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4-Threonine-Oxytocin: A More Active and Specific Oxytocic Agent than Oxytocin

Abstract

SINCE the original synthesis of oxytocin1, the principal uterine contracting and milk ejecting hormone of the posterior pituitary gland, more than 200 analogues have been synthesized in a number of laboratories and the structure–function relationships of the parent hormone have been elucidated pharmacologically2. We now wish to report the synthesis and properties of 4-threonine-oxytocin, an analogue of oxytocin in which the glutamine residue in the four position is replaced by a threonine residue. This analogue has strikingly greater activities in the isolated rat uterus and fowl vasodepressor assays than oxytocin itself, and possesses specifically weaker vasopressor and antidiuretic activities than oxytocin. We believe that study of this analogue may help (a) in elucidating the nature of hormone-receptor interactions, (b) from the standpoint of the phylogeny of the neuro-hypophysial hormones, and (c) in clinical use.

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References

  1. du Vigneaud, V., Ressler, C., Swan, J. M., Roberts, C. W., Katsoyannis, P. G., and Gordon, S., J. Amer. Chem. Soc., 75, 4879 (1953).

    Article  CAS  Google Scholar 

  2. Berde, B., and Boissonnas, R. A., in Neurohypophysial Hormones and Similar Polypeptides (edit. by Berde, B.), 802 (Springer-Verlag, Berlin, 1968).

    Google Scholar 

  3. Merrifleld, R. B., J. Amer. Chem. Soc., 85, 2149 (1963).

    Article  Google Scholar 

  4. Manning, M., J. Amer. Chem. Soc., 90, 1348 (1968).

    Article  CAS  Google Scholar 

  5. Baxter, J. W. M., Manning, M., and Sawyer, W. H., Biochemistry, 8, 3592 (1969).

    Article  CAS  PubMed  Google Scholar 

  6. Manning, M., Wuu, T. C., and Baxter, J. W. M., J. Chromatog., 38, 396 (1968).

    Article  CAS  Google Scholar 

  7. Sawyer, W. H., in The Pituitary Gland (edit. by Harris, G. W., and Donovan, B. T.), 3, 288 (Butterworth, London, 1966).

    Google Scholar 

  8. Flouret, G., and du Vigneaud, V., J. Med. Chem., 12, 1036 (1969).

    Article  Google Scholar 

  9. Katsoyannis, P. G., and du Vigneaud, V., J. Biol. Chem., 233, 1352 (1958).

    CAS  PubMed  Google Scholar 

  10. Berde, B., and Konzett, H., Med. Exp., 2, 317 (1960).

    CAS  Google Scholar 

  11. Geschwind, I. L., Colloques Internationaux du Centre National de la Recherche Scientifique, No. 177, 385 (1969).

    Google Scholar 

  12. Sawyer, W. H., Wuu, T. C., Baxter, J. W. M., and Manning, M., Endocriology, 85, 385 (1969).

    Article  CAS  Google Scholar 

  13. Hope, D. B., Murti, V. V. S., and du Vigneaud, V., J. Biol. Chem., 237, 1563 (1962).

    CAS  PubMed  Google Scholar 

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MANNING, M., SAWYER, W. 4-Threonine-Oxytocin: A More Active and Specific Oxytocic Agent than Oxytocin. Nature 227, 715–716 (1970). https://doi.org/10.1038/227715a0

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