Format

Send to

Choose Destination
J Am Chem Soc. 2017 Sep 13;139(36):12406-12409. doi: 10.1021/jacs.7b07272. Epub 2017 Sep 1.

Cyanine Conformational Restraint in the Far-Red Range.

Author information

1
Laboratory of Chemical Biology, NIH/NCI/CCR , 376 Boyles Street, Frederick, Maryland 21702, United States.
2
Department of Biotechnology and Biophysics, Julius Maximilian University Würzburg , Am Hubland 97074 Würzburg, Germany.
3
Optical Microscopy and Analysis Laboratory, NIH/NCI/CCR , 1050 Boyles Street, Frederick, Maryland 21702, United States.
4
School of Molecular Sciences and The Biodesign Institute at Arizona State University , Tempe, Arizona 85287, United States.
5
Optical Microscopy and Analysis Laboratory, Leidos Biomedical Res. Inc., Frederick National Laboratory for Cancer Research , Frederick, Maryland 21702, United States.
6
Laboratory of Protein Dynamics and Signaling, NIH/NCI/CCR , 1050 Boyles Street, Frederick, Maryland 21702, United States.

Abstract

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.

PMID:
28862842
DOI:
10.1021/jacs.7b07272
[Indexed for MEDLINE]

Supplemental Content

Full text links

Icon for American Chemical Society
Loading ...
Support Center