A Novel Ergot Alkaloid as a 5-HT1A Inhibitor Produced by Dicyma sp.

Journal of Medicinal Chemistry

Volumn 46, Issue 24, 2003, Pages 5117-5120

  Vázquez, María J ^a   Roa, Ana M ^a   Reyes, Fernando ^c   Vega, Alfonso ^d   Rivera Sagredo, Alfonso ^e   Thomas, David R ^b   Díez, Emilio ^a   Hueso Rodríguez, Juan A ^a  

^a GLAXOSMITHKLINE   (Spain)

^b GLAXOSMITHKLINE   (United Kingdom)

^c PHARMAMAR S A   (Spain)

^d DGP   (Spain)

^e ELI LILLY AND COMPANY   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DOPAMINE 2 RECEPTOR; ERGOLINE DERIVATIVE; ERGOT ALKALOID; KETANSERIN; SB 272183; SEROTONIN 1A ANTAGONIST; SEROTONIN 1A RECEPTOR; SEROTONIN 1B RECEPTOR; SEROTONIN 2A RECEPTOR; SEROTONIN 2C RECEPTOR; SEROTONIN 6 RECEPTOR; SEROTONIN 7 RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ANXIETY DISORDER; ARTICLE; CHO CELL; CONTROLLED STUDY; DEPRESSION; DICYMA; DRUG ISOLATION; DRUG RECEPTOR BINDING; DRUG STRUCTURE; FUNGUS; HELA CELL; HUMAN; HUMAN CELL; MASS SPECTROMETRY; NEUROTRANSMISSION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ANIMALS; ASCOMYCOTA; BRAIN; CELL MEMBRANE; ERGOLINES; ERGOT ALKALOIDS; GUANOSINE 5'-O-(3-THIOTRIPHOSPHATE); MAGNETIC RESONANCE SPECTROSCOPY; RADIOLIGAND ASSAY; RECEPTOR, SEROTONIN, 5-HT1A; SEROTONIN ANTAGONISTS;

EID: 0242691710     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0341204     Document Type: Article

References (23)

1. Hartig, P. R. Molecular biology of 5-HT receptors. Trends Pharmacol. Sci. 1989, 10, 64-69.
2. 1A receptor gene. J. Biol. Chem. 1990, 256, 5825-5832.
3. 1A receptors are critically involved in the anxiolytic effects of 8-OH-DPAT. Psychopharmacology 1996, 125, 89-91.
4. Lopez-Rodriguez M. L.; Ayala D.; Benhamu B.; Morcillo M. J.; Viso A. Arylpiperazine derivatives acting at 5-HT1A receptors. Curr. Med. Chem. 2002, 9, 443-469.
5. Sylte I.; Bronowska A.; Dahl S. G. Ligand induced conformational states of the 5-HT1A receptor. Eur. J. Pharmacol. 2001, 416, 33-41.
6. Ninomiya, I.; Kiguchi, T. In The Alkaloids: Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: San Diego, 1990; Vol. 38.
7. Stadler, P. A.; Floss, H. G. In Natural Products and Drugs Development; Krogsgaard-Larsen, P.; Christensen, S. B.; Kofod H., Eds. Munksgaard: Copenhagen, 1984.
8. Fuxe, K.; Ogren, S. O.; Agnati, L. F.; Anderson, K., Kall H.; Köhler, C.; Fredholm, B. In Advances in Biochemical Psychopharmacology; Goldstein, M.; Calne, D. B.; Lieberman, A.; Thorner, M. O., Eds.; Raven Press: New York, 1980; Vol. 23, pp 41-62
9. Johnston, A. L.; File, S. E. 5-HT and anxiety: promises and pitfalls. Pharmacol. Biochem., Behav. 1986, 24, 1467-1470.
10. Hollister, L. E.; Claghorn, J. L. New antidepressants, Annu. Rev. Pharmacol., Toxicol. 1993, 32, 165-177.
11. Peroutka, S. J.; Sleight, A. J.; McCarthy, B. G.; Pierce, P. A.; Schmidt, A. W.; Hekmatpanah, C. R. The clinical utility of pharmacological agents that act at serotonin receptors. J. Neuropsych. Clin. Neurosci. 1989, 1, 253-262.
12. Perellino, N. C.; Malyszko, J.; Ballabio, M.; Gioia, B.; Minghetti, A. Identification of ergobine, a new natural peptide ergot alkaloid. J. Nat. Prod. 1993, 56, 489-493.
13. Janet-Siems, K.; Kaloga, M.; Eich, E. Ergobalansine/ergobalansinine, a proline-free peptide-type alkaloid of the fungal genus Balansia, is a constituent of Ipomoea piurensis. J. Nat. Prod. 1994, 57, 1304-1306.
14. Perri, L.; Pitman, I. H.; Rae, I. D.; Winkler, D. A.; Andrews, P. R. Conformational analysis of the ergot alkaloids ergotamine and ergotaminine. J. Med. Chem. 1982, 25, 937-942.
15. 1A receptor agonist-antagonist binding affinity differences as a measure of intrinsic activity in recombinant and native tissue systems. Br. J. Pharmacol. 2000, 130, 1108-1114.
16. Nichols, D. E.; Frescas, S.; Marona-Lewicka, D.; Kurrasch-Orbaugh, D. M. Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD). J. Med. Chem. 2002, 45, 4344-4349.
17. Roberts, C.; Price, G. W.; Middlemiss, D. N. Ligands for the investigation of 5-HT autoreceptor function. Brain Res. Bull. 2001, 56, 463-469.
18. Roberts, C.; Watson, J.; Burton, M.; Price, G.; Jones, B. Functional characterization of the 5-HT terminal autoreceptor in Guinea-pig brain cortex. Br. J. Pharmacol. 1996, 117, 384-388.
19. 1D receptor antagonist in native tissue. J. Pharmacol. 2001, 133, 797-806.
20. To, Z. P.; Bonhaus, D. W.; Eglen, R. M.; Jakeman, L. B. Characterization and distribution of putative 5-HT7 receptors in guinea pig brain. Br. J. Pharmacol. 1996, 115, 107-116.
21. Bowen, W. P.; Jerman, J. C. Non linear regression using spreadsheets. Trends Pharmacol. Sci. 1995, 16, 413-417.
22. 50) of an enzymatic reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
23. 1D receptor subtypes. J. Recept. Signal Transduction Res. 1995, 15, 199-211.