Biological Properties of Opioid Peptides Replacing Tyr at Position 1 by 2,6-Dimethyl-Tyr

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概要

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• To understand the effect of the replacement of Tyr residue at position 1 in opioid peptides by 2,6-dimethyl-Tyr (Dmt) on the biological property, chiral (D or L) Dmt^1 analogs of Leu-enkephalin (Enk) and Tyr-D-Arg-Phe-βAla-NH_2 (YRFB) were synthesized and their enzymatic stabilities, in vitro bioactivities and receptor binding affinities compared with those of parent peptides. [L-Dmt^1]Enk (1) exhibited 4-fold higher stability against aminopeptidase-M and possessed dramatically increased activities in guinea pig ilium (GPI) (187-fold) and mouse vas deferens (MVD) (131-fold) assays, and in rat brain receptor binding assays (356-fold at μ receptor and 46-fold at δ receptor) as compared to Enk. [L-Dmt^1]YRFB (3) also exhibited increased activties in GPI (46-fold) and MVD (177-fold) assays, and in the binding assays (69-fold at μ receptor and 341-fold at δ receptor) as compared to the parent peptide. [D-Dmt^1]Enk (2) and [D-Dmt^1]YRFB (4) exhibited activities with diminished or lesser potency than the parent peptide in all assays. These results indicate that there is a tendency for μ affinity to be enhanced more than δ affinity with introduction of L-Dmt into δ ligand peptide (Enk), and for δ affinity to be enhanced more than μ affinity in case of μ ligand peptide (YRFB), resulting in reduced receptor selectivities at the receptors.

• 公益社団法人日本薬学会の論文
• 1999-10-15

著者

• 山城 祐子

  Faculty Of Pharmaceutical Sciences Kobe Gakuin University

• 山本 譲

  Faculty Of Pharmaceutical Sciences Kanazawa University

• AMBO Akihiro

  Tohoku Pharmaceutical University

• SASAKI Yusuke

  Tohoku Pharmaceutical University

• Ambo A

  Tohoku Pharmaceutical University

• Ouchi H

  Tohoku Pharmaceutical Univ. Sendai Jpn

• Ouchi Hidekazu

  Tohoku College Of Pharmacy

• Yamamoto Y

  Tohoku Univ. Sendai Jpn

• Sasaki Y

  Institute Of Natural Medicine University Of Toyama

• Yamamoto Y

  Pharmaceutical Research Laboratory Hokuriku Seiyaku Co. Ltd.

• Yamamoto Y

  School Of Pharmaceutical Sciences Toho University

• YAMAMOTO Yutaka

  Tohoku Pharmaceutical University

• SUTO Takuya

  Tohoku Pharmaceutical University

• Yamamoto Yoshio

  Pharmaceutical Research Division Takeda Chemical Industries Ltd.

• Yamamoto Y

  大阪薬科大学

• 山本 靖夫

  School Of Pharmaceutical Sciences Toho University

• Sasaki Youhei

  Faculty Of Pharmaceutical Sciences Hoshi University

• Sasaki Yusuke

  Tohoku College Of Pharmacy

• Sasaki Yohei

  Department Of Medicinal Plant Science Hoshi University

• Yamamoto Yutaka

  Tohoku College of Pharmacy

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