Synthesis and systematic evaluation of symmetric sulfonated centrally C C bonded cyanine near-infrared dyes for protein labelling

The most commonly used near-infrared cyanine dyes contain an aryl ether that is not fully stable towards nucleophiles. Replacement of the aryl ether by a more stable carbon-carbon bond can improve the stability. In this work we have synthesized a series of four negatively-charged symmetrical Csingle...

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Bibliographic Details
Published in:Dyes and pigments 2016-09, Vol.132, p.7-19
Main Authors: van der Wal, Steffen, Kuil, Joeri, Valentijn, A. Rob P.M., van Leeuwen, Fijs W.B.
Format: Article
Language:English
Subjects:
Aromatic compounds
Bonding
Chemical bonds
Conjugation
Cyanine dyes
Dyes
Ethers
Fluorescence
Image guided surgery
Stability
Stacking
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Summary:The most commonly used near-infrared cyanine dyes contain an aryl ether that is not fully stable towards nucleophiles. Replacement of the aryl ether by a more stable carbon-carbon bond can improve the stability. In this work we have synthesized a series of four negatively-charged symmetrical Csingle bond C bond-containing Cy7 derivatives and compared them to the known dyes indocyanine green (ICG) and IRDye 800CW. The extent of stacking of these Csingle bond C bond-containing dyes was higher than reported for aryl ether dyes, but stacking could be minimized by altering the surface charge of the molecules and by introducing sulfonate groups. Furthermore, the degree of stacked dye in an antibody-dye conjugate was similar to the degree of stacking of free dye under labeling conditions. In our view, Csingle bond C bond-containing Cy7 dyes provide a chemical platform, based on which one can improve the photophysical properties and stacking behavior, thereby generating interesting additions to the conjugation toolbox available for e.g. antibodies.
ISSN:0143-7208
1873-3743
DOI:10.1016/j.dyepig.2016.03.054