Two New Opioid Delta-Receptor Ligands: A Highly Selective Agonist and a Potent Selective Antagonist in in Vitro Isolated Preparations
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概要
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N, N-Diallyl derivatives of enkephalin analogues were chemically synthesized, and their biological activities were estimated in in vitro isolated preparations. N, N-Diallyl-[D-Ala<SUP>2</SUP>, D-Leu<SUP>5</SUP>]-enkephalin [test compound I] at doses up to 10 μM did not inhibit the electrically-evoked contractions of guinea-pig ileum, which had been suggested to contain opioid mu- and kappa-receptors, but it significantly depressed the contractions of mouse vas deferens, which had been indicated to contain mu-, kappa- and delta-receptors, suggesting that test compound I did not act on both mu- and kappa-receptors, but acted on delta-receptors. Additionally, the K<SUB>e</SUB> (equilibrium dissociation constant) values againsttest compound I of naloxone were approximately 30 nM and similar to those of Mr 2266, also indicating that test compound I acted as a delta agonist. Moreover, the K<SUB>e</SUB> values of ICI 154129 against compound I were approximately 340 nM, strongly suggesting that test compound I acted as a delta agonist. The K<SUB>e</SUB> values of bis-[N, N-diallyl-[D-Ala<SUP>2</SUP>, Leu<SUP>5</SUP>]-enkephalyl]-cystine [test compound II] against [D-Ala<SUP>2</SUP>, D-Leu<SUP>5</SUP>]-enkephalin in mouse vas deferens and morphine or ethylketocyclazocine in guinea-pig ileum were 44.9 nM and 5.00 or 11.3 μM, respectively, showing that test compound II was a potent selective opioid delta antagonist. In conclusion, among compounds synthesized, two new opioid delta-receptor ligands, one being a highly selective agonist and the other being a potent selective antagonist in in vitro isolated preparations, were found in the present study.
著者
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Inoue Hideyuki
Department Of Chemistry And Materials Science Tokyo Institute Of Technology
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Aoki Kazuko
Departamento Sistemas Biologicos Universidad Autonoma Metropolitana-xochimilco
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OKA Tetsuo
Department of Clinical Pharmacology, School of Medicine, Tokai University
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Ueki Masaaki
Department of Anesthesia, Nishiwaki Municipal Hospital:Department of Anesthesia and Perioperative Medicine, Kobe University
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KAJIWARA Midori
Department of Pharmacology, School of Medicine, Tokai University
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SHINOZAKI Kozo
Department of Applied Chemistry, Science University of Tokyo
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INOUE Hideyuki
Department of Applied Chemistry, Science University of Tokyo
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