6- N,N -Dimethylamino-2,3-Naphthalimide a New Environment-Sensitive Fluorescent Probe in δ -Selective and μ -Selective Opioid Peptides

A new environment-sensitive fluorophore, 6- N , N -dimethylamino-2,3-naphthalimide (6DMN) was introduced in the δ -selective opioid agonist H-Dmt-Tic-Glu-NH 2 and in the μ -selective opioid agonist endomorphin-2 (H-Tyr-Pro-Phe-Phe-NH 2 ). 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-(CH 2 ) 5 -CO-Dap(6DMN)-NH 2 (1) and H-Dmt-Tic-Glu-Dap(6DMN)-NH 2 )] (2) were identified as potential fluorescent probes showing properties suitable for studies of distribution and internalization of δ -opioid receptors by confocal laser scanning microscopy.

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