TY - JOUR
T1 - Cyanine Conformational Restraint in the Far-Red Range
AU - Michie, Megan S.
AU - Götz, Ralph
AU - Franke, Christian
AU - Bowler, Matthew
AU - Kumari, Nikita
AU - Magidson, Valentin
AU - Levitus, Marcia
AU - Loncarek, Jadranka
AU - Sauer, Markus
AU - Schnermann, Martin J.
N1 - Funding Information:
M.J.S. thanks Dr. Joseph Barchi, NCI-CCR, for NMR assistance and Dr. James Kelley, NCI-CCR, for mass spectrometric analysis. This work was supported by the Intramural Research Program of the National Institutes of Health, National Cancer Institute, Center for Cancer Research. M.S. acknowledges funding by the DFG (ReceptorLight TRR 166). Dr. Luke Lavis, Janelia Research Campus, Howard Hughes Medical Institute, is acknowledged for assistance with fluorescence quantum yield determination and helpful discussions.
Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/9/13
Y1 - 2017/9/13
N2 - 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.
AB - 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.
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U2 - 10.1021/jacs.7b07272
DO - 10.1021/jacs.7b07272
M3 - Article
C2 - 28862842
AN - SCOPUS:85029577839
SN - 0002-7863
VL - 139
SP - 12406
EP - 12409
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 36
ER -