Lysosomal ATP imaging in living cells by a water-soluble cationic polythiophene derivative

Highly Selective Fluorescence Sensing and Imaging of ATP Using a Boronic Acid Groups-Bearing Polythiophene Derivate

“…From the changes in ATP concentrations-dependent fluorescence intensities (Figure S5, Supplementary Materials), the detection limit was estimated to be 2.07 × 10 −9 M based on the 3 σ /slope (where σ is the standard deviation of the background and slope is the sensitivity) [24,38]. Such a low detection limit should be very competitive with most of previously reported fluorescence or colorimetric probes for ATP [18,19,20,21,22,23,24,25] (Table S1, Supplementary Materials). The high sensitivity of L for ATP should be closely related to the strong synergetic interactions between L and ATP.…”

“…Among various CPs, polythiophene (PT) derivatives have received extensive attention because of their sensitive chain conformation transition responsive to external stimuli [7,8,18,19,20,21], providing unique advantages over other CPs on keeping the balance between simplicity (colorimetric mode) and sensitivity (fluorescence mode). In previous reports including ours, several PTs derivatives have been designed for the fluorescent detection of ATP with moderate selectivity and sensitivity [19,22,23,24,25]. These reported PT-based ATP probes contain generally cationic groups on their side chains, for example, quaternary ammonium [18,19,25,26], imidazolium [22], or phosphonium [23], to offer essential water solubility and recognition site for ATP.…”

“…In previous reports including ours, several PTs derivatives have been designed for the fluorescent detection of ATP with moderate selectivity and sensitivity [19,22,23,24,25]. These reported PT-based ATP probes contain generally cationic groups on their side chains, for example, quaternary ammonium [18,19,25,26], imidazolium [22], or phosphonium [23], to offer essential water solubility and recognition site for ATP. Thus, in most cases, electrostatic interaction is the primary driving force for the binding of polymer probes with ATP, resulting in these assays being sensitive to ionic strength.…”

Molecular Design, Synthetic Strategies, and Applications of Cationic Polythiophenes

“…The precipitate obtained was washed several times with a saturated solution of tetrabutylammonium chloride to obtain the corresponding polymer. Poly­(1 H -imidazolium-1-ethyl-3-{2-[(4-methyl-3-thienyl)-oxy]­ethyl}) chloride 25b was synthesized by Huang et al using a similar method to that described by Ho ( vide supra ), with FeCl 3 (3.8 equiv) in chloroform (5 mL) at 45 °C for 5 days. The syntheses of poly­(1 H -imidazolium-1,2-dimethyl-3-{3-[(4-methyl-3-thienyl)-oxy]­propyl}) chloride 29 and poly­(1 H -imidazolium-1,2-dimethyl-3-{2-[(4-methyl-3-thienyl)-oxy]­ethyl}) chloride 30 were similar to the preparation of polymer 25a except for the bromide substitution, where 1,2-dimethylimidazole was used instead of methyl imidazole .…”

“…Aside from CPTs with traditional linear chains, those with extended higher dimensional structures (branched) have also been reported, providing unique molecular architectures and novel functionalities. − This review also presents the challenges in preparing CPTs, since some of these compounds are not readily obtained by polymerization of the corresponding reactive monomers using FeCl 3 method. This review highlights the newer applications of CPTs other than sensing − and as a material component in optoelectronic devices and supercapacitors. − CPTs have been used in chiral self-assembly with DNA and sugars, as a nonviral gene-delivery system, , as material for monitoring and detection of various biological processes like cell targeting and imaging, ,− and for biomedical applications as a membrane probe and as anticancer, antifungal, or antibacterial agents with or without light activation. ,− This review only includes the articles containing cationic polythiophenes and those polythiophenes possessing polyaminated groups published in the last 17 years. Although there are other polythiophenes containing anionic or zwitterionic charged groups or cationic polymer containing thiophene moieties, these structures are beyond the scope of this review (except those that are used to compare with the CPTs , ).…”