Design, Synthesis and Some uses of Receptor-Specific Agonists and Antagonists of Vasopressin and Oxytocin

References

• Michell R. H., Kirk C. J., Billah M. M. Hormonal stimulation of phosphatidylinositol breakdown, with particular reference to the hepatic effects of vasopressin. Biochem Soc Trans. 1979; 7: 861–865
   PubMedGoogle Scholar
• Jard S. Mechanisms of action of vasopressin and vasopressin antagonists. Kidney Intnl. 1988; 34(suppl 26)S38–S42
   Google Scholar
• Jard S., Barberis C., Audigier S., Tribollet E. Neurohypophyseal hormone receptor systems in brain and periphery. Prog. Brain Res. 1987; 72: 173–187
   PubMed Web of Science ®Google Scholar
• Berde B., Boissonnas R. A. Basic pharmacological properties of synthetic analogues and homologues of the neurohypophysial hormones. Neurohypophysial hormones and similar polypeptides, Handbook of Experimental Pharmacology, B. Berde. Springer, Berlin 1968; Vol 23: 802–870
   Google Scholar
• du Vigneaud V., Ressler C., Swan J. M., Katosoyannis P. G., Roberts C. W. The synthesis of oxytocin. J. Amer. Chem. Soc. 1954; 76: 3115–3121
   Web of Science ®Google Scholar
• du Vigneaud V., Gish D. T., Katsoyannis P. G. A synthetic preparation possessing biological properties associated with arginine-vasopressin. J. Amer. Chem. Soc. 1954; 76: 4751–4752
   Web of Science ®Google Scholar
• Hruby V. J., Smith C. S. Structure-activity relationships of neurohypophysial peptides. Chemistry, Biology, and medicine of neurohypophysial hormones and their analogs, C. W. Smith, S. Udenfriend, J. Meienhofer. Academic Press, Orlando, FL 1987; Vol. 8: 77–207, The Peptides
   Google Scholar
• Lebl M. Analogs with inhibitory properties. Handbook of neurohypophyseal hormone analogs, K. Jost, M. Lebl, F. Brtnik. CRC Press, Boca Raton, FL 1988; Vol. 2: 17–74, part 1
   Google Scholar
• Kinter L. B., Huffman W. F., Stassen F. L. Antagonists of the antidiuretic activity of vasopressin. Am. J. Physiol. 1985; 254: F165–77
   Google Scholar
• Manning M., Sawyer W. H. Discovery, development and some uses of vasopressin and oxytocin antagonists. J. Lab. Clin. Med. 1989; 114: 617–632
   PubMed Web of Science ®Google Scholar
• Manning M., Grzonka Z., Sawyer W. H. Synthesis of posterior pituitary hormones and hormone analogues. The pituitary, C. Beardwell, G. Robertson. Butterworths, London 1981; 265–296
   Google Scholar
• Sawyer W. H., Manning M. Experimental uses of neurohypophysial hormone analogs. Trends in Endocrinol and Metab. 1989; 48–50
   PubMed Web of Science ®Google Scholar
• Manning M., Sawyer W. H. Antagonists of vasopressin and oxytocin: Current status and future perspectives. Vasopressin, S. Jard, R. Jamison. Colloque Inserm/John Libbey Eurotext, London 1991; 297–309
   Google Scholar
• Merrifield R. B. Solid phase synthesis I. The synthesis of a tetrapeptide. J. Amer. Chem. Soc. 1963; 85: 2149–2154
   Web of Science ®Google Scholar
• Schwartz J., Derdowska I., Sobocinska M., Kupryszewski G. A potent new synthetic analog of vasopressin with relative agonist specificity for the pituitary. Endocrinol. 1991; 129: 1107–1109
   PubMed Web of Science ®Google Scholar
• Yamamura Y., Ogawa H., Chihara T., Kondo K., Onogawa T., Nakamura S., Mori T., Tominaga M., Yabuuchi Y. OPC-21268, an orally effective, nonpeptide vasopressin V1 receptor antagonist. Science 1991; 252: 572–574
   PubMed Web of Science ®Google Scholar
• Yamamura Y., Ogawa H., Yamashita H., Chihara T., Miyamoto H., Nakamura S., Onogawa T., Yamashita T., Hosokawa T., Mori T., Tominaga M., Yabuuchi Y. Characterization of a novel aquaretic agent, OPC-31260, as an orally effective, nonpeptide vasopressin V2 receptor antagonist. Br. J. Pharmacol. 1992; 105: 787–791
   PubMed Web of Science ®Google Scholar
• Freidinger R. M., Williams P. D., Tung R. D., Bock M. G., Pettibone D. J., Clineschmidt B. V., DiPardo R. M., Erb J. M., Garsky V. M., Gould N. P., Kaufman M. J., Lundell D. S., Perlow D. S., Whittier W. L., Veber D. F. Cyclic hexapeptide oxytocin antagonists potency-, selectivity-, and solubility-enhancing modifications. J. Med. Chem. 1990; 33: 1843–1845
   PubMed Web of Science ®Google Scholar
• Nestor J. J., Jr., Ferger M. F., du Vigneaud V. [1-β-mercapto-β, β pentamethylenepropionic acid] oxytocin, a potent inhibitor of oxytocin. J. Med. Chem. 1975; 18: 284–287
   PubMed Web of Science ®Google Scholar
• Elands J., Barberis C., Jard S., Tribollet E., Dreifuss J. J., Bankowski K., Manning M., Sawyer W. H. 125I-labelled d(CH2)5[Tyr(Me)2 Tyr-NH29]OVT: a selective oxytocin receptor ligand. Eur. J. Pharmacol. 1987; 147: 197–207
   Web of Science ®Google Scholar
• Lutz W., Londowski J. M., Sanders M., Salisbury J., Kumar R. A vasopressin analog that binds but does not activate V1 or V2 vasopressin receptors is not internalized into cells that express V1 or V2 receptors. J. Biol. Chem. 1992; 267: 1109–1115
   PubMed Web of Science ®Google Scholar
• Kruszynski M., Lammek B., Manning M., Seto J., Haldar J., Sawyer W. H. [1-(β-mercapto-β, β-cyclopentamethylenepropionic acid), 2-(0-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
   PubMed Web of Science ®Google Scholar
• Manning M., Stoev S., Bankowski K., Misicka A., Lammek B., Wo N. C., Sawyer W. H. Synthesis and some pharmacological properties of potent and selective antagonists of the vasopressor (V1-receptor) response to arginine vasopressin. J. Med. Chem. 1992; 35: 382–388
   PubMed Web of Science ®Google Scholar
• Bankowski K., Manning M., Haldar J., Sawyer W. H. Design and synthesis of potent antagonists of the vasopressor response to arginine vasopressin. J. Med. Chem. 1978; 21: 850–853
   PubMed Web of Science ®Google Scholar
• Manning M., Stoev S., Kolodziejczyk A., Klis W. A., Kruszynski M., Misicka A., Olma A., Wo N. C., Sawyer W. H. Design of potent and selective linear antagonists of the vasopressor (V1-receptor) responses to vasopressin. J. Med. Chem. 1990; 33: 3079–3086
   PubMed Web of Science ®Google Scholar
• Sawyer W. H., Pang P. K. T., Seto J., McEnroe M., Lammek B., Manning M. Vasopressin analogs that antagonize antidiuretic responses by rats to the antidiuretic hormone. Science 1981; 212: 49–51
   PubMed Web of Science ®Google Scholar
• Manning M., Lammek B., Kolodziejczyk A., Seto J., Sawyer W. H. Synthetic antagonists of in vivo antidiuretic and vasopressor responses to arginine vasopressin. J. Med. Chem. 1981; 24: 701–706
   PubMed Web of Science ®Google Scholar
• Manning M., Przybylski J. P., Olma A., Klis W. A., Kruszynski M., Wo N. C., Pelton G. H., Sawyer W. H. No requirement of cyclic conformation for binding of antagonists to vasopressin receptors. Nature 1987; 329: 839–840
   PubMed Web of Science ®Google Scholar
• Trinder D., Stephenson J. M., Gao X., Phillips P. A., Risvanis J., Johnston C. I. [3H]desGly-NH29-d(CH2)5[D-Ileu2 Ileu4]AVP: An AVP V2 Receptor Antagonist Radioligand. Peptides 1991; 12: 1195–1200
   PubMed Web of Science ®Google Scholar
• Elands J., Barberis C., Jard S. [3H]-[Thr4 Gly7]OT: a highly selective ligand for central and peripheral OT receptors. Am. J. Physiol. 1988; 254: E31
   Google Scholar
• Marchingo A. J., Abrahams J. M., Woodcock E. A., Smith A. I., Mendelsohn F. A. O., Johnston C. I. Properties of [3H]1-desamino-8-D-arginine vasopressin as a radioligand for vasopressin V2-receptors in rat kidney. Endocrinology 1988; 122: 1328–1336
   PubMed Web of Science ®Google Scholar
• Schmidt A., Audigier S., Barbaris C., Jard S., Manning M., Kolodziejczyk A. S., Sawyer W. H. A radioiodinated linear vasopressin antagonist: A ligand with high affinity and specificity for V1a receptors. FEBS. Lett. 1991; 282: 77–81
   PubMed Web of Science ®Google Scholar
• Zaoral M., Kolc J., Sorm 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. of Czech. Chem. Comm. 1967; 32: 1250–1257
   Google Scholar
• Akerlund M., Stromberg P., Hauksson A., Andersen L. F., Lyndrup J., Melin P. Inhibition of uterine contractions of premature labour with an oxytocin analogue. Results from a pilot study. Brit. J. Obstet. Gynaecol. 1987; 94: 1040–1045
   PubMedGoogle Scholar
• Gavras H., Ribeiro A. B., Kohlmann O., Saragoca M., Mulinari R. A., Ramos O., Gavras I. Effects of a specific inhibitor of the vascular action of vasopressin in humans. Hypertension 1984; 6: 1156–1160, (suppl.)
   Web of Science ®Google Scholar
• Ruffalo R. R., Jr., Brooks D. P., Huffman W. F., Poste G. From vasopressin antagonist to agonist: A saga of surprise. Drug News and Perspectives 1991; 4: 217–222
   Google Scholar
• Lammek B., Bankowski K., Misicka A., Manning M., Seto J., Sawyer W. H. 2–0-alkyl-tyrosine derivatives of 1-deamino-arginine vasopressin: highly specific and potent antidiuretic agonists. J. Med. Chem. 1989; 32: 244–247
   PubMed Web of Science ®Google Scholar
• Lowbridge J., Manning M., Seto J., Haldar J., Sawyer W. H. Synthetic antagonists of in vivo responses by the rat uterus to oxytocin. J. Med. Chem. 1979; 22: 565–569
   PubMed Web of Science ®Google Scholar
• Bankowski K., Manning M., Seto J., Haldar J., Sawyer W. H. Design and synthesis of potent in vivo antagonists of oxytocin. Int. J. Pept. Protein Res. 1980; 16: 382–391
   PubMedGoogle Scholar
• Manning M., Kruszynski M., Bankowski K., Olma A., Lammek B., Cheng L. L., Klis W. A., Seto J., Haldar J., Sawyer W. H. Solid phase synthesis of 16 potent (selective and nonselective) in vivo antagonists of oxytocin. J. Med. Chem. 1989; 32: 382–391
   PubMed Web of Science ®Google Scholar
• Manning M., Klis W. A., Przybylski J., Kruszynski M., Olma A., Bankowski K., Lammek B., Wo N. C., Sawyer W. H. Linear antagonists of arginine vasopressin and oxytocin. Peptides, G. Jung, E. Bayer. Walter de Gruyter, Berlin 1989; 552–555
   Google Scholar
• Lowbridge J., Manning M., Haldar J., Sawyer W. H. [1-β-mercapto-β, β-cyclopentamethylenepropanoic acid, 4-valine, 8-D-arginine] vasopressin, a potent and selective inhibitor of the vasopressor response to arginine vasopressin. J. Med. Chem. 1978; 21: 313–315
   PubMed Web of Science ®Google Scholar
• Manning M., Klis W. A., Przybylski J. P., Kruszynski M., Olma A., Wo N. C., Pelton G. H., Sawyer W. H. Novel linear antagonists of the antidiuretic (V2) and vasopressor (V1) responses to vasopressin. Int. J. Pept. Protein Res. 1988; 32: 455–467
   PubMedGoogle Scholar
• Manning M., Kolodziejczyk A. S., Stoev S., Klis W. A., Wo N. C., Sawyer W. H. (1990) Highly potent and selective Tyr-NH29 containing linear V1 antagonists; D-Tyr2-containing linear V2-antagonists: potential radioiodinated ligands for vasopressin receptors. Peptides 1990, Proc. 21st Eur. Pep. Symp. 1990, E. Giralt, D. Andreu. ESCOM, Leiden, 665–667
   Google Scholar
• Antoni F. A. Novel ligand specificity of pituitary vasopressin receptors in the rat. Neuroendocrinology 1984; 39: 186–188
   PubMed Web of Science ®Google Scholar
• Rivier C., Rivier J., Mormede P., Vale W. Studies of the nature of the interaction between vasopressin and corticotropin-releasing factor on adrenocorticotropin release in the rat. Endocrinology 1984; 115: 882–886
   PubMed Web of Science ®Google Scholar