Molecular Receptors for Recognition and Sensing of Nucleotides

Abstract

Nucleotides are constituents of nucleic acids and they have a variety of functions in cellular metabolism. Synthetic receptors and sensors are required to reveal the role of nucleotides in living organisms and mechanisms of signal transduction events. In recent years, a large number of nucleotide‐selective synthetic receptors have been devised, which utilize different molecular designs and sensing mechanisms. This Minireview presents recent progress in the design of synthetic molecular receptors for selective recognition of nucleotides in aqueous solution. The binding properties of receptors and the origins of their selectivity for a particular nucleotide are discussed.

Anthracene‐Based Cyclophanes with Selective Fluorescent Responses for TTP and GTP: Insights into Recognition and Sensing Mechanisms

“…Fluorescence titrations with other nucleoside triphosphates revealed as ignificant enhancement of fluorescence, with ATPg iving the most pronounced effect for 1 and 2.I nterestingly,t he addition of pyrophosphate (the reference anion) resulted in much smaller changes in fluorescence spectra of receptors and to lower binding constants. This result implies the importance of additional interactions formed in theh ost-guestc omplexes between nucleobases and macrocycles that increase the overall binding affinity,a sc ompared with pyrophosphate.T hese interactions can be dispersion interactions between the nucleobase and the anthracene ring or hydrogen-bondingi nteractions between the nucleobase andthe linker.Wefound an interesting behavior of receptor 1 and 3 in titration experiments with nucleotides, which [2,5] For cases in which we observed changes in the monomerexcimer ratio, it is clear that binding modes I or III are formed ( Figure 4D). In these complexes, the nucleobase has either hydrogen-bonding interactions with the linker or dispersion interactions with the anthracene ring, or even interacts with both parts of the macrocycle simultaneously.B inding mode II should not be the case for our receptors because neither of the tested nucleotides showede nhancement of the excimer band together with the decrease of the monomer band.…”

“…Addition of some nucleotides ( 1 +ATP, 1 +TTP, 3 +UTP) influenced the ratio of the monomer and excimer emission (Figure A) with clear isosbestic points, while other nucleotides induce simultaneous changes of both bands, enhancement or quenching (Figure B, C). Overall, three interaction modes in receptor–nucleotide complexes have been reported: I , II and III , as exemplified for receptor 3 in Figure D …”

“…Therefore, new hosts for recognition and sensing of nucleotides, as well as understanding how to design such systems and their mechanisms of action are of great interest. Despite significant progress in this area in the past years, the challenge to bind and detect nucleotides with high selectively remains …”

“…Despite significant progress in this area in the past years, the challenge to bind andd etect nucleotides with high selectively remains. [2,5] Cyclophanes attractc onsiderable attention among scientists and they are tested in different applications in chemistry and biology. [15] Macrocyclesw ith dye molecules in their structures show ah igh potentialf or diverse analytical applications.…”

Tuning the anion binding properties of lanthanide receptors to discriminate nucleoside phosphates in a sensing array

“…3,4 Signicant research effort is focussed on developing synthetic receptors for nucleoside phosphate anions, due to the critical roles they play in biological processes, including energy transduction, phosphorylation, cellular signalling and DNA synthesis. 5,6 The creation of receptors capable of binding and differentiating nucleoside phosphate anions (e.g. ATP, ADP, AMP, GTP, GDP, UDP) under physiological conditions could underpin exciting new sensing tools for biomedical research and drug discovery, 7 but it is very challenging due to the similarities in anion structure, size and charge.…”