Syntheses and biological evaluation of analogs of luteinizing hormone-releasing hormone (LH-RH) modified in position 2, 3, 4 or 5

N. Yanaihara, T. Hashimoto, C. Yanaihara, K. Tsuji, Y. Kenmochi, F. Ashizawa, T. Kaneko, H. Oka, S. Saito, A. Arimura, Andrew V Schally

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Abstract

Syntheses by the conventional methods as well as the chemical, physical and biological properties are described of the following analogs of the LH-releasing hormone (LH-RH): [Leu3]-LH-RH, [Phe3]-LH-RH, [Trp2] [His3]-LH-RH, Des-Trp3-LH-RH, Des-His2-[Phe5]-LH-RH, [Ala4]-LH-RH, [Phe5]-LH-RH and [Ala4] [Phe5]-LH-RH. In vivo assays showed that [Leu3]-LH-RH did not release LH in doses as high as 5 - 25 μg, having less than 0.0008% of LH-RH activity, while [Phe3]-LH-RH had 0.43% of the LH-RH activity of natural LH-RH. The LH-RH activities of [Trp2] [His3]-LH-RH, Des-Trp3-LH-RH and Des-His2-[Phe5]-LH-RH were extremely low. On the other hand, [Ala4]-LH-RH, [Phe5]-LH-RH and [Ala4] [Phe5]-LH-RH had significant LH-RH activity. The structure-activity relationship of LH-RH is discussed on the basis of these findings.

Original languageEnglish
Pages (from-to)64-73
Number of pages10
JournalBiochemical and Biophysical Research Communications
Volume52
Issue number1
DOIs
StatePublished - May 1 1973
Externally publishedYes

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Gonadotropin-Releasing Hormone

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics
  • Molecular Biology

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Syntheses and biological evaluation of analogs of luteinizing hormone-releasing hormone (LH-RH) modified in position 2, 3, 4 or 5. / Yanaihara, N.; Hashimoto, T.; Yanaihara, C.; Tsuji, K.; Kenmochi, Y.; Ashizawa, F.; Kaneko, T.; Oka, H.; Saito, S.; Arimura, A.; Schally, Andrew V.

In: Biochemical and Biophysical Research Communications, Vol. 52, No. 1, 01.05.1973, p. 64-73.

Research output: Contribution to journalArticle

Yanaihara, N. ; Hashimoto, T. ; Yanaihara, C. ; Tsuji, K. ; Kenmochi, Y. ; Ashizawa, F. ; Kaneko, T. ; Oka, H. ; Saito, S. ; Arimura, A. ; Schally, Andrew V. / Syntheses and biological evaluation of analogs of luteinizing hormone-releasing hormone (LH-RH) modified in position 2, 3, 4 or 5. In: Biochemical and Biophysical Research Communications. 1973 ; Vol. 52, No. 1. pp. 64-73.
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abstract = "Syntheses by the conventional methods as well as the chemical, physical and biological properties are described of the following analogs of the LH-releasing hormone (LH-RH): [Leu3]-LH-RH, [Phe3]-LH-RH, [Trp2] [His3]-LH-RH, Des-Trp3-LH-RH, Des-His2-[Phe5]-LH-RH, [Ala4]-LH-RH, [Phe5]-LH-RH and [Ala4] [Phe5]-LH-RH. In vivo assays showed that [Leu3]-LH-RH did not release LH in doses as high as 5 - 25 μg, having less than 0.0008{\%} of LH-RH activity, while [Phe3]-LH-RH had 0.43{\%} of the LH-RH activity of natural LH-RH. The LH-RH activities of [Trp2] [His3]-LH-RH, Des-Trp3-LH-RH and Des-His2-[Phe5]-LH-RH were extremely low. On the other hand, [Ala4]-LH-RH, [Phe5]-LH-RH and [Ala4] [Phe5]-LH-RH had significant LH-RH activity. The structure-activity relationship of LH-RH is discussed on the basis of these findings.",
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AU - Yanaihara, N.

AU - Hashimoto, T.

AU - Yanaihara, C.

AU - Tsuji, K.

AU - Kenmochi, Y.

AU - Ashizawa, F.

AU - Kaneko, T.

AU - Oka, H.

AU - Saito, S.

AU - Arimura, A.

AU - Schally, Andrew V

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AB - Syntheses by the conventional methods as well as the chemical, physical and biological properties are described of the following analogs of the LH-releasing hormone (LH-RH): [Leu3]-LH-RH, [Phe3]-LH-RH, [Trp2] [His3]-LH-RH, Des-Trp3-LH-RH, Des-His2-[Phe5]-LH-RH, [Ala4]-LH-RH, [Phe5]-LH-RH and [Ala4] [Phe5]-LH-RH. In vivo assays showed that [Leu3]-LH-RH did not release LH in doses as high as 5 - 25 μg, having less than 0.0008% of LH-RH activity, while [Phe3]-LH-RH had 0.43% of the LH-RH activity of natural LH-RH. The LH-RH activities of [Trp2] [His3]-LH-RH, Des-Trp3-LH-RH and Des-His2-[Phe5]-LH-RH were extremely low. On the other hand, [Ala4]-LH-RH, [Phe5]-LH-RH and [Ala4] [Phe5]-LH-RH had significant LH-RH activity. The structure-activity relationship of LH-RH is discussed on the basis of these findings.

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