Reversible photoswitching of the DNA-binding properties of styrylquinolizinium derivatives through photochromic [2 + 2] cycloaddition and cycloreversion

Sarah Kölsch, Heiko Ihmels, Jochen Mattay, Norbert Sewald and Brian O. Patrick
Beilstein J. Org. Chem. 2020, 16, 111–124. https://doi.org/10.3762/bjoc.16.13

Supporting Information

Supporting Information File 1: Additional spectroscopic data, detailed experimental procedures, 1H NMR spectra, and crystallographic data.
Format: PDF Size: 1.4 MB Download

Cite the Following Article

Reversible photoswitching of the DNA-binding properties of styrylquinolizinium derivatives through photochromic [2 + 2] cycloaddition and cycloreversion
Sarah Kölsch, Heiko Ihmels, Jochen Mattay, Norbert Sewald and Brian O. Patrick
Beilstein J. Org. Chem. 2020, 16, 111–124. https://doi.org/10.3762/bjoc.16.13

How to Cite

Kölsch, S.; Ihmels, H.; Mattay, J.; Sewald, N.; Patrick, B. O. Beilstein J. Org. Chem. 2020, 16, 111–124. doi:10.3762/bjoc.16.13

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 202.7 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Schlosser, J.; Ihmels, H. Photocontrolled Binding of Styrylnaphthyridine Ligands to Abasic Site-Containing DNA by Reversible [2+2] Cycloaddition and Cycloreversion. Chemistry (Weinheim an der Bergstrasse, Germany) 2024, 30, e202400423. doi:10.1002/chem.202400423
  • Dohmen, C.; Ihmels, H. Photoinduced [2+2] and [4+4] Cycloaddition and Cycloreversion Reactions for the Development of Photocontrollable DNA Binders. ChemPhotoChem 2024, 8. doi:10.1002/cptc.202300318
  • Berdnikova, D. V. Aurones: Unexplored Visible-Light Photoswitches for Aqueous Medium. Chemistry (Weinheim an der Bergstrasse, Germany) 2024, 30, e202304237. doi:10.1002/chem.202304237
  • Schlosser, J.; Fedorova, O.; Fedorov, Y.; Ihmels, H. Photoinduced in situ generation of DNA-targeting ligands: DNA-binding and DNA-photodamaging properties of benzo[c]quinolizinium ions. Beilstein journal of organic chemistry 2024, 20, 101–117. doi:10.3762/bjoc.20.11
  • Schlosser, J.; Stötzel, N.; Fedorov, Y.; Ihmels, H. Photoinduced Reactions of Styrylpyridine Derivatives for the In Situ Formation of Selective Ligands for Apyrimidinic DNA. ChemPhotoChem 2023, 7. doi:10.1002/cptc.202300159
  • Dohmen, C.; Ihmels, H. Switching between DNA binding modes with a photo- and redox-active DNA-targeting ligand, part II: the influence of the substitution pattern. Organic & biomolecular chemistry 2023, 21, 5799–5808. doi:10.1039/d3ob00879g
  • Zhang, M.-s.; Chu, Y.; Wu, Z.; Guo, Y.-r.; Shi, Y.-n.; Wang, C.; Wang, M.-q.; Zhong, Y.-q.; Zhang, H.-y.; Wang, Y.-n.; Wang, J.; Zhao, G.-j. Ultrafast spectroscopic study on non-adiabatic UV protection mechanism of hemicyanines. Chinese Journal of Chemical Physics 2023, 36, 25–34. doi:10.1063/1674-0068/cjcp2104078
  • Mizuno, K. Photochemistry of aromatic compounds (2019–2020). Photochemistry; The Royal Society of Chemistry, 2022; pp 125–200. doi:10.1039/9781839167676-00125
  • Wang, Z.; Amjaour, H.; Robertson, J. E. M.; Azizov, D.; Ugrinov, A.; Chu, Q. R. A recyclable thermoset with built-in thermocleavable group developed from a cis-cyclobutane-1,2-dicarboxylic acid. Chemical communications (Cambridge, England) 2022, 58, 8850–8853. doi:10.1039/d2cc01502a
  • Saifutiarova, A. E.; Fedorov, Y. V.; Maurel, F.; Gulakova, E. N.; Karnoukhova, V. A.; Fedorova, O. A. Highly regioselective and stereoselective photodimerization of azine-containing stilbenes in neat condition: An efficient synthesis of novel cyclobutanes with heterocyclic substituents. Journal of Photochemistry and Photobiology A: Chemistry 2022, 427, 113804. doi:10.1016/j.jphotochem.2022.113804
  • Berdnikova, D. V. Photoswitches for controllable RNA binding: a future approach in the RNA-targeting therapy. Chemical communications (Cambridge, England) 2021, 57, 10819–10826. doi:10.1039/d1cc04241f
  • Ramos-Soriano, J.; Galan, M. C. Photoresponsive Control of G-Quadruplex DNA Systems. JACS Au 2021, 1, 1516–1526. doi:10.1021/jacsau.1c00283
  • Bosch, P.; Marcelo, G.; Matamoros-Recio, A.; Sucunza, D.; Mendicuti, F.; Domingo, A.; Vaquero, J. J. A new family of fluorescent pyridazinobenzimidazolium cations with DNA binding properties. Dyes and Pigments 2021, 192, 109443. doi:10.1016/j.dyepig.2021.109443
  • Orehovec, I.; Matković, M.; Pehar, I.; Majhen, D.; Piantanida, I. Bis-Pyrene Photo-Switch Open- and Closed-Form Differently Bind to ds-DNA, ds-RNA and Serum Albumin and Reveal Light-Induced Bioactivity. International journal of molecular sciences 2021, 22, 4916. doi:10.3390/ijms22094916
  • Bortolozzi, R.; Ihmels, H.; Schulte, R.; Stremmel, C.; Viola, G. Synthesis, DNA-binding and antiproliferative properties of diarylquinolizinium derivatives. Organic & biomolecular chemistry 2021, 19, 878–890. doi:10.1039/d0ob02298e
  • Pithan, P. M.; Steup, S.; Ihmels, H. Cation-induced ring-opening and oxidation reaction of photoreluctant spirooxazine-quinolizinium conjugates. Beilstein journal of organic chemistry 2020, 16, 904–916. doi:10.3762/bjoc.16.82
  • Berdnikova, D. V.; Heider, J.; Ihmels, H.; Sewald, N.; Pithan, P. M. Photoinduced release of DNA‐binding ligands from the [4+4] dimers of benzo[b]quinolizinium and anthracene derivatives. ChemPhotoChem 2020, 4, 520–525. doi:10.1002/cptc.202000015
Other Beilstein-Institut Open Science Activities