Heptamethine Cyanine Dyes with a Robust C-C
Bond at the Central Position of the Chromophore
Hyeran Lee,J. Christian Mason, andSamuel Achilefu*
Department of Radiology, Washington University,
St. Louis, Missouri 63110
achilefus@mir.wustl.edu
Received June 21, 2006
Abstract:
Novel, highly fluorescent, monofunctional, water-soluble
heptamethine cyanine dyes containing a robust C-C bond
at the central position of the near-infrared fluorophore system
were prepared by the Suzuki-Miyaura method. The reaction
proceeded efficiently to replace the meso-chlorine atom with
a carboxy-functionalized aryl moiety and afforded the desired
compounds in high yields. This methodology is particularly
attractive due to its versatility and the utilization of environmentally friendly water as solvent. The new compounds
possess excellent spectral properties and readily label bioactive molecules on solid support. The results demonstrate
the potential of using the new compounds as fluorescent
antennae for molecular imaging, spectroscopy, microscopy,
and chemical or biological molecular recognition studies.
