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Volumn 40, Issue 23, 1997, Pages 3739-3748

Betidamino acid scan of the GnRH antagonist acyline

Author keywords

[No Author keywords available]

Indexed keywords

ACYLINE; AZALINE B; BETIDAMINO ACID DERIVATIVE; GLYCINE DERIVATIVE; GONADORELIN ANTAGONIST; LUTEINIZING HORMONE; UNCLASSIFIED DRUG;

EID: 9844268498     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970024p     Document Type: Article
Times cited : (23)

References (48)
  • 1
    • 0002995352 scopus 로고
    • Novel antagonists of GnRH: A compendium of their physicochemical properties, activities, relative potencies and efficacy in humans
    • GnRH Analogues. The State of the Art 1993; Lunenfeld, B., Insler, V., Eds.; The Parthenon Publishing Group: Carnforth, Lancaster
    • Rivier, J. Novel antagonists of GnRH: a compendium of their physicochemical properties, activities, relative potencies and efficacy in humans. In Proceedings of the 3rd International Symposium on GnRH Analogues in Cancer and Human Reproduction; GnRH Analogues. The State of the Art 1993; Lunenfeld, B., Insler, V., Eds.; The Parthenon Publishing Group: Carnforth, Lancaster, 1993; pp 13-26.
    • (1993) Proceedings of the 3rd International Symposium on GnRH Analogues in Cancer and Human Reproduction , pp. 13-26
    • Rivier, J.1
  • 3
    • 0023708204 scopus 로고
    • Luteinizing hormone-releasing hormone (LHRH) antagonists
    • Dutta, A. S. Luteinizing hormone-releasing hormone (LHRH) antagonists. Drugs Future 1988, 13, 43-57.
    • (1988) Drugs Future , vol.13 , pp. 43-57
    • Dutta, A.S.1
  • 4
    • 0000400728 scopus 로고
    • The development of safer GnRH antagonists: Strategy and status
    • Bouchard, P., Haour, F., Franchiniont, P., Schatz, B., Eds.; Elsevier: Paris, France
    • Karten, M. J.; Hoeger, C. A.; Hook, W. A.; Lindbert, M. C.; Naqvi, R. H. The development of safer GnRH antagonists: strategy and status. In Recent Progress on GnRH and Gonadal Peptides; Bouchard, P., Haour, F., Franchiniont, P., Schatz, B., Eds.; Elsevier: Paris, France, 1990; pp 147-158.
    • (1990) Recent Progress on GnRH and Gonadal Peptides , pp. 147-158
    • Karten, M.J.1    Hoeger, C.A.2    Hook, W.A.3    Lindbert, M.C.4    Naqvi, R.H.5
  • 6
    • 0022472366 scopus 로고
    • New effective gonadotropin releasing hormone antagonists with minimal potency for histamine release in vitro
    • Rivier, J.; Porter, J.; Rivier, C.; Perrin, M.; Corrigan, A.; 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.
    • (1986) J. Med. Chem. , vol.29 , pp. 1846-1851
    • Rivier, J.1    Porter, J.2    Rivier, C.3    Perrin, M.4    Corrigan, A.5    Hook, W.A.6    Siraganian, R.P.7    Vale, W.W.8
  • 13
    • 0000015666 scopus 로고
    • Benzotriazole-assisted synthesis of monoacyl aminals and their peptide derivatives
    • Katritzky, A. R.; Urogdi, L.; Mayence, A. Benzotriazole-assisted synthesis of monoacyl aminals and their peptide derivatives. J. Org. Chem. 1990, 55, 2206-2214.
    • (1990) J. Org. Chem. , vol.55 , pp. 2206-2214
    • Katritzky, A.R.1    Urogdi, L.2    Mayence, A.3
  • 14
    • 0027241297 scopus 로고
    • An α-aminoglycine derivative suitable for solid-phase peptide synthesis using Fmoc strategy
    • Qasmi, D.; René, L.; Badet, B. An α-aminoglycine derivative suitable for solid-phase peptide synthesis using Fmoc strategy. Tetrahedron Lett. 1993, 34, 3861-3862.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 3861-3862
    • Qasmi, D.1    René, L.2    Badet, B.3
  • 17
    • 0000780654 scopus 로고    scopus 로고
    • Orthogonally protected N-methyl-substituted α-aminoglycines
    • Jiang, G.-C.; Simon, L.; Rivier, J. E. Orthogonally protected N-methyl-substituted α-aminoglycines. Protein Pept. Lett. 1996, 3, 219-224.
    • (1996) Protein Pept. Lett. , vol.3 , pp. 219-224
    • Jiang, G.-C.1    Simon, L.2    Rivier, J.E.3
  • 18
    • 0029837607 scopus 로고    scopus 로고
    • Peptide chemistry: Development of high-performance liquid chromatography and capillary zone electrophoresis
    • Miller, C.; Rivier, J. Peptide chemistry: Development of high-performance liquid chromatography and capillary zone electrophoresis. Biopolymers 1996, 40, 265-317.
    • (1996) Biopolymers , vol.40 , pp. 265-317
    • Miller, C.1    Rivier, J.2
  • 19
    • 0000695923 scopus 로고
    • A CFF91-based continuum solvation model: Solvation free energies of small organic molecules and conformations of the alanine dipeptide in solution
    • Schmidt, A. B.; Fine, R. M. A CFF91-based continuum solvation model: Solvation free energies of small organic molecules and conformations of the alanine dipeptide in solution. Mol. Sim. 1994, 13, 347-365.
    • (1994) Mol. Sim. , vol.13 , pp. 347-365
    • Schmidt, A.B.1    Fine, R.M.2
  • 21
    • 0022665939 scopus 로고
    • Gonadotropin-releasing hormone analog design. Structure-function studies toward the development of agonists and antagonists: Rationale and perspective
    • Karten, M. J.; Rivier, J. E. Gonadotropin-releasing hormone analog design. Structure-function studies toward the development of agonists and antagonists: rationale and perspective. Endocrine Rev. 1986, 7, 44-66.
    • (1986) Endocrine Rev. , vol.7 , pp. 44-66
    • Karten, M.J.1    Rivier, J.E.2
  • 22
    • 0007097512 scopus 로고
    • An overview of GnRH antagonists development: Two decades of progress
    • Crowley, W. F., Jr., Conn, P. M., Eds.; Springer-Verlag: New York
    • Karten, M. J. An overview of GnRH antagonists development: Two decades of progress. In Modes of Action of GnRH and GnRH Analogs; Crowley, W. F., Jr., Conn, P. M., Eds.; Springer-Verlag: New York, 1992; pp 277-297.
    • (1992) Modes of Action of GnRH and GnRH Analogs , pp. 277-297
    • Karten, M.J.1
  • 23
    • 0002476761 scopus 로고
    • Hypothalamic hypophysiotropic hormones: Review on the design of synthetic analogs
    • Loffet, A., Ed.; Editions de L'Universites: Bruxelles, Belgium
    • Rivier, J.; Brown, M.; Rivier, C.; Ling, N.; Vale, W. Hypothalamic hypophysiotropic hormones: review on the design of synthetic analogs. In Peptides 1976; Loffet, A., Ed.; Editions de l'Universites: Bruxelles, Belgium, 1976; pp 427-521.
    • (1976) Peptides 1976 , pp. 427-521
    • Rivier, J.1    Brown, M.2    Rivier, C.3    Ling, N.4    Vale, W.5
  • 24
    • 0027484160 scopus 로고
    • Single point D-substituted corticotropin releasing factor analogs: Effects on potency and physicochemical characteristics
    • Rivier, J.; Rivier, C.; Galyean, R.; Miranda, A.; Miller, C.; Craig, A. G.; Yamamoto, G.; Brown, M.; Vale, W. Single point D-substituted corticotropin releasing factor analogs: Effects on potency and physicochemical characteristics. J. Med. Chem. 1993, 36, 2851-2859.
    • (1993) J. Med. Chem. , vol.36 , pp. 2851-2859
    • Rivier, J.1    Rivier, C.2    Galyean, R.3    Miranda, A.4    Miller, C.5    Craig, A.G.6    Yamamoto, G.7    Brown, M.8    Vale, W.9
  • 25
    • 0016591067 scopus 로고
    • 8]-somatostatin: An analog of somatostatin more potent than the native molecule
    • 8]-somatostatin: An analog of somatostatin more potent than the native molecule. Biochem. Biophys. Res. Commun. 1975, 65, 746-751.
    • (1975) Biochem. Biophys. Res. Commun. , vol.65 , pp. 746-751
    • Rivier, J.1    Brown, M.2    Vale, W.3
  • 26
    • 0015811931 scopus 로고
    • Synthetic analogs of the hypothalamic luteinizing hormone releasing factor with increased agonist or antagonist properties
    • Monahan, M.; Amoss, M.; Anderson, H.; Vale, W. Synthetic analogs of the hypothalamic luteinizing hormone releasing factor with increased agonist or antagonist properties. Biochemistry 1973, 12, 4616-4620.
    • (1973) Biochemistry , vol.12 , pp. 4616-4620
    • Monahan, M.1    Amoss, M.2    Anderson, H.3    Vale, W.4
  • 27
    • 0026644295 scopus 로고
    • Con format ional analysis of a highly potent, constrained gonadotropin-releasing hormone antagonist. II. Molecular Dynamics simulations
    • Rizo, J.; Koerber, S. C.; Bienstock, R. J.; Rivier, J.; Gierasch, L. M.; Hagler, A. T. Con format ional analysis of a highly potent, constrained gonadotropin-releasing hormone antagonist. II. Molecular Dynamics simulations. J. Am. Chem. Soc. 1992, 114, 2860-2871.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 2860-2871
    • Rizo, J.1    Koerber, S.C.2    Bienstock, R.J.3    Rivier, J.4    Gierasch, L.M.5    Hagler, A.T.6
  • 28
    • 0027436493 scopus 로고
    • Conformational analysis of a highly potent dicyclic gonadotropin-releasing hormone antagonist by nuclear magnetic resonance and molecular dynamics
    • 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.
    • (1993) J. Med. Chem. , vol.36 , pp. 3265-3273
    • Bienstock, R.J.1    Rizo, J.2    Koerber, S.C.3    Rivier, J.E.4    Hagler, A.T.5    Gierasch, L.M.6
  • 29
    • 9844249131 scopus 로고
    • Application of the Mansch approach to design GnRH analogs using Topliss' manual method
    • Brunfeldt, K., Ed.; Scriptor: Copenhagen, Denmark
    • Rivier, J.; Rivier, C.; Perrin, M.; Porter, J.; Vale, W. Application of the Mansch approach to design GnRH analogs using Topliss' manual method. In Peptides 1980; Brunfeldt, K., Ed.; Scriptor: Copenhagen, Denmark, 1981; pp 566-571.
    • (1981) Peptides 1980 , pp. 566-571
    • Rivier, J.1    Rivier, C.2    Perrin, M.3    Porter, J.4    Vale, W.5
  • 30
    • 0020962258 scopus 로고
    • Antagonists of the luteinizing hormone releasing hormone with pyridylalanines which completely inhibit ovulation at nanogram dosage
    • Folkers, K.; Bowers, C. Y.; Kubiak, T.; Stepinski, J. Antagonists of the luteinizing hormone releasing hormone with pyridylalanines which completely inhibit ovulation at nanogram dosage. Biochem. Biophys. Res. Commun. 1983, 111, 1089-1095.
    • (1983) Biochem. Biophys. Res. Commun. , vol.111 , pp. 1089-1095
    • Folkers, K.1    Bowers, C.Y.2    Kubiak, T.3    Stepinski, J.4
  • 33
    • 0020655656 scopus 로고
    • GnRH binding to rat anterior pituitary membrane homogenates: Comparison of antagonists and agonists using radiolabeled antagonist and agonist
    • 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.
    • (1983) Mol. Pharmacol. , vol.23 , pp. 44-51
    • Perrin, M.H.1    Haas, Y.2    Rivier, J.E.3    Vale, W.W.4
  • 35
    • 0021846048 scopus 로고
    • Improved antagonists of luteinizing hormone-releasing hormone modified in position 7
    • Hocart, S. J.; Nekola, M. V.; Coy, D. H. Improved antagonists of luteinizing hormone-releasing hormone modified in position 7. J. Med. Chem. 1985, 28, 967.
    • (1985) J. Med. Chem. , vol.28 , pp. 967
    • Hocart, S.J.1    Nekola, M.V.2    Coy, D.H.3
  • 38
    • 0022665939 scopus 로고
    • GnRH analog design Structure-function studies toward the development of agonists and antagonists: Rationale and perspective
    • Karten, M. J.; Rivier, J. E. GnRH analog design Structure-function studies toward the development of agonists and antagonists: Rationale and perspective. Endocrine Rev. 1986, 7, 44-66.
    • (1986) Endocrine Rev. , vol.7 , pp. 44-66
    • Karten, M.J.1    Rivier, J.E.2
  • 42
    • 0022689993 scopus 로고
    • Use of carboethoxysulfenyl chloride (Sce-Cl) for disulfide bond formation
    • Le Nguyen, D.; Rivier, J. Use of carboethoxysulfenyl chloride (Sce-Cl) for disulfide bond formation. Int. J. Pept. Protein Res. 1986, 27, 285-292.
    • (1986) Int. J. Pept. Protein Res. , vol.27 , pp. 285-292
    • Le Nguyen, D.1    Rivier, J.2
  • 43
    • 0014772602 scopus 로고
    • Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides
    • 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.
    • (1970) Anal. Biochem. , vol.34 , pp. 595-598
    • Kaiser, E.1    Colescott, R.L.2    Bossinger, C.D.3    Cook, P.I.4
  • 44
    • 0021325781 scopus 로고
    • Reversed phase HPLC: Preparative purification of synthetic peptides
    • Rivier, J.; McClintock, R.; Galyean, R.; Anderson, H. Reversed phase HPLC: Preparative purification of synthetic peptides. J. Chromatogr. 1984, 288, 303-328.
    • (1984) J. Chromatogr. , vol.288 , pp. 303-328
    • Rivier, J.1    McClintock, R.2    Galyean, R.3    Anderson, H.4
  • 45
    • 0016592212 scopus 로고
    • Inhibition of the pre-ovulatory proestrous gonadotropin surge, ovulation and pregnancy with a peptide analogue of luteinizing hormone releasing hormone
    • 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.
    • (1975) Endocr. Res. Commun. , vol.2 , pp. 1-23
    • Corbin, A.1    Beattie, C.W.2
  • 46
    • 0021092590 scopus 로고
    • Comparison of the effect of several GnRH antagonists on LH secretion, receptor binding and ovulation
    • Rivier, C.; Rivier, J.; Perrin, M.; Vale, W. Comparison of the effect of several GnRH antagonists on LH secretion, receptor binding and ovulation. Biol. Reprod. 1983, 29, 374-378.
    • (1983) Biol. Reprod. , vol.29 , pp. 374-378
    • Rivier, C.1    Rivier, J.2    Perrin, M.3    Vale, W.4
  • 47
    • 0022597406 scopus 로고
    • Stress-induced inhibition of reproductive functions: Role of endogenous corticotropin-releasing factor
    • Rivier, C.; Rivier, J.; Vale, W. Stress-induced inhibition of reproductive functions: Role of endogenous corticotropin-releasing factor. Science 1986, 231, 607-609.
    • (1986) Science , vol.231 , pp. 607-609
    • Rivier, C.1    Rivier, J.2    Vale, W.3
  • 48
    • 0024566412 scopus 로고
    • In the rat, interleukin-1α acts at the level of the brain and the gonads to interfere with gonadotropin and sex steroid secretion
    • Rivier, C.; Vale, W. In the rat, interleukin-1α acts at the level of the brain and the gonads to interfere with gonadotropin and sex steroid secretion. Endocrinology 1989, 124, 2105-2109.
    • (1989) Endocrinology , vol.124 , pp. 2105-2109
    • Rivier, C.1    Vale, W.2


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