Quantum Yield of DNA Strand Breaks under Photoexcitation of a Molecular Ruby

Wang, Cui; Ebel, Kenny; Heinze, Katja; Resch‐Genger, Ute; Bald, Ilko

doi:10.1002/chem.202203719

Cited by 7 publications

(6 citation statements)

References 99 publications

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“…Nevertheless, these lesions, namely DNA base oxidations, often require alkaline treatment to lead to a strand cleavage, so that the DNA damage remained mainly unnoticed in the employed assay. At the same time, it has been reported that 1 O 2 can also efficiently induce single-strand breaks directly [ 89 ], so that the observed low DNA cleavage under aerobic conditions may be assigned to such a reaction. Moreover, it should be noted that both 3 O 2 and 1 O 2 [ 46 ] might react with other intermediates formed during the photoreaction, for example by the reaction with C-radicals 4 and 5 to give peroxides such as 6 ( Scheme 4 ), by cycloaddition of 1 O 2 to alkene and diene units, or by deactivation of the excited state in a triplet-triplet annihilation [ 90 ], all of which leading to a reduced photocleavage efficiency.…”

Section: Resultsmentioning

confidence: 99%

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

Schlosser,

Fedorova,

Fedorov

et al. 2024

Beilstein J. Org. Chem.

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The photoreactions of selected styrylpyridine derivatives to the corresponding benzo[c]quinolizinium ions are described. It is shown that these reactions are more efficient in aqueous solution (97–44%) than in organic solvents (78–20% in MeCN). The quinolizinium derivatives bind to DNA by intercalation with binding constants of 6–11 × 104 M−1, as shown by photometric and fluorimetric titrations as well as by CD- and LD-spectroscopic analyses. These ligand–DNA complexes can also be established in situ upon 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, even under anaerobic conditions. Investigations of the mechanism of the DNA damage revealed the involvement of intermediate hydroxyl radicals and C-centered radicals. Under aerobic conditions, singlet oxygen only contributes to marginal extent to the DNA damage.

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Section: Resultsmentioning

confidence: 99%

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

Schlosser,

Fedorova,

Fedorov

et al. 2024

Beilstein J. Org. Chem.

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“…Very recently, the DNA single and double strand breaks induced by irradiation of a molecular ruby have been quantified, which opens a new field of application for the Lab-on-a-DNA origami approach. 124 …”

Section: Discussionmentioning

confidence: 99%

Lab-on-a-DNA origami: nanoengineered single-molecule platforms

et al. 2023

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“… 2023 29 e202203719 . 1 The [Cr(ddpd) 2 ] 3+ complex induces DNA strand breaks under UV/vis light, making it a potential photosensitizer for photodynamic therapy. By combining DNA origami technology with atomic force microscopy, the quantum yield of strand breaks was quantified to be between 1 and 4% .…”

Section: Key Referencesmentioning

confidence: 99%

“…Panel D shows (1) the molecular structure of the photosensitizer [Cr(ddpd) 2 ][BF 4 ] 3 and (2) quantum yields for strand breakage in ss- and ds-DNA sequences. Adapted with permission from ref ( 1 ). Copyright 2023 Wiley-VCH.…”

Section: Dna Damage Induced Upon Vuv Irradiation (30–220 Nm; 620–413 Ev)mentioning

confidence: 99%

Unraveling the Complexity of DNA Radiation Damage Using DNA Nanotechnology

Ameixa,

Bald

2024

Acc. Chem. Res.

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Conspectus Radiation cancer therapies use different ionizing radiation qualities that damage DNA molecules in tumor cells by a yet not completely understood plethora of mechanisms and processes. While the direct action of the radiation is significant, the byproducts of the water radiolysis, mainly secondary low-energy electrons (LEEs, <20 eV) and reactive oxygen species (ROS), can also efficiently cause DNA damage, in terms of DNA strand breakage or DNA interstrand cross-linking. As a result, these types of DNA damage evolve into mutations hindering DNA replication, leading to cancer cell death. Concomitant chemo-radiotherapy explores the addition of radiosensitizing therapeutics commonly targeting DNA, such as platinum derivatives and halogenated nucleosides, to enhance the harmful effects of ionizing radiation on the DNA molecule. Further complicating the landscape of DNA damage are secondary structures such as G-quadruplexes occurring in telomeric DNA. These structures protect DNA from radiation damage, rendering them as promising targets for new and more selective cancer radiation treatments, rather than targeting linear DNA. However, despite extensive research, there is no single paradigm approach to understanding the mysterious way in which ionizing radiation causes DNA damage. This is due to the multidisciplinary nature of the field of research, which deals with multiple levels of biological organization, from the molecular building blocks of life toward cells and organisms, as well as with complex multiscale radiation-induced effects. Also, intrinsic DNA features, such as DNA topology and specific oligonucleotide sequences, strongly influence its response to damage from ionizing radiation. In this Account, we present our studies focused on the absolute quantification of photon- and low-energy electron-induced DNA damage in strategically selected target DNA sequences. Our methodology involves using DNA origami nanostructures, specifically the Rothemund triangle, as a platform to expose DNA sequences to either low-energy electrons or vacuum-ultraviolet (VUV, <15 eV) photons and subsequent atomic force microscopy (AFM) analysis. Through this approach, the effects of the DNA sequence, incorporation of halogenated radiosensitizers, DNA topology, and the radiation quality on radiation-induced DNA strand breakage have been systematically assessed and correlated with fundamental photon- and electron-driven mechanisms underlying DNA radiation damage. At lower energies, these mechanisms include dissociative electron attachment (DEA), where electrons attach to DNA molecules causing strand breaks, and dissociative photoexcitation of DNA. Additionally, further dissociative processes such as photoionization and electron impact contribute to the complex cascade of DNA damage events induced by ionizing radiation. We expect that emerging DNA origami-based approaches will lead to a paradigm shift in research fields associated with DNA damage and suggest future directions, which can foster the development of technological a...

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Quantum Yield of DNA Strand Breaks under Photoexcitation of a Molecular Ruby

Cited by 7 publications

References 99 publications

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

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

Lab-on-a-DNA origami: nanoengineered single-molecule platforms

Unraveling the Complexity of DNA Radiation Damage Using DNA Nanotechnology

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