New Polyfluorinated Cyanine Dyes for Selective NIR Staining of Mitochondria

Abstract

In this communication, the synthesis of three unknown polyfluorinated cyanine dyes and their application as selective markers for mitochondria are presented. By incorporating fluorous side chains into cyanine dyes, their remarkable photophysical properties were enhanced. To investigate their biological application, several different cell lines were incubated with the synthesized cyanine dyes. It was discovered that the presented dyes can be utilized for selective near‐infrared‐light (NIR) staining of mitochondria, with very low cytotoxicity determined by MTT assay. This is the first time that polyfluorinated cyanine fluorophores are presented as selective markers for mitochondria. Due to the versatile applications of polyfluorinated fluorophores in bioimaging and materials science, it is expected that the presented fluorophores will be stimulating for the scientific community.

Synthesis and Applications of Selected Fluorine-Containing Fluorophores

“…This reaction affords the final product at a 49% yield for 93 and 18% yield for 94, as reported earlier by the Henary group [72]. [73]. These polyfluorinated heterocycles 98-100 are then alkylated with methyl iodide to render indolium salts 101-103.…”

“…The synthesis of polyfluorinated cyanine dyes designed by Braun et al begins with a bromine-containing heterocycle reacting with compounds 95-97 to generate the fluorinated heterocycles necessary in Scheme 19[73]. These polyfluorinated heterocycles 98-100 are then alkylated with methyl iodide to render indolium salts 101-103.…”

“…Scheme 19. Synthesis of polyfluorinated cyanine dyes[73].Another synthesis for fluorine containing cyanine dyes is shown in Scheme 20, which begins with the reaction of carboxylic acid derivative 107 and cyclopentanone under acidic conditions. The second step shows the formation of the fluorinated heterocycle 108 reacting with indolium-containing half dye to form chromenylium-cyanine 109 in acetic anhydride[74].…”

Lanthanide conjugates as versatile instruments for therapy and diagnostics

“…This can be achieved, e.g., by using peptidomimetics such as functionalized peptoids. [12][13][14][15][16] To avoid the cytotoxicity of free metal ions, which is mainly caused by binding to endogenous metalloproteins and subsequent structure disruption, the metals are tightly complexed with multidentate ligands. [17][18][19][20] The most prominent chelators are the macrocyclic 1,4,7,10-tetraazacyclododecane-1,4,7,10tetraacetate (DOTA) and its analogs ( Fig.…”

The Aggregation Regularity Effect of Multiarylpyrroles on Their Near‐Infrared Aggregation‐Enhanced Emission Property

“…Near-infrared (NIR) fluorescent dyes have attracted significant attention duet ot heir wide use in many fields, such as biological imaging and tumor treatment, which originates from their deep tissue penetration, reduced background autofluorescence and minimal damage to biological samples. [1][2][3][4][5] However,t raditional NIR fluorescentm olecules are usually composed of pconjugated large planars tructures, which can emit strongf luorescence in dilute solution but are weaklye missive or even nonfluorescent in the aggregated state. This phenomenoni s usually called aggregation-caused quenching (ACQ), which limits their biological applications because most NIR dyes are hydrophobic and prone to aggregation in living organisms.…”