A review of the design, synthesis and biological activity of the bicyclic hexapeptide tachykinin NK2 antagonist MEN 10627

Regulatory Peptides

Volumn 65, Issue 1, 1996, Pages 55-59

  Quartara, Laura ^a   Pavone, Vincenzo ^b   Pedone, Carlo ^b   Lombardi, Angelina ^b   Renzetti, Anna Rita ^c   Maggi, Carlo Alberto ^a  

^a Menarini Ricerche SpA   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^c Laboratori Guidotti SpA   (Italy)

Author keywords

Conformation; Cyclization; Drug delivery; In vivo activity; Metabolic stability; Selectivity

Indexed keywords

CYCLO(GLUTAMINYLTRYPTOPHYLPHENYLALANYLGLYCYLLEUCYLMETHIONYL); MEN 10627; NEUROKININ A DERIVATIVE; SAREDUTANT; TACHYKININ RECEPTOR ANTAGONIST;

ANIMAL TISSUE; BLADDER; CONTROLLED STUDY; DRUG ACTIVITY; HAMSTER; HUMAN; HUMAN TISSUE; ILEUM; INTRAGASTRIC DRUG ADMINISTRATION; INTRANASAL DRUG ADMINISTRATION; INTRAVENOUS DRUG ADMINISTRATION; NONHUMAN; PRIORITY JOURNAL; PULMONARY ARTERY; RABBIT; RAT; RECEPTOR BINDING; REVIEW;

ANIMALIA; CRICETINAE; ORYCTOLAGUS CUNICULUS;

EID: 0030603859     PISSN: 01670115     EISSN: None     Source Type: Journal    
DOI: 10.1016/0167-0115(96)00072-9     Document Type: Review

References (29)

1. [1] Gante, J., Peptidomimedcs-tailored enzyme inhibitors, Angew. Chem. Int. Ed. Engl., 33 (1994) 1699-1720.
2. [2] Otsuka, M. and Yoshioka, K., Neurotransmitter function of mammalian TKs, Physiol. Rev., 73 (1993) 229-307.
3. [3] Buck, S.H., Burcher, E., Shults, C.W., Lovenberg, W. and O'Donahue, M.H., Novel pharmacology of substance K binding sites: a third type of tachykinin receptor, Science, 226 (1984) 987-989.
4. [4] Masu, Y., Nakayama, K., Tamaki, H., Harada, Y., Kuno, M. and Nakanishi, S., cDNA cloning of bovine substance K receptor through oocyte expression system, Nature, 329 (1987) 836-838.
5. [5] Lee, C.M., Campbell, N.J., Williams, B.J. and Iversen, L.L., Multiple tachykinin binding sites in peripheral tissues and in brain, Eur. J. Pharmacol., 130 (1986) 209-217.
6. [6] Regoli, D., Drapeau, G., Dion, S. and d'Orleans-Juste, P., Pharmacological receptors for substance P and neurokinins, Life Sci., 40 (1987) 109-117.
7. [7] Maggi, C. A., Patacchini, R., Rovero, P and Giachetti, A., Tachykinin receptors and receptor antagonists, J. Auton. Pharmacol., 13 (1993) 23-93.
8. 2 receptor antagonists, Regul. Pept., 46 (1993) 9-19.
9. 2 tachykinin receptor in the mediation of spinal reflex excitability in the rat, Neuroscience, 44 (1991) 483-490.
10. [10] Nagy, I. Maggi, C.A., Dray, A., Woolf, C.J. and Urban, L., The role of neurokinins and NMDA receptors in synaptic transmission from capsaicin-sensitive primary afferents in the rat spinal cord in vitro, Neuroscience, 52 (1993) 1029-1037.
11. 2 receptor antagonist SR 48,968 inhibits thalamic responses evoked by thermal but not mechanical nociception, Eur. J. Pharmacol., 237 (1993) 143-146.
12. 2 receptor antagonists in the mouse light-dark box, Eur. J. Pharmacol., 250 (1993) R11-R12.
13. 8 analogues, Biochemistry, 30 (1991) 10175-10181.
14. [14] Williams, B.J., Curtis, N.R., McKnight, A.T., Maguire, J.J., Young, S.C., Veber, D.F. and Baker, R., Cyclic peptides as selective tachykinin antagonists, J. Med. Chem., 36 (1993) 2-10.
15. [15] McKnight, A.T., Maguire, J.J., Elliott, N.J., Fletcher, A.E., Foster, A.C., Tridgett, R., Williams, B.J., Longmore J. and Iversen, L.L., Pharmacological specificity of novel, synthetic, cyclic peptides as antagonists at tachykinin receptors, Br. J. Pharmacol., 104 (1991) 355-360.
16. [16] Wollborn, U., Brunne, R.M., Harting, J., Holzemann, G. and Leibfritz, D., Comparative conformational analysis and in vitro pharmacological evaluation of three cyclic hexapeptide NK-2 antagonists, Int. J. Pept. Protein Res., 41 (1993) 376.
17. [17] Pavone, V., Lombardi, A., Pedone, C., Quartara, L. and Maggi, C.A., A new potent and highly selective, long lasting, peptide based neurokinin A antagonist: rational design of MEN 10,627, In: R.S. Hodges and J.A. Smith (Eds.), Peptides, Chemistry, Structure and Biology, Proceedings of the Thirteenth American Peptide Symposium, ESCOM, Leiden, 1994, p. 487.
18. 6)cyclo(2β-5β). J. Chem. Soc. Perk. Trans., II (1995) 987-993.
19. [19] Horwell, D.C., Howson, W., Naylor, D. and Willems, M.G., The design of polar β-turn dipeptide mimetics, Bioorg. Med. Chem. Lett., 5 (1995) 1445-1450.
20. 2 receptors, J. Pharmacol. Exp. Ther., 271 (1994) 1489-1500.
21. [21] Rovero, P., Quartara, L. and Fabbri, G., Synthesis of cyclic peptides on solid support, Tetrahedron Lett., 32 (1991) 2639-2642.
22. [22] Caciagli, V., Cardinall, F., Hänsicke, A., Liotine, T., Tuchalski, G., Bonelli, F., Centini, F., Sisto, S. and Lombardi, P., Large scale continuous flow synthesis of MEN 10627 a new potent neurokinin A antagonist cyclic peptide, In: R. Epton (Ed.), Innovation and Perspectives in Solid Phase Synthesis, Mayflower Worldwide, Birmingham, 1994, pp. 465-468.
23. 3 antagonist in the guinea-pig but not in the rat, Biochem. Biophys. Res. Commun., 191 (1993) 180-187.
24. 3 receptor in guinea-pig and rat cerebral cortex, Br. J. Pharmacol., 110 (1993) 59P.
25. 2 receptor antagonist, Eur. J. Pharmacol., 234 (1993) 83-90.
26. 2 tachykinin receptor subtypes, Br. J. Pharmacol., 104 (1991) 91-96.
27. 2 receptors mediate the non-cholinergic bronchospastic response to capsaicin and vagal stimulation in guinea-pigs, J. Auton, Pharmacol., 15 (1995) 49-54.
28. 2 receptor selective antagonist MEN 10,627 in rat small intestine, Jpn. J. Pharmacol., 65 (1994) 281-283.
29. [29] Pavone, V., Lombardi, A., Maggi, C.A., Quartara, L. and Pedone, C., Conformational rigidity versus flexibility in a novel peptidic neurokinin A receptor antagonist, J. Pept. Sci., 4 (1995) 227-235.