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

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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
Pages (from-to)1848-1851
Number of pages4
JournalBiochemistry
Volume14
Issue number9
StatePublished - Dec 1 1975
Externally publishedYes

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Gonadotropin-Releasing Hormone
Derivatives
Gonadotropins
Peptides
Alanine
Rats

ASJC Scopus subject areas

  • Biochemistry

Cite this

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.

Polyfluoroalkylamine derivatives of luteinizing hormone-releasing hormone. / Coy, David H.; Vilchez-Martinez, Jesus A.; Coy, Esther J.; Nishi, Nozumu; Arimura, Akira; Schally, Andrew V.

In: Biochemistry, Vol. 14, No. 9, 01.12.1975, p. 1848-1851.

Research output: Contribution to journalArticle

Coy, DH, Vilchez-Martinez, JA, Coy, EJ, Nishi, N, Arimura, A & Schally, AV 1975, 'Polyfluoroalkylamine derivatives of luteinizing hormone-releasing hormone', Biochemistry, vol. 14, no. 9, pp. 1848-1851.
Coy DH, Vilchez-Martinez JA, Coy EJ, Nishi N, Arimura A, Schally AV. Polyfluoroalkylamine derivatives of luteinizing hormone-releasing hormone. Biochemistry. 1975 Dec 1;14(9):1848-1851.
Coy, David H. ; Vilchez-Martinez, Jesus A. ; Coy, Esther J. ; Nishi, Nozumu ; Arimura, Akira ; Schally, Andrew V. / Polyfluoroalkylamine derivatives of luteinizing hormone-releasing hormone. In: Biochemistry. 1975 ; Vol. 14, No. 9. pp. 1848-1851.
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