Polyfluoroalkylamine Derivatives of Luteinizing Hormone-Releasing Hormone

David H. Coy, Jesus A. Vilchez-martinez, Esther J. Coy, Nozumu Nishi, Akira Arimura, Andrew V. Schally

Research output: Contribution to journalArticle

21 Scopus citations

Abstract

A series of C-terminally fluorinated analogs of luteinizing hormone-releasing hormone (LH-RH) was synthesized by a combination of solid-phase and classical techniques and found to have interesting properties when assayed for LH- and FSH-releasing activities over a prolonged period of time in immature male rats. One of the peptides, desGly10-LH-RH-2,2,2-trifluoroethylamide, was found to be about nine times more effective than LH-RH in releasing LH, or approximately twice as active as the corresponding alkylamide peptide, desGly10-LH-RH-ethylamide. However, desGly10-LH-RH-2,2,3,3,3-pentafluoropropylamide was only slightly more active than LH-RH and considerably less active than the corresponding propylamide analog. A family of peptides was also prepared containing D-alanine in position six of the chain in conjunction with the C-terminal modifications. D-Ala6,desGly10-LH-RH-2,2,2-trifluoroethylamide, surprisingly, gave patterns of gonadotropin release which were only as intense and virtually identical with those obtained with D-Ala6,desGly10-LH-RH-ethylamide which in turn releases about 20 times more LH than a similar dose of LH-RH. D-Ala6,desGly10-LH-RH-propylamide also gave almost identical patterns of gonadotropin release. D-Ala6,desGly10,LH-RH-2,2,3,3,3-pentafluoropropylamide was considerably less potent, being only five times more effective than LH-RH.

Original languageEnglish (US)
Pages (from-to)1848-1851
Number of pages4
JournalBiochemistry
Volume14
Issue number9
DOIs
StatePublished - May 1 1975
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry

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    Coy, D. H., Vilchez-martinez, J. A., Coy, E. J., Nishi, N., Arimura, A., & Schally, A. V. (1975). Polyfluoroalkylamine Derivatives of Luteinizing Hormone-Releasing Hormone. Biochemistry, 14(9), 1848-1851. https://doi.org/10.1021/bi00680a007