Monofunctional near-infrared fluorochromes for imaging applications.
In this report, the development of a new class of monocarboxylate functionalized cyanine derivatives using improved synthetic procedures is detailed. The employed synthetic strategy relies on efficient nucleophilic attack of alkyl-thiols on cyanine dyes bearing chloro-substituted polymethinic linkers. Monocarboxylate derivatized fluorochromes (CyTE dyes) can be prepared in one step in greater than 90% yield without the need for additional purification. Several of the fluorochromes synthesized by this route show no tendency to aggregate in aqueous solution and have excitation and emission maxima greater than 800 nm. The potential utility of the CyTE fluorochromes was demonstrated through direct labeling of phage displaying a vascular cellular adhesion molecule-1 (VCAM-1) targeting peptide. Endothelial cell internalization of the VCAM-1 targeted phage was monitored via near-infrared fluorescence microscopy.
Hilderbrand
Scott A
SA
Center for Molecular Imaging Research, Massachusetts General Hospital, Harvard Medical School, Room 5406, 149 13th Street, Charlestown, Massachusetts 02129, USA.
Kelly
Kimberley A
KA
Weissleder
Ralph
R
Tung
Ching-Hsuan
CH
D000818:Animals; D045744:Cell Line, Tumor; D005456:Fluorescent Dyes / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry*; D051379:Mice; D008856:Microscopy, Fluorescence / Q000295:instrumentation* / Q000379:methods*; D015394:Molecular Structure; D013057:Spectrum Analysis
D005456:Fluorescent Dyes