Flexibility and Preorganization of Fluorescent Nucleobase-Pyrene Conjugates Control DNA and RNA Recognition
| Autor: | Josipa Matić, Anders Foller Füchtbauer, L. Marcus Wilhelmsson, Ivo Piantanida, Biserka Žinić, Željka Ban |
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| Rok vydání: | 2020 |
| Předmět: |
Poly U
DNA/RNA recognition hydrogen bonding fluorescent nucleobase pyrene intramolecular pre-organization Stereochemistry Pharmaceutical Science 010402 general chemistry 01 natural sciences Fluorescence Article Analytical Chemistry Nucleobase lcsh:QD241-441 chemistry.chemical_compound lcsh:Organic chemistry Drug Discovery Physical and Theoretical Chemistry Fluorescent Dyes RNA Double-Stranded Pyrenes 010405 organic chemistry Hydrogen bond Chemistry Circular Dichroism Organic Chemistry Water RNA DNA 3. Good health 0104 chemical sciences Poly C Spectrometry Fluorescence Chemistry (miscellaneous) Poly G Solvents Nucleic Acid Conformation Molecular Medicine Pyrene Poly A Selectivity Linker |
| Zdroj: | Molecules Volume 25 Issue 9 Molecules, Vol 25, Iss 2188, p 2188 (2020) |
| ISSN: | 1420-3049 |
| Popis: | We synthesized a new amino acid-fluorescent nucleobase derivative (qAN1-AA) and from it two new fluorescent nucleobase&ndash fluorophore (pyrene) conjugates, whereby only the analogue with the longer and more flexible linker (qAN1-pyr2) self-folded into intramolecularly stacked qAN1/pyrene conformation, yielding characteristic, 100 nm-red-shifted emission (&lambda max = 500 nm). On the contrary, the shorter and more rigid linker resulted in non-stacked conformation (qAN1-pyr1), characterized by the emission of free pyrene at &lambda max = 400 nm. Both fluorescent nucleobase&ndash fluorophore (pyrene) conjugates strongly interacted with ds-DNA/RNA grooves with similar affinity but opposite fluorescence response (due to pre-organization), whereas the amino acid-fluorescent base derivative (qAN1-AA) was inactive. However, only intramolecularly self-folded qAN1-pyr2 showed strong fluorescence selectivity toward poly U (Watson&ndash Crick complementary to qAN1 nucleobase) and poly A (reverse Hoogsteen complementary to qAN1 nucleobase), while an opposite emission change was observed for non-complementary poly G and poly C. Non-folded analogue (qAN1-pyr1) showed no ss-RNA selectivity, demonstrating the importance of nucleobase-fluorophore pre-organization. |
| Databáze: | OpenAIRE |
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