6-N,N-Dimethylamino-2,3-naphthalimide: A New Environment-Sensitive Fluorescent Probe in δ- and μ-Selective Opioid Peptides
- 17 May 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 49 (12) , 3653-3658
- https://doi.org/10.1021/jm060343t
Abstract
A new environment-sensitive fluorophore, 6-N,N-(dimethylamino)-2,3-naphthalimide (6DMN) was introduced in the δ-selective opioid peptide agonist H-Dmt-Tic-Glu-NH2 and in the μ-selective opioid peptide agonist endomorphin-2 (H-Tyr-Pro-Phe-Phe-NH2). Environment-sensitive fluorophores are a special class of chromophores that generally exhibit a low quantum yield in aqueous solution but become highly fluorescent in nonpolar solvents or when bound to hydrophobic sites in proteins or membranes. New fluorescent δ-selective irreversible antagonists (H-Dmt-Tic-Glu-NH-(CH2)5-CO-Dap(6DMN)-NH2 (1) and H-Dmt-Tic-Glu-Dap(6DMN)-NH2 (2)) were identified as potential fluorescent probes showing good properties for use in studies of distribution and internalization of δ receptors by confocal laser scanning microscopy.Keywords
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