Tripeptide Analogues of Melanocyte-stimulating Hormone Release

Tripeptide Analogues of Melanocyte-stimulating Hormone Release-Inhibiting. Hormone (Pro-Leu-Gly-NH2) as Inhibitors of Oxotremorine-Induced Tremor...
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Journal of Medicinal Chemistry, 1979, Vol. 22, No. 8 931

Tripeptide Analogues of MIF

(45) S. Moore, J. Biol. Chem., 238, 235 (1963). (46) A. M. Felix, C.-T. Wang, A. A. Liebman, C. M. Delany, T.

(38) W. H. Sawyer, Endocrinology, 63, 694 (1958). (39) H. 0. Schild, Br. J. Pharmacol. Chemother., 2,189 (1947). (40) J. Fiihr, J. Kaczmarczyk, and C. D. Kriittgen, Klin. Wochschr., 33, 729 (1955). (41) B. F. Gisin, Helv. Chim. Acta, 56, 142 (1973). (42) E. Kaiser, R. L. Colescott, C. D. Bossinger, and P. I. Cook, Anal. Biochem. 34, 595 (1970). (43) J. Meienhofer, A. Trzeciak, R. T. Havran, and R. Walter, J. Am. Chem. SOC.,92, 7199 (1970). (44) G. L. Ellman, Arch. Biochem. Biophys., 82, 70 (1959).

Mowles, B. A. Burghardt, A. M. Charnecki, and J. Meienhofer, Int. J. Pept. Protein Res., 10, 299 (1977). (47) For details of amino acid analysis procedure for A3-Pro,see ref 7b. (48) D. B. Hope, V. V. S. Murti, and V. du Vigneaud, J. Biol. Chem., 237, 1563 (1962). (49) 0. H. Lowry, N. J. Rosebrough, A. L. Farr,and R. J. Randall, J. Biol. Chem., 193, 265 (1951).

Tripeptide Analogues of Melanocyte-stimulating Hormone Release-Inhibiting Hormone (Pro-Leu-Gly-NH2)as Inhibitors of Oxotremorine-Induced Tremor Sven Bjorkman,* Staffan Castensson, and Hans Sievertsson Department of Organic Pharmaceutical Chemistry, Biomedical Center, University of Uppsala, S-751 23 Uppsala, Sweden. Received February 20, 1979

Fourteen di- and tripeptide analogues of MIF, Pro-Leu-Gly-NH,,have been synthesized and assayed for inhibition of oxotremorine-inducedtremor. Replacement of Pro by HCO-Pro or cyclopentanecarboxylicacid gave inactive analogues, while some peptides of the general structure