Design and Synthesis of a Conformationally Restricted Analogue of the EFGH-Ring System of Ciguatoxin

Heterocycles ◽  
2009 ◽  
Vol 79 (1) ◽  
pp. 325 ◽  
Author(s):  
Masayuki Inoue ◽  
Masahiro Hirama ◽  
Nayoung Lee
2004 ◽  
Vol 14 (9) ◽  
pp. 2041-2046 ◽  
Author(s):  
Lichun Sun ◽  
Natalya I Vasilevich ◽  
Joseph A Fuselier ◽  
Simon J Hocart ◽  
David H Coy

1988 ◽  
Vol 31 (2) ◽  
pp. 284-295 ◽  
Author(s):  
Hing L. Sham ◽  
Giorgio Bolis ◽  
Herman H. Stein ◽  
Stephen W. Fesik ◽  
Patrick A. Marcotte ◽  
...  

1994 ◽  
Vol 37 (11) ◽  
pp. 1586-1601 ◽  
Author(s):  
Hubert Josien ◽  
Solange Lavielle ◽  
Alie Brunissen ◽  
Monique Saffroy ◽  
Yvette Torrens ◽  
...  

1992 ◽  
Vol 35 (10) ◽  
pp. 1710-1721 ◽  
Author(s):  
Stephen F. Martin ◽  
Richard E. Austin ◽  
Christopher J. Oalmann ◽  
William R. Baker ◽  
Stephen L. Condon ◽  
...  

2021 ◽  
Author(s):  
Patrick Eiring ◽  
Ryan McLaughlin ◽  
Siddharth Matikonda ◽  
HAN ZHONGYING ◽  
Lennart Grabenhorst ◽  
...  

Cyanine dyes are exceptionally useful probes for a range of fluorescence-based applications. We recently demonstrated that appending a ring system to the pentamethine cyanine ring system improves the quantum yield and extends the fluorescence lifetime. Here, we report an optimized synthesis of persulfonated variants that enable efficient labeling of nucleic acids and proteins. We demonstrate that a bifunctional sulfonated tertiary amide significantly improves the optical properties of the resulting bioconjugates. These new conformationally restricted cyanines are compared to parent species in a range of contexts including their use on a DNA-nano-antenna, in single-molecule Förster resonance energy transfer (FRET) applications, far-red fluorescence lifetime imaging microscopy (FLIM), and single-molecule localization microscopy. These efforts define contexts in which eliminating cyanine isomerization provides meaningful benefits to imaging performance.


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