Effect of a novel selective and potent phosphinic peptide inhibitor of endopeptidase 3.4.24.16 on neurotensin-induced analgesia and neuronal inactivation

British Journal of Pharmacology

Volumn 121, Issue 4, 1997, Pages 705-710

  Vincent, Bruno ^a   Jiracek, Jirì ^b,d   Noble, Florence ^c   Loog, Mart ^a,e   Roques, Bernard ^c   Dive, Vincent ^b   Vincent, Jean Pierre ^a   Checler, Frédéric ^a  

^a INSTITUT DE PHARMACOLOGIE MOLÉCULAIRE ET CELLULAIRE   (France)

^b DIF   (France)

^c INSERM   (France)

^d INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^e UNIVERSITY OF TARTU   (Estonia)

Author keywords

Analgesia; Chemistry; Combinatorial; Inactivation; Neurons; Neurotensin; Peptidase inhibitor; Phosphinic peptide

Indexed keywords

AMINOPEPTIDASE; DIPEPTIDYL PEPTIDASE IV; NEUROTENSIN; PROLYL ENDOPEPTIDASE; PROTEINASE INHIBITOR;

ANALGESIA; ANIMAL CELL; ANIMAL TISSUE; ARTICLE; ENZYME INHIBITION; MOUSE; NERVE CELL; NONHUMAN; PRIORITY JOURNAL; RAT;

ANALGESIA; ANIMALS; MALE; METALLOENDOPEPTIDASES; MICE; NEURONS; NEUROTENSIN; OLIGOPEPTIDES; PEPTIDYL-DIPEPTIDASE A; PHOSPHINES; RATS;

EID: 0030958889     PISSN: 00071188     EISSN: None     Source Type: Journal    
DOI: 10.1038/sj.bjp.0701182     Document Type: Article

References (38)

1. BARELLI, H., DIVE, V., YIOTAKIS, A., VINCENT, J.P. & CHECLER, F. (1992). Potent inhibition of endopeptidase 24.16 and endopeptidase 24.15 by the phosphonamide peptide N-(phenylethylphosphonyl)-Gly-LPro-L-aminohexanoic acid. Biochem. J., 287, 621-625.
2. BARELLI, H., FOX-THRELKELD, J.E.T., DIVE, V., DANIEL, E.E., VINCENT, J.P. & CHECLER, F. (1994). Role of endopeptidase 3.4.24.16 in the catabolism of neurotensin, in vivo, in the vascularly perfused dog ileum. Br. J. Pharmacol., 112, 127-132.
3. BARELLI, H., VINCENT, J.P. & CHECLER, F. (1991). Rat brain endopeptidase 24-15: specificity towards opioids, tachykinins and neurotensin-related peptides. Comparison with the neurotensin degrading metallopeptidase endopeptidase 24-16. Neurochemistry, Life Sci. Adv., 10, 115-124.
4. BRADFORD, M.M. (1976). A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem., 72, 248-259.
5. CHABRY, J., CHECLER, F., VINCENT, J.P. & MAZELLA, J. (1990). Colocalization of neurotensin receptors and of the neurotensin-degrading enzyme endopeptidase 24-16 in primary cultures of neurones. J. Neurosci., 10, 3916-3921.
6. CHECLER, F. (1991). Peptidases and neuropeptide-inactivating mechanisms in the circulation and in the gastrointestinal tractus. In Neuropeptide Function in the Gastrointestinal Tract. ed. Daniel, E.D. pp. 273-307. Boston: CRC Press.
7. CHECLER, F. (1993). Neuropeptide-degrading peptidases. In Methods in Neurotransmitter and Neuropeptide Research. Part 2. ed. Nagatsu, T., Parvez, H., Naoi, M. & Parvez, S. pp. 375-418. Amsterdam: Elsevier Science Publishers.
8. CHECLER, F., BARELLI, H., KITABGI, P. & VINCENT, J.P. (1988). Neurotensin metabolism in various tissues from central and peripheral origins. Ubiquitous involvement of a novel neurotensin degrading metalloendopeptidase. Biochimie, 70, 75-82.
9. CHECLER, F., BARELLI, H. & VINCENT, J.P. (1989). Tissue distribution of a novel neurotensin-degrading metallopeptidase. An immunological approach using monospecific polyclonal antibodies. Biochem. J., 257, 549-554.
10. CHECLER, F., MAZELLA, J., KITABGI, P. & VINCENT, J.P. (1986a). High affinity receptor sites and rapid proteolytic inactivation of neurotensin in primary cultured neurons. J. Neurochem., 47, 1742-1748.
11. CHECLER, F., VINCENT, J.P. & KITABGI, P. (1986b). Purification and characterization of a novel neurotensin degrading peptidase from rat brain synaptic membranes. J. Biol. Chem., 261, 11274-11281.
12. CHECLER, F., VINCENT, J.P. & KITABGI, P. (1983). Degradation of neurotensin by rat brain synaptic membranes. Involvement of a thermolysin-like metalloendopeptidase (enkephalinase), angiotensin-converting enzyme and other unidentified peptidases. J. Neurochem., 41, 375-384.
13. CLINESCHMIDT, B.V., MCGUFFIN, J.V. & BUNTING, P.B. (1979). Neurotensin: antinocisponsive action in rodents. Eur. J. Pharmacol., 54, 129-139.
14. COQUEREL, A., DUBUC, I., KITABGI, P. & COSTENTIN, J.A. (1988). Potentiation by thiorphan and bestatin of the naloxone-insensitive analgesic effects of neurotensin and neuromedin N. Neurochem. Int., 12, 361-366.
15. COQUEREL, A., DUBUC, I., MENARD, J.F., KITABGI, P. & COSTENTIN, J. (1986). Naloxone-insensitive potentiation of neurotensin hypothermic effect by the enkephalinase inhibitor thiorphan. Brain Res., 398, 386-389.
16. DAUCH, P., BARELLI, H., VINCENT, J.P. & CHECLER, F. (1991a). Fluorimetric assay of the neurotensin-degrading metalloendopeptidase, endopeptidase 24-16. Biochem. J., 280, 412-426.
17. DAUCH, P., VINCENT, J.P. & CHECLER, F. (1991b). Specific inhibition of endopeptidase 24.16 by dipeptides. Eur. J. Biochem., 202, 269-276.
18. DAVIS, T.P., GILLESPIE, T.J. & KONINGS, P.N.M. (1992). Specificity of neurotensin metabolism by regional rat brain slices. J. Neurochem., 58, 608-617.
19. EDDY, N.B. & LEIMBLACH, D. (1991). Synthetic analgesics (11): dithienylbutenyl and dithienylbutylamines. J. Pharmacol. Exp. Ther., 107, 385-393.
20. HUGGINS, C.G. & THAMPI, N.S. (1968). A simple method for the determination of angiotensin I converting enzyme. Life Sci., 7, 633-639.
21. JIRÀCEK, J., YIOTAKIS, A., VINCENT, B., CHECLER, F. & DIVE, V. (1996). Development of the first potent and selective inhibitor of the zinc-endopeptidase 3.4.24.16 using a systematic approach based on combinatorial chemistry of phosphinic peptides. J. Biol. Chem., 271, 19606-19611.
22. KITABGI, P. (1989). Neurotensin modulates dopamine neurotransmission at several levels along brain dopaminergic pathways. Neurochem. Int., 14, 111-119.
23. KITABGI, P., DUBUC, I., NOUEL, D., COSTENTIN, J., CUBER, J.-C., FULCRAND, H., DOULUT, S., RODRIGUEZ, M. & MARTINEZ, J. (1992). Effects of thiorphan, bestatin and a novel metallopeptidase inhibitor JMV 390-1 on the recovery of neurotensin and neuromedin N released from mouse hypothalamus. Neurosci. Lett., 142, 200-204.
24. KONKOY, C.S., WATERS, S.M. & DAVIS, T.P. (1994). Acute administration of neuroleptics decreases neurotensin metabolism on intact, regional rat brain slices. J. Pharmacol. Exp. Ther., 269, 555-563.
25. LITTLEWOOD, G.M., IVERSEN, L.L. & TURNER, A.J. (1988). Neuropeptides and their peptidases: functional considerations. Neurochem. Int., 12, 383-389.
26. MCKELVY, J.F. & BLUMBERG, S. (1986). Inactivation and metabolism of neuropeptides. Ann. Rev. Neurosci., 9, 415-434.
27. MENTLEIN, R. & DAHMS, P. (1994). Endopeptidases 24.16 and 24.15 are responsible for the degradation of somatostatin, neurotensin and other neuropeptides by cultivated rat cortical astrocytes. J. Neurochem., 62, 27-36.
28. MEUNIER, J.C., MOLLEREAU, C., TOLL, L., SUAUDEAU, C., MOISAND, C., ALVINERIE, P., BUTOUR, J.L., GUILLEMOT, J.C., FERRARA, P., MONSARRAT, B., MAZARGUIL, H., VASSART, G., PARMENTIER, M. & COSTENTIN, J. (1995). Isolation and structure of the endogenous agonist of opioid receptor-like ORL1 receptor. Nature, 377, 532-535.
29. MONTIEL, J.L., CORNILLE, F., ROQUES, B.P. & NOBLE, F. (1997). Nociceptin/orphanin FQ metabolism. Role of aminopeptidase and endopeptidase 3.4.24.15. J. Neurochem., 68, 354-361.
30. NEMEROFF, C.B., LUTTINGER, D. & PRANGE, A.J. (1980). Neurotensin: central nervous system effects of a neuropeptide. Trends Neurosci., 3, 212-215.
31. ONDETTI, M.A., RUBIN, B. & CUSHMAN, D.W. (1977). Design of specific inhibitors of angiotensin-converting enzyme: new class of orally antihypertensive agents. Science, 196, 441-444.
32. REINSCHEID, R.K., NOTHACKER, H.P., BOURSON, A., ARDATI, A., HENNINGSEN, R.A., BUNZOW, J.R., GRANDY, D.K., LANGEN, H., MONSMA, Jr, F.J. & CIVELLI, O. (1995). Orphanin FQ: a neuropeptide that activates an opioid-like G protein-coupled receptor. Science, 270, 792-794.
33. SCHMIDT, C., PHYROUX, J., NOBLE, F., FOURNIÉ-ZALUSKI, M.C. & ROQUES, B.P. (1991). Analgesic responses elicited by endogenous enkephalins (protected by mixed peptidase inhibitors) in a variety of morphine-sensitive noxious tests. Eur. J. Pharmacol., 192, 253-262.
34. TURNER, A.J., MATSAS, R. & KENNY, A.J. (1985). Are there neuropeptide-specific peptidases? Biochem. Pharmacol., 34, 1347-1356.
35. VINCENT, B., BEAUDET, A., DAUCH, P., VINCENT, J.P. & CHECLER, F. (1996). Distinct properties of neuronal and astrocytic endopeptidase 3.4.24.16: a study on differentiation, subcellular distribution and secretion processes. J. Neurosci., 16, 5049-5059.
36. VINCENT, B., DIVE, V., YIOTAKIS, A., SMADJA, C., MALDONADO, R., VINCENT, J.P. & CHECLER, F. (1995). Phosphorus-containing peptides as mixed inhibitors of endopeptidase 3.4.24.15 and 3.4.24.16: effect on neurotensin degradation in vitro and in vivo. Br. J. Pharmacol., 115, 1053-1063.
37. VINCENT, B., VINCENT, J.P. & CHECLER, F. (1994). Neurotensin and neuromedin N undergo distinct catabolic processes in astrocytes and primary cultured neurons. Eur. J. Biochem., 221, 297-306.
38. YIOTAKIS, A., VASSILOU, S., JIRACEK, J. & DIVE, V. (1996). Protection of hydroxyphosphinyl function of phosphinic dipeptides by adamantyl. Application to the solid-phase synthesis of phosphinic peptides. J. Org. Chem., 61, 6601-6605.