[3H]LY303870, a novel nonpeptide radioligand for the NK-1 receptor

Journal of Neurochemistry

Volumn 66, Issue 3, 1996, Pages 1095-1102

  Gehlert, D R ^a   Schober, D A ^a   Hipskind, P A ^a   Gitter, B D ^a   Howbert, J J ^a,b  

^a ELI LILLY AND COMPANY   (United States)

^b Darwin Molecular Corporation   (United States)

Author keywords

Autoradiography; Guinea pig; Migraine; Pain; Substance P

Indexed keywords

2 BENZHYDRYL 3 (2 IODOBENZYLAMINO)QUINUCLIDINE; 2 BENZHYDRYL 3 (2 METHOXYBENZYLAMINO) 1 AZABICYCLO[2.2.2]OCTANE; 2 [1 IMINO 2 (2 METHOXYPHENYL)ETHYL] 7,7 DIPHENYLPERHYDROISOINDOL 4 ONE; 3 (1H INDOL 3 YL) 1 [N (2 METHOXYBENZYL)ACETYLAMINO] 2 [N [2 [4 (1 PIPERIDINYL) 1 PIPERIDINYL]ACETYL]AMINO]PROPANE; 3 (2 METHOXYBENZYLAMINO) 2 PHENYLPIPERIDINE; 5 AMINOVALERYLSUBSTANCE P [7-11][9 PROLINE 10 (N METHYLLEUCINE)]; ELEDOISIN; LANEPITANT; LY 306740; LY 307679; N [2 [N ACETYL N (2 METHOXYBENZYL)AMINO] 1 (1H INDOL 3 YLMETHYL)ETHYL] 4 CYCLOHEXYLPIPERAZINE 1 ACETAMIDE; NEUROKININ; NEUROKININ 1 RECEPTOR; NEUROKININ A; NEUROKININ B; NEUROKININ B [7 METHYLPHENYLALANINE]; PHYSALAEMIN; SUBSTANCE P; TACHYKININ RECEPTOR ANTAGONIST; UNCLASSIFIED DRUG; INDOLE DERIVATIVE; PIPERIDINE DERIVATIVE; TRITIUM;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; AUTORADIOGRAPHY; CONTROLLED STUDY; CORPUS STRIATUM; DRUG ANTAGONISM; DRUG COMPETITION; DRUG POTENCY; DRUG RECEPTOR BINDING; ENANTIOMER; GUINEA PIG; LIGAND BINDING; NONHUMAN; PRIORITY JOURNAL; ANIMAL; BINDING SITE; BRAIN; CELL LINE; HUMAN; METABOLISM; TISSUE DISTRIBUTION;

ANIMALIA; CAVIA PORCELLUS; SUS SCROFA; TRITIUM;

ANIMALS; AUTORADIOGRAPHY; BINDING SITES; BRAIN; CELL LINE; CORPUS STRIATUM; GUINEA PIGS; HUMANS; INDOLES; PIPERIDINES; RECEPTORS, NEUROKININ-1; SUBSTANCE P; TISSUE DISTRIBUTION; TRITIUM;

EID: 0029670937     PISSN: 00223042     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1471-4159.1996.66031095.x     Document Type: Article

References (37)

1. Achard D., Trunchon A., and Peyronel J.-F. (1994) Perhydrothio-pyranopyrrole derivatives: a novel series of potent and selective nonpeptide NK1 antagonists. Bioorg. Med. Chem. Lett. 4, 669-672.
2. 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, 248-254.
3. Cascieri M. A., Ber E., Fong T. M., Sadowski S., Bansal A., Swain C., Seward E., Frances B., Burns D., and Strader C. D. (1992) Characterization of the binding of a potent, selective, radioiodinated antagonist to the human neurokinin-1 receptor. Mol. Pharmacol. 42, 458-463.
4. Dam T. V. and Quirion R. (1986) Pharmacological characterization and autoradiographic localization of substance P receptors in guinea pig brain. Peptides 7, 855-864.
5. Danks J. A., Rothman R. B., Cascieri M. A., Chicchi G. G., Liang T., and Herkenham M. (1986) A comparative autoradiographic study of the distributions of substance P and eledoism binding sites in rat brain. Brain Res. 385, 273-281.
6. 1 receptor antagonist. Eur. J. Pharmacol 250, 403-413.
7. Fong T. M., Yu H., and Strader C. D. (1992) Molecular basis for the species selectivity of the neurokinin 1 receptor antagonist CP-96,345 and RP 67580. J. Biol. Chem. 267, 25668-25671.
8. Garret C., Carruette A., Fardin S., Moussaoui S., Peyronel J.-F., Blanchard J.-C., and Laduron P. M. (1991) Pharmacological properties of a potent and selective nonpeptide substance P antagonist. Proc Natl. Acad. Sci. USA 88, 10208-10212.
9. 3H]-substance P in rat cerebral cortex. Brain Res. 601, 34-40
10. Gerard N. P., Eddy R. L., Shows T. B., and Gerard G. (1990) The human neurokinin A receptor. J. Biol. Chem. 265, 20455-20462,
11. Gerard N., Garraway L. A., Eddy R. L., Shows T. B., Iijima H., Paquet J.-L., and Gerard G. (1991) Human substance P (NK1): organization of the gene, chromosomal localization, and functional expression. Biochemistry 30, 10640-10646.
12. Gether U., Johansen T. E., Snider R. M., Lowe J. A., Nakanishi S., and Schwartz T. W. (1993a) Different binding epitopes on the NK-1 receptor for substance P and a non-peptide antagonist. Nature 362, 345-348.
13. Gether U., Yokota Y., Emonds-Alt X., Breliére J.-C., Lowe J. A., Snider R. M., Nakanishi S., and Schwartz T. W. (1993b) Two nonpeptide tachykinin antagonists act through epitopes on corresponding segments of the NK-1 and NK-2 receptors. Proc. Natl. Acad. Sci. USA 90, 6194-6198.
14. Gitter B. D., Waters D. C., Bruns R. F., Mason N. R., Nixon J. A., and Howbert J. J. (1991) Species differences in affinities of non-peptide antagonists for substance P receptors. Eur. J. Pharmacol. 197, 237-238.
15. Gitter B. D., Bruns R. F., Waters D. C., Howbert J. J., Threlkeld P. G., Nixon J. A., Lobb K. L., Mason N. R., Stengel P. W., Cockerham S. L., Silbaugh S. A., Gehlert D. R., Schober D. A., Iyengar S., Calligaro D. O., Regoli D., and Hipskind P. (1995) Pharmacological characterization of LY303870: a novel, potent and selective non-peptide substance P (NK-1) receptor antagonist. J. Pharmacol. Exp. Ther. 27, 737-744.
16. Guard S. and Watson S. P. (1991) Tachykinin receptor types: classification and membrane signaling mechanisms. Neurochem. Int. 18, 149-165.
17. Hershey A. D. and Krause J. E. (1990) Molecular characterization of a functional cDNA encoding for rat substance P receptor. Science 247, 958-962.
18. Hipskind P. A., Howbert J. J., Cho S., Cronin J. S., Fort S. L., Ginah F. O., Hansen G. J., Huff B. E., Lobb K. L., Martinelli M. J., Murray A. R., Nixon J. A., Staszak M. A., and Copp J. D. (1995) Practical and enantiospecific synthesis of LY303870, a novel NK-1 antagonist. J. Org. Chem. 60, 7033-7070.
19. Hopkins B., Powell S. J., Danks P., Briggs I., and Graham A. (1991) Isolation and characterization of the human lung NK-1 receptor cDNA. Biochem. Biophys. Res. Commun. 180, 1110-1117.
20. Huang R.-R., Cheung A. H., Mazina K. E., Strader C. D., and Fong T. M. (1992) cDNA sequence and heterologous expression of the human neurokinin-3 receptor Biochem. Biophys. Res. Commun. 184, 966-972.
21. Kris R. M., South V., Saltzman A., Felder S., Ricca G. A., Jaye M., Huebner K., Kagan J., Croce C. M., and Schlessinger J. (1991) Cloning and expression of the human substance K receptor and analysis of its role in mitogenesis. Cell Growth Differ. 2, 15-22.
22. MacLeod A. M., Merchant K. J., Cascieri M. A., Sadowski S., Ber E., Swain C. J., and Baker R. (1993) N-Acyl-L-tryptophan benzyl esters: potent substance P receptor antagonists. J. Med. Chem. 36, 2044-2045.
23. 1) receptor antagonist. Science 251, 437-439
24. Mills S. G., Wu M. T., MacCoss M., Budhu R., Dorn C P., Cascieri M. A., Sadowski S., Strader C. D., and Greenlee W. J. (1993) 1,4-Diacylpiperazine-2-(S)-[(N-aminoalkyl)carboamides] as novel, potent substance P receptor antagonists. Bioorg. Med. Chem. Lett. 3, 2707-2712.
25. Mussap C. J., Geraghty D. P., and Burcher E. (1993) Tachykinin receptors: a radioligand binding perspective. J. Neurochem. 60, 1987-2009.
26. Nakanishi S. (1991) Mammalian tachykinin receptors. Annu. Rev. Neurosci. 14, 123-136.
27. Quirion R., Dam T.-V., and Guard S. (1991) Selective neurokinin receptor radioligands. Ann. NY Acad. Sci. 632, 137-144.
28. 3H]-cis-3-[(2-methoxybenzyl)-amino]-2-phenylpiperidine, a highly potent and selective nonpeptide substance P receptor antagonist radioligand. J. Med. Chem. 36, 3197-3201.
29. Sachais B. S., Snider R. M., Lowe J. A., and Krause J. E. (1993) Molecular basis for the species selectivity of the substance-P antagonist CP-96,345. J. Biol. Chem. 268, 2319-2323.
30. Sasai Y. and Nakanishi S. (1989) Molecular cloning of rat substance K receptor and ils mRNAs. Biochem. Biophys. Res. Commun. 165, 695-702.
31. 2+ channels. Eur. J. Pharmacol. 215, 351-352.
32. Shigemoto R., Yokota Y., Tsuchida K., and Nakanishi S. (1990) Cloning and expression of a rat neuromedin K receptor cDNA J. Biol. Chem. 265, 623-628.
33. 1) receptor. Science 251, 435-437.
34. Tabart M. and Peyronel J.-F. (1994) Synthesis of RPR-100893, prototype of a new series of potent and selective non peptide NK1 antagonists: the triarylperhydroisoindolols. Bioorg. Med. Chem. Lett. 4, 673-676.
35. Takeda Y., Chou K. B., Takeda J., Sachais B. S., and Krause J. E. (1991) Molecular cloning, structural characterization and functional expression of cDNA clones. Biochem. Biophys. Res Commun. 179, 1232-1240.
36. 125I] physalaemin. Brain Res. 332, 299-307.
37. Yokota Y., Sasai Y., Tanaka K., Fujiwara T., Tsuchida K., Shigemoto R., Kakizuka A., Ohkubo H., and Nakanishi S. (1989) Molecular characterization of a functional cDNA for the rat substance P receptor. J. Biol. Chem. 264, 17649-17652.