Dansylated analogues of the opioid peptide [Dmt1]DALDA: in vitro activity profiles and fluorescence parameters.

• Authors: Irena Berezowska , Carole Lemieux , Nga N Chung , Bogumil Zelent , Peter W Schiller
• Languages of publication: EN

Abstracts

EN

Dansylated analogues of the potent and selective μ opioid peptide agonist [Dmt1]DALDA (H-Dmt-D-Arg-Phe-Lys-NH2; Dmt = 2',6'-dimethyltyrosine) were prepared either by substitution of Nβ-dansyl-α,β-diaminopropionic acid or Nε-dansyllysine for Lys4, or by attachment of a dansyl group to the C-terminal carboxamide function via a linker. All three analogues displayed high μ agonist potency in vitro and the C-terminally dansylated one retained significant μ receptor selectivity. The three analogues showed interesting differences in their fluorescence emission maxima and quantum yields, indicating that the dansyl group in two of them was engaged in intramolecular hydrophobic interactions. These dansylated [Dmt1]DALDA analogues represent valuable tools for binding studies, cellular uptake and intracellular distribution studies, and tissue distribution studies.

Keywords

EN

fluorescence spectroscopy; opioid activity profile in vitro; fluorescence quantum yield; opioid peptides; fluorescent opioid peptide analogues; [Dmt1]DALDA

• Publisher: Polish Biochemical Society
• Journal: Acta Biochimica Polonica
• Year: 2004
• Volume: 51
• Issue: 1
• Pages: 107-113

Dates

published

2004

received

2003-10-31

revised

2004-02-10

accepted

2004-02-20

Contributors

author

Irena Berezowska

• Laboratory of Chemical Biology and Peptide Research, Clinical Research Institute of Montreal, Montreal, Quebec, Canada

author

Carole Lemieux

• Laboratory of Chemical Biology and Peptide Research, Clinical Research Institute of Montreal, Montreal, Quebec, Canada

author

Nga N Chung

• Laboratory of Chemical Biology and Peptide Research, Clinical Research Institute of Montreal, Montreal, Quebec, Canada

author

Bogumil Zelent

• Department of Biochemistry and Biophysics, University of Pennsylvania, School of Medicine, Philadelphia, U.S.A.

author

Peter W Schiller

• Laboratory of Chemical Biology and Peptide Research, Clinical Research Institute of Montreal, Montreal, Quebec, Canada

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