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. 2006 Jun 15;49(12):3653-8.
doi: 10.1021/jm060343t.

6-N,N-dimethylamino-2,3-naphthalimide: a new environment-sensitive fluorescent probe in delta- and mu-selective opioid peptides

M Eugenio Vázquez  1 , Juan B Blanco, Severo Salvadori, Claudio Trapella, Roberto Argazzi, Sharon D Bryant, Yunden Jinsmaa, Lawrence H Lazarus, Lucia Negri, Elisa Giannini, Roberta Lattanzi, Mariantonella Colucci, Gianfranco Balboni
Affiliations

6-N,N-dimethylamino-2,3-naphthalimide: a new environment-sensitive fluorescent probe in delta- and mu-selective opioid peptides

M Eugenio Vázquez et al. J Med Chem. .

Abstract

A new environment-sensitive fluorophore, 6-N,N-(dimethylamino)-2,3-naphthalimide (6DMN) was introduced in the delta-selective opioid peptide agonist H-Dmt-Tic-Glu-NH(2) and in the mu-selective opioid peptide 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 delta-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 good properties for use in studies of distribution and internalization of delta receptors by confocal laser scanning microscopy.

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Figures

Figure 1
Figure 1
Functional bioactivity of compounds 1 and 2 on MVD. Inhibition of DEL C induced twitch by (2) (10 and 100 nM) and (1) (0.3 and 1 nM) were conducted as given in the experimental section using MVD preparations.
Figure 2
Figure 2
Microscopic visualization of compound 1 in NG108-15 cells: (left) NG108-15 cells with fluorescence compound; (right) non-specific binding obtained by preincubation with the opioid receptor antagonist naloxone.
See this image and copyright information in PMC

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References

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