Femtosecond photoisomerization of azobenzene-derivative binding to DNA

Chen, Tao; Igarashi, Kazumasa; Nakagawa, Naofumi; Yamane, Kunio; Fujii, Tomoyuki; Asanuma, Hiroyuki; Yamashita, Mikio

doi:10.1016/j.jphotochem.2011.08.007

Cited by 3 publications

(3 citation statements)

References 24 publications

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“…However, it is also possible that electronic interactions, including both energy and charge transfer between the azobenzene and the nucleic acid bases , are modulating the quantum yield by changing the energy relaxation pathways available to the azobenzene on an ultrafast time scale . In this case, one would explain the sequence-dependent differences in quantum yield as arising from different electronic interactions between the azobenzene and the different bases.…”

Section: Resultsmentioning

confidence: 99%

“…25 However, it is also possible that electronic interactions, including both energy and charge transfer between the azobenzene and the nucleic acid bases 11,26 are modulating the quantum yield by changing the energy relaxation pathways available to the azobenzene on an ultrafast time scale. 27 In this case, one would explain the sequence-dependent differences in quantum yield as arising from different electronic interactions between the azobenzene and the different bases. To test this alternative hypothesis, Figure 4 plots the photoisomerization quantum yield (bars) for the azobenzene incorporated in the middle of 18-base ssDNAs comprising polydeoxyadenosine (poly(dA)), polydeoxycytidine (poly(dC)), and polydeoxythymidine (poly(dT)).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Photoisomerization Quantum Yield of Azobenzene-Modified DNA Depends on Local Sequence

et al. 2013

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Photoswitch-modified DNA is being studied for applications including light-harvesting molecular motors, photocontrolled drug delivery, gene regulation, and optically mediated assembly of plasmonic metal nanoparticles in DNA-hybridization assays. We study the sequence and hybridization dependence of the photoisomerization quantum yield of azobenzene attached to DNA via the popular d-threoninol linkage. Compared to free azobenzene we find that the quantum yield for photoisomerization from trans to cis form is decreased 3-fold (from 0.094 ± 0.004 to 0.036 ± 0.002) when the azobenzene is incorporated into ssDNA, and is further reduced 15-fold (to 0.0056 ± 0.0008) for azobenzene incorporated into dsDNA. In addition, we find that the quantum yield is sensitive to the local sequence including both specific mismatches and the overall sequence-dependent melting temperature (Tm). These results serve as design rules for efficient photoswitchable DNA sequences tailored for sensing, drug delivery, and energy-harvesting applications, while also providing a foundation for understanding phenomena such as photonically controlled hybridization stringency.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Photoisomerization Quantum Yield of Azobenzene-Modified DNA Depends on Local Sequence

et al. 2013

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“…We focused on a strategy based on halogenides (iodide, bromide) of azo derivatives and glycosyl thiols as electrophilic and nucleophilic partners, respectively, in a palladium-catalyzed Buchwald-Hartwig-Migita cross-coupling reaction (Figure 1). [17] Although azobenzene derivatives bearing sulfide motifs have already been reported, [18,19] direct thioarylation of azoswitches, to the best of our knowledge, has never been disclosed. Moreover, systematic studies on the influence of sulfur-based substituents on photochromic and thermal relaxation properties of azobenzene derivatives are lacking.…”

Section: Introductionmentioning

confidence: 99%

Sulfur and Azobenzenes, a Profitable Liaison: Straightforward Synthesis of Photoswitchable Thioglycosides with Tunable Properties

Berry

Despras

2022

Chemistry A European J

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Azobenzene photoswitches are valuable tools for controlling properties of molecular systems with light. We have been investigating azobenzene glycoconjugates to probe carbohydrate-protein interactions and to design glycoazobenzene macrocycles with chiroptical and physicochemical properties modulated by light irradiation. To date, direct conjugation of glycosides to azobenzenes was performed by reactions providing target compounds in limited yields. We therefore sought a more effective and reliable coupling method. In this paper, we report on a straightforward thioarylation of azobenzene derivatives with glycosyl thiols as well as other thiols, thereby increasing the scope of azobenzene conjugation. Even challenging unsymmetrical conjugates can be achieved in good yields via sequential or one-pot procedures. Importantly, red-shifted azoswitches, which are addressed with visible light, were easily functionalized. Additionally, by oxidation of the sulfide bridge to the respective sulfones, both the photochromic and the thermal relaxation properties of the core azobenzene can be tuned. Utilizing this option, we realized orthogonal three-state photoswitching in mixtures containing two distinct azobenzene thioglycosides.

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Dioxidomolybdenum(VI) complexes of azo-hydrazones: Structural investigation, DNA binding and cytotoxicity studies

et al. 2022

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Femtosecond photoisomerization of azobenzene-derivative binding to DNA

Cited by 3 publications

References 24 publications

Photoisomerization Quantum Yield of Azobenzene-Modified DNA Depends on Local Sequence

Photoisomerization Quantum Yield of Azobenzene-Modified DNA Depends on Local Sequence

Sulfur and Azobenzenes, a Profitable Liaison: Straightforward Synthesis of Photoswitchable Thioglycosides with Tunable Properties

Dioxidomolybdenum(VI) complexes of azo-hydrazones: Structural investigation, DNA binding and cytotoxicity studies

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