Selective Fluorimetric Detection of Pyrimidine Nucleotides in Neutral Aqueous Solution with a Styrylpyridine-Based Cyclophane

Author:

Schlosser Julika1,Hebborn Julian F. M.1,Berdnikova Daria V.1ORCID,Ihmels Heiko1ORCID

Affiliation:

1. Department of Chemistry-Biology, Research Center of Micro- and Nanochemistry and (Bio)Technology (Cµ), University of Siegen, Adolf-Reichwein-Str. 2, 57068 Siegen, Germany

Abstract

A styrylpyridine-containing cyclophane with diethylenetriamine linkers is presented as a host system whose association with representative nucleotides was examined with photometric and fluorimetric titrations. The spectrometric titrations revealed the formation of 1:1 complexes with log Kb values in the range of 2.3–3.2 for pyrimidine nucleotides TMP (thymidine monophosphate), TTP (thymidine triphosphate) and CMP (cytidine monophosphate) and 3.8–5.0 for purine nucleotides AMP (adenosine monophosphate), ATP (adenosine triphosphate), and dGMP (deoxyguanosine monophosphate). Notably, in a neutral buffer solution, the fluorimetric response to the complex formation depends on the type of nucleotide. Hence, quenching of the already weak fluorescence was observed with the purine bases, whereas the association of the cyclophane with pyrimidine bases TMP, TTP, and CMP resulted in a significant fluorescence light-up effect. Thus, it was demonstrated that the styrylpyridine unit is a useful and complementary fluorophore for the development of selective nucleotide-targeting fluorescent probes based on alkylamine-linked cyclophanes.

Funder

Deutsche Forschungsgemeinschaft

University of Siegen

Publisher

MDPI AG

Subject

Organic Chemistry,Inorganic Chemistry,Electrochemistry,Chemistry (miscellaneous)

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