Fluorescence-based chemosensors that recognize anions of physiological significance and biomedical relevance in water are of utmost importance. Among the several anions ubiquitous in biological system, pyrophosphate (PPi) anion has a pivotal role in regulating cellular metabolic processes. To selectively differentiate the PPi anion, the chemists have utilized a metal-ligand-based approach that enables the formation of a metal-chemosensor ensemble that strongly interacts with PPi to obtain a fluorescent response. However, this method is an indirect approach to anion sensing as the sensor is metal-dependent, and the huge excess of metal used may be detrimental to enzyme-based application. In this regard, we report a serendipitously discovered water-soluble metal-free fluorescent PPi sensor that is composed of an amino acid (AA) coupled to fluorescent reporter 3-HNA (3-Hydroxy napthoic acid). The fluorescence emission intensity of the molecule is ~30-fold enhanced at 500 nm in the presence of PPi. The emission signal enhancement is also observed in the presence of phosphate and vanadate, which are chemically related to pyrophosphate anion in terms of geometry and basicity. Through proton NMR and fluorescence-based experiments, we have shown the sensing mechanism of the molecule is attributed to intermolecular proton transfer from the fluorescent chemosensor to the anion, depending on the basicity. Furthermore, we have shown the utility of the chemosensor to detect PPi in a routinely used bioanalytical application, polymerase chain reaction (PCR), to track DNA amplification. Overall, we have demonstrated a simple water-soluble metal-free chemosensor that detects biologically relevant chemically related anions.

A metal-free anion sensor to detect pyrophosphate and its chemical relatives in water

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27th CRSI National Symposium in Chemistry

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