Jablonski, Artur and Fritz, Yannic and Wagenknecht, Hans-Achim and Czerwieniec, Rafal and Bernas, Tytus and Trzybinski, Damian and Wozniak, Krzysztof and Kowalski, Konrad (2017) Pyrene-nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 13. pp. 2521-2534. ISSN 1860-5397,
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Fluorescent pyrene-linker-nucleobase (nucleobase = thymine, adenine) conjugates with carbonyl and hydroxy functionalities in the linker were synthesized and characterized. X-ray single-crystal structure analysis performed for the pyrene-C(O)CH2CH2-thymine (2) conjugate reveals dimers of molecules 2 stabilized by hydrogen bonds between the thymine moieties. The photochemical characterization showed structure-dependent fluorescence properties of the investigated compounds. The conjugates bearing a carbonyl function represent weak emitters as compared to compounds with a hydroxy function in the linker. The self-assembly properties of pyrene nucleobases were investigated in respect to their binding to single and double strand oligonucleotides in water and in buffer solution. In respect to the complementary oligothymidine Tin template in water, compounds 3 and 5 both show a self-assembling behavior according to canonical base-base pairing. However, in buffer solution, derivative 5 was much more effective than 3 in binding to the T-10 template. Furthermore the adenine derivative 5 binds to the double-stranded (dA)(10)-T-10 template with a self-assembly ratio of 112%. Such a high value of a self-assembly ratio can be rationalized by a triple-helix-like binding, intercalation, or a mixture of both. Remarkably, compound 5 also shows dual staining pattern in living HeLa cells. Confocal microscopy confirmed that 5 predominantly stains mitochondria but it also accumulates in the nucleoli of the cells.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | DNA; THYMINE; FLUORESCENCE; DERIVATIVES; ENERGY; ASSEMBLIES; SYSTEMS; PROBES; SET; confocal microscopy; luminescence; nucleobases; oligonucleotide binding; pyrene; X-ray |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Physikalische und Theoretische Chemie > Chair of Chemistry III - Physical Chemistry (Molecular Spectroscopy and Photochemistry) > Prof. Dr. Hartmut Yersin |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 14 Dec 2018 13:19 |
| Last Modified: | 01 Mar 2019 07:40 |
| URI: | https://pred.uni-regensburg.de/id/eprint/1826 |
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