An uracil-linked hydroxyflavone probe for the recognition of ATP

• Published in: Beilstein journal of organic chemistry Vol. 14; no. 1; pp. 747 - 755
• Main Authors: Bojtár, Márton, Janzsó-Berend, Péter Zoltán, Mester, Dávid, Hessz, Dóra, Kállay, Mihály, Kubinyi, Miklós, Bitter, István
• Format: Journal Article
• Language: English
• Published: Germany Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 2018; Beilstein-Institut
• Subjects: 3-hydroxyflavone; ATP sensing; base-pairing; Chemical sensors; Chemistry; Electrostatic properties; Fluorescence spectroscopy; fluorescent probes; Full Research Paper; Materials science; nucleotide recognition; Nucleotides; Physical chemistry; Physiology; Sensors; Uracil; Hungary; 3-hydroxyflavone; ATP sensing; base-pairing; nucleotide recognition; fluorescent probes
• ISSN: 1860-5397; 2195-951X; 1860-5397
• DOI: 10.3762/bjoc.14.63

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.
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.
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.