Photoinduced in situ generation of DNA-targeting ligands: DNA-binding and DNA-photodamaging properties of benzo[c]quinolizinium ions

• Julika Schlosser,
• Olga Fedorova,
• Yuri Fedorov and
• Heiko Ihmels

Beilstein J. Org. Chem. 2024, 20, 101–117, doi:10.3762/bjoc.20.11

• irradiation of the styrylpyridines and formation of the intercalator directly in the presence of DNA. In addition to the DNA-binding properties, the tested benzo[c]quinolizinium derivatives also operate as photosensitizers, which induce DNA damage at relative low concentrations and short irradiation times

• ; heterocycles; photocyclization; photosensitizer; styrylpyridines; Introduction DNA intercalators – most often represented by small planar heteroaromatic compounds – play an important role as chemotherapeutic agents [1][2][3][4]. Specifically, upon intercalation into the DNA double helix such ligands can cause

• spectrometry. In all cases, the E-configuration of the alkene double bonds was indicated by characteristic coupling constants of the alkene protons (3JH–H = 16 Hz). Absorption properties and photoreactions of styrylpyridine derivatives In acetonitrile solution, the styrylpyridines 2a–g exhibited long

Azologization and repurposing of a hetero-stilbene-based kinase inhibitor: towards the design of photoswitchable sirtuin inhibitors

• Christoph W. Grathwol,
• Nathalie Wössner,
• Sören Swyter,
• Adam C. Smith,
• Enrico Tapavicza,
• Robert K. Hofstetter,
• Anja Bodtke,
• Manfred Jung and
• Andreas Link

Beilstein J. Org. Chem. 2019, 15, 2170–2183, doi:10.3762/bjoc.15.214

• oxidized to phenantrene in the presence of oxygen [48]. In high concentrations, (E)-stilbene furthermore undergoes photocyclodimerization to cyclobutane derivatives [49]. Photoisomerization and photocyclization are also reported for 3-styrylpyridines, forming two regioisomeric dihydroazaphenanthrenes that