An uracil-linked hydroxyflavone probe for the recognition of ATP

Márton Bojtár, Péter Zoltán Janzsó-Berend, Dávid Mester, Dóra Hessz, M. Kállay, M. Kubinyi, I. Bitter

Research output: Contribution to journalArticle

3 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)747-755
Number of pages9
JournalBeilstein Journal of Organic Chemistry
Volume14
DOIs
Publication statusPublished - Jan 1 2018

Fingerprint

Uracil
Adenosine Triphosphate
Nucleotides
Fluorophores
Complexation
Molecules
Fluorescence spectroscopy
Coulomb interactions
Scaffolds
Availability

Keywords

  • 3-hydroxyflavone
  • ATP sensing
  • Base-pairing
  • Fluorescent probes
  • Nucleotide recognition

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

An uracil-linked hydroxyflavone probe for the recognition of ATP. / Bojtár, Márton; Janzsó-Berend, Péter Zoltán; Mester, Dávid; Hessz, Dóra; Kállay, M.; Kubinyi, M.; Bitter, I.

In: Beilstein Journal of Organic Chemistry, Vol. 14, 01.01.2018, p. 747-755.

Research output: Contribution to journalArticle

Bojtár, Márton ; Janzsó-Berend, Péter Zoltán ; Mester, Dávid ; Hessz, Dóra ; Kállay, M. ; Kubinyi, M. ; Bitter, I. / An uracil-linked hydroxyflavone probe for the recognition of ATP. In: Beilstein Journal of Organic Chemistry. 2018 ; Vol. 14. pp. 747-755.
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