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

Kölsch, Sarah; Ihmels, Heiko; Mattay, Jochen; Sewald, Norbert; Patrick, Brian O.

doi:10.3762/bjoc.16.13

Cited by 17 publications

(11 citation statements)

References 87 publications

(117 reference statements)

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“…The chemical structures of the products were confirmed by 1D and 2D NMR spectroscopy ( 1 H, 13 C, COSY, HSQC, HMBC), mass spectrometry and elemental analysis. Specifically, the products showed the characteristic 1 H NMR shifts of the E ‐configured alkene double bonds ( 3 J H−H =16 Hz) [22] …”

Section: Resultsmentioning

confidence: 99%

“…Another strategy to increase the selectivity of DNA‐binding ligands has been realized with photo‐active compounds, whose association with the target DNA can be switched on or off by light [21–26] . In these cases, a substrate, which does not bind to DNA, may be delivered close to the nucleic acid without an effect, whereas the DNA‐binding ligand is formed directly upon irradiation.…”

Section: Introductionmentioning

confidence: 99%

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Photoinduced Reactions of Styrylpyridine Derivatives for the In Situ Formation of Selective Ligands for Apyrimidinic DNA

Schlosser,

Stötzel,

Fedorov

et al. 2023

ChemPhotoChem

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The photocyclization reaction of sterically demanding styrylpyridine derivatives was investigated and shown to depend on the type of substituent. With this method, a 2,2‐diphenyl‐1,3‐benzodioxolo‐annelated benzo[c]quinolizinium was synthesized, and its association with regular and abasic site‐containing DNA (AP‐DNA) was investigated by absorption, fluorescence, circular and linear dichroism spectroscopy. Specifically, this ligand binds preferentially to AP‐DNA relative to regular duplex DNA, and the AP‐DNA/ligand complex is formed in situ upon irradiation of the styrylpyridine substrate in the presence of the DNA.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photoinduced Reactions of Styrylpyridine Derivatives for the In Situ Formation of Selective Ligands for Apyrimidinic DNA

Schlosser,

Stötzel,

Fedorov

et al. 2023

ChemPhotoChem

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“…While being an emerging area, studies concerning the photoregulation of G4 structures are less common than examples of photoregulation of duplex DNA hairpins. 44 − 63 In this Perspective, we focus our attention on the most recent examples of photoresponsive G4-based systems and the strategies used to engineer these systems toward a variety of applications. For a more comprehensive overview regarding photoresponsive control of oligonucleotide structures, the reader is referred to another recent review.…”

Section: Introductionmentioning

confidence: 99%

Photoresponsive Control of G-Quadruplex DNA Systems

Ramos‐Soriano

Galan

2021

JACS Au

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G-quadruplex (G4) oligonucleotide secondary structures have recently attracted significant attention as therapeutic targets owing to their occurrence in human oncogene promoter sequences and the genome of pathogenic organisms. G4s also demonstrate interesting catalytic activities in their own right, as well as the ability to act as scaffolds for the development of DNA-based materials and nanodevices. Owing to this diverse range of opportunities to exploit G4 in a variety of applications, several strategies to control G4 structure and function have emerged. Interrogating the role of G4s in biology requires the delivery of small-molecule ligands that promote its formation under physiological conditions, while exploiting G4 in the development of responsive nanodevices is normally achieved by the addition and sequestration of the metal ions required for the stabilization of the folded structure. Although these strategies prove successful, neither allows the system in question to be controlled externally. Meanwhile, light has proven to be an attractive means for the control of DNA-based systems as it is noninvasive, can be delivered with high spatiotemporal precision, and is orthogonal to many chemical and biological processes. A plethora of photoresponsive DNA systems have been reported to date; however, the vast majority deploy photoreactive moieties to control the stability and assembly of duplex DNA hybrids. Despite the unique opportunities afforded by the regulation of G-quadruplex formation in biology, catalysis, and nanotechnology, comparatively little attention has been devoted to the design of photoresponsive G4-based systems. In this Perspective, we consider the potential of photoresponsive G4 assemblies and examine the strategies that may be used to engineer these systems toward a variety of applications. Through an overview of the main developments in the field to date, we highlight recent progress made toward this exciting goal and the emerging opportunities that remain ripe for further exploration in the coming years.

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“…Similarly, it was shown that DNA helicity can be somewhat changed by photo-switchable small molecules [ 14 ]. Lately, significant progress was made by Ihmels et al, demonstrating a wide range of heterocyclic systems, which can be finely tuned [ 15 , 16 , 17 , 18 ]. In addition, very recently new photo-switchable non-covalently interacting optoepigenetic tools for conditional modulation of nucleosomal DNA accessibility were reported [ 19 ].…”

Section: Introductionmentioning

confidence: 99%

Bis-Pyrene Photo-Switch Open- and Closed-Form Differently Bind to ds-DNA, ds-RNA and Serum Albumin and Reveal Light-Induced Bioactivity

Orehovec

Matković

Pehar

et al. 2021

IJMS

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Newly designed and synthesized diarylethene (DAE) derivatives with aliphatic amine sidearms and one with two pyrenes, revealed excellent photo-switching property of central DAE core in MeOH and water. The only exception was bis-pyrene analogue, its DAE core very readily photochemically closed, but reversible opening completely hampered by aromatic stacking interaction of pyrene(s) with cyclic DAE. In this process, pyrene fluorescence showed to be a reliable monitoring method, an open form characterized by strong emission at 480 nm (typical for pyrene-aggregate), while closed form emitted weakly at 400 nm (typical for pyrene-DAE quenching). Only open DAE-bis-pyrene form interacted measurably with ds-DNA/RNA by flexible insertion in polynucleotide grooves, while self-stacked closed form did not bind to DNA/RNA. For the same steric reasons, flexible open DAE-bis-pyrene form was bound to at least three different binding sites at bovine serum albumin (BSA), while rigid, self-stacked closed form interacted dominantly with only one BSA site. Preliminary screening of antiproliferative activity against human lung carcinoma cell line A549 revealed that all DAE-derivatives are non-toxic. However, bis-pyrene analogue efficiently entered cells and located in the cytoplasm, whereby irradiation by light (315–400 nm) resulted in a strong, photo-induced cytotoxic effect, typical for pyrene-related singlet oxygen species production.

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

Cited by 17 publications

References 87 publications

Photoinduced Reactions of Styrylpyridine Derivatives for the In Situ Formation of Selective Ligands for Apyrimidinic DNA

Photoinduced Reactions of Styrylpyridine Derivatives for the In Situ Formation of Selective Ligands for Apyrimidinic DNA

Photoresponsive Control of G-Quadruplex DNA Systems

Bis-Pyrene Photo-Switch Open- and Closed-Form Differently Bind to ds-DNA, ds-RNA and Serum Albumin and Reveal Light-Induced Bioactivity

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