Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Cyanine Conformational Restraint in the Far-Red Range

Cyanine Conformational Restraint in the Far-Red Range
Ralph Götz, Martin J. Schnermann, Nikita Kumari, Matthew Bowler, Megan S. Michie, Markus Sauer, Christian Franke, Valentin Magidson, Jadranka Loncarek, Marcia Levitus
Far-red cyanine fluorophores find extensive use in modern microscopy despite modest quantum yields. To improve the photon output of these molecules, we report a synthetic strategy that blocks the major deactivation pathway: excited-state trans-to-cis polyene rotation. In the key transformation, a protected dialdehyde precursor undergoes a cascade reaction to install the requisite tetracyclic ring system. The resulting molecules exhibit the characteristic features of conformational restraint, including improved fluorescence quantum yield and extended lifetime. Moreover, these compounds recover from hydride reduction with dramatically improved efficiency. These observations enable efficient single-molecule localization microscopy in oxygenated buffer without addition of thiols. Enabled by modern organic synthesis, these studies provide a new class of far-red dyes with promising spectroscopic and chemical properties.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b07272

DOI: 10.1021/jacs.7b07272

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