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.
Publication types
-
Research Support, N.I.H., Intramural
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Animals
-
Binding, Competitive
-
Cell Line, Tumor
-
Fluorescent Dyes / chemical synthesis*
-
Fluorescent Dyes / chemistry
-
Fluorescent Dyes / pharmacology
-
Guinea Pigs
-
Imides / chemistry*
-
In Vitro Techniques
-
Male
-
Mice
-
Muscle Contraction
-
Naphthalenes / chemistry*
-
Naphthalimides
-
Neuroblastoma
-
Neuromuscular Junction / drug effects
-
Neuromuscular Junction / physiology
-
Oligopeptides / chemical synthesis*
-
Oligopeptides / chemistry
-
Oligopeptides / pharmacology
-
Opioid Peptides / chemical synthesis*
-
Opioid Peptides / chemistry
-
Opioid Peptides / pharmacology
-
Radioligand Assay
-
Receptors, Opioid, delta / agonists*
-
Receptors, Opioid, delta / metabolism
-
Receptors, Opioid, mu / agonists*
-
Receptors, Opioid, mu / metabolism
-
Structure-Activity Relationship
Substances
-
2',6'-dimethyltyrosyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid-glutamamide
-
6-N,N-dimethylamino-2,3-naphthalimide
-
Fluorescent Dyes
-
Imides
-
Naphthalenes
-
Naphthalimides
-
Oligopeptides
-
Opioid Peptides
-
Receptors, Opioid, delta
-
Receptors, Opioid, mu
-
endomorphin 2