Surprising pharmacological activity of analogues designed by substitution of position 3 in arginine vasopressin (AVP) and 8-D-arginine vasopressin with L-2-naphthylalanine

Journal of Pharmacy and Pharmacology

Volumn 48, Issue 3, 1996, Pages 316-319

  Lammek, Bernard ^a   Konieczna, Ewa ^a   Trzeciak, Henryk I ^b   Kozłowski, Artur ^b   Szymkowiak, Jacek ^b   Stojko, Rafał ^b   Kupryszewski, Gotfryd ^a  

^a UNIVERSITY OF GDA SK   (Poland)

^b MEDICAL UNIVERSITY OF SILESIA   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE DERIVATIVE; ARGIPRESSIN DERIVATIVE; VASOPRESSIN V1 RECEPTOR; VASOPRESSIN V2 RECEPTOR;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIDIURESIS; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; INTRAVENOUS DRUG ADMINISTRATION; MALE; NONHUMAN; PRESSOR RESPONSE; RAT;

EID: 0029951427     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.2042-7158.1996.tb05924.x     Document Type: Article

References (22)

1. Dekanski, J. (1952) The quantitative assay of vasopressin. Br. J. Pharmacol. 7: 567-572
2. Feder, P. I., Hobson, D. W., Olson, C. T., Joiner, R. L., Mathews, M. C. (1991) Stagewise adaptative dose allocation for quantal response dose-response studies. Neurosci. Biobehav. Rev. 15: 109-114
3. Hlavacek, J. (1987) Important structural modifications. Noncoded amino acids. In: Jost, K., Lebl, M., Brtnik, F. (eds) CRC Handbook of Neurohypophyseal Hormone Analogs, Vol. I, Part 2, CRC Press, Boca Raton, pp 109-129
4. Holton, P. (1948) A modification of the method of Dale and Lindlaw for standardization of posterior pituitary extract. Br. J. Pharmacol. 3: 328-341
5. Jost, K., Prohazka, Z., Cort, J. H., Barth, T., Skopkowa, J., Prusik, Z., Sorm, F. (1974) Synthesis and some biological activities of analogues of deamino-vasopressin with disulphide bridge altered to a thioether bridge. Coll. Czechoslov. Chem. Commun. 39: 2835-2856
6. Lammek, B., Rekowski, P., Kupryszewski, G., Melin, P., Ragnarsson, U. (1988) Synthesis of arginine-vasopressins, modified in position 1 and 2, as antagonists of vasopressor response to the parent hormone. J. Med. Chem. 31: 603-606
7. Lammek, B., Derdowska, I., Kupryszewski, G., Slaninova, J., Barth, T., Hrbas, P. (1989) Synthesis, biological activity and receptor binding affinity of six new antagonists of [8-L-arginine]-vasopressin. Collect. Czech. Chem. Commun. 54: 3374-3380
8. Manning, M. (1968) Synthesis by the Merrifield method of a protected nonapeptide amide with the amino acid sequence of oxytocin. J. Am. Chem. Soc. 90: 1348-1349
9. Manning, M., Sawyer, W. H. (1985) Development of selective agonists and antagonists of vasopressin and oxytocin. In: Schrier, R. W. (ed.) Vasopressin, Raven Press, New York, pp 131-144
10. Manning, M., Coy, E., Sawyer, W. H. (1970) Solid-phase synthesis of [4-threonine] oxytocin. A more potent and specific oxytocic agent than oxytocin. Biochemistry 9: 3925-3930
11. Manning, M., Balaspiri, L., Moehring, J. Haldar, J., Sawyer, W. H. (1976) Synthesis and some pharmacological properties of deamino[4-threonine,8-D-arginine]vasopressin and deamino[8-D-arginine]vasopressin, highly potent and specific antidiuretic peptides, and [8-D-argmine]vasopressin. and deamino-arginine vasopressin. J. Med. Chem. 19: 842-845
12. Manning, M., Grzonka, Z., Sawyer, W. H. (1981) Synthesis of posterior pituitary hormones and hormone analogues In: Beardwell. C., Robinson, G. (eds) The Pituitary, Butterworth, Kent, UK, pp 265-296
13. Manning, M., Bańkowski, K., Sawyer, W. H. (1987) Selective agonists and antagonists of vasopressin In: Gash, D. M., Boer, G. J. (eds) Vasopressin, Plenum Publishing Corporation, New York, pp 335-368
14. Munsick, R. A. (1960) Effect of magnesium ion on the response of the rat uterus to neurohypophyseal hormones and analogues. Endocrinology 66: 451-469
15. Sawyer, W. H. (1958) Differences in the antidiuretic responses of rats to the intravenous administration of lysine and arginine vasopressin. Endocrinology 63: 694-698
16. 2 a new scale for the measurement of drug antagonism. Br. J. Pharmacol. 2: 189-206
17. Slaninova, J. (1987) Fundamental biological evaluation. In: Jost, K., Lebl, M., Brtnik, F. (eds) CRC Handbook of Neurohypophyseal Hormone Analogs, Vol 1, CRC Press, Boca Raton, pp 83-107
18. Stürmer, F. (1968) Bioassay procedures for neurohypophysial hormones and similar polypeptides In: Berde, B. (ed.) Handbook of Experimental Pharmacology, Springer Verlag, Berlin-Heidelberg-New York, pp 130-189
19. Tallarida, R. J., Murray, R. B. (1987) Manual of pharmacologic calculations. Springer Verlag, Berlin-Heideiberg-New York
20. Thibonnier, M. (1990) Vasopressin agonists and antagonists. Horm. Res. 34: 124-128
21. Vavra, I , Machova, A., Krejci, I. (1974) Antidiuretic action of (1-deamino-8-D-arginine) vasopressin in unanaesthetised rats. J. Pharmacol. Exp. Ther. 188: 241-247
22. Zaoral, M. (1985) Vasopressin analogs with high and specific antidiuretic activity. Int. J. Pept. Protein Res. 25: 561-574