An uracil-linked hydroxyflavone probe for the recognition of ATP.

Márton Bojtár,Péter Zoltán Janzsó-Berend,István Bitter,Dóra Hessz,Dávid Mester,Miklós Kubinyi,Mihály Kállay

doi:10.3762/bjoc.14.63

Márton Bojtár, Péter Zoltán Janzsó-Berend + Show 5 more

Open Access

https://doi.org/10.3762/bjoc.14.63

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Abstract

Background: Nucleotides are essential molecules in living systems due to their paramount importance in various physiological processes. In the past years, numerous attempts were made to selectively recognize and detect these analytes, especially ATP using small-molecule fluorescent chemosensors. Despite the various solutions, the selective detection of ATP is still challenging due to the structural similarity of various nucleotides. In this paper, we report the conjugation of a uracil nucleobase to the known 4’-dimethylamino-hydroxyflavone fluorophore.Results: The complexation of this scaffold with ATP is already known. The complex is held together by stacking and electrostatic interactions. To achieve multi-point recognition, we designed the uracil-appended version of this probe to include complementary base-pairing interactions. The theoretical calculations revealed the availability of multiple complex structures. The synthesis was performed using click chemistry and the nucleotide recognition properties of the probe were evaluated using fluorescence spectroscopy.Conclusions: The first, uracil-containing fluorescent ATP probe based on a hydroxyflavone fluorophore was synthesized and evaluated. A selective complexation with ATP was observed and a ratiometric response in the excitation spectrum.

Highlights

Nucleotides play essential roles in various physiological processes, such as energy transportation [1], DNA synthesis [2] and cell signaling events [3]
The first, uracil-containing fluorescent ATP probe based on a hydroxyflavone fluorophore was synthesized and evaluated
The former ensures a good solubility of ATP in water and generates an electrostatic field around it while the latter is required for associations with similar planar hydrophobic molecules involved in the biochemical processes of ATP [34]

Summary

Results

The complexation of this scaffold with ATP is already known. The complex is held together by stacking and electrostatic interactions. To achieve multi-point recognition, we designed the uracil-appended version of this probe to include complementary base-pairing interactions. The theoretical calculations revealed the availability of multiple complex structures. The synthesis was performed using click chemistry and the nucleotide recognition properties of the probe were evaluated using fluorescence spectroscopy

Conclusions

Introduction

Results and Discussion

Conclusion

Synthetic procedures