From nucleus to mitochondria to lysosome selectivity switching in a cyanine probe: The phenolic to methoxy substituent conversion affects probe’s selectivity

A NIR Emitting Cyanine with Large Stokes’ Shift for Mitochondria and Identification of their Membrane Potential Disruption

“…The introduction of fluorescent-microscopy-based visualization has made a remarkable impact on mitochondria identification and tracking due to their high specificity and sensitivity. [10][11][12][13][14][15][16][17][18][19][20][21][22] The development of fluorescent dyes for studying mitochondrial morphological dynamics via fluorescent microscopy-based techniques are important to understand mitochondria related disease conditions (i. e., mitochondrial dysfunction). [23][24][25] An ideal mitochondrial selective fluorescent dye should exhibit high sensitivity towards mitochondrial membrane potential which is the key indicator of the mitochondrial dysfunction.…”

“…[23][24][25] An ideal mitochondrial selective fluorescent dye should exhibit high sensitivity towards mitochondrial membrane potential which is the key indicator of the mitochondrial dysfunction. [24,26,27] The fundamental function of the cellular mitochondria is to produce ATP via oxidative phosphorylation to fulfill cellular energy requirements. [28][29][30][31][32][33] The mitochondrial membrane potential gradient ( ~ψ) generated across the mitochondrial inner membrane is the key driving force for the oxidative phosphorylation process.…”

“…[12] In another study, when the amino group is replaced with an oxygen-based donor group, the resulting benzothiazolium derivatives also exhibited good selectivity toward mitochondria. [14,27] Stemming from our general interests in searching for NIR-emitting mitochondrial probes, we now disclose a highly photostable mitochondria selective probe ExCy (Scheme 1), which exhibited an attractive NIR emission (λ em � 730 nm) with a large Stokes' shift (> 100 nm). When using ExCy for visualization of mitochondria, the probe exhibited high sensitivity towards mitochondrial membrane potential changes, leading to its application in detecting mitochondrial membrane potential dysfunction in live cells via fluorescence confocal microscopy.…”

Large Stokes shift benzothiazolium cyanine dyes with improved intramolecular charge transfer (ICT) for cell imaging applications

“…32,[52][53][54][55][56] Among these diverse cyanine acceptor groups, benzothiazolium derivatives (see Scheme 1) play a crucial role due to their broad applicability as fluorescence imaging probes. 29,31,35,47,55,[57][58][59][60][61] Benzothiazolium-based fluorescent dyes have been recently reported for their specificity towards subcellular components such as mitochondria, lysosomes, and nucleus/DNA. 4,40,50,[62][63][64][65][66][67] In addition, many benzothiazolium derived fluorescent dyes have been designed and developed for numerous chemical and biological sensing applications.…”

Novel (Phenothiazinyl)Vinyl-Pyridinium Dyes and Their Potential Applications as Cellular Staining Agents

“…Fluorescent probes, particularly emitting in NIR, based on polymethine dyes [2], polyfluorinated cyanine dyes [3], and cyanine-benzothiazole hybrid system [4] revealed high selectivity towards mitochondria. The lysosomal compartment of different cell lines such as HF-P4, BLM, U-2 OS and A-2058 were selectivity labeled by fluorescent Coumarin Troger's base derivatives with cyanine substituents [5].…”