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Fluorescent-labeled bioconjugates of the opioid peptides biphalin and DPDPE incorporating fluorescein-maleimide linkers.
- Source :
-
Future medicinal chemistry [Future Med Chem] 2017 Jun; Vol. 9 (9), pp. 859-869. Date of Electronic Publication: 2017 Jun 21. - Publication Year :
- 2017
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Abstract
- Aim: The conjugation of fluorescent labels to opioid peptides is an extremely challenging task, which needs to be overcome to create new classes of probes for biological assays.<br />Materials & Methods: Three opioid peptide analogs of biphalin and [D-Pen2,5]-Enkephalin (DPDPE) containing a fluorescein-maleimide motif were synthesized.<br />Results & Discussion: The biphalin analog 17 binds to opioid receptors with K <subscript>i</subscript> <superscript>μ</superscript> = 530 ± 90 nM and K <subscript>i</subscript> <superscript>δ</superscript> = 69.8 ± 16.4 nM. We then tested the ability of the compounds to stimulate G-protein-coupling, 17 activated μ-receptor expressing cells (EC <subscript>50</subscript> = 16.7 ± 6.7 nM, E <subscript>Max</subscript> = 76 ± 4%) as well as δ-receptor expressing cells (EC <subscript>50</subscript> = 42 ± 10 nM, E <subscript>Max</subscript> = 34 ± 8%). However, 17 was not able to fluorescently label receptor in live or fixed cells.<br />Conclusion: Our data suggest that the biphalin scaffold could be employed to develop fluorescent ligands with the appropriate fluorescent motif, and suggest a means for further probe development.
Details
- Language :
- English
- ISSN :
- 1756-8927
- Volume :
- 9
- Issue :
- 9
- Database :
- MEDLINE
- Journal :
- Future medicinal chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 28635314
- Full Text :
- https://doi.org/10.4155/fmc-2016-0232