Solid-Phase Synthesis and Opioid Activities of [D-Ala^2]Deltorphin II Analogs
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概要
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[D-Ala^2]Deltorphin II (DL-II) analogs having various aliphatic amino acids at positions 5 and 6 were synthesized by a solid-phase method and their opioid activites on electrically inducewd guinea pig ileum (GPI) and mouse vas deferens (MVD) preparations were determined. During the synthesis of an analog, [tert-leucine(Tle)^<5,6>]DL-II, we encountered difficulty in the coupling reaction between Tle^5 and Tle^6 with the usual diisopropylcarbodiimide (DIPCDI)-mediated tert-butoxycarbonyl (Boc) strategy, though the other analogs could be successfully synthesized. We found that the fluorenylmethoxycarbonyl (Fmoc)-Tle/DIPCDI/1-hydroxybenztriazole method was very useful for the synthesis of such a peptide having a sterically hindered sequence. Acid hydrolysis studies of the synthetic analogs suggested that the steric hindrance of consecutive aliphatic amino acid sequences depend upon the degree of branching at the β-carbon atom of the amino acids. In the MVD assay, two analogs, [Ala^<5,6>] and [Tle^<5,6>]DL-II showed remarkably low potencies while other analogs with Nva^<5,6>, Nle^<5,6>, Ile^<5,6>, Leu^<5,6> and Mle^<5,6> substituted for Val^<5,6>(DL-II) showed comparable or slightly lower potencies than DL-II. In the GPI assay, no remarkable changes in potency were observed between DL-II and this series of analogs. Conformational aspects of synthetic analogs were examined by comparing the circular dichroism spectra.
- 社団法人日本薬学会の論文
- 1993-08-15
著者
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鈴木 謙次
東北薬科大学
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安保 明博
Tohoku College of Pharmacy
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佐々木 有亮
Tohoku College of Pharmacy
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鈴木 謙次
Tohoku College of Pharmacy
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緑川 京子
Tohoku College of Pharmacy
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