Design, synthesis, and evaluation of the antipsychotic potential of orally bioavailable neurotensin (8-13) analogues containing non-natural arginine and lysine residues

Neuropharmacology

Volumn 49, Issue 8, 2005, Pages 1149-1159

  Hadden, M Kyle ^a   Orwig, Kevin S ^a   Kokko, Kyle P ^a   Mazella, Jean ^b   Dix, Thomas A ^a,c  

^a MEDICAL UNIVERSITY OF SOUTH CAROLINA   (United States)

^b CNRS   (France)

^c Argolyn Biosciences Inc   (United States)

Author keywords

Amino acid analogues; Arginine; Blood brain barrier; Lysine; Neurotensin; Peptides; Schizophrenia

Indexed keywords

DEXAMPHETAMINE; NEUROTENSIN DERIVATIVE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; HYPOTHERMIA; LOCOMOTION; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; SCHIZOPHRENIA;

ANIMALS; ANTIPSYCHOTIC AGENTS; AREA UNDER CURVE; ARGININE; BIOLOGICAL AVAILABILITY; CATALEPSY; CENTRAL NERVOUS SYSTEM STIMULANTS; DEXTROAMPHETAMINE; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; HALOPERIDOL; INJECTIONS, INTRAPERITONEAL; LYSINE; MALE; MOTOR ACTIVITY; NEUROTENSIN; PEPTIDE FRAGMENTS; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, NEUROTENSIN;

EID: 27744477471     PISSN: 00283908     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.neuropharm.2005.06.010     Document Type: Article

References (40)

1. E.B. Binder, B. Kinkead, M.J. Owens, and C.B. Nemeroff The role of neurotensin in the pathophysiology of schizophrenia and the mechanism of action of antipsychotic drugs Biol. Psychiatry 50 11 2001 856 872
2. G. Bissette, C.B. Nemeroff, P.T. Loosen, A.J. Prange Jr., and M.A. Lipton Hypothermia and intolerance to cold induced by intracisternal administration of the hypothalamic peptide neurotensin Nature 262 5569 1976 607 609
3. H. Bitterman, J. Einsiedel, H. Hubner, and P. Gmeiner Evaluation of lactam-bridged neurotensin analogues adjusting ψ(Pro10) close to the experimentally derived bioactive conformation of NT(8-13) J. Med. Chem. 47 22 2004 5587 5590
4. R.T. Borchardt Optimizing oral absorption of peptides using prodrug strategies J. Controlled Release 62 1-2 1999 231 238
5. M. Boules, L. Warrington, A. Fauq, D. McCormick, and E. Richelson A novel neurotensin analog blocks cocaine- and d-amphetamine-induced hyperactivity Eur. J. Pharmacol. 426 1-2 2001 73 76
6. N.A. Breslin, R.L. Suddath, G. Bissette, C.B. Nemeroff, P. Lowrimore, and D.R. Weinberger CSF concentrations of neurotensin in schizophrenia: an investigation of clinical and biochemical correlates Schizophr. Res. 12 1 1994 35 41
7. P.S. Burton, R.A. Conradi, N.F. Ho, A.R. Hilgers, and R.T. Borchardt How structural features influence the biomembrane permeability of peptides J. Pharm. Sci. 85 12 1996 1336 1340
8. R. Carraway, and S.E. Leeman Structural requirements for the biological activity of neurotensin, a new vasoactive peptide J. Meienhofer Peptides: Chemistry, Structure and Biology 1975 Ann Arbor Science Ann Arbor 679 685
9. R.A. Conradi, A.R. Hilgers, N.F. Ho, and P.S. Burton The influence of peptide structure on transport across Caco-2 cells Pharm. Res. 8 12 1991 1453 1460
10. B. Cusack, D.J. McCormick, Y.P. Pang, T. Souder, R. Garcia, A. Fauq, and E. Richelson Pharmacological and biochemical profiles of unique neurotensin 8-13 analogs exhibiting species selectivity, stereoselectivity, and superagonism J. Biol. Chem. 270 31 1995 18359 18366
11. O.C. Dermer, and M.T. Edmison Orientation in aromatic substitution by the benzenesulfonimide radical J. Am. Chem. Soc. 77 1 1955 70 73
12. S. Gangwar, S.D. Jois, T.J. Siahaan, D.G. Vander Velde, V.J. Stella, and R.T. Borchardt The effect of conformation on membrane permeability of an acyloxyalkoxy-linked cyclic prodrug of a model hexapeptide Pharm. Res. 13 11 1996 1657 1662
13. D.L. Garver, G. Bissette, J.K. Yao, and C.B. Nemeroff Relation of CSF neurotensin concentrations to symptoms and drug response of psychotic patients Am. J. Psychiatry 148 4 1991 484 488
14. M.K. Hadden, K.P. Kokko, and T.A. Dix Asymmetric synthesis of ω-bromo-2(S)-methyl acids as precursors for novel arginine, lysine and mercapto residues Synth. Commun. 35 12 2005 1675 1680
15. D.L. Heyl, A.M. Sefler, J.X. He, T.K. Sawyer, D.J. Wustrow, H.C. Akunne, M.D. Davis, T.A. Pugsley, T.G. Heffner, and A.E. Corbin Structure-activity and conformational studies of a series of modified C-terminal hexapeptide neurotensin analogues Int. J. Pept. Protein Res. 44 3 1994 233 238
16. K.J. Kennedy, J.T. Lundquist IV, T.L. Simandan, C.C. Beeson, and T.A. Dix Asymmetric synthesis of non-natural homologues of lysine Bioorg. Med. Chem. Lett. 14 1997 1937 1940
17. K.J. Kennedy, T.L. Simandan, and T.A. Dix A facile route to cyclic and acyclic alkyl-arginines Synth. Commun. 28 4 1998 741 746
18. K.J. Kennedy, J.T. Lundquist IV, T.L. Simandan, K.P. Kokko, C.C. Beeson, and T.A. Dix Design rationale, synthesis, and characterization of non-natural analogs of the cationic amino acids arginine and lysine J. Pept. Res. 55 4 2000 348 358
19. B. Kinkead, E.B. Binder, and C.B. Nemeroff Does neurotensin mediate the effects of antipsychotic drugs? Biol. Psychiatry 46 3 1999 340 351
20. G.T. Knipp, D.G. Vander Velde, T.J. Siahaan, and R.T. Borchardt The effect of beta-turn structure on the passive diffusion of peptides across Caco-2 cell monolayers Pharm. Res. 14 10 1997 1332 1340
21. K.P. Kokko, and T.A. Dix Monitoring neurotensin[8-13] degradation in human and rat serum utilizing matrix-assisted laser desorption/ionization time-of-flight mass spectrometry Anal. Biochem. 308 2002 34 41
22. K.P. Kokko, M.K. Hadden, K.S. Orwig, J. Mazella, and T.A. Dix In vitro analysis of stable, receptor-selective neurotensin[8-13] analogues J. Med. Chem. 46 19 2003 4141 4148
23. K.P. Kokko, H.B. Hooper, and T.A. Dix Synthesis of cyclic and acyclic N(α)-methyl-N(ω)-alkyl-l-arginine analogues Tetrahedron Lett. 45 2004 2151 2153
24. K.P. Kokko, M.K. Hadden, K.L. Price, K.S. Orwig, R.E. See, and T.A. Dix In vivo behavioral effects of stable, receptor-selective neurotensin[8-13] analogues that cross the blood-brain barrier Neuropharmacology 48 3 2005 417 425
25. S. Luca, J.F. White, A.K. Sohal, D.V. Filippov, J.H. van Boom, R. Grisshammer, and M. Baldus The conformation of neurotensin bound to its G protein-coupled receptor Proc. Natl Acad. Sci. U.S.A. 100 19 2003 10706 10711
26. J.T. Lundquist IV, and T.A. Dix Synthesis and human neurotensin receptor binding activities of neurotensin(8-13) analogues containing position 8 alpha-azido-N-alkylated derivatives of ornithine, lysine, and homolysine J. Med. Chem. 42 23 1999 4914 4918
27. ω) analogues of arginine J. Org. Chem. 64 1999 9265 9267
28. J.T. Lundquist IV, E.E. Büllesbach, and T.A. Dix Synthesis of neurotensin(9-13) analogues exhibiting enhanced human neurotensin receptor binding affinities Bioorg. Med. Chem. Lett. 10 5 2000 453 455
29. J.T. Lundquist IV, and J.C. Pelletier Improved solid-phase peptide synthesis method utilizing alpha-azide-protected amino acids Org. Lett. 3 5 2001 781 783
30. R. Machida, T. Tokumura, Y. Tsuchiya, A. Sasaki, and K. Abe Pharmacokinetics of novel hexapeptides with neurotensin activity in rats Biol. Pharm. Bull. 16 1 1993 43 47
31. S.O. Ogren The behavioural pharmacology of typical and atypical antipsychotic drugs J.G. Csernansky Handbook of Experimental Pharmacology vol. 120 1996 Springer Berlin 225 266
32. F.W. Okumu, G.M. Pauletti, D.G. Vander Velde, T.J. Siahaan, and R.T. Borchardt Effect of restricted conformational flexibility on the permeation of model hexapeptides across Caco-2 cell monolayers Pharm. Res. 14 2 1997 169 175
33. Y.P. Pang, B. Cusack, K. Groshan, and E. Richelson Proposed ligand binding site of the transmembrane receptor for neurotensin(8-13) J. Biol. Chem. 271 25 1996 15060 15068
34. Richelson, E., Cusack, B., Pang, Y.P., McCormick, D.J., Fauq, A., Tyler, B.M., Boules, M., 2001. Neo-tryptophan. United States Patent and Trademark Office. USA, Mayo Foundation for Medical Education and Research.
35. J.L. Sadoul, J. Mazella, S. Amar, P. Kitabgi, and J.P. Vincent Preparation of neurotensin selectively iodinated on the tyrosine 3 residue. Biological activity and binding properties on mammalian neurotensin receptors Biochem. Biophys. Res. Commun. 120 3 1984 812 819
36. A.M. Sefler, J.X. He, T.K. Sawyer, K.E. Holub, D.O. Omecinsky, M.D. Reily, V. Thanabal, H.C. Akunne, and W.L. Cody Design and structure-activity relationships of C-terminal cyclic neurotensin fragment analogues J. Med. Chem. 38 2 1995 249 257
37. R.P. Sharma, P.G. Janicak, G. Bissette, and C.B. Nemeroff CSF neurotensin concentrations and antipsychotic treatment in schizophrenia and schizoaffective disorder Am. J. Psychiatry 154 7 1997 1019 1021
38. K.M. Skoog, S.T. Cain, and C.B. Nemeroff Centrally administered neurotensin suppresses locomotor hyperactivity induced by d-amphetamine but not by scopolamine or caffeine Neuropharmacology 25 7 1986 777 782
39. B.M. Tyler-McMahon, M. Boules, and E. Richelson Neurotensin: peptide for the next millennium Regul. Pept. 93 1-3 2000 125 136
40. B.M. Tyler-McMahon, J.A. Stewart, F. Farinas, D.J. McCormick, and E. Richelson Highly potent neurotensin analog that causes hypothermia and antinociception Eur. J. Pharmacol. 390 1-2 2000 107 111