Synthesis and biological activity of endomorphin-2 analogs incorporating piperidine-2-, 3- or 4-carboxylic acids instead of proline in position 2

Chemical Biology and Drug Design

Volumn 72, Issue 1, 2008, Pages 91-94

  Staniszewska, Renata ^a   Fichna, Jakub ^a   Gach, Katarzyna ^a   Toth, Geza ^b   Poels, Jeroen ^c   Vanden Broeck, Jozef ^c   Janecka, Anna ^a  

^a MEDICAL UNIVERSITY OF LODZ   (Poland)

^b INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

^c UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

receptor agonist; Binding studies; Calcium based functional assay; Enzymatic degradation; Unnatural amino acids

Indexed keywords

AEQUORIN; CALCIUM; CARBOXYLIC ACID DERIVATIVE; DELTORPHIN 2; ENDOMORPHIN 2; ENDOMORPHIN 2 DERIVATIVE; ENDORPHIN DERIVATIVE; ISONIPECOTIC ACID; MU OPIATE RECEPTOR; NIPECOTIC ACID 2 ENDOMORPHIN 2; PIPERIDINE 2 CARBOXYLIC ACID; PIPERIDINE 3 CARBOXYLIC ACID; PROLINE;

ANIMAL TISSUE; ARTICLE; ASSAY; BINDING AFFINITY; BIOLOGICAL ACTIVITY; BRAIN HOMOGENATE; CALCIUM CELL LEVEL; CONTROLLED STUDY; DRUG DEGRADATION; DRUG HALF LIFE; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; IC 50; LUMINESCENCE; NONHUMAN; PRIORITY JOURNAL; RAT;

AMINO ACID SUBSTITUTION; ANIMALS; BRAIN CHEMISTRY; CARBOXYLIC ACIDS; INHIBITORY CONCENTRATION 50; OLIGOPEPTIDES; PIPERIDINES; PROLINE; RATS; RECEPTORS, OPIOID, MU;

RATTUS;

EID: 45449111798     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2008.00678.x     Document Type: Article

References (13)

1. Zadina J.E., Hackler L., Ge L.J., Kastin A.J. (1997) A potent and selective endogenous agonist for the mu-opiate receptor. Nature 386: 499 502.
2. Janecka A., Staniszewska R., Fichna J. (2007) Endomorphin analogs. Curr Med Chem 14: 3201 3208.
3. Yamazaki T., Ro S., Goodman M., Chung N.N., Schiller P.W. (1993) A topochemical approach to explain morphiceptin bioactivity. J Med Chem 36: 708 719.
4. Podlogar B.L., Paterlini M.G., Ferguson D.M., Leo G.C., Demeter D.A., Brown F.K., Reitz A.B. (1998) Conformational analysis of the endogenous mu-opioid agonist endomorphin-1 using NMR spectroscopy and molecular modeling. FEBS Lett 439: 13 20.
5. Schiller P.W., Weltrowska G., Berezowska I., Nguyen T.M., Wilkes B.C., Lemieux C., Chung N.N. (1999) The TIPP opioid peptide family: development of delta antagonists, delta agonists, and mixed mu agonist/delta antagonists. Biopolymers 51: 411 425.
6. Cardillo G., Gentilucci L., Melchiorre P., Spampinato S. (2000) Synthesis and binding activity of endomorphin-1 analogues containing beta-amino acids. Bioorg Med Chem Lett 10: 2755 2758.
7. Doi M., Asano A., Komura E., Ueda Y. (2002) The structure of an endomorphin analogue incorporating 1-aminocyclohexane-1-carboxlylic acid for proline is similar to the beta-turn of Leu-enkephalin. Biochem Biophys Res Commun 297: 138 142.
8. Toth G., Keresztes A., Tomboly C., Peter A., Fulop F., Tourwe D., Navratilowa E., Varga E., Roeske W.R., Yamamura H.I., Szucs M., Borsodi A. (2004) New endomorphin analogs with mu;-agonist andδ-antagonist properties. Pure Appl Chem 76: 951 957.
9. Tsuda Y., Kawakami T., Yamada T., Isozaki K., Shimohigashi Y., Ambo A., Sasaki Y., Okada Y. (2006) Synthesis and biological activity of endomorphin-2 analogues containing Pro mimics. Proc 42nd Japanese Pept Symposium Pept Sci 43: 321.
10. Fichna J., do-Rego J.C., Chung N.N., Lemieux C., Schiller P.W., Poels J., Vanden Broeck J., Costentin J., Janecka A. (2007) Synthesis and characterization of potent and selective mu-opioid receptor antagonists, [Dmt(1), D-2-Nal(4)]endomorphin-1 (Antanal-1) and [Dmt(1), D-2-Nal(4)] endomorphin-2 (Antanal-2). J Med Chem 50: 512 520.
11. Fichna J., Janecka A., Bailly L., Marsais F., Costentin J., do-Rego J.C. (2006) In vitro characterization of novel peptide inhibitors of endomorphin-degrading enzymes in the rat brain. Chem Biol Drug Des 68: 173 175.
12. Sakurada S., Zadina J.E., Kastin A.J., Katsuyama S., Fujimura T., Murayama K., Yuki M., Ueda H., Sakurada T. (1999) Differential involvement of mu-opioid receptor subtypes in endomorphin-1- and -2-induced antinociception. Eur J Pharmacol 372: 25 30.
13. Paterlini M.G., Avitabile F., Ostrowski B.G., Ferguson D.M., Portoghese P.S. (2000) Stereochemical requirements for receptor recognition of the mu-opioid peptide endomorphin-1. Biophys J 78: 590 599.