Synthesis of somatostatin mimetics based on 1-deoxynojirimycin

Vincent Chagnault; Jérô Lalot; Paul V. Murphy

doi:10.1002/cmdc.200800038

Synthesis of somatostatin mimetics based on 1-deoxynojirimycin

Vincent Chagnault
, Jérô Lalot
, Paul V. Murphy

University College Dublin

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

15 Citations (Scopus)

Abstract

The synthesis of novel somatostatin mimetics from 1-deoxynojirimycin (DNJ) is described. The dipeptide mimetic, which respectively displayed the side chains of tryptophan and lysine at the nitrogen and O6 atoms of the iminosugar scaffold is a ligand (K_i=3.2 μM) for the human somatostatin receptor subtype 4 (hSSTR4) but has lower affinity (K_i>100 μM) for hSSTR5. A benzylated analogue of the Trp-Lys mimetic displays higher affinity for hSSTR5 (K_i=5 μM).

Original language	English
Pages (from-to)	1071-1076
Number of pages	6
Journal	ChemMedChem
Volume	3
Issue number	7
DOIs	https://doi.org/10.1002/cmdc.200800038
Publication status	Published - 14 Jul 2008
Externally published	Yes

Keywords

1-deoxynojirimycin
Carbohydrates
Peptidomimetics
Scaffolds
Somatostatin

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10.1002/cmdc.200800038

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title = "Synthesis of somatostatin mimetics based on 1-deoxynojirimycin",

abstract = "The synthesis of novel somatostatin mimetics from 1-deoxynojirimycin (DNJ) is described. The dipeptide mimetic, which respectively displayed the side chains of tryptophan and lysine at the nitrogen and O6 atoms of the iminosugar scaffold is a ligand (Ki=3.2 μM) for the human somatostatin receptor subtype 4 (hSSTR4) but has lower affinity (Ki>100 μM) for hSSTR5. A benzylated analogue of the Trp-Lys mimetic displays higher affinity for hSSTR5 (Ki=5 μM).",

keywords = "1-deoxynojirimycin, Carbohydrates, Peptidomimetics, Scaffolds, Somatostatin",

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AU - Chagnault, Vincent

AU - Lalot, Jérô

AU - Murphy, Paul V.

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Y1 - 2008/7/14

N2 - The synthesis of novel somatostatin mimetics from 1-deoxynojirimycin (DNJ) is described. The dipeptide mimetic, which respectively displayed the side chains of tryptophan and lysine at the nitrogen and O6 atoms of the iminosugar scaffold is a ligand (Ki=3.2 μM) for the human somatostatin receptor subtype 4 (hSSTR4) but has lower affinity (Ki>100 μM) for hSSTR5. A benzylated analogue of the Trp-Lys mimetic displays higher affinity for hSSTR5 (Ki=5 μM).

AB - The synthesis of novel somatostatin mimetics from 1-deoxynojirimycin (DNJ) is described. The dipeptide mimetic, which respectively displayed the side chains of tryptophan and lysine at the nitrogen and O6 atoms of the iminosugar scaffold is a ligand (Ki=3.2 μM) for the human somatostatin receptor subtype 4 (hSSTR4) but has lower affinity (Ki>100 μM) for hSSTR5. A benzylated analogue of the Trp-Lys mimetic displays higher affinity for hSSTR5 (Ki=5 μM).

KW - 1-deoxynojirimycin

KW - Carbohydrates

KW - Peptidomimetics

KW - Scaffolds

KW - Somatostatin

UR - https://www.scopus.com/pages/publications/54849203700

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DO - 10.1002/cmdc.200800038

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SP - 1071

EP - 1076

JO - ChemMedChem

JF - ChemMedChem

IS - 7

ER -

Synthesis of somatostatin mimetics based on 1-deoxynojirimycin

Abstract

Keywords

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