peptides; Opioid receptor; Receptor selectivity

Indexed keywords

DELTA OPIATE RECEPTOR; MU OPIATE RECEPTOR; TETRAPEPTIDE;

ARTICLE; CONFORMATIONAL TRANSITION; DRUG BINDING SITE; DRUG CONFORMATION; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; LIGAND BINDING; PRIORITY JOURNAL; RECEPTOR AFFINITY;

BINDING SITES; BINDING, COMPETITIVE; ENKEPHALINS; LIGANDS; MODELS, MOLECULAR; MUTAGENESIS, SITE-DIRECTED; PEPTIDES, CYCLIC; PHENYLALANINE; PROTEIN BINDING; PROTEIN CONFORMATION; RADIOLIGAND ASSAY; RECEPTORS, OPIOID, DELTA; RECEPTORS, OPIOID, MU; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 0036945574     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.2002.21061.x     Document Type: Article

References (22)

1. Mosberg, H.I., Hurst, R., Hruby, V.J., Gee, K., Yamamura, H.I., Galligan, J.J. & Burks, T.F. (1983) Bis-penicillamine enkephalins: highly improved specificity toward delta opioid receptors. Proc. Natl Acad. Sci. USA 80, 5871-5874.
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 enhanced delta opioid receptor selectivity and potency. Life Sci. 43, 1013-1020.
3. 1H NMR data. J. Am. Chem. Soc. 116, 429-436.
4. 1 replacements in the cyclic δ receptor selective tetrapeptide Tyr-c[D-Cys-Phe-D-Pen]OH (JOM-13). J. Med. Chem. 37, 4371-4383.
5. 3 replacements in the cyclic δ receptor selective tetrapeptide Tyr-c[D-Cys-Phe-D-Pen]OH (JOM-13). J. Med. Chem. 37, 4384-4391.
6. Mosberg, H.I., Dua, R.K., Pogozheva, I.D. & Lomize, A.L. (1996) Development of a model for the δ opioid receptor pharmacophore. 4. Residue 3 dehydrophenyl-alanine analogues of Tyr-c[D-Cys-Phe-D-Pen]OH (JOM-13) confirm required gauche orientation of aromatic sidechain. Biopolymers 38, 221-234.
7. Ho, J.C. (1997) Development of a model for the μ opioid receptor pharmacophore. PhD Thesis, University of Michigan.
8. Pogozheva, I.D., Lomize, A.L. & Mosberg, H.I. (1997) The transmembrane 7-a-bundle of rhodopsin: distance geometry calculation with hydrogen bonding constraints. Biophys. J. 72, 1963-1985.
9. Pogozheva, I.D., Lomize, A.L. & Mosberg, H.I. (1998) Three-dimensional structures of opioid receptors from distance geometry using hydrogen bonding constraints. Biophys. J. 75, 612-634.
10. Lomize, A.L., Pogozheva, I.D. & Mosberg, H.I. (1999) Structural organization of G protein-coupled receptors. J. Computer-Aided Mol. Design 13, 1-29.
11. Bourne, H.R. & Meng, E.C. (2000) Rhodopsin sees the light. Science 289, 733-734.
12. Palczewski, K., Kumasaka, T., Hori, T., Behnke, C.A., Motoshima, H., Fox, B.A., Le Trong, I., Teller, D.C., Okada, T., Stenkamp, R.E., Yamamoto, M. & Miyano, M. (2000) Crystal structure of rhodopsin: a G protein-coupled receptor. Science 289, 739-745.
13. Kobilka, B., Gether, U., Seifert, R., Lin, S. & Ghanouni, P. (1998) Examination of ligand-induced conformational changes in the beta2 adrenergic receptor. Life Sci. 62, 1509-1512.
14. Gether, U., Lin, S., Ghanouni. P., Ballesteros, J.A., Weinstein, H. & Kobilka, B.K. (1997) Agonists induce conformational changes in transmembrane domains III and VI of the beta2 adrenoceptor. EMBO J. 16, 6737-6747.
15. Farrens, D.L., Altenbach, C., Yang, K., Hubbell, W.L. & Khorana, H.G. (1996) Requirement of rigid-body motion of transmembrane helices for light activation of rhodopsin. Science 274, 768-770.
16. Befort, K., Tabbara, L.P., Bausch, S., Chavkin, C., Evans, C. & Kieffer, B.L. (1996) 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.
17. Befort, K., Tabbara, L.P., Kling, D., Maigret, B. & Kieffer, B.L. (1996) Role of aromatic transmembrane residues of the δ-opioid receptor in ligand recognition. J. Biol. Chem. 271, 10161-10168.
18. Surratt, C.K., Johnson, P.S., Moriwaki, A., Seidleck, B.K., Blaschak, C.J., Wang, J.B. & Uhl, G.R. (1994) Opiate receptor. Charged transmembrane domain amino acids are criticai for agonist recognition and intrinsic activity. J. Biol. Chem. 269, 20548-20553.
19. Mansour, A., Taylo, R.L.P., Fine, J.L., Thompson, R.C., Hoversten, M.T., Mosberg, H.I., Watson, S.J. & Akil, H. (1997) Key residues defining the mu-opioid receptor binding pocket: a site-directed mutagenesis study. J. Neurochem. 68, 344-353.
20. Befort, K., Zilliox, C., Filliol, D., Yue, S. & Kieffer, B.L. (1999) Constitutive activation of the delta opioid receptor by mutations in transmembrane domains III and VII. J. Biol. Chem 274, 28058-28066.
21. Mansour, A., Hoversten, M.T., Taylor, L.P., Watson, S.J. & Akil, H. (1995) The cloned mu, delta and kappa receptors and their endogenous ligands: evidence for two opioid peptide recognition cores. Brain Res. 700, 89-98.
22. 50) of an enzymatic reaction. Biochem. Pharmacol. 22, 3099-3108.