Selective Fluorimetric Detection of Pyrimidine Nucleotides in Neutral Aqueous Solution with a Styrylpyridine-Based Cyclophane
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 <i>K&l...
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MDPI AG
2023-05-01
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| Series: | Chemistry |
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| Online Access: | https://www.mdpi.com/2624-8549/5/2/82 |
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| author | Julika Schlosser Julian F. M. Hebborn Daria V. Berdnikova Heiko Ihmels |
| author_facet | Julika Schlosser Julian F. M. Hebborn Daria V. Berdnikova Heiko Ihmels |
| author_sort | Julika Schlosser |
| collection | DOAJ |
| description | 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 <i>K</i><sub>b</sub> 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. |
| first_indexed | 2024-03-11T02:38:47Z |
| format | Article |
| id | doaj.art-5e4178bc73594cb3b37dc366fe0cbd93 |
| institution | Directory Open Access Journal |
| issn | 2624-8549 |
| language | English |
| last_indexed | 2024-03-11T02:38:47Z |
| publishDate | 2023-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Chemistry |
| spelling | doaj.art-5e4178bc73594cb3b37dc366fe0cbd932023-11-18T09:45:39ZengMDPI AGChemistry2624-85492023-05-01521220123210.3390/chemistry5020082Selective Fluorimetric Detection of Pyrimidine Nucleotides in Neutral Aqueous Solution with a Styrylpyridine-Based CyclophaneJulika Schlosser0Julian F. M. Hebborn1Daria V. Berdnikova2Heiko Ihmels3Department of Chemistry-Biology, Research Center of Micro- and Nanochemistry and (Bio)Technology (Cµ), University of Siegen, Adolf-Reichwein-Str. 2, 57068 Siegen, GermanyDepartment of Chemistry-Biology, Research Center of Micro- and Nanochemistry and (Bio)Technology (Cµ), University of Siegen, Adolf-Reichwein-Str. 2, 57068 Siegen, GermanyDepartment of Chemistry-Biology, Research Center of Micro- and Nanochemistry and (Bio)Technology (Cµ), University of Siegen, Adolf-Reichwein-Str. 2, 57068 Siegen, GermanyDepartment of Chemistry-Biology, Research Center of Micro- and Nanochemistry and (Bio)Technology (Cµ), University of Siegen, Adolf-Reichwein-Str. 2, 57068 Siegen, GermanyA 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 <i>K</i><sub>b</sub> 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.https://www.mdpi.com/2624-8549/5/2/82fluorescent dyesnucleotide recognitionheterocycleshost–guest chemistry |
| spellingShingle | Julika Schlosser Julian F. M. Hebborn Daria V. Berdnikova Heiko Ihmels Selective Fluorimetric Detection of Pyrimidine Nucleotides in Neutral Aqueous Solution with a Styrylpyridine-Based Cyclophane Chemistry fluorescent dyes nucleotide recognition heterocycles host–guest chemistry |
| title | Selective Fluorimetric Detection of Pyrimidine Nucleotides in Neutral Aqueous Solution with a Styrylpyridine-Based Cyclophane |
| title_full | Selective Fluorimetric Detection of Pyrimidine Nucleotides in Neutral Aqueous Solution with a Styrylpyridine-Based Cyclophane |
| title_fullStr | Selective Fluorimetric Detection of Pyrimidine Nucleotides in Neutral Aqueous Solution with a Styrylpyridine-Based Cyclophane |
| title_full_unstemmed | Selective Fluorimetric Detection of Pyrimidine Nucleotides in Neutral Aqueous Solution with a Styrylpyridine-Based Cyclophane |
| title_short | Selective Fluorimetric Detection of Pyrimidine Nucleotides in Neutral Aqueous Solution with a Styrylpyridine-Based Cyclophane |
| title_sort | selective fluorimetric detection of pyrimidine nucleotides in neutral aqueous solution with a styrylpyridine based cyclophane |
| topic | fluorescent dyes nucleotide recognition heterocycles host–guest chemistry |
| url | https://www.mdpi.com/2624-8549/5/2/82 |
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