Unsulfated C-terminal 7-peptide of cholecystokinin: A new ligand of the opiate receptor

Schiller, Peter W.; Lipton, A.; Horrobin, David F.; Bodanszky, Miklos

doi:10.1016/0006-291x(78)91149-x

Cited by 138 publications

(103 citation statements)

References 9 publications

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“…K e values for the δ antagonists were determined with the ratio of IC 50 values obtained with DPDPE in the MVD assay in the presence and absence of a fixed antagonist concentration [11] . Opioid receptor binding studies were performed as described in detail elsewhere [9] . Binding affinities for μ and δ receptors were determined by displacing, [ Yvon-Spex spectrofluorometer equipped with a Hammamatsu R2658P photomultiplier tube.…”

Section: Methodsmentioning

confidence: 99%

Aladan scanning: The structure-activity relationship of dynorphin A

Chen

Yang

Weng

2009

Sci. China Ser. B-Chem.

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An unnatural amino acid, β-[6′ -(N, N-dimethyl)amino-2′ -naphthoyl]alanine (Ald) showing polarity-sen sitive fluorescence characteristics, was synthesized. A thorough Ald-scan of dynorphin A (Dyn A), the putative endogenous ligand for κ opioid receptors, was then performed. Replacement of the amino acid residues in positions 5, 8, 10, 12 or 14 of Dyn A(1-13)-NH 2 with Ald resulted in compounds that had almost equal κ binding affinity compared with that of the parent compound; on the other hand, substitution of residues in position 1 or 4 with Ald decreased κ-receptor binding affinity. These results indicate that Tyr and Phe in Dyn A are very important for maintaining its κ-opioid activity. Evidence from receptor binding assay clearly displays that [Ald 5 ]Dyn A(1-13)-NH 2 is a highly selective κ-opioid receptor agonist. An evaluation of the interaction of Ald-containing Dyn A(1-13)-NH 2 analogues with SDS and DPC micelles was also performed. Interestingly, [Ald 1 ]Dyn A(1-13)-NH 2 and [Ald 4 ]DynA(1-13)-NH 2 showed quite different fluorescence emission maxima in SDS and DPC micelles. This indicates that both peptides are sensitive to electronic properties of the polar surface of the micelles. aladan, dynorphin A, fluorescent amino acid, fluorescent peptide

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Section: Methodsmentioning

confidence: 99%

Aladan scanning: The structure-activity relationship of dynorphin A

Chen

Yang

Weng

2009

Sci. China Ser. B-Chem.

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“…9,10 K e values for the ␦ antagonists were determined from the ratio of IC 50 values obtained with H-Tyr-c[D-PenGly-Phe-D-Pen]OH (DPDPE) in the MVD assay in the presence and absence of a fixed antagonist concentration.…”

Section: Bioassays and Receptor Binding Assaysmentioning

confidence: 99%

[Aladan³]TIPP: A fluorescent δ‐opioid antagonist with high δ‐receptor binding affinity and δ selectivity

et al. 2004

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“…The GPI [10] and MVD [11] bioassays were carried out as reported in detail elsewhere [7,12]. A log dose-response curve was determined with [Leu 5 ]enkephalin as standard for each ileum and vas preparation and IC 50 values of the compounds being tested were normalized according to a published procedure [13].…”

Section: Bioassaysmentioning

confidence: 99%

Synthesis of a novel side-chain to side-chain cyclized enkephalin analogue containing a carbonyl bridge

Pawlak¹,

Chung²,

Schiller³

et al. 1997

J. Peptide Sci.

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A novel type of cyclic opiod peptide analogue, cyclo(N e ,N e H -carbonyl-D-Lys 2 ,Lys 5 )enkephalinamide, was prepared from a linear precursor peptide. The peptide was synthesized on the Merrifield resin and also by a combination of the solid-phase technique and the classical method in solution. In both cases the cyclization was performed by reaction of bis(4-nitrophenyl)carbonate with the free side-chain amino groups of the two lysine residues. The described method permits the convenient preparation of novel peptide analogues cyclized via a ureido group incorporating the side-chain amino groups of two a,o-diamino acid residues. The cyclic enkephalin analogue containing a 21-membered ring structure showed preference for m over d opioid

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Unsulfated C-terminal 7-peptide of cholecystokinin: A new ligand of the opiate receptor

Cited by 138 publications

References 9 publications

Aladan scanning: The structure-activity relationship of dynorphin A

Aladan scanning: The structure-activity relationship of dynorphin A

[Aladan³]TIPP: A fluorescent δ‐opioid antagonist with high δ‐receptor binding affinity and δ selectivity

Synthesis of a novel side-chain to side-chain cyclized enkephalin analogue containing a carbonyl bridge

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Unsulfated C-terminal 7-peptide of cholecystokinin: A new ligand of the opiate receptor

Cited by 138 publications

References 9 publications

Aladan scanning: The structure-activity relationship of dynorphin A

Aladan scanning: The structure-activity relationship of dynorphin A

[Aladan3]TIPP: A fluorescent δ‐opioid antagonist with high δ‐receptor binding affinity and δ selectivity

Synthesis of a novel side-chain to side-chain cyclized enkephalin analogue containing a carbonyl bridge

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[Aladan³]TIPP: A fluorescent δ‐opioid antagonist with high δ‐receptor binding affinity and δ selectivity