Structure-based design in drug discovery - the application of a peptoid drug design strategy for the development of non-peptide neuropeptide receptor ligands

Bibliography

• GANELLIN RC: Medicinal Chemistry Principles and Practice.King FD (Ed.), The Royal Society of Chemistry (1994):185–205.
   Google Scholar
• OLSON GL, BOLIN DR, BONNER MP et al.: Concepts andprogress in the development of peptide mimetics. Med. Chem. (1993) 36:3039–3049.
   Web of Science ®Google Scholar
• BOHM H-J, KLEBE G: What can we learn from molecularrecognition in protein - ligand complexes for the design of new drugs ?Angew. Chem. Int Ed. Engl. (1996) 35:2588–2614.
   Google Scholar
• HAGIWARA D, MIYAKE H, MORIMOTO H et al: Studies on neurokinin antagonists. 2. Design and structure-activ-ity relationships of novel trip eptide substance P antago-nists. J Med. Chem. (1992) 35:3184–3191.
   Google Scholar
• GIANNIS A, KOLTER T: Peptidomimetics for receptor ligands - development and medical perspectives. Angew. Chem. Int. Ed. Engl. (1993) 32:1244-1267. An excellent review of recently published peptide receptor ligands.
   Google Scholar
• BALKENHOHL F, VON DEM BUSSCHE-HUNNEFELD C, LANSKY A, ZECHEL C: Combinatorial synthesis of small organic molecules. Angew. Chem. Int. Ed. Engl. (1996) 35:2288–2337.
   Web of Science ®Google Scholar
• HORWELL DC, HOWSON W, REES DC: Peptoid design. Drug Design Disc. (1994) 12:63–75.
   PubMedGoogle Scholar
• HORWELL DC: The peptoid approach to the design of non-peptide, small molecule agonists and antagonists of neuropeptides. TibTech. (1995) 13:132–134.
   PubMed Web of Science ®Google Scholar
• FARMER PS, ARIENS EJ: Speculations on the design of non-peptidic peptidomimetics. Trends Pharmacol. Sci.(1982) 5:362-365. Seminal concepts on the design of non-peptide receptor ligands.
   Google Scholar
• SCHVVYZER R: Organisation and transduction of peptide information. Trends Pharmacol. Sci. (1980) 3:327–331.
   Google Scholar
• MARTINEZ J: In: Comprehensive Medicinal Chemistry. Em-mett J (Ed.), Pergamon (1990) 3:925.
   Google Scholar
• RICH DH: In: Comprehensive Medicinal Chemistry. Sammes PG (Ed.), Pergamon (1990) 2:391.
   Google Scholar
• STEWART JM: The design of peptide hormone ana-logues. Trends Pharmacol Sci. (1982) 5:300–304.
   Google Scholar
• PETSKO GA: For medicinal purposes. Nature (1996) 384 (Suppl.):7–9.
   Google Scholar
• TURK J, PANSE, GT, MARSHALL GR: Studies with a-methyl amino acids resolution and amino protection. J. Org. Chem. (1975) 40:953–955.
   PubMed Web of Science ®Google Scholar
• FINCHAM CI, HORWELL DC, RATCLIFFE GS, REES DC: Theuse of a proline ring as a conformational restraint in CCK-B receptor dipeptoids. Bioorg. Med. Chem. Lett. (1992) 2:403–406.
   Web of Science ®Google Scholar
• HIGGINBOTTOM M, KNEEN C, RATCLIFFE GS: Rationallydesigned dipeptoid analogues of CCK. A Free-Wil-son/Fujita-Ban analysis of some a-methyltryptophan derivatives as CCK-B antagonists. J. Med. Chem. (1992) 35:1572–1577.
   Google Scholar
• CRAWLEY JN, CORWIN RL: Biological actions of cholecystokinin. Peptides (1994) 15:731-755. Excellent comprehensive review of the biology of CCK.
   Google Scholar
• TRIVEDI BK: Cholecystokinin receptor antagonists: cur- rent status. Curr. Med. Chem. (1994) 1:313–327.
   Google Scholar
• ITO H, SOGABE H, SATOH Y: CCK-A receptor antago-nists. Drugs Fut. (1995) 20:587–599.
   Google Scholar
• HORWELL DC: Development of CCK-B antagonists. Neuropeptides (1991) 19 (Suppl.):57–64.
   Google Scholar
• PINCUS MR, MURPHY RB, CARTY RP et al.: Conforma-tional analysis of possible biologically active (receptor bound) conformations of peptides derived from cholecystokinin, ceulein and little gastrin and the opi-ate peptide met-enkephalin. Peptides (1988) 9:145–152.
   PubMedGoogle Scholar
• HORWELL DC, HUGHES J, HUNTER JC etal: Rationallydesigned dipeptoid analogues of CCK. a-Methyltrypto-phan derivatives as highly selective and orally active gastrin and CCK-B antagonists with potent anxiolytic properties .j Med. Chem. (1991) 34:404–414.
   Google Scholar
• BODEN PR. PINNOCK RD, PRITCHARD MC, WOODRUFFGN: Evaluation of a series of novel CCK-B antagonists using a functional assay in the rat central nervous system. Br. J. Pharmacol (1994) 112:666–670.
   PubMed Web of Science ®Google Scholar
• HAYWARD NJ, HARDING M, LLOYD SAC etal.: The effectof CCK-B/gastrin antagonists on stimulated gastric acid secretion in the anaesthetised rat. Br. J. Pharmacol (1991) 104:973–977.
   Google Scholar
• SCHMASSMANN A, GARNER A, FLOGERZI B et al: Cholecystokinin type B receptor antagonist PD 136450 is a partial secretory agonist in the stomach and a full agonist in the pancreas of the rat. Gut (1994) 35:270–274
   PubMed Web of Science ®Google Scholar
• HUGHES J, DOCKRAY GJ, HILL D et al.: Characterisationof novel peptoid agonists for the CCK-A receptor. Regul Peptides (1996) 65:15–22.
   PubMed Web of Science ®Google Scholar
• BURGAUD BGM, HORVVELL DC, PRITCHARD MC, BERNADN, MARTINEZ J: The asymmetric synthesis of non-pep-tide CCK-A receptor agonists. Tetrahedron: Asymmetry (1995) 6:1081–1084.
   Web of Science ®Google Scholar
• BODEN PR, HIGGINBOT TOM, HILL DR etal: Cholecystok-inin dipeptoid antagonists: design, synthesis and anx-iolytic profile of some novel CCK-A and CCK-B selective and mixed CCK-A/CCK-B antagonists. J. Med. Chem. (1993) 36:552–565.
   PubMed Web of Science ®Google Scholar
• HILL DR, SHAW TM, GRAHAM W etal: Autoradiographicdetection of cholecystokinin-A receptors in primate brain using 125Bolton Hunter CCK-8 and 3H-MK-329. J. Neurosci. (1990) 10:1070–1081.
   PubMed Web of Science ®Google Scholar
• MACDONALD JK, PARNAVELAS JG, KARAMANLIDIS AN etaL: The morphology and distribution of peptide con-taining neurons in the adult and developing visual cortex of the rat. J. Neurocytol. (1982) 11:881–895.
   PubMedGoogle Scholar
• SOMOGYI P, HODGSON AJ, SMITH AD et al: Differentpopulations of GABAergic neurons in the visual cortex and hippocampus of cat contain somatostatin- or cholecystokinin-immunoreactive material. J. Neurosci. (1984) 4:2590–2603.
   PubMed Web of Science ®Google Scholar
• DEMEULEMEESTER H, VAN DESANDE F, ORBAN GA et al.:Heterogeneity of GABAergic cells in cat visual cortex. J. Neurosci. (1988) 8(3):988–1000.
   PubMed Web of Science ®Google Scholar
• HARVEY SC: In: The Pharmacological Basis of Therapeutics,7th edition. Goodmann AG, Gilman IS (Eds.), Macmillan (1985):339–371.
   Google Scholar
• DAUGE V, STEIMES P, DERRIEN M et al.: CCK-8 effects onmotivational and emotional states of rats involve CCKA receptors of the postereo-median pare of the nucleus accumbens. Pharmacol Biochem. Behav. (1989) 34:157–163.
   PubMed Web of Science ®Google Scholar
• SINGH L, LEWIS AS, FIELD MJ et al.: Evidence for an involvement of the brain cholecystokinin B receptor in anxiety. Proc. Natl. Acad. Sci. USA (1991) 88:1130–1133.
   PubMed Web of Science ®Google Scholar
• RATAUD J, DARCHE F, PIOT 0 et al.: Arodolytic effect of CCK-antagonists on plus-maze behavior in mice. Brain Res. (1991) 548(1–2):315–317.
   Google Scholar
• HENDRIE CA, DOURISH CT: Anxiolytic profile of thecholecystokinin antagonist devazepide in mice. Br. J. Pharmacol. (1990) 99:138P.
   Google Scholar
• RAVARD S, DOURISH CT, IVERSEN SD: Evidence that the anxiolytic-like effects of the CCK antagonists devazepide and L-365,260 in the elevated plus maze paradigm in rats are mediated by CCK receptors. Br. J. Pharmacol. (1990) 10:576P.
   Google Scholar
• SINGH L, FIELD MJ, HILL DR et al.: Peptoid CCK receptor antagonists: pharmacological evaluation of CCK, CCKB and mixed CCKA/B receptor antagonists. Eur. J Pharma-col. (1995) 286:185–191.
   PubMed Web of Science ®Google Scholar
• VAN MEGAN HJGM, VVESTENBERG HGM, DEN BOER JA et al: Cholecystokinin in anxiety. Eur. Neuropsychophar-macol (1996) 6:263–280.
   PubMed Web of Science ®Google Scholar
• SINGH L, FIELD MJ, HUGHES J et al.: The behavioural properties of CI-988, a selective cholecystokinins recep-tor antagonist. Br. J. Pharmacol (1991) 104:239–245.
   PubMed Web of Science ®Google Scholar
• HUGHES J, BODEN P, COSTALL B et al.: Development of a class of selective cholecystokinin type B receptor antagonists having potent anxiolytic activity. Proc. Natl. Acad. Sci. USA (1990) 87:6728–6732.
   PubMed Web of Science ®Google Scholar
• POVVELL KR, BARRETT JE: Evaluation of the effects of PD134308 (CI-988), a CCK-B antagonist, on the punished responding of squirrel monkeys. Neuropeptides (1991) 19:75–78.
   PubMed Web of Science ®Google Scholar
• DAWSON GR, RUPNIAK NMJ, IVERSEN SD et al.: Lack of effect of CCK-B receptor antagonists in ethological and conditioned animal screens for anxiolytic drugs. Psy-chopharmacol (1995) 121:109–117.
   PubMed Web of Science ®Google Scholar
• INNIS RB, SNYDER SH: Distinct cholecystokinin recep-tors in brain and pancreas. Proc. Natl. Acad. Sci USA (1986) 77:6917–6921.
   Google Scholar
• SINGH L, FIELD MJ, VASS CA et al.: The antagonism of benzodiazepine withdrawal efects by the selective cholecystokinin-B receptor antagonist CI-988. Br. J. Pharmacol. (1992) 105:8–10.
   PubMed Web of Science ®Google Scholar
• STENGAARD-PEDERSEN K, LARSSON LI: Localization andopiate receptor binding of enkephalin, CCK and ACTH/betaendorphin in therat central nervouss ystem. Peptides (1984) 23:715–718.
   Google Scholar
• VAN DIJK A, RICHARDS JG, TRZECIAK A et al.: Cholecystokinin receptors: biochemical demonstra-tions and autoradioraphical localization in rat brain and pancreas using H cholecystokinin as radioligand. Neurosci. (1984) 4:1021–1033.
   PubMed Web of Science ®Google Scholar
• BARBAZ BS, HALL NR, LIEBMAN JM: Antagonism of mor-phine analgesia by CCK8S does not extend to all assays nor all opiate analgesics. Peptides (1989) 9:1295–1300.
   Web of Science ®Google Scholar
• FARIS PL, KOMISARUK BR, WATKINS LR, MAYER DJ: Evi-dence for the neuropeptide cholecystokinin as an an-tagonist of opiate analgesia. Science (1983) 219:310–312.
   PubMed Web of Science ®Google Scholar
• DOURISH CT, O'NEILL ME, COUGHLAN J etal.: The selec-tive CCKB receptor antagonist L365,260 enhances mor-phine analgesia and prevents morphine tolerance in the rat. Eur. j Pharmacol (1990) 176:3544.
   Google Scholar
• SINGH L, OLES RJ, FIELD MJ etal: Effect of CCK receptor antagonists on the antinociceptive, reinforcing and gut motility properties ofmorphine. Br. J. Pharmacol (1996) 118:1317–1325.
   PubMed Web of Science ®Google Scholar
• WIESENFELD-HALLIN Z, XU X-J, HUGHES J, HORWELL DC, HOKFELT T: PD 134308, a selective anugonist of cholecystokinintype-B receptors, enhances the analge-sic effect of morphine and synergistically interacts with intrathecal galanin to depress spinal nociceptive re-felexes . Proc. Natl. Acad. Sci. USA (1990) 87:7105–7109.
   PubMed Web of Science ®Google Scholar
• MARSHALL FH, BARNES S, HUGHES J et al.: Cholecystok-inin modulates the release of dopamine from the ante-rior and posterior nucleus accumbens by two different mechanisms. J. Neurochem. (1991) 56:917–922.
   PubMed Web of Science ®Google Scholar
• HIGGINS GA, NGUYEN P, SELLERS EM: Morphine place conditioning is differentially affected by CCK-A and CCK-B receptor antagonists. Brain Res. (1992) 572:208–215.
   PubMed Web of Science ®Google Scholar
• CARR GD, FIBIGER HC, PHILLIPS AG: Conditioned place preference as a measure of drug reward. In: The Neuro-pharmacological Basis of Reward. Liebman JM, Cooper SJ (Eds.), Oxford University Press, Oxford (1989):264–319.
   Google Scholar
• SPYRAKI C, FIBIGER HC, PHILLIPS AG: Attenuation of heroin reward in rats by disruption of the mesolimbic dopamine system. Psychopharmacology (1983) 79:278–283.
   PubMed Web of Science ®Google Scholar
• HOKFELT T, REHFELD JF, SKIRBOLL LR et al: Evidence for co-existence of dopamine and CCK in mesolimbic neu-rones. Nature (1980) 285:476–478.
   PubMed Web of Science ®Google Scholar
• VACCARINO FJ, KOOB GF: Microinjections of nanogram amounts of sulfated cholecystokinin octapeptide into the rat nucleus accumbens attenuate brain stimulation reward. Neurosci. Lett. (1984) 52:6166.
   Google Scholar
• SINGH L, FIELD MJ, HUNTER JC et al.: Modulation of the in vivo actions of morphine by the mixed CCIcus receptor antagonist PD 142898. Eur.j Pharmacol. (1996) 307:283–289.
   PubMed Web of Science ®Google Scholar
• REGOLI D, BOUDON A, FAUCHERE J-L: Receptors andantagonists for subslance P and related peptides. Phar-macol Rev. (1994) 46(0551–599.
   PubMed Web of Science ®Google Scholar
• MAGGI CA, PATACCHINI R, ROVERO P, GIACHETTI A: Tachykinin receptors and tachykinin receptor antago-nists. J. Auton. Pharmacol (1993) 13:23–93.
   PubMedGoogle Scholar
• LAVELLE S, BEAUJOUAN JC, TORRENS Y et al.: Central nervous system receptors fortachykinins: structure-ac-tivity relationships and biochemical studies. In: Sub-stance P Metabolism and Biological Actions. Jordan CC, Oehme P (Eds.), Taylor and Francis, London (1985):85.
   Google Scholar
• LEANDER S, HAKANSON R, ROSELL S et al: A specific substance P antagonist blocks smooth muscle contrac-tions induced by non-cholinergic noradrenergic nerve stimulation. Nature (1981) 294:467–469.
   PubMed Web of Science ®Google Scholar
• ROSELL S, FOLKERS K: Substance P antagonists: a new type of pharmacological tool. Trends Pharmacol Sci. (1991) 3:211–211.
   Google Scholar
• MCKNIGHT AT, MAGUIRE JJ et al: Pharmacological speci- ficity of novel, synthetic, cyclic peptides as antagonists at tachykinin receptors. Br. J. Pharmacol. (1991) 104:355–360.
   PubMed Web of Science ®Google Scholar
• MCKNIGHT AT, MAGUIRE JJ eta].: Pharmacological speci-ficity of synthetic peptides as antagonists at tachykinin receptors. Regul Pep. (1988) 12:127.
   Google Scholar
• BOYLE S, GUARDS et al: Rational design of high affinity tachykinin NK2 receptor antagonists. Bioorg. Med. Chem. (1994) 2(2):101–113.
   PubMedGoogle Scholar
• BOYLE S, GUARDS et al: Rational design of high affinity tachykininNKi receptor antagonists. Bioorg. Med. Chem. (1994) 2 (5):357–370.
   PubMedGoogle Scholar
• HELLBERG S, ERIKSSON L et al.: Minimum analogue peptide sets (MAPS) for quantitative structure-activity relationships. Int J. Pept Protein Res. (1991) 37:414–424.
   PubMedGoogle Scholar
• HORWELL DC, HOWSON W, RATCLIFFE GS, REES DC: The design of a dipeptide library for screening at peptide receptor sites. Bioorg Med. Chem. Lett (1993) 3(5):799–802.
   Web of Science ®Google Scholar
• BODEN P, EDEN JM et al.: Use of a dipeptide chemical library in the development of non-peptide tachykinin NK3 receptor selective antagonists. J. Med. Chem. (1996) 39(8):1664–1675
   PubMed Web of Science ®Google Scholar
• HORWELL DC, RATCLIFFE G, ROBERTS E: Stabilities of typtophanylphenethylamides to acid and alkaline con-ditions. Bioorg. Med. Chem. Leff. (1991) 1:169–172.
   Web of Science ®Google Scholar
• MICHELOT R, MAYER M et al.: Activity of the C-terminal part of substance P on guinea-pig ileum and trachea preparations 1. N-Acylated pentapeptides SP (7–11) . Eur. J. Med. Chem. (1988) 23:243–247.
   Google Scholar
• BODEN P, EDEN JM eta].: The rational development of small molecule tachykinin NK3 receptor selective an-tagonists - the utilisation of a dipeptide chemical library in drug design. Bioorg. Med. Chem. Lett. (1994) 4 (14): 1679–1684.
   Google Scholar
• BODEN P, EDEN JM et al: The development of a novel series of non-pe ptide tachykinin NK3 receptor selective antagonists. Bioorg Med. Chem. Len. (1995) 5(16):1773–1778.
   Web of Science ®Google Scholar
• ANDREWS PLR, RAPEPORT WG, SANGER GJ: Neurophar-macology of emesis induced by anticancer therapy. Trends Pharmacol. Sci. (1988) 9:334–341.
   PubMedGoogle Scholar
• GARDNER CJ, BOUNTRA C, BUNCE KT et al: Antiemeticactivity of neurokinin NKi receptor antagonists is me-diated centrally in the ferret. Br. J. Pharmacol (1994) 112:516P.
   Web of Science ®Google Scholar
• BOUNTRA C, BUNCE K, DALE T eta].: Anti-emetic profileof a nonpeptide neurokinin NKi receptor antagonist, CP-99,994, in ferrets. Eur. j Pharmacol (1993) 249:R3–R4.
   Google Scholar
• TATTERSALL FD, RYCROFT W, HARGREAVES RJ, HILL RG: The tachykinin NKi receptor antagonist CP-99,994 at-tenuates cisplatin induced emesis in the ferret. Eur. Pharmacol (1993) 250:R5–R6.
   PubMed Web of Science ®Google Scholar
• GARDNER CJ, TWISSELL DJ, DALE TJ eta].: The broad-spec-trum antiemetic activity of the novel non-peptide tachykinin NKi receptor antagonist GR203040. Br. J. Pharmacol (1995) 116:3158–3163.
   Google Scholar
• WATSON JW, GONSALVES SF, FOSSA AA eta].: The antie-metic effects of CP99,994 in the ferret and the dog: role of the NKi receptor. Br. J. Pharmacol (1995) 115:84–94.
   Google Scholar
• MORROW GR, HICKOK JT, ROSENTHAL SN: Progress in reducing nausea and emesis. Cancer (1995) 76 (3):343–357.
   PubMed Web of Science ®Google Scholar
• RUDD JA, NAYLOR RJ: An interaction of ondansetron anddexamethasone antagonizing cisplatin-induced acute and delayed emesis in the ferret Br. J. Pharmacol. (1996) 118:209–214.
   Google Scholar
• SINGH L, FIELD MJ, HUGHES J et al.: The NKi receptorantagonist PD154075 blocks cisplatin-induced delayed emesis in the ferret. Eur.j Pharmacol (1997) 321:209–216.
   PubMed Web of Science ®Google Scholar
• EDEN JM, HALL MD, HIGGINBOTTOM M et al.: PD 165929 the first high affinity non-peptide neuromedin-B (NMB) receptor selective antagonist. Bioorg. Med. Chem. Lett. (1996) 6:2617–2622.
   Web of Science ®Google Scholar