Characterization of the effects of opiorphin and sialorphin and their analogs substituted in position 1 with pyroglutamic acid on motility in the mouse ileum

Journal of Peptide Science

Volumn 19, Issue 3, 2013, Pages 166-172

  Kamysz, Elzbieta ^a   Salaga, Maciej ^b   Sobczak, Marta ^b   Kamysz, Wojciech ^c   Fichna, Jakub ^b  

^a MEDICAL UNIVERSITY OF LODZ   (Poland)

^b UNIVERSITY OF GDA SK   (Poland)

^c MEDICAL UNIVERSITY OF GDANSK   (Poland)

Author keywords

Animal models of gastrointestinal motility; Enkephalins; Mouse ileum; Opiorphin; Sialorphin; Structure activity relationship studies

Indexed keywords

DELTA OPIATE RECEPTOR; ENZYME INHIBITOR; METENKEPHALIN; OPIORPHIN; PYROGLUTAMIC ACID; SIALORPHIN; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; DRUG EFFECT; DRUG SYNTHESIS; ELECTRIC FIELD; GASTROINTESTINAL MOTILITY; GASTROINTESTINAL TRANSIT; ILEUM CONTRACTION; ILEUM MOTILITY; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; SMOOTH MUSCLE CONTRACTILITY; SOLID PHASE SYNTHESIS;

ANIMALS; DOSE-RESPONSE RELATIONSHIP, DRUG; GASTROINTESTINAL TRANSIT; ILEUM; MALE; MICE; MICE, INBRED C57BL; MUSCLE CONTRACTION; MUSCLE, SMOOTH; OLIGOPEPTIDES; PROTEIN PRECURSORS; RATS; SALIVARY PROTEINS AND PEPTIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

ANIMALIA;

EID: 84874019775     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.2486     Document Type: Article

References (28)

1. Hughes J, Smith TW, Kosterlitz HW, Fothergill LA, Morgan BA, Morris HR. Identification of two related pentapeptides from the brain with potent opiate agonist activity. Nature 1975; 258: 577-580.
2. Noble F, Smadja C, Valverde O, Maldonado R, Coric P, Turcaud S, Fournie-Zaluski MC, Roques BP. Pain-suppressive effects on various nociceptive stimuli (thermal, chemical, electrical and inflammatory) of the first orally active enkephalin-metabolizing enzyme inhibitor RB 120. Pain 1997; 73: 383-391.
3. Jutkiewicz EM. RB101-mediated protection of endogenous opioids: potential therapeutic utility? CNS Drug Rev. 2007; 13: 192-205.
4. Fournie-Zaluski MC, Chaillet P, Bouboutou R, Coulaud A, Cherot P, Waksman G, Costentin J, Roques BP. Analgesic effects of kelatorphan, a new highly potent inhibitor of multiple enkephalin degrading enzymes. Eur. J. Pharmacol. 1984; 102: 525-528.
5. Fournie-Zaluski MC, Coric P, Turcaud S, Lucas E, Noble F, Maldonado R, Roques BP. "Mixed inhibitor-prodrug" as a new approach toward systemically active inhibitors of enkephalin-degrading enzymes. J. Med. Chem. 1992; 35: 2473-2481.
6. Noble F, Soleilhac JM, Soroca-Lucas E, Turcaud S, Fournie-Zaluski MC, Roques BP. Inhibition of the enkephalin-metabolizing enzymes by the first systemically active mixed inhibitor prodrug RB 101 induces potent analgesic responses in mice and rats. J. Pharmacol. Exp. Ther. 1992; 261: 181-190.
7. Kayser V, Fournie-Zaluski MC, Guilbaud G, Roques BP. Potent antinociceptive effects of kelatorphan (a highly efficient inhibitor of multiple enkephalin-degrading enzymes) systemically administered in normal and arthritic rats. Brain Res. 1989; 497: 94-101.
8. Maldonado R, Feger J, Fournie-Zaluski MC, Roques BP. Differences in physical dependence induced by selective mu or delta opioid agonists and by endogenous enkephalins protected by peptidase inhibitors. Brain Res. 1990; 520: 247-254.
9. Noble F, Coric P, Fournie-Zaluski MC, Roques BP. Lack of physical dependence in mice after repeated systemic administration of the mixed inhibitor prodrug of enkephalin-degrading enzymes, RB101. Eur. J. Pharmacol. 1992; 223: 91-96.
10. Noble F, Turcaud S, Fournie-Zaluski MC, Roques BP. Repeated systemic administration of the mixed inhibitor of enkephalin-degrading enzymes, RB101, does not induce either antinociceptive tolerance or cross-tolerance with morphine. Eur. J. Pharmacol. 1992; 223: 83-89.
11. Maldonado R, Dauge V, Callebert J, Villette JM, Fournie-Zaluski MC, Feger J, Roques BP. Comparison of selective and complete inhibitors of enkephalin-degrading enzymes on morphine withdrawal syndrome. Eur. J. Pharmacol. 1989; 165: 199-207.
12. Wisner A, Dufour E, Messaoudi M, Nejdi A, Marcel A, Ungeheuer MN, Rougeot C. Human opiorphin, a natural antinociceptive modulator of opioid-dependent pathways. Proc. Natl. Acad. Sci. U.S.A. 2006; 103: 17979-17984.
13. Rougeot C, Messaoudi M, Hermitte V, Rigault AG, Blisnick T, Dugave C, Desor D, Rougeon F. Sialorphin, a natural inhibitor of rat membrane-bound neutral endopeptidase that displays analgesic activity. Proc. Natl. Acad. Sci. U.S.A. 2003; 100: 8549-8554.
14. Tian XZ, Chen J, Xiong W, He T, Chen Q. Effects and underlying mechanisms of human opiorphin on colonic motility and nociception in mice. Peptides 2009; 30: 1348-1354.
15. Rougeot C, Robert F, Menz L, Bisson JF, Messaoudi M. Systemically active human opiorphin is a potent yet non-addictive analgesic without drug tolerance effects. J. Physiol. Pharmacol. 2010; 61: 483-490
16. Javelot H, Messaoudi M, Garnier S, Rougeot C. Human opiorphin is a naturally occurring antidepressant acting selectively on enkephalin-dependent delta-opioid pathways. J. Physiol. Pharmacol. 2010; 61: 355-362.
17. Davies KP, Tar M, Rougeot C, Melman A. Sialorphin (the mature peptide product of Vcsa1) relaxes corporal smooth muscle tissue and increases erectile function in the ageing rat. BJU Int. 2007; 99: 431-435.
18. Thanawala V, Kadam VJ, Ghosh R. Enkephalinase inhibitors: potential agents for the management of pain. Curr. Drug Targets 2008; 9: 887-894.
19. Rosa M, Arsequell G, Rougeot C, Calle LP, Marcelo F, Pinto M, Centeno NB, Jimenez-Barbero J, Valencia G. Structure-activity relationship study of opiorphin, a human dual ectopeptidase inhibitor with antinociceptive properties. J. Med. Chem. 2012; 55: 1181-1188.
20. Seebach D, Lukaszuk A, Patora-Komisarska K, Podwysocka D, Gardiner J, Ebert MO, Reubi JC, Cescato R, Waser B, Gmeiner P, Hubner H, Rougeot C. On the terminal homologation of physiologically active peptides as a means of increasing stability in human serum - neurotensin, opiorphin, B27-KK10 epitope, NPY. Chem. Biodivers. 2011; 8: 711-739.
21. Barlos K, Chatzi O, Gatos D, Stavropoulos G. 2-Chlorotrityl chloride resin. Studies on anchoring of Fmoc-amino acids and peptide cleavage. Int. J. Pept. Protein Res. 1991; 37: 513-520.
22. Friligou I, Papadimitriou E, Gatos D, Matsoukas J, Tselios T. Microwave-assisted solid-phase peptide synthesis of the 60-110 domain of human pleiotrophin on 2-chlorotrityl resin. Amino Acids 2011; 40: 1431-1440.
23. Rizzolo F, Testa C, Lambardi D, Chorev M, Chelli M, Rovero P, Papini AM. Conventional and microwave-assisted SPPS approach: a comparative synthesis of PTHrP(1-34)NH(2). J. Pept. Sci. 2011; 17: 708-714.
24. Palasek SA, Cox ZJ, Collins JM. Limiting racemization and aspartimide formation in microwave-enhanced Fmoc solid phase peptide synthesis. J. Pept. Sci. 2007; 13: 143-148.
25. Davies KP. The role of opiorphins (endogenous neutral endopeptidase inhibitors) in urogenital smooth muscle biology. J. Sex. Med. 2009; 6(Suppl 3): 286-291.
26. Riviere PJ, Liberge M, Murillo-Lopez D, Bueno L. Opposite central and peripheral control by endogenous opioids of intestinal motility in fed rats. Br. J. Pharmacol. 1989; 98: 236-242.
27. Cummins PM, O'Connor B. Pyroglutamyl peptidase: an overview of the three known enzymatic forms. Biochim. Biophys. Acta 1998; 1429: 1-17.
28. Albert Z, Szewczuk A. Pyrrolidonyl peptidase in some avian and rodent tissues. Histochemical localization and biochemical studies. Acta Histochem. 1972; 44: 98-105.