Studies on Peptides. CXXXI. Synthesis of Adrenorphin and Enkephalin Analogs

NOBUTAKA FUJII; MITSUYA SAKURAI; SUZUMITSU KUNO; HARUAKI YAJIMA; MASAMICHI SATOH; MARIKO MATSUSHITA; NORIKO YAMAMOTO; HIROSHI TAKAGI; ZENGMU WANG; WI LEE; PENFENG WANG

doi:10.1248/cpb.33.4326

Studies on Peptides. CXXXI. Synthesis of Adrenorphin and Enkephalin Analogs

NOBUTAKA FUJII, MITSUYA SAKURAI, SUZUMITSU KUNO, HARUAKI YAJIMA, MASAMICHI SATOH, MARIKO MATSUSHITA, NORIKO YAMAMOTO, HIROSHI TAKAGI, ZENGMU WANG, WI LEE, PENFENG WANG

Author information

NOBUTAKA FUJII
MITSUYA SAKURAI
SUZUMITSU KUNO
HARUAKI YAJIMA
MASAMICHI SATOH
MARIKO MATSUSHITA
NORIKO YAMAMOTO
HIROSHI TAKAGI
ZENGMU WANG
WI LEE
PENFENG WANG
Author's Organization：
Faculty of Pharmaceutical Sciences, Kyoto University
Faculty of Pharmaceutical Sciences, Kyoto University
Faculty of Pharmaceutical Sciences, Kyoto University
Faculty of Pharmaceutical Sciences, Kyoto University
Faculty of Pharmaceutical Sciences, Kyoto University
Faculty of Pharmaceutical Sciences, Kyoto University
Faculty of Pharmaceutical Sciences, Kyoto University
Faculty of Pharmaceutical Sciences, Kyoto University
Department of Chemistry, Jilin University, Changchun, People's Republic of China
Department of Chemistry, Jilin University, Changchun, People's Republic of China
Department of Chemistry, Jilin University, Changchun, People's Republic of China

Keywords: analgesic activity

JOURNAL FREE ACCESS

1985 Volume 33 Issue 10 Pages 4326-4332

DOI https://doi.org/10.1248/cpb.33.4326

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Abstract

Adrenorphin, H-Tyr-Gly-Gly-Phe-Met-Arg-Arg-Val-NH₂, and its D-Met (O)²-analog were synthesized. In addition, analogs of [Arg⁶, Phe⁷] enkephalin substituted at the 2nd position by D-Ala and D-Met (O) were also synthesized, together with four other enkephalin analogs. Among these compounds, [D-Met (O)²] adrenorphin exhibited high analgesic activity (29.1 times that of morphine) antagonized by naloxone, when administered intracisternally to mice.

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