carbocyanines and quinoline

In the review on "Cyanine Dyes Containing Quinoline Moieties: History, Synthesis, Optical Properties and Applications" (K. Ilina, M. Henary, Chem Eur. J. 2021, 27, 2430; https://doi.org/10.1002/chem.202003697), some essential aspects were incorrectly described and discussed. To avoid further confusion, this correspondence tries to clarify both the structures and the history of some cyanine and apocyanine dyes that were not presented sufficiently.

Topics: Carbocyanines; Coloring Agents; Fluorescent Dyes; Quinolines

Unsymmetrical cyanine dyes, such as thiazole orange, are useful for the detection of nucleic acids with fluorescence because they dramatically enhance the fluorescence upon binding to nucleic acids. Herein, we synthesized a series of unsymmetrical cyanine dyes and evaluated their fluorescence properties. A systematic structure-property relationship study has revealed that the dialkylamino group at the 2-position of quinoline in a series of unsymmetrical cyanine dyes plays a critical role in the fluorescence enhancement. Four newly designed unsymmetrical cyanine dyes showed negligible intrinsic fluorescence in the free state and strong fluorescence upon binding to double-stranded DNA (dsDNA) with a quantum yield of 0.53 to 0.90, which is 2 to 3 times higher than previous unsymmetrical cyanine dyes. A detailed analysis of the fluorescence lifetime revealed that the dialkylamino group at the 2-position of quinoline suppressed nonradiative decay in favor of increased fluorescence quantum yield. Moreover, these newly developed dyes were able to stain the nucleus specifically in fixed HeLa cells examined by using a confocal laser-scanning microscope.

Topics: Carbocyanines; DNA Probes; Fluorescent Dyes; HeLa Cells; Humans; Limit of Detection; Microscopy, Confocal; Molecular Structure; Phantoms, Imaging; Quinolines