Abstract
Affinity labels (irreversible ligands) are useful pharmacological tools to study receptor structure and function. As part of a program to prepare affinity labels based on opioid peptides, we developed a general synthetic strategy to introduce different electrophilic labeling moieties (i.e. isothiocyanate and bromoacetamide) via a p-amino functionality on a phenylalanine residue. The affinity labelling groups were incorporated into the Phe4 position of the delta opioid receptor antagonists ICI-174,864 (1) and N,N-dibenzyl leucine enkephalin (2). Using an orthogonal Boc/Fmoc protection strategy, the common peptide precursors were assembled in solution, the affinity labels introduced and the peptides deprotected. In cloned δ receptors expressed in CHO cells (3), only the isothiocyanate derivative of N,N-dibenzyl leucine enkephalin exhibited wash-resistant inhibition of [3H]DPDPE binding.
| Original language | English |
|---|---|
| Pages (from-to) | 171-172 |
| Number of pages | 2 |
| Journal | Regulatory Peptides |
| Volume | 54 |
| Issue number | 1 |
| DOIs | |
| State | Published - Nov 10 1994 |
| Externally published | Yes |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Endocrinology
- Physiology
- Neuroscience(all)
Cite this
Synthesis of enkephalin-based affinity labels for delta opioid receptors. / Maeda, DY; Murray, Thomas F.; Roth, JE; Aldrich, JV.
In: Regulatory Peptides, Vol. 54, No. 1, 10.11.1994, p. 171-172.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis of enkephalin-based affinity labels for delta opioid receptors
AU - Maeda, DY
AU - Murray, Thomas F.
AU - Roth, JE
AU - Aldrich, JV
PY - 1994/11/10
Y1 - 1994/11/10
N2 - Affinity labels (irreversible ligands) are useful pharmacological tools to study receptor structure and function. As part of a program to prepare affinity labels based on opioid peptides, we developed a general synthetic strategy to introduce different electrophilic labeling moieties (i.e. isothiocyanate and bromoacetamide) via a p-amino functionality on a phenylalanine residue. The affinity labelling groups were incorporated into the Phe4 position of the delta opioid receptor antagonists ICI-174,864 (1) and N,N-dibenzyl leucine enkephalin (2). Using an orthogonal Boc/Fmoc protection strategy, the common peptide precursors were assembled in solution, the affinity labels introduced and the peptides deprotected. In cloned δ receptors expressed in CHO cells (3), only the isothiocyanate derivative of N,N-dibenzyl leucine enkephalin exhibited wash-resistant inhibition of [3H]DPDPE binding.
AB - Affinity labels (irreversible ligands) are useful pharmacological tools to study receptor structure and function. As part of a program to prepare affinity labels based on opioid peptides, we developed a general synthetic strategy to introduce different electrophilic labeling moieties (i.e. isothiocyanate and bromoacetamide) via a p-amino functionality on a phenylalanine residue. The affinity labelling groups were incorporated into the Phe4 position of the delta opioid receptor antagonists ICI-174,864 (1) and N,N-dibenzyl leucine enkephalin (2). Using an orthogonal Boc/Fmoc protection strategy, the common peptide precursors were assembled in solution, the affinity labels introduced and the peptides deprotected. In cloned δ receptors expressed in CHO cells (3), only the isothiocyanate derivative of N,N-dibenzyl leucine enkephalin exhibited wash-resistant inhibition of [3H]DPDPE binding.
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UR - http://www.scopus.com/inward/citedby.url?scp=0028099973&partnerID=8YFLogxK
U2 - 10.1016/0167-0115(94)90445-6
DO - 10.1016/0167-0115(94)90445-6
M3 - Article
VL - 54
SP - 171
EP - 172
JO - Regulatory Peptides
JF - Regulatory Peptides
SN - 0167-0115
IS - 1
ER -