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 microM) for the human somatostatin receptor subtype 4 (hSSTR4) but has lower affinity (K(i)>100 microM) for hSSTR5. A benzylated analogue of the Trp-Lys mimetic displays higher affinity for hSSTR5 (K(i)=5 microM).
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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1-Deoxynojirimycin / chemistry
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1-Deoxynojirimycin / pharmacology*
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Binding, Competitive
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Biomimetic Materials / chemical synthesis
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Biomimetic Materials / pharmacology*
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Hormones / chemical synthesis
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Hormones / pharmacology
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Humans
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Imino Sugars / chemistry
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Imino Sugars / pharmacology
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Ligands
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Lysine / chemistry
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Lysine / pharmacology
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Models, Molecular
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Receptors, Somatostatin / metabolism*
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Somatostatin / analogs & derivatives
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Somatostatin / chemical synthesis
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Somatostatin / pharmacology*
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Tryptophan / chemistry
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Tryptophan / pharmacology
Substances
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Hormones
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Imino Sugars
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Ligands
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Receptors, Somatostatin
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somatostatin receptor subtype-4
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1-Deoxynojirimycin
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Somatostatin
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Tryptophan
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Lysine