New potent enkephalin analogs containing trifluoromethylamino acid residues

Iwao Ojima; Koji Kato; Fabian A. Jameison; John Conway; Kazuaki Nakahashi; Masaki Hagiwara; Tetsuhisa Miyamae; Hans E. Radunz

doi:10.1016/S0960-894X(01)81068-4

New potent enkephalin analogs containing trifluoromethylamino acid residues

Iwao Ojima
, Koji Kato
, Fabian A. Jameison
, John Conway
, Kazuaki Nakahashi
, Masaki Hagiwara
, Tetsuhisa Miyamae
, Hans E. Radunz

Chemistry

Stony Brook University
Fuji Chemical Industries, Ltd.
Merck KGaA

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

A series of new methionine-enkephalin analogs containing trifluoronorvaline (TFNV) or trifluoronorleucine (TFNL) in place of Gly² or Gly³ are synthesized. The new analogs bearing (D)-TFNV in place of Gly² exhibit ca. 100,000 times enhancement in in vivo analgesic activity in comparison with methionine-enkephalin. The in vitro binding assays for mu, delta and kappa receptors reveal that this enhancement is not based on the much stronger binding to these receptors, but mainly due to the extremely efficient inhibition of degradation by aminopeptidase(s).

Original language	English
Pages (from-to)	219-222
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	2
Issue number	3
DOIs	https://doi.org/10.1016/S0960-894X(01)81068-4
State	Published - 1992

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title = "New potent enkephalin analogs containing trifluoromethylamino acid residues",

abstract = "A series of new methionine-enkephalin analogs containing trifluoronorvaline (TFNV) or trifluoronorleucine (TFNL) in place of Gly2 or Gly3 are synthesized. The new analogs bearing (D)-TFNV in place of Gly2 exhibit ca. 100,000 times enhancement in in vivo analgesic activity in comparison with methionine-enkephalin. The in vitro binding assays for mu, delta and kappa receptors reveal that this enhancement is not based on the much stronger binding to these receptors, but mainly due to the extremely efficient inhibition of degradation by aminopeptidase(s).",

author = "Iwao Ojima and Koji Kato and Jameison, \{Fabian A.\} and John Conway and Kazuaki Nakahashi and Masaki Hagiwara and Tetsuhisa Miyamae and Radunz, \{Hans E.\}",

year = "1992",

doi = "10.1016/S0960-894X(01)81068-4",

language = "English",

volume = "2",

pages = "219--222",

journal = "Bioorganic and Medicinal Chemistry Letters",

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TY - JOUR

T1 - New potent enkephalin analogs containing trifluoromethylamino acid residues

AU - Ojima, Iwao

AU - Kato, Koji

AU - Jameison, Fabian A.

AU - Conway, John

AU - Nakahashi, Kazuaki

AU - Hagiwara, Masaki

AU - Miyamae, Tetsuhisa

AU - Radunz, Hans E.

PY - 1992

Y1 - 1992

N2 - A series of new methionine-enkephalin analogs containing trifluoronorvaline (TFNV) or trifluoronorleucine (TFNL) in place of Gly2 or Gly3 are synthesized. The new analogs bearing (D)-TFNV in place of Gly2 exhibit ca. 100,000 times enhancement in in vivo analgesic activity in comparison with methionine-enkephalin. The in vitro binding assays for mu, delta and kappa receptors reveal that this enhancement is not based on the much stronger binding to these receptors, but mainly due to the extremely efficient inhibition of degradation by aminopeptidase(s).

AB - A series of new methionine-enkephalin analogs containing trifluoronorvaline (TFNV) or trifluoronorleucine (TFNL) in place of Gly2 or Gly3 are synthesized. The new analogs bearing (D)-TFNV in place of Gly2 exhibit ca. 100,000 times enhancement in in vivo analgesic activity in comparison with methionine-enkephalin. The in vitro binding assays for mu, delta and kappa receptors reveal that this enhancement is not based on the much stronger binding to these receptors, but mainly due to the extremely efficient inhibition of degradation by aminopeptidase(s).

UR - https://www.scopus.com/pages/publications/0026775845

U2 - 10.1016/S0960-894X(01)81068-4

DO - 10.1016/S0960-894X(01)81068-4

M3 - Article

AN - SCOPUS:0026775845

SN - 0960-894X

VL - 2

SP - 219

EP - 222

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 3

ER -

New potent enkephalin analogs containing trifluoromethylamino acid residues

Abstract

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