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Review
. 2023 Aug:75:102335.
doi: 10.1016/j.cbpa.2023.102335. Epub 2023 Jun 1.

Rejuvenating old fluorophores with new chemistry

Martin J Schnermann  1 , Luke D Lavis  2
Affiliations
Review

Rejuvenating old fluorophores with new chemistry

Martin J Schnermann et al. Curr Opin Chem Biol. 2023 Aug.

Abstract

The field of organic chemistry began with 19th century scientists identifying and then expanding upon synthetic dye molecules for textiles. In the 20th century, dye chemistry continued with the aim of developing photographic sensitizers and laser dyes. Now, in the 21st century, the rapid evolution of biological imaging techniques provides a new driving force for dye chemistry. Of the extant collection of synthetic fluorescent dyes for biological imaging, two classes reign supreme: rhodamines and cyanines. Here, we provide an overview of recent examples where modern chemistry is used to build these old-but-venerable classes of optically responsive molecules. These new synthetic methods access new fluorophores, which then enable sophisticated imaging experiments leading to new biological insights.

Keywords: Cyanine; Fluorescence; Imaging; Microscopy; Organic chemistry; Rhodamine.

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Conflict of interest statement

Declaration of competing interest The authors declare the following financial interests/personal relationships that may be considered as potential competing interests: Luke Lavis reports a relationship with Eikon Therapeutics that includes consulting or advisory and equity or stocks; patent and patent applications with inventor Luke Lavis are assigned to HHMI.

Figures

Figure 1.
Figure 1.. Early developments in dye chemistry.
(A) Synthesis of mauveine (1). (B) Synthesis of cyanine dye 2. (C) Synthesis of pararosaniline (4). (D) Synthesis of tetramethylrhodamine (7). (E) Examples of dye chemistry inspiring medicinal chemistry.
Figure 2.
Figure 2.. Modern chemical approaches for rhodamine dye synthesis.
(A) Synthesis of rhodamines using Pd-catalyzed cross-coupling and structures of exemplar dyes: JF549 (12) and JFX554 (13). (B) Condensation–oxidation of 3-aminophenols and lactols yields dyes such as 14. (C) Synthesis of rhodamines using metalation of dibromides and structure of thiophene-containing Si-rhodamine 15. (D) Use of masked acyl cyanide (16) to derivatize fluorinated rhodamines via SNAr and structure of bioavailable JFX673-HaloTag ligand (17).
Figure 3.
Figure 3.. Modern chemical approaches for cyanine dye synthesis.
(A) Synthesis of conformationally restricted cyanine dyes and representative compound 18. (B) Use of Zincke salts in the synthesis of heptamethine dyes such as 19. (C) Replacing the indoline units in cyanine dyes with flavylium moieties yields SWIR-absorbing dyes including 20. (D) Synthesis of nonamethine dyes and representative compounds 21 and 22.
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References

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