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Volumn 5, Issue 11, 1999, Pages 472-490

Synthesis and structure-activity investigation of novel vasopressin hypotensive peptide agonists

Author keywords

Hypotensive; Vasodepressor; Vasopressin

Indexed keywords

ANTIHYPERTENSIVE AGENT; ARGIPRESSIN DERIVATIVE; RECEPTOR SUBTYPE; VASOPRESSIN V1 RECEPTOR; VASOPRESSIN V2 RECEPTOR;

EID: 0032758539     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1387(199911)5:11<472::AID-PSC217>3.0.CO;2-A     Document Type: Article
Times cited : (11)

References (79)
  • 2
    • 0343114783 scopus 로고    scopus 로고
    • Discovery of novel selective hypotensive analogues of a vasopressin antagonist
    • Ramage R, Epton R (eds). Mayflower Scientific Ltd.: UK
    • Manning M, Stoev S, Wo NC, Chan WY. Discovery of novel selective hypotensive analogues of a vasopressin antagonist. In Peptides 1996, Ramage R, Epton R (eds). Mayflower Scientific Ltd.: UK, 1998; 615-616.
    • (1998) Peptides 1996 , pp. 615-616
    • Manning, M.1    Stoev, S.2    Wo, N.C.3    Chan, W.Y.4
  • 3
    • 0031647812 scopus 로고    scopus 로고
    • Discovery of novel selective hypotensive vasopressin peptides: A new vasodilating vasopressin receptor?
    • Vasopressin and Oxytocin: Molecular, Cellular and Clinical Research, Zingg HH, Bichet DC, Bourque C (eds)
    • Chan WY, Wo NC, Stoev S, Cheng L-L, Manning M. Discovery of novel selective hypotensive vasopressin peptides: a new vasodilating vasopressin receptor? In Vasopressin and Oxytocin: Molecular, Cellular and Clinical Research, Zingg HH, Bichet DC, Bourque C (eds). Adv. Exptl. Med. Biol. 1998; 449: 451-453.
    • (1998) Adv. Exptl. Med. Biol. , vol.449 , pp. 451-453
    • Chan, W.Y.1    Wo, N.C.2    Stoev, S.3    Cheng, L.-L.4    Manning, M.5
  • 4
    • 0031760550 scopus 로고    scopus 로고
    • Discovery of novel selective hypotensive vasopressin peptides that exhibit little or no functional interactions with known oxytocin/vasopressin receptors
    • Chan WY, Wo NC, Stoev S, Cheng L-L, Manning M. Discovery of novel selective hypotensive vasopressin peptides that exhibit little or no functional interactions with known oxytocin/vasopressin receptors. Br. J. Pharmacol. 1998; 125: 803-811.
    • (1998) Br. J. Pharmacol. , vol.125 , pp. 803-811
    • Chan, W.Y.1    Wo, N.C.2    Stoev, S.3    Cheng, L.-L.4    Manning, M.5
  • 5
    • 0021720889 scopus 로고
    • Vasopressin causes endothelium-dependent relaxations of the canine basilar artery
    • Katusic ZS, Sheperd JT, Vanhoutte PM. Vasopressin causes endothelium-dependent relaxations of the canine basilar artery. Circ. Res. 1984; 55: 575-579.
    • (1984) Circ. Res. , vol.55 , pp. 575-579
    • Katusic, Z.S.1    Sheperd, J.T.2    Vanhoutte, P.M.3
  • 7
    • 0031951116 scopus 로고    scopus 로고
    • Structural bases of vasopressin/oxytocin receptor function
    • Barberis C, Mouillac B, Durroux T. Structural bases of vasopressin/oxytocin receptor function. J. Endocrinol. 1998; 156: 223-229.
    • (1998) J. Endocrinol. , vol.156 , pp. 223-229
    • Barberis, C.1    Mouillac, B.2    Durroux, T.3
  • 8
    • 0018897308 scopus 로고
    • [1-β-Mercapto-β,β-cyclopentamethylenepropionic acid, 2-(O-methyl) tyrosine] arginine-vasopressin and [1-β-mercapto-β,β-cyclopentamethylenepropionic acid] arginine-vasopressin, two highly potent antagonists of the vasopressor response to arginine-vasopressin
    • Kruszynski M, Lammek B, Manning M, Seto J, Haldar J, Sawyer WH. [1-(β-Mercapto-β,β-cyclopentamethylenepropionic acid, 2-(O-methyl) tyrosine] arginine-vasopressin and [1-(β-mercapto-β,β-cyclopentamethylenepropionic acid] arginine-vasopressin, two highly potent antagonists of the vasopressor response to arginine-vasopressin. J. Med. Chem. 1980; 23: 364-368.
    • (1980) J. Med. Chem. , vol.23 , pp. 364-368
    • Kruszynski, M.1    Lammek, B.2    Manning, M.3    Seto, J.4    Haldar, J.5    Sawyer, W.H.6
  • 13
    • 0032956960 scopus 로고    scopus 로고
    • An investigation of position 3 in arginine vasopressin with aliphatic, aromatic, conformationally restricted, polar and charged amino acids
    • Stoev S, Cheng L-L, Olma A, Klis WA, Manning M, Sawyer WH, Wo NC, Chan WY. An investigation of position 3 in arginine vasopressin with aliphatic, aromatic, conformationally restricted, polar and charged amino acids. J. Peptide Sci. 1999; 5: 141-153.
    • (1999) J. Peptide Sci. , vol.5 , pp. 141-153
    • Stoev, S.1    Cheng, L.-L.2    Olma, A.3    Klis, W.A.4    Manning, M.5    Sawyer, W.H.6    Wo, N.C.7    Chan, W.Y.8
  • 15
    • 0004725589 scopus 로고
    • Basic pharmacological properties of synthetic analogues and homologues of the neurohypophysial hormones
    • Berde B (ed.). Springer Verlag: Berlin
    • Berde B, Boissonnas RA. Basic pharmacological properties of synthetic analogues and homologues of the neurohypophysial hormones. In Neurohypophysial Hormones and Similar Polypeptides, Handbook of Experimental Pharmacology, vol. 23, Berde B (ed.). Springer Verlag: Berlin, 1968; 802-870.
    • (1968) Neurohypophysial Hormones and Similar Polypeptides, Handbook of Experimental Pharmacology , vol.23 , pp. 802-870
    • Berde, B.1    Boissonnas, R.A.2
  • 16
    • 0000515280 scopus 로고
    • The design of peptide hormone analogs
    • Academic Press: New York
    • Rudinger J. The design of peptide hormone analogs. In Ariens Drug Design, vol 2. Academic Press: New York, 1971; 319-419.
    • (1971) Ariens Drug Design , vol.2 , pp. 319-419
    • Rudinger, J.1
  • 17
    • 0017687370 scopus 로고
    • Design of neurohypophysial peptides which exhibit selective agonistic and antagonistic properties
    • Manning M, Lowbridge J, Haldar J, Sawyer WH. Design of neurohypophysial peptides which exhibit selective agonistic and antagonistic properties. Federation Proc. 1977; 36: 1848-1852.
    • (1977) Federation Proc. , vol.36 , pp. 1848-1852
    • Manning, M.1    Lowbridge, J.2    Haldar, J.3    Sawyer, W.H.4
  • 18
    • 0019500323 scopus 로고
    • Neurohypophysial peptides: Design of tissue-specific agonists and antagonists
    • Sawyer WH, Grzonka Z, Manning M. Neurohypophysial peptides: design of tissue-specific agonists and antagonists. Molec. Cell. Endocrinol. 1981; 22: 117-134.
    • (1981) Molec. Cell. Endocrinol. , vol.22 , pp. 117-134
    • Sawyer, W.H.1    Grzonka, Z.2    Manning, M.3
  • 19
    • 0001161443 scopus 로고
    • Selective agonists and antagonists of vasopressin
    • Gash DM, Boer GJ (eds). Plenum Press: New York
    • Manning M, Bankowski K, Sawyer WH. Selective agonists and antagonists of vasopressin. In Vasopressin, Principles and Properties, Gash DM, Boer GJ (eds). Plenum Press: New York, 1987; 335-368.
    • (1987) Vasopressin, Principles and Properties , pp. 335-368
    • Manning, M.1    Bankowski, K.2    Sawyer, W.H.3
  • 20
    • 0003372827 scopus 로고
    • Structure-activity relationships of neurohypophysial peptides
    • Udenfriend S, Meienhofer J (eds). Academic Press: Orlando, FL
    • Hruby VJ, Smith CW. Structure-activity relationships of neurohypophysial peptides. In The Peptides, vol. 8, Udenfriend S, Meienhofer J (eds). Academic Press: Orlando, FL, 1987; 77-207.
    • (1987) The Peptides , vol.8 , pp. 77-207
    • Hruby, V.J.1    Smith, C.W.2
  • 21
    • 0000545447 scopus 로고
    • Tables of analogs
    • Jost K, Lebl M, Brtnik F (eds). CRC Press: Boca Raton, FL
    • Lebl M, Jost K, Brtnik F. Tables of analogs. In Handbook of Neurohypophysial Hormone Analogs, vol. 2, part 2, Jost K, Lebl M, Brtnik F (eds). CRC Press: Boca Raton, FL, 1987; 127-267.
    • (1987) Handbook of Neurohypophysial Hormone Analogs , vol.2 , Issue.2 PART , pp. 127-267
    • Lebl, M.1    Jost, K.2    Brtnik, F.3
  • 22
    • 0023852168 scopus 로고
    • Antagonists of the antidiuretic activity of vasopressin
    • Kinter LB, Huffman WF, Stassen FL. Antagonists of the antidiuretic activity of vasopressin. Am. J. Physiol. 1988; 254: F165-F177.
    • (1988) Am. J. Physiol. , vol.254
    • Kinter, L.B.1    Huffman, W.F.2    Stassen, F.L.3
  • 23
    • 0024801647 scopus 로고
    • Discovery, development and some uses of vasopressin and oxytocin antagonists
    • Manning M, Sawyer WH. Discovery, development and some uses of vasopressin and oxytocin antagonists. J. Lab. Clin. Med. 1989; 114: 617-632.
    • (1989) J. Lab. Clin. Med. , vol.114 , pp. 617-632
    • Manning, M.1    Sawyer, W.H.2
  • 24
    • 0027532677 scopus 로고
    • Design, synthesis and some uses of receptor specific agonists and antagonists of vasopressin and oxytocin
    • Manning M, Sawyer WH. Design, synthesis and some uses of receptor specific agonists and antagonists of vasopressin and oxytocin. J. Receptor Res. 1993; 13: 195-214.
    • (1993) J. Receptor Res. , vol.13 , pp. 195-214
    • Manning, M.1    Sawyer, W.H.2
  • 27
    • 0019830566 scopus 로고
    • Synthetic antagonists of in vivo antidiuretic and vasopressor responses to arginine vasopressin
    • Manning M, Lammek B, Kolodziejczyk A, Seto J, Sawyer WH. Synthetic antagonists of in vivo antidiuretic and vasopressor responses to arginine vasopressin. J. Med. Chem. 1981; 24: 701-706.
    • (1981) J. Med. Chem. , vol.24 , pp. 701-706
    • Manning, M.1    Lammek, B.2    Kolodziejczyk, A.3    Seto, J.4    Sawyer, W.H.5
  • 28
    • 0008122240 scopus 로고
    • 2-O-methyl and 2-O-ethyl-tyrosine derivatives of [8-arginine] vasopressin analogs: Highly specific antidiuretic agonists
    • Bankowski K, Lammek B, Kruszynski M, Manning M, Seto J, Sawyer WH. 2-O-methyl and 2-O-ethyl-tyrosine derivatives of [8-arginine] vasopressin analogs: highly specific antidiuretic agonists. Coll. Czech. Chem. Commun. 1988; 53: 2617-2626.
    • (1988) Coll. Czech. Chem. Commun. , vol.53 , pp. 2617-2626
    • Bankowski, K.1    Lammek, B.2    Kruszynski, M.3    Manning, M.4    Seto, J.5    Sawyer, W.H.6
  • 29
    • 0024579003 scopus 로고
    • 2-O-Alkyltyrosine derivatives of 1-deamino-arginine-vasopressin: Highly specific and potent antidiuretic agonists
    • Lammek B, Bankowski K, Misicka A, Manning M, Seto J, Sawyer WH. 2-O-Alkyltyrosine derivatives of 1-deamino-arginine-vasopressin: Highly specific and potent antidiuretic agonists. J. Med. Chem. 1989; 32: 244-247.
    • (1989) J. Med. Chem. , vol.32 , pp. 244-247
    • Lammek, B.1    Bankowski, K.2    Misicka, A.3    Manning, M.4    Seto, J.5    Sawyer, W.H.6
  • 30
    • 0021034548 scopus 로고
    • Potent antagonists of the antidiuretic response to arginine-vasopressin based on modifications of [1-(β-mercapto-β,β-cyclopentamethylenepropionic acid), 2-D-phenylalanine, 4-valine] arginine-vasopressin at position 4
    • Manning M, Olma A, Klis WA, Seto J, Sawyer WH. Potent antagonists of the antidiuretic response to arginine-vasopressin based on modifications of [1-(β-mercapto-β,β-cyclopentamethylenepropionic acid), 2-D-phenylalanine, 4-valine] arginine-vasopressin at position 4. J. Med. Chem. 1983; 26: 1607-1613.
    • (1983) J. Med. Chem. , vol.26 , pp. 1607-1613
    • Manning, M.1    Olma, A.2    Klis, W.A.3    Seto, J.4    Sawyer, W.H.5
  • 31
    • 0021271889 scopus 로고
    • Potent and selective antagonists of the antidiuretic response to arginine-vasopressin based on modifications of [1-β-mercapto-β,β-pentamethylenepropionic acid, 2-D-isoleucine, 4-valine]arginine-vasopressin at position 4
    • Manning M, Nawrocka E, Misicka A, Olma A, Klis WA, Seto J, Sawyer WH. Potent and selective antagonists of the antidiuretic response to arginine-vasopressin based on modifications of [1-β-mercapto-β,β-pentamethylenepropionic acid), 2-D-isoleucine, 4-valine]arginine-vasopressin at position 4. J. Med. Chem. 1984; 27: 423-429.
    • (1984) J. Med. Chem. , vol.27 , pp. 423-429
    • Manning, M.1    Nawrocka, E.2    Misicka, A.3    Olma, A.4    Klis, W.A.5    Seto, J.6    Sawyer, W.H.7
  • 33
    • 0023665377 scopus 로고
    • Invertebrate vasopressin/oxytocin homologs: Characterization of peptides from Conus Geographus and Conus Striatus Venoms
    • Cruz LJ, de Santos V, Zafaralla GC, Ramilo CA, Zeikus R, Gray WR, Olivera BM. Invertebrate vasopressin/oxytocin homologs: characterization of peptides from Conus Geographus and Conus Striatus Venoms. J. Biol. Chem. 1987; 262: 15821-15824.
    • (1987) J. Biol. Chem. , vol.262 , pp. 15821-15824
    • Cruz, L.J.1    De Santos, V.2    Zafaralla, G.C.3    Ramilo, C.A.4    Zeikus, R.5    Gray, W.R.6    Olivera, B.M.7
  • 34
    • 0025330375 scopus 로고
    • Invertebrate neuropeptides resembling vasotocin and some analogues: Synthesis and pharmacological properties
    • Kruszynski M, Manning M, Wo NC, Sawyer WH. Invertebrate neuropeptides resembling vasotocin and some analogues: Synthesis and pharmacological properties. Experientia 1990; 46: 771-773.
    • (1990) Experientia , vol.46 , pp. 771-773
    • Kruszynski, M.1    Manning, M.2    Wo, N.C.3    Sawyer, W.H.4
  • 38
    • 2442751778 scopus 로고
    • 4-Substituted analogs of deamino-D-arginine-vasopressin: Biological potencies and structure-activity relationships related to position 4
    • Rich HD, Gross E (eds). Pierce Chemical: Rockford, IL
    • Plis̄ka V, Melin P, Carlsson L. 4-Substituted analogs of deamino-D-arginine-vasopressin: biological potencies and structure-activity relationships related to position 4. In Peptides: Synthesis. Structure, Function, Proceedings of the 7th American Peptide Symposium, Rich HD, Gross E (eds). Pierce Chemical: Rockford, IL, 1981; 717-720.
    • (1981) Peptides: Synthesis. Structure, Function, Proceedings of the 7th American Peptide Symposium , pp. 717-720
    • Pliska, V.1    Melin, P.2    Carlsson, L.3
  • 39
    • 0021348914 scopus 로고
    • Influence of sarcosine or N-methylalanine in position 7 on the antagonistic properties of [1-deaminopenicillamine]-and [1-(β-mercapto-β,β-cyclopentamethylene-propionic acid)]-vasopressin
    • Gazis D, Schwartz IL, Lammek B, Grzonka Z. Influence of sarcosine or N-methylalanine in position 7 on the antagonistic properties of [1-deaminopenicillamine]-and [1-(β-mercapto-β,β-cyclopentamethylene-propionic acid)]-vasopressin. Int. J. Peptide Protein Res. 1984; 28: 78-83.
    • (1984) Int. J. Peptide Protein Res. , vol.28 , pp. 78-83
    • Gazis, D.1    Schwartz, I.L.2    Lammek, B.3    Grzonka, Z.4
  • 42
    • 0020679299 scopus 로고
    • Synthesis and some pharmacological properties of oxytocin and vasopressin analogues with sarcosine or N-methyl-L-alanine in position 7
    • Grzonka Z, Lammek B, Kasprzykowski F, Gazis D, Schwartz L. Synthesis and some pharmacological properties of oxytocin and vasopressin analogues with sarcosine or N-methyl-L-alanine in position 7. J. Med. Chem. 1983; 26: 555-559.
    • (1983) J. Med. Chem. , vol.26 , pp. 555-559
    • Grzonka, Z.1    Lammek, B.2    Kasprzykowski, F.3    Gazis, D.4    Schwartz, L.5
  • 43
    • 0015581876 scopus 로고
    • Solid-phase synthesis and pressor potency of [1-deamino-9-ethylenediamine]-lysine-vasopressin
    • Glass JD, du Vigneaud V. Solid-phase synthesis and pressor potency of [1-deamino-9-ethylenediamine]-lysine-vasopressin. J. Med. Chem. 1973; 16: 160-161.
    • (1973) J. Med. Chem. , vol.16 , pp. 160-161
    • Glass, J.D.1    Du Vigneaud, V.2
  • 46
    • 0000960777 scopus 로고
    • Amino acids and peptides. LXXI. Synthesis of 1-deamino-8-D-γ-aminobutyrine-vasopressin, 1-deamino-8-D-lysine-vasopressin, and 1-deamino-8-D-arginine-vasopressin
    • Zaoral M, Kolc J, Šorm F. Amino acids and peptides. LXXI. Synthesis of 1-deamino-8-D-γ-aminobutyrine-vasopressin, 1-deamino-8-D-lysine-vasopressin, and 1-deamino-8-D-arginine-vasopressin. Coll. Czech. Chem. Commun. 1967; 32: 1250-1257.
    • (1967) Coll. Czech. Chem. Commun. , vol.32 , pp. 1250-1257
    • Zaoral, M.1    Kolc, J.2    Šorm, F.3
  • 47
    • 0015789667 scopus 로고
    • Solid-phase synthesis of [1-deamino-4-valine]-8-D-arginine-vasopressin (DVDAVP). A highly potent and specific antidiuretic agent possessing protracted effects
    • Manning M, Balaspiri L, Acosta M, Sawyer WH. Solid-phase synthesis of [1-deamino-4-valine]-8-D-arginine-vasopressin (DVDAVP). A highly potent and specific antidiuretic agent possessing protracted effects. J. Med. Chem. 1973: 16: 975-978.
    • (1973) J. Med. Chem. , vol.16 , pp. 975-978
    • Manning, M.1    Balaspiri, L.2    Acosta, M.3    Sawyer, W.H.4
  • 48
    • 0016382468 scopus 로고
    • Structural changes in the arginine vasopressin molecule that enhance antidiuretic activity and specificity
    • Sawyer WH, Acosta M, Balaspiri L, Manning M. Structural changes in the arginine vasopressin molecule that enhance antidiuretic activity and specificity. Endocrinology 1974; 94: 1106-1115.
    • (1974) Endocrinology , vol.94 , pp. 1106-1115
    • Sawyer, W.H.1    Acosta, M.2    Balaspiri, L.3    Manning, M.4
  • 49
    • 0001540256 scopus 로고
    • Enzymatic cleavage of glycinamide from vasopressin and proposed structure for the pressor-antidiuretic hormone of the posterior pituitary
    • du Vigneaud V, Lawler HC, Popenoe EA. Enzymatic cleavage of glycinamide from vasopressin and proposed structure for the pressor-antidiuretic hormone of the posterior pituitary. J. Am. Chem. Soc. 1953; 75: 4880-4881.
    • (1953) J. Am. Chem. Soc. , vol.75 , pp. 4880-4881
    • Du Vigneaud, V.1    Lawler, H.C.2    Popenoe, E.A.3
  • 50
    • 0017279977 scopus 로고
    • Synthetic metabolites of neurohypophyseal hormones [des-9-glycinamide] oxytocin and [des-9-glycinamide,des-8-leucine] oxytocin
    • Walter R, Havran RT, Schwartz IL. Synthetic metabolites of neurohypophyseal hormones [des-9-glycinamide] oxytocin and [des-9-glycinamide,des-8-leucine] oxytocin. J. Med. Chem. 1976; 19: 328-330.
    • (1976) J. Med. Chem. , vol.19 , pp. 328-330
    • Walter, R.1    Havran, R.T.2    Schwartz, I.L.3
  • 54
    • 20744456789 scopus 로고
    • Solid phase peptide synthesis. I. The synthesis of a tetrapeptide
    • Merrifield RB. Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J. Am. Chem. Soc. 1963; 85: 2149-2154.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 2149-2154
    • Merrifield, R.B.1
  • 55
    • 0001611730 scopus 로고
    • Solid-phase peptide synthesis. III. An improved synthesis of bradykinin
    • Merrifield RB. Solid-phase peptide synthesis. III. An improved synthesis of bradykinin. Biochemistry 1964; 3: 1385-1390.
    • (1964) Biochemistry , vol.3 , pp. 1385-1390
    • Merrifield, R.B.1
  • 57
    • 2442727383 scopus 로고    scopus 로고
    • Exploring the structure/function relationships of novel vasopressin hypotensive peptides
    • Bajusz S, Hudecz F (eds). Akademic Kiadô: Budapest, Hungary
    • Manning M, Stoev S, Cheng L-L, Wo NC, Chan WY. Exploring the structure/function relationships of novel vasopressin hypotensive peptides. In Peptides 1998, Bajusz S, Hudecz F (eds). Akademic Kiadô: Budapest, Hungary, 1999; 56-57.
    • (1999) Peptides 1998 , pp. 56-57
    • Manning, M.1    Stoev, S.2    Cheng, L.-L.3    Wo, N.C.4    Chan, W.Y.5
  • 58
    • 0014704672 scopus 로고
    • New method for the synthesis of peptides: Activation of the carboxyl group with dicyclohexylcarbodiimide by using 1-hydroxy-benzotriazole as additives
    • Koenig W, Geiger R. New method for the synthesis of peptides: activation of the carboxyl group with dicyclohexylcarbodiimide by using 1-hydroxy-benzotriazole as additives. Chem. Ber. 1970; 103: 788-798.
    • (1970) Chem. Ber. , vol.103 , pp. 788-798
    • Koenig, W.1    Geiger, R.2
  • 59
    • 0014432614 scopus 로고
    • Synthesis by the Merrifield method of a protected nonapeptide amide with the amino acid sequence of oxytocin
    • Manning M. Synthesis by the Merrifield method of a protected nonapeptide amide with the amino acid sequence of oxytocin. J. Am. Chem. Soc. 1968; 90: 1348-1349.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 1348-1349
    • Manning, M.1
  • 60
    • 0030625001 scopus 로고    scopus 로고
    • Position three in vasopressin antagonist tolerates conformationally restricted and aromatic amino acid substitutions: A striking contrast with vasopressin agonists
    • Manning M, Cheng L-L, Stoev S, Klis WA, Nawrocka E, Olma A, Sawyer WH, Wo NC, Chan WY. Position three in vasopressin antagonist tolerates conformationally restricted and aromatic amino acid substitutions: a striking contrast with vasopressin agonists. J. Peptide Sci. 1997; 3: 31-46.
    • (1997) J. Peptide Sci. , vol.3 , pp. 31-46
    • Manning, M.1    Cheng, L.-L.2    Stoev, S.3    Klis, W.A.4    Nawrocka, E.5    Olma, A.6    Sawyer, W.H.7    Wo, N.C.8    Chan, W.Y.9
  • 61
    • 0001034894 scopus 로고
    • A method of synthesis of long peptide chains using a synthesis of oxytocin as an example
    • Bodanszky M, du Vigneaud V. A method of synthesis of long peptide chains using a synthesis of oxytocin as an example. J. Am. Chem. Soc. 1959; 81: 5688-5691.
    • (1959) J. Am. Chem. Soc. , vol.81 , pp. 5688-5691
    • Bodanszky, M.1    Du Vigneaud, V.2
  • 62
    • 0003359140 scopus 로고
    • Active esters and resins in peptide synthesis
    • Bodanszky M, Sheehan JT. Active esters and resins in peptide synthesis. Chem. Ind. 1964; 1423-1424.
    • (1964) Chem. Ind. , pp. 1423-1424
    • Bodanszky, M.1    Sheehan, J.T.2
  • 63
    • 0000219437 scopus 로고
    • A synthetic preparation possessing biological properties associated with arginine-vasopressin
    • du Vigneaud V, Gish DT, Katsoyannis PG. A synthetic preparation possessing biological properties associated with arginine-vasopressin. J. Am. Chem. Soc. 1954; 76: 4751-5752.
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 4751-5752
    • Du Vigneaud, V.1    Gish, D.T.2    Katsoyannis, P.G.3
  • 65
    • 0000046837 scopus 로고
    • A highly potent analogue of oxytocin, desamino-oxytocin
    • Hope DV, Murti VVS, du Vigneaud V. A highly potent analogue of oxytocin, desamino-oxytocin. J. Biol. Chem. 1962; 237: 1563-1566.
    • (1962) J. Biol. Chem. , vol.237 , pp. 1563-1566
    • Hope, D.V.1    Murti, V.V.S.2    Du Vigneaud, V.3
  • 66
    • 0017861160 scopus 로고
    • Solid phase synthesis of somatosatatin and glucagon-selective analogs in gram quantities
    • Rivier J, Kaiser R, Galyean R. Solid phase synthesis of somatosatatin and glucagon-selective analogs in gram quantities. Biopolymers 1978; 17, 1927-1938.
    • (1978) Biopolymers , vol.17 , pp. 1927-1938
    • Rivier, J.1    Kaiser, R.2    Galyean, R.3
  • 67
    • 0014402250 scopus 로고
    • The purification of synthetic oxytocin and analogues by gel filtration on Sephadex G-15
    • Manning M, Wuu TC, Baxter JWM. The purification of synthetic oxytocin and analogues by gel filtration on Sephadex G-15. J. Chromatogr. 1968; 38: 396-398.
    • (1968) J. Chromatogr. , vol.38 , pp. 396-398
    • Manning, M.1    Wuu, T.C.2    Baxter, J.W.M.3
  • 68
    • 0001641316 scopus 로고
    • The quantitative assay of vasopressin
    • Dekanski J. The quantitative assay of vasopressin. Br. J. Pharmacol. 1952; 7: 567-572.
    • (1952) Br. J. Pharmacol. , vol.7 , pp. 567-572
    • Dekanski, J.1
  • 69
    • 0000918627 scopus 로고
    • Biologic assays for oxytocin and vasopressin
    • Sawyer WH. Biologic assays for oxytocin and vasopressin. Methods Med. Res. 1961; 9: 210-219.
    • (1961) Methods Med. Res. , vol.9 , pp. 210-219
    • Sawyer, W.H.1
  • 70
    • 72849154573 scopus 로고
    • Effect of magnesium ion on the response of the rat uterus to neurohypophysical hormones and analogues
    • Munsick RA. Effect of magnesium ion on the response of the rat uterus to neurohypophysical hormones and analogues. Endocrinology 1960; 66: 451-457.
    • (1960) Endocrinology , vol.66 , pp. 451-457
    • Munsick, R.A.1
  • 71
    • 84957417090 scopus 로고
    • A modification of the method of Dale and Laidlaw for standardization of posterior pituitary extract
    • Holton P. A modification of the method of Dale and Laidlaw for standardization of posterior pituitary extract. Br. J. Pharmacol. 1948; 3: 328-334.
    • (1948) Br. J. Pharmacol. , vol.3 , pp. 328-334
    • Holton, P.1
  • 72
    • 84982328496 scopus 로고
    • pA, a new scale of the measurement of drug antagonism
    • Schild HO. pA, a new scale of the measurement of drug antagonism. Br. J. Pharmacol Chemother. 1958; 2: 189-206.
    • (1958) Br. J. Pharmacol Chemother. , vol.2 , pp. 189-206
    • Schild, H.O.1
  • 73
    • 0015991040 scopus 로고
    • [1-β-mercaptoβ,β-diethyl-propionic acid]-8-lysine-vasopressin, a potent inhibitor of 8-lysine-vasopressin and of oxytocin
    • Dyckes DF, Nestor JJ Jr, Ferger MF, du Vigneaud V. [1-β-mercaptoβ,β-diethyl-propionic acid]-8-lysine-vasopressin, a potent inhibitor of 8-lysine-vasopressin and of oxytocin. J. Med. Chem. 1974; 17: 250-252.
    • (1974) J. Med. Chem. , vol.17 , pp. 250-252
    • Dyckes, D.F.1    Nestor Jr., J.J.2    Ferger, M.F.3    Du Vigneaud, V.4
  • 74
    • 0015622907 scopus 로고
    • Solid-phase synthesis and some pharmacological properties of 4-threonine analogs of vasopressins and vasotocin and of arginine-vasopressin and arginine-vasotocin
    • Manning M, Coy EJ, Sawyer WH, Acosta M. Solid-phase synthesis and some pharmacological properties of 4-threonine analogs of vasopressins and vasotocin and of arginine-vasopressin and arginine-vasotocin. J. Med. Chem. 1973; 16: 463-466.
    • (1973) J. Med. Chem. , vol.16 , pp. 463-466
    • Manning, M.1    Coy, E.J.2    Sawyer, W.H.3    Acosta, M.4
  • 75
    • 33747866223 scopus 로고
    • The preparation of Merrifield-resins through total esterification with cesium salts
    • Gisin, BF. The preparation of Merrifield-resins through total esterification with cesium salts. Helv. Chim. Acta 1973; 56: 1476-1482.
    • (1973) Helv. Chim. Acta , vol.56 , pp. 1476-1482
    • Gisin, B.F.1
  • 76
    • 0019477851 scopus 로고
    • A convenient method for O-alkylation of N-substituted tyrosines using a crown ether
    • Kolodziejczyk AM, Manning M. A convenient method for O-alkylation of N-substituted tyrosines using a crown ether. J. Org. Chem. 1981; 46: 1944-1946.
    • (1981) J. Org. Chem. , vol.46 , pp. 1944-1946
    • Kolodziejczyk, A.M.1    Manning, M.2
  • 77
    • 0016612021 scopus 로고
    • [1-β-mercapto-β,β-pentamethylenepropionic acid oxytocin, a potent inhibitor of oxytocin
    • Nestor JJ Jr, Ferger MF, du Vigneaud V. [1-β-mercapto-β,β-pentamethylenepropionic acid) oxytocin, a potent inhibitor of oxytocin. J. Med. Chem. 1975; 18: 284-287.
    • (1975) J. Med. Chem. , vol.18 , pp. 284-287
    • Nestor Jr., J.J.1    Ferger, M.F.2    Du Vigneaud, V.3
  • 78
    • 49549139072 scopus 로고
    • Reactifs de couplage peptidique. IV. (1)-l'hexafluorophosphate de benzotriazolyl N-oxytris-dimethylamino phosphonium (B.O.P.)
    • Castro B, Dormoy JR, Evin G, Selve C. Reactifs de couplage peptidique. IV. (1)-l'hexafluorophosphate de benzotriazolyl N-oxytris-dimethylamino phosphonium (B.O.P.). Tetrahedron Lett. 1975; 14: 1219-1222.
    • (1975) Tetrahedron Lett. , vol.14 , pp. 1219-1222
    • Castro, B.1    Dormoy, J.R.2    Evin, G.3    Selve, C.4
  • 79
    • 70349907134 scopus 로고
    • B.O.P.: A new peptide coupling reagent exemplified in the synthesis of somatostatin
    • Loffet A (ed.). Editions de L'Universite de Bruxelles
    • Castro B, Dormoy JR, Evin G, Selve C. B.O.P.: A new peptide coupling reagent exemplified in the synthesis of somatostatin. In Peptides 1976, Loffet A (ed.). Editions de L'Universite de Bruxelles: 1976; 79-83.
    • (1976) Peptides 1976 , pp. 79-83
    • Castro, B.1    Dormoy, J.R.2    Evin, G.3    Selve, C.4


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