Deltorphin analogs restricted via a urea bridge: Structure and opioid activity

Journal of Peptide Science

Volumn 14, Issue 7, 2008, Pages 830-837

  Zieleniak, Agnieszka ^a   Rodziewicz Motowidło, Sylwia ^b   Rusak, Łukasz ^b   Chung, Nga N ^c   Czaplewski, Cezary ^b   Witkowska, Ewa ^a   Schiller, Peter W ^c   Ciarkowski, Jerzy ^b   Izdebski, Jan ^a  

^a UNIVERSITY OF WARSAW   (Poland)

^b UNIVERSITY OF GDA SK   (Poland)

^c CLIN RESEARCH INSTITUTE OF MONTREAL   (Canada)

Author keywords

Conformation; Deltorphin; NMR; Opioid cyclopeptides; SAR

Indexed keywords

DELTORPHIN; DELTORPHIN DERIVATIVE;

ANIMAL TISSUE; ARTICLE; DRUG ACTIVITY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; GUINEA PIG; ILEUM; MOLECULAR DYNAMICS; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; VAS DEFERENS;

ANALGESICS, OPIOID; ANIMALS; COMPUTER SIMULATION; ILEUM; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OLIGOPEPTIDES; STRUCTURE-ACTIVITY RELATIONSHIP; SWINE; UREA;

CAVIA;

EID: 48249117533     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1010     Document Type: Article

References (24)

1. Espamer V, Melchiorri P, Falconieri-Erspamer G, Negri L, Corsi R, Severini C, Barra D, Simmaco M, Krell G. Deltorphins: a family of naturally occurring peptides with high affinity and selectivity for delta opioid binding sites. Proc. Natl. Acad. Sci. U.S.A. 1989; 86: 5188-5192.
2. Montecucchi PC, de Castiglione R, Piani S, Gozzini L, Erspamer V. Amino acid composition and sequence of dermorphin, a novel opiate-like peptide from the skin of Phyllomedusa sauvagei. Int. J. Pept. Protein Res. 1981; 17: 275-283.
3. Filip K, Oleszczuk M, Pawlak D, Wójcik J, Chung NN, Schiller PW, Izdebski J. Potent side-chain to side-chain cyclized dermorphin analogues containing a carbonyl bridge. J. Pept. Sci. 2003; 9: 649-657.
4. Filip K, Oleszczuk M, Wójcik J, Chung NN, Schiller PW, Pawlak D, Zieleniak A, Parcińska A, Witkowska E, Izdebski J. Cyclic enkephalin and dermorphin analogues containing a carbonyl bridge. J. Pept. Sci. 2005; 11: 347-352.
5. Witkowska E, Nowakowski M, Oleszczuk M, Filip K, Ciszewska M, Chung NN, Schiller PW, Wójcik J, Izdebski J. Ureido group containing cyclic dermorphin(1-7) analogues: synthesis, biology and conformation. J. Pept. Sci. 2007; 13: 519-528.
6. Paton WDM. The action of morphine and related substances on contraction and on acetylcholine output of coaxially stimulated guinea pig ileum. Br. J. Pharmacol. 1957; 12: 119-127.
7. Henderson G, Hughes J, Kosterlitz H. A new example of a morphine sensitive neuroeffector junction. Br. J. Pharmacol. 1972; 46: 764-766.
8. Schiller PW, Lipton A, Horrobin DF, Bodanszky M. Unsulfated C-terminal 7-peptide of cholecystokinin: a new ligand of the opiate receptor. Biochem. Biophys. Res. Commun. 1978; 85: 1332-1338.
9. DiMaio J, Schiller PW. A Cyclic enkephalin analog with high in vivo opiate activity. Proc. Natl. Acad. Sci. U.S.A. 1980; 77: 7162-716X.
10. 65-analogue. Eur. J. Pharmacol. 1979; 58: 11-18.
11. Bartles C, Xia T, Billeter M, Günter P, Wütrich K. The program XEASY for the computer-supperted NMR spectral analysis of biological macromolecules. J. Biomol. NMR 1995; 6: 1-10.
12. Case DA, Darden TA. Cheatham TE III, Simmerling CL, Wang J, Duke RE, Luo K, Merz KM, Wang B, Pearlman DA, Crowley M, Brozell S, Tsui V, Gohlke H, Mongan J, Hornak V, Cui G, Beroza P, Schafmeister C, Caldwell JW, Ross WS, Kollman PA. AMBER 8. University of California: San Francisco, CA, 2004.
13. Schmidt MW, Baldridge KK, Boatz JA, Elbert ST, Gordon MS, Jensen JH, Koseki S, Matsunaga N, Nguyen KA, Su S, Windus TL, Dupuis M, Montgomery JA. General atomic and molecular electronic structure system. J. Comp. Chem. 1993; 14: 1347-1363.
14. Pigache A, Cieplak P, Dupradeau F-Y. Automatic and highly reproducible RESP and ESP charge derivation: application to the development of programs RED and XRED. In 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004.
15. Allen FH. The Cambridge structural database: a quarter of a million crystal structures and rising. Acta Cryst. 2002, B58, 380-388.
16. Pearlman DA. How is an NMR structure best defined? An analysis of molecular dynamics distance-based approaches. J. Biomol. NMR 1994; 4: 1-16.
17. Essmann U, Perera L, Berkowitz ML, Darden T, Lee H, Pedersen LG. A smooth particle mesh Ewald method. J. Chem. Phys. 1995; 103: 8577-8593.
18. Koradi K, Billeter M, Wüthrich K. MOLMOL: a program for display and analysis of macromolecular structures. J. Mol. Graphics 1996; 14: 52-55.
19. Shendrovich MD, Liao S, Qian X, Hruby VJ. A three-demensional model of the δ - opioid pharmacophore: comparative molecular modelling of peptide and nonpeptide ligands. Biopolymers 2000; 53: 565-580.
20. Wu Y-C, Lin J-S, Hwang C-C. Structure - activity relationships of αS1-casomorphin using AM1 calculations and molecular dynamics simulations. J. Phys. Chem. B 2007; 111: 7377-7383.
21. Nikiforovich GV, Hruby VJ, Parakash OM, Gehrig CA. Topographical requirements for δ-selective opioid-peptides. Biopolymers 1991; 31: 941-955.
22. Malicka J, Czaplewski C, Groth M, Wiczk W, Oldziej S, Łankiewicz L, Ciarkowski J, Liwo A. Use of NMR and fluorescence spectroscopy as well as theoretical conformational analysis in conformation-activity studies of cyclic enkephalin analogues. Curr. Top. Med. Chem. 2004; 4: 123-133.
23. Nikiforovich GV, Balodis J, Shenderovich MD, Golbraikh AA. Conformational features responsible for binding of cyclic analogs of enkephalin to opioid receptors. Int. J. Pept. Protein Res. 1990; 34: 88-96.
24. Mierke DF, Lucietto P, Schiller PW, Goodman M. Conformational studies of diastereoisomeric cyclic enkephalins by 1H-NMR and computer simulations. Biopolymers 1987; 26: 1573-1586.