Solid-phase synthetic strategy and bioevaluation of a labeled delta-opioid receptor ligand Dmt-Tic-Lys for in vivo imaging

Jatinder S Josan; David L Morse; Liping Xu; Maria Trissal; Brenda Baggett; Peg Davis; Josef Vagner; Robert J Gillies; Victor J Hruby

doi:10.1021/ol900200k

Solid-phase synthetic strategy and bioevaluation of a labeled delta-opioid receptor ligand Dmt-Tic-Lys for in vivo imaging

Org Lett. 2009 Jun 18;11(12):2479-82. doi: 10.1021/ol900200k.

Authors

Jatinder S Josan¹, David L Morse, Liping Xu, Maria Trissal, Brenda Baggett, Peg Davis, Josef Vagner, Robert J Gillies, Victor J Hruby

Affiliation

¹ Department of Chemistry, BIO5 Institute, The University of Arizona, Tucson, Arizona 85721, USA.

Abstract

A general solid-phase synthetic strategy is developed to prepare fluorescent and/or lanthanide-labeled derivatives of the delta-opioid receptor (deltaOR) ligand H-Dmt-Tic-Lys(R)-OH. The high delta-OR affinity (K(i) = 3 nM) and desirable in vivo characteristics of the Cy5 derivative 1 suggest its usefulness for structure-function studies and receptor localization and as a high-contrast noninvasive molecular marker for live imaging ex vivo or in vivo.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Affinity Labels
Animals
Carbocyanines* / chemistry
Diagnostic Imaging
Fluorescent Dyes* / chemistry
Isoquinolines / chemical synthesis*
Ligands
Mice
Receptors, Opioid, delta / chemistry
Receptors, Opioid, delta / metabolism*
Stereoisomerism

Substances

Affinity Labels
Carbocyanines
Fluorescent Dyes
Isoquinolines
Ligands
Receptors, Opioid, delta
cyanine dye 5

Abstract

Publication types

MeSH terms

Substances

Grants and funding