Design of monocyclic (1-3) and dicyclic (1-3/4-10) gonadotropin releasing hormone (GnRH) antagonists

Journal of Medicinal Chemistry

Volumn 43, Issue 5, 2000, Pages 797-806

  Rivier, Jean E ^a   Porter, John ^a   Cervini, Laura A ^a   Lahrichi, Sabine L ^a   Kirby, Dean A ^a   Struthers, R Scott ^b   Koerber, Steven C ^a   Rivier, Catherine L ^a  

^a SALK INSTITUTE FOR BIOLOGICAL STUDIES   (United States)

^b NEUROCRINE BIOSCIENCES INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GONADORELIN ANTAGONIST; GONADORELIN RECEPTOR;

ARTICLE; CHIRALITY; DRUG CONFORMATION; DRUG DESIGN; DRUG POTENCY; DRUG RECEPTOR BINDING; NONHUMAN; OVULATION INHIBITION; RAT; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

ANIMALS; CELL LINE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ELECTROPHORESIS, CAPILLARY; FEMALE; GONADOTROPIN-RELEASING HORMONE; HORMONE ANTAGONISTS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MODELS, MOLECULAR; OVULATION; PEPTIDES, CYCLIC; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0034624840     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9901172     Document Type: Article

References (50)

1. Karten, M. J.; Rivier, J. E. GnRH analogue design Structure-function studies toward the development of agonists and antagonists: Rationale and perspective. Endocr. Rev. 1986, 7, 44-66.
2. Matsuo, H.; Baba, Y.; Nair, R. M.; Arimura, A.; Schally, A. V. Structure of the porcine LH-and FSH-releasing hormone. I. The proposed amino acid sequence. Biochem. Biophys. Res. Commun. 1971, 43, 1334-1339.
3. Burgus, R.; Butcher, M.; Amoss, M.; Ling, N.; Monahan, M.; Rivier, J.; Fellows, R.; Blackwell, R.; Vale, W.; Guillemin, R. Primary structure of the ovine hypothalamic luteinizing hormone-releasing factor (LRF). Proc. Natl. Acad. Sci. U.S.A. 1972, 69, 278-282.
4. Sprecher, R. F.; Momany, F. A. On the conformation of luteinizing hormone-releasing hormone, nuclear overhauser observations. Biochem. Biophys. Res. Commun. 1979, 87, 72-77.
5. Kopple, K. D. Peptide backbone-folding in LHRH and analogues. In Peptides: Synthesis-Structure-Function; Rich, D. H., Gross, E., Eds.; Pierce Chemical Co.: Rockford, IL, 1983; pp 295-298.
6. Kopple, K. D. Nitroxyl-induced T1 relaxation rates as a probe of conformation in peptide hormones. Int. J. Pept. Protein Res. 1983, 21, 43-48.
7. Momany, F. A. Conformational energy analysis of the molecule, luteinizing hormone-releasing hormone. 1. Native decapeptide. J. Am. Chem. Soc. 1976, 98, 2990-2996.
8. Momany, F. A. Conformational energy analysis of the molecule, luteinizing hormone-releasing hormone. 2. Tetrapeptide and decapeptide analogues. J. Am. Chem. Soc. 1976, 98, 2996-3000.
9. Chandrasekaren, R.; Lakshminarayanan, A. V.; Pandya, U. V.; Ramachandran, G. N. Conformation of the LL and LD hairpin bends with internal hydrogen bonds in proteins and peptides. Biochim. Biophys. Acta 1973, 303, 14-27.
10. Monahan, M.; Amoss, M.; Anderson, H.; Vale, W. Synthetic analogues of the hypothalamic luteinizing hormone releasing factor with increased agonist or antagonist properties. Biochemistry 1973, 12, 4616-4620.
11. Tonelli, A. E. The effects of isolated N-methylated residues on the conformational characteristics of polypeptides. Biopolymers 1976, 15, 1615-1622.
12. Rivier, J. E.; Struthers, R. S.; Porter, J.; Lahrichi, S. L.; Jiang, G.; Cervini, L. A.; Ibea, M.; Kirby, D. A.; Koerber, S. C.; Rivier, C. L. Design of potent dicyclic (4-10/5-8) gonadotropin releasing hormone (GnRH) antagonists. J. Med. Chem. 2000, 43, 784-796.
13. Rizo, J.; Koerber, S. C.; Bienstock, R. J.; Rivier, J.; Hagler, A. T.; Gierasch, L. M. Conformational analysis of a highly potent, constrained gonadotropin-releasing hormone antagonist. I. Nuclear magnetic resonance. J. Am. Chem. Soc. 1992, 114, 2852-2859.
14. Rizo, J.; Koerber, S. C.; Bienstock, R. J.; Rivier, J.; Gierasch, L. M.; Hagler, A. T. Conformational analysis of a highly potent, constrained gonadotropin-releasing hormone antagonist. II. Molecular Dynamics simulations. J. Am. Chem. Soc. 1992, 114, 2860-2871.
15. Bienstock, R. J.; Rizo, J.; Koerber, S. C.; Rivier, J. E.; Hagler, A. T.; Gierasch, L. M. Conformational analysis of a highly potent dicyclic gonadotropin-releasing hormone antagonist by nuclear magnetic resonance and molecular dynamics. J. Med. Chem. 1993, 36, 3265-3273.
16. Rivier, J.; Koerber, S.; Rivier, C.; Porter, J.; Hagler, A. Design, computer derived structure and biological activity of two bicyclic gonadotropin releasing hormone (GnRH) antagonist. In Current Research in Protein Chemistry: Technique, Structure & Function; Villafranca, J., Ed.; Academic Press: 1990; pp 273-281.
17. Meirovitch, H.; Koerber, S. C.; Rivier, J. E.; Hagler, A. T. Computer simulation of the free energy of peptides with the local states method: analogues of gonadotropin releasing hormone in the random coil and stable states. Biopolymers 1994, 34, 815-839.
18. Rivier, J.; Vale, W.; Burgus, R.; Ling, N.; Amoss, M.; Blackwell, R.; Guillemin, R. Synthetic luteinizing hormone releasing factor analogues Series of short chain amide LRF homologues converging to the amino terminus. J. Med. Chem. 1973, 16, 545-549.
19. Rabinovich, A. K.; Rivier, J. E. Accelerated protocols for solid-phase peptide synthesis at elevated temperature. Am. Biotechnol. Lab. 1994, June, 48-51.
20. Rabinovich, A. K.; Rivier, J. E. SPPS using high temperature. In Peptides: Chemistry, Structure and Biology; Hodges, R. S., Smith, J. A., Eds.; ESCOM Science Publishers: B. V., Leiden, The Netherlands, 1994; pp 71-73.
21. Rivier, J. E.; Miranda, M. T. M. Solid-phase peptide synthesis at elevated temperature: Optimized conditions. In Synthesis of Peptides and Peptidomimetics; Goodman, M., Felix, A., Moroder, L., Toniolo, C., Eds.; Georg Thieme Verlag: Stuttgart, Germany, 1999; Vol. E22, in press.
22. Felix, A. M.; Heimer, E. P.; Wang, C. T.; Lambros, T. J.; Fournier, A.; Mowles, T. F.; Maines, S.; Campbell, R. M.; Wegrzynski, B. B.; Toome, V.; Fry, D.; Madison, V. S. Synthesis, biological activity and conformational analysis of cyclic GRF analogues. Int. J. Pept. Protein Res. 1988, 32, 441-454.
23. Rivier, J.; Kupryszewski, G.; Varga, J.; Porter, J.; Rivier, C.; Perrin, M.; Hagler, A.; Struthers, S.; Corrigan, A.; Vale, W. Design of potent cyclic gonadotropin releasing hormone (GnRH ) antagonists. J. Med. Chem. 1988, 31, 677-682.
24. Rivier, J. Use of trialkylamraonium phosphate (TAAP) buffers in reverse phase HPLC for high resolution and high recovery of peptides and proteins. J. Liq. Chromatog. 1978, 1, 343-367.
25. Hoeger, C. A.; Galyean, R. F.; Boublik, J.; McClintock, R. A.; Rivier, J. E. Preparative reversed phase high performance liquid chromatography. II. Effects of buffer pH on the purification of synthetic peptides. Biochromatography 1987, 2, 134-142.
26. Porter, J.; Dykert, J.; Rivier, J. Synthesis, resolution and characterization of ring substituted phenylalanines and tryptophans. Int. J. Pept. Protein Res. 1987, 30, 13-21.
27. Corbin, A.; Beattie, C. W. Inhibition of the pre-ovulatory proestrous gonadotropin surge, ovulation and pregnancy with a peptide analogue of luteinizing hormone releasing hormone. Endocr. Res. Commun. 1975, 2, 1-23.
28. Rivier, J.; Rivier, C.; Perrin, M.; Porter, J.; Vale, W. LHRH analogues as antiovulatory agents. In LHRH and Its Analogues - Contraceptive and Therapeutic Applications. Advances in Reproduction; Vickery, B. H., Nestor, J. J., Jr., Hafez, E. S. E., Eds.; MTP Press: Lancaster, Boston, The Hague, 1984; pp 11-22.
29. Ljungqvist, A.; Feng, D.-M.; Hook, W.; Shen, Z.-X.; Bowers, C.; Folkers, K. Antide and related antagonists of luteinizing hormone release with long action and oral activity. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 8236-8240.
30. Miranda, A.; Koerber, S. C.; Gulyas, J.; Lahrichi, S.; Craig, A. G.; Corrigan, A.; Hagler, A.; Rivier, C.; Vale, W. W.; Rivier, J. E. Conformationally restricted competitive antagonists of human/rat corticotropin-releasing factor. J. Med. Chem. 1994, 37, 1450-1459.
31. Rivier, J.; Porter, J.; Rivier, C.; Perrin, M.; Corrigan, A. Z.; Hook, W. A.; Siraganian, R. P.; Vale, W. W. New effective gonadotropin releasing hormone antagonists with minimal potency for histamine release in vitro. J. Med. Chem. 1986, 29, 1846-1851.
32. Rivier, J.; Porter, J.; Hoeger, C.; Theobald, P.; Craig, A. G.; Dykert, J.; Corrigan, A.; Perrin, M.; Hook, W. A.; Siraganian, R. P.; Vale, W.; Rivier, C. Gonadotropin releasing hormone antagonists with Nω-triazolyl-ornithine, -lysine or -para-aminophenylalanine residues at positions 5 and 6. J. Med. Chem. 1992, 35, 4270-4278.
33. Rivier, J. E.; Jiang, G.; Porter, J.; Hoeger, C.; Craig, A. G.; Corrigan, A. Z.; Vale, W. W.; Rivier, C. L. GnRH antagonists: novel members of the azaline B family. J. Med. Chem. 1995, 38, 2649-2662.
34. 3+ or α-COO group on helix stability. Proteins 1989, 5, 1-7.
35. Rizo, J.; Sutton, R. B.; Breslau, J.; Koerber, S. C.; Porter, J.; Hagler, A. T.; Rivier, J.; Gierasch, L. M. A novel conformation in a highly potent, constrained gonadotropin releasing hormone antagonist. J. Am. Chem. Soc. 1996, 118, 970-976.
36. Rivier, J. E.; Jiang, G.; Struthers, R. S.; Koerber, S. C.; Porter, J.; Cervini, L. A.; Kirby, D. A.; Craig, A. G.; Rivier, C. L. Design of potent dicyclic (1-5/4-10) gonadotropin releasing hormone (GnRH) antagonists. J. Med. Chem. 2000, 43, 807-818.
37. Koerber, S.; Rizo, J.; Struthers, R. S.; Rivier, J. Consensus bioactive conformation of cyclic GnRH antagonists defined by NMR and molecular modeling. J. Med. Chem. 2000, 43, 819-828.
38. Märki, W.; Spiess, J.; Taché, Y.; Brown, M.; Rivier, J. E. Total solid-phase synthesis of porcine gut gastrin releasing peptide (GRP). a mammalian bombesin. J. Am. Chem. Soc. 1981, 103, 3178-3185.
39. Jiang, G.-C.; Simon, L.; Rivier, J. E. Orthogonally protected N-methyl-substituted α-aminoglycines. Protein Pept. Lett. 1996, 3, 219-224.
40. Stewart, J. M.; Young, J. D. Solid-Phase Peptide Synthesis; Pierce Chemical Co.: Rockford, IL, 1969.
41. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 1970, 34, 595-598.
42. Felix, A. M.; Wang, C.-T.; Heimer, E. P.; Fournier, A. Applications of BOP reagent in solid-phase synthesis. II. Solid-phase side-chain to side-chain cyclizations using BOP reagent. Intl. J. Pept. Protein Res. 1988, 31, 231-238.
43. Miller, C.; Rivier, J. Peptide chemistry: Development of high-performance liquid chromatography and capillary zone electrophoresis. Biopolymers 1996, 40, 265-317.
44. Miller, C.; Rivier, J. Analysis of synthetic peptides by capillary-zone electrophoresis in organic/aqueous buffers. J. Pept. Res. 1998, 51, 444-451.
45. Eidne, K. A.; Sellar, R. E.; Couper, G.; Anderson, L.; Taylor, P. L. Molecular cloning and characterisation of the rat pituitary gonadotropin-releasing hormone (GnRH) receptor. Mol. Cell. Endocrinol. 1992, 90, R5-R9.
46. Kaiser, U. B.; Zhao, D.; Cardone, G. R.; Chin, W. W. Isolation and characterization of cDNAs encoding the rat pituitary gonadotropin-releasing hormone receptor. Biochem. Biophys. Res. Commun. 1992, 189, 1645-1652.
47. Perrin, M. H.; Bilezikjian, L. M.; Hoeger, C.; Donaldson, C. J.; Rivier, J. E.; Haas, Y.; Vale, W. W. Molecular and functional characterization of GnRH receptors cloned from rat pituitary and a mouse pituitary tumor cell line. Biochem. Biophys. Res. Commun. 1993, 191, 1139-1144.
48. Perrin, M. H.; Haas, Y.; Rivier, J. E.; Vale, W. W. GnRH binding to rat anterior pituitary membrane homogenates: Comparison of antagonists and agonists using radiolabeled antagonist and agonist. Mol. Pharmacol. 1983, 23, 44-51.
49. Maple, J.; Dinur, U.; Hagler, A. T. Derivation of ferce fields for molecular mechanics and dynamics from Ab Initio energy surfaces. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 5350-5354.
50. Maple, J. R.; Thacher, T. S.; Dinur, U.; Hagler, A. T. Biosym force field research results in new techniques for the extraction of inter-and intramolecular forces. Chem. Des. Auto. News 1990, 5, 5-10.