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

Abstract

A boronic acid groups-bearing polythiophene derivate (L) was designed and synthesized for highly sensitive fluorescence detection of ATP based on a multisite-binding coupled with analyte-induced aggregation strategy. L has a polythiophene backbone as fluorophores and two functional side groups, i.e., quaternary ammonium group and boronic acid group, as multibinding sites for ATP. When various structural analogues such as ADP, AMP, and various inorganic phosphates were added into the aqueous solution of L, only ATP caused a remarkable fluorescence quenching of about 60-fold accompanied by obvious color changes of solution from yellow to purple. The detection limit is estimated to be 2 nM based on 3σ/slope. With the advantage of good water solubility, low toxicity, and highly selective response to ATP, L was successfully utilized as a probe to real-time assay activity of adenylate kinase (ADK) and map fluorescent imaging of ATP in living cells.

Design and development of imidazo[4,5-f] [1,10] phenanthroline-Zn(ii) based fluorescent probes for specific recognition of ATP with tunable optical responses and probing the enzymatic hydrolysis of ATP by alkaline phosphatase

“…99, 104 and 106) and some of them were not able to detect ATP selectively over other important biological phosphate anions and nucleotides (ref. 23, 98, 101–103 and 105). More importantly, none of these sensing platforms were utilized to develop real-time fluorescent assays to evaluate the enzymatic activity of ALP.…”

Peculiarities of the Fluorescence Quenching in the ATP – Calix[4]arene C-107 Aqueous Solutions

“…Complexes of multicharged ions are more interesting, since their connection to ATP is also associated with the presence of anions in the triphosphate part of ATP [7]. In addition to the electrostatic interaction, hydrophobic, 𝜋-𝜋 stacking interactions can be formed, or hydrogen bonds can appear, that is, accompanied by the complexation of ATP with more complex molecular systems, which are often used to visualize the presence of ATP [8][9][10][11].…”

The Magical Combination of Polymer Science and Fluorometry

“…The authors then demonstrated its application for sensing oxygen in model tumor spheroids. Zhao et al developed a fluorescence sensor for adenosine triphosphate (ATP) in aqueous solution and HeLa cells using polythiophene that bore boronic acid and quaternary ammonium moieties [12]. The boronic acid and quaternary ammonium groups in the polymer bound to the diol and phosphate groups in ATP, respectively.…”