Synthesis and Pharmacological Evaluation of Dual Labeled Delta Opioid Receptor Peptides

Peck, Angela M.; Kumar, Vivek; Murray, Thomas F.; Aldrich, Jane V.

doi:10.1007/978-0-387-26575-9_228

Cited by 1 publication

(3 citation statements)

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“…We had previously successfully prepared several peptides containing both an isothiocyanate group and a hydroxyl-containing amino acid (Table 1), indicating that the occurrence of this side reaction is dependent on the conformation of the final peptide. In the second case the bromoacetamide derivative of a peptide containing a C-terminal His 6 tag (see below) underwent a side reaction with one of the His residues (Peck et al, 2006). …”

Section: Resultsmentioning

confidence: 99%

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Solid Phase Synthesis and Application of Labeled Peptide Derivatives: Probes of Receptor-Opioid Peptide Interactions

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Solid phase synthetic methodology has been developed in our laboratory to incorporate an affinity label (a reactive functionality such as isothiocyanate or bromoacetamide) into peptides (Leelasvatanakij, L. and Aldrich, J. V. (2000) J. Peptide Res. 56, 80), and we have used this synthetic strategy to prepare affinity label derivatives of a variety of opioid peptides. To date side reactions have been detected only in two cases, both involving intramolecular cyclization. We have identified several peptide-based affinity labels for δ opioid receptors that exhibit wash-resistant inhibition of binding to these receptors and are valuable pharmacological tools to study opioid receptors. Even in cases where the peptide derivatives do not bind covalently to their target receptor, studying their binding has revealed subtle differences in receptor interactions with particular opioid peptide residues, especially Phe residues in the N-terminal "message" sequences. Solid phase synthetic methodology for the incorporation of other labels (e.g. biotin) into the C-terminus of peptides has also been developed in our laboratory (Kumar, V. and Aldrich, J. V. (2003) Org. Lett. 5, 613). These two synthetic approaches have been combined to prepare peptides containing multiple labels that can be used as tools to study peptide ligand-receptor interactions. These solid phase synthetic methodologies are versatile strategies that are applicable to the preparation of labeled peptides for a variety of targets in addition to opioid receptors.

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Section: Resultsmentioning

confidence: 99%

“…1) (Peck et al, 2006). Because the His tag consists of amino acids, these peptides can be synthesized using the strategy described for peptide-based affinity labels.…”

Section: Resultsmentioning

confidence: 99%