Synthesis and Biological Properties of the 2-l-β-(Pyrazolyl-1)alanine Analogs of Luteinizing Hormone-Releasing Hormone and Thyrotropin-Releasing Hormone

David H. Coy; Yoshihiro Hirotsu; Tommie W. Redding; Esther J. Coy; Andrew V. Schally

doi:10.1021/jm00243a018

Synthesis and Biological Properties of the 2-l-β-(Pyrazolyl-1)alanine Analogs of Luteinizing Hormone-Releasing Hormone and Thyrotropin-Releasing Hormone

David H. Coy, Yoshihiro Hirotsu, Tommie W. Redding, Esther J. Coy, Andrew V. Schally

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

Abstract

The luteinizing hormone-releasing hormone (LH-RH) analog, <Glu-Pyr(1)Ala-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH₂, and the thyrotropin-releasing hormone (TRH) analog, <Glu-Pyr(1)Ala-Pro-NH₂, were synthesized by azide couplings of the dipeptide hydrazide, <Glu-Pyr(1)Ala-NHNH₂, to the C-terminal octapeptide of LH-RH and to proline amide, respectively. In an ovariectomized, steroid-blocked rat assay, the LH-RH analog was found to have only 1% of the LH-releasing activity of the natural hormone. The TRH analog was 1.5 times more effective than TRH itself in releasing TSH in vivo from the anterior pituitary of mice. This peptide is one of two synthetic peptides so far discovered which are more potent than TRH.

Original language	English (US)
Pages (from-to)	948-949
Number of pages	2
Journal	Journal of Medicinal Chemistry
Volume	18
Issue number	9
DOIs	https://doi.org/10.1021/jm00243a018
State	Published - Sep 1 1975
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

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Synthesis and Biological Properties of the 2-l-β-(Pyrazolyl-1)alanine Analogs of Luteinizing Hormone-Releasing Hormone and Thyrotropin-Releasing Hormone. / Coy, David H.; Hirotsu, Yoshihiro; Redding, Tommie W.; Coy, Esther J.; Schally, Andrew V.

In: Journal of Medicinal Chemistry, Vol. 18, No. 9, 01.09.1975, p. 948-949.

Research output: Contribution to journal › Article › peer-review

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title = "Synthesis and Biological Properties of the 2-l-β-(Pyrazolyl-1)alanine Analogs of Luteinizing Hormone-Releasing Hormone and Thyrotropin-Releasing Hormone",

abstract = "The luteinizing hormone-releasing hormone (LH-RH) analog, <Glu-Pyr(1)Ala-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2, and the thyrotropin-releasing hormone (TRH) analog, <Glu-Pyr(1)Ala-Pro-NH2, were synthesized by azide couplings of the dipeptide hydrazide, <Glu-Pyr(1)Ala-NHNH2, to the C-terminal octapeptide of LH-RH and to proline amide, respectively. In an ovariectomized, steroid-blocked rat assay, the LH-RH analog was found to have only 1% of the LH-releasing activity of the natural hormone. The TRH analog was 1.5 times more effective than TRH itself in releasing TSH in vivo from the anterior pituitary of mice. This peptide is one of two synthetic peptides so far discovered which are more potent than TRH.",

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AU - Coy, David H.

AU - Hirotsu, Yoshihiro

AU - Redding, Tommie W.

AU - Coy, Esther J.

AU - Schally, Andrew V.

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N2 - The luteinizing hormone-releasing hormone (LH-RH) analog, <Glu-Pyr(1)Ala-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2, and the thyrotropin-releasing hormone (TRH) analog, <Glu-Pyr(1)Ala-Pro-NH2, were synthesized by azide couplings of the dipeptide hydrazide, <Glu-Pyr(1)Ala-NHNH2, to the C-terminal octapeptide of LH-RH and to proline amide, respectively. In an ovariectomized, steroid-blocked rat assay, the LH-RH analog was found to have only 1% of the LH-releasing activity of the natural hormone. The TRH analog was 1.5 times more effective than TRH itself in releasing TSH in vivo from the anterior pituitary of mice. This peptide is one of two synthetic peptides so far discovered which are more potent than TRH.

AB - The luteinizing hormone-releasing hormone (LH-RH) analog, <Glu-Pyr(1)Ala-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2, and the thyrotropin-releasing hormone (TRH) analog, <Glu-Pyr(1)Ala-Pro-NH2, were synthesized by azide couplings of the dipeptide hydrazide, <Glu-Pyr(1)Ala-NHNH2, to the C-terminal octapeptide of LH-RH and to proline amide, respectively. In an ovariectomized, steroid-blocked rat assay, the LH-RH analog was found to have only 1% of the LH-releasing activity of the natural hormone. The TRH analog was 1.5 times more effective than TRH itself in releasing TSH in vivo from the anterior pituitary of mice. This peptide is one of two synthetic peptides so far discovered which are more potent than TRH.

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Synthesis and Biological Properties of the 2-l-β-(Pyrazolyl-1)alanine Analogs of Luteinizing Hormone-Releasing Hormone and Thyrotropin-Releasing Hormone

Abstract

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