Synthesis of azobenzene-tethered DNA for reversible photo-regulation of DNA functions: hybridization and transcription

Asanuma, Hiroyuki; Liang, Xingguo; Nishioka, H.; Matsunaga, Daijiro; Liu, Mingzhe; Komiyama, Makoto

doi:10.1038/nprot.2006.465

Cited by 288 publications

(270 citation statements)

References 18 publications

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“…Experimental Section Synthesis of oligonucleotides:O ligonucleotides consisting of only native bases (nDNA-1, nDNA-2, and nDNA-3) were supplied by Integrated DNA Te chnologies, Inc. We synthesized phosphoramidite monomers modified with unmodified Azo or SDM-Azo as described previously. [34][35][36] Oligonucleotides xDNA-1, 2, and 3h aving Azo units or SDM-Azo units were purchased from Nihon Te chno Service Co. Ltd. (Tsukuba, Japan).…”

Section: Resultsmentioning

confidence: 99%

“…Previously,A sanumaa nd co-workers demonstrated the photo-control of association and dissociation of aD NA duplex by introducing an azobenzene derivative into DNA through d-threoninol as as caffold. [34][35][36] Introduction of multiple azobenzenes allowed efficient photo-regulation of duplex formation. [37] With these photo-responsive DNAs, photo-driven nanomachines, [38] photo-switchable DNAzymes, [39,40] and ap hoto-controllable DNA-buckyball have been created.…”

Section: Introductionmentioning

confidence: 99%

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DNA Microcapsule for Photo‐Triggered Drug Release Systems

et al. 2017

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In this study we constructed spherical photo‐responsive microcapsules composed of three photo‐switchable DNA strands. These strands first formed a three‐way junction (TWJ) motif that further self‐assembled to form microspheres through hybridization of the sticky‐end regions of each branch. To serve as the photo‐switch, multiple unmodified azobenzene (Azo) or 2,6‐dimethyl‐4‐(methylthio)azobenzene (SDM‐Azo) were introduced into the sticky‐end regions via a d‐threoninol linker. The DNA capsule structure deformed upon trans‐to‐cis isomerization of Azo or SDM‐Azo induced by specific light irradiation. In addition, photo‐triggered release of encapsulated small molecules from the DNA microcapsule was successfully achieved. Moreover, we demonstrated that photo‐triggered release of doxorubicin caused cytotoxicity to cultured cells. This biocompatible photo‐responsive microcapsule has potential application as a photo‐controlled drug‐release system.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

DNA Microcapsule for Photo‐Triggered Drug Release Systems

et al. 2017

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“…Because it occupies the fibrinogen-binding pocket, only 15Apt can inhibit thrombin-mediated coagulation (23). Next, the regulatory domain is composed of the complementary sequence to 15Apt, but with azobenzene molecules inserted into the phosphate backbone of the DNA sequence using an automated DNA synthesizer (31). Finally, the linking domain ties the inhibitory and regulatory domains together.…”

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confidence: 99%

Using photons to manipulate enzyme inhibition by an azobenzene-modified nucleic acid probe

Kim

Phillips

Liu

et al. 2009

Proc. Natl. Acad. Sci. U.S.A.

145

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The ability to inhibit an enzyme in a specific tissue with high spatial resolution combined with a readily available antidote should find many biomedical applications. We have accomplished this by taking advantage of the cis-trans photoisomerization of azobenzene molecules. Specifically, we positioned azobenzene moieties within the DNA sequence complementary to a 15-base-long thrombin aptamer and then linked the azobenzene-modified cDNA to the aptamer by a polyethylene glycol (PEG) linker to make a unimolecular conjugate. During the photoisomerization of azobenzene by visible light, the inhibition of thrombin is disabled because the probe hybridizes with the cDNA in the trans-azobenzene conformation so that the aptamer cannot bind its target thrombin. However, when UV light is applied, melting of the hairpin structure (duplex) is induced via trans-to-cis conversion, thereby changing conformation of the aptamer and making the aptamer free to bind to and inhibit its target thrombin. By using standard clotting assays, we measured the IC 200 of various probe designs in both states and concluded the feasibility of using photon energy to temporally and spatially regulate these enzymatic reactions. Thus, we can report the development of DNA probes in the form of photon-controllable (thrombin) inhibitors, termed PCIs, and we expect that this approach will be highly beneficial in future biomedical and pharmaceutical applications.anticoagulation ͉ aptamer ͉ enzyme inhibitor ͉ photo controllable ͉ thrombine O ver the last decade, extensive research has been devoted to the study of phototransformable molecules based on photochromism chemistry. This science has been applied to photooptical technology and such photomodulated devices as eyeglasses called Transitions (1-4). A photochromic compound has 2 molecular states: stable and relatively unstable. The 2 states are interchangeable by the effect of irradiation using different wavelengths and differ from one another in terms of both physical and chemical properties. The photoconversion mechanism can largely be divided into 3 transformation types: photochromic tautomerism, cis-trans isomerization, and photocyclization. Briefly, photoisomerization is a process in which molecular structural change between isomers is caused by photoexcitation. Therefore, because isomerization causes a conformational change that can change the overall structure of a molecule, cis-trans isomerization is an intriguing mechanism that can be used to regulate mechanical devices and biological reactions (5-8).As one of the most popular phototransformable molecules in use today, azobenzene and its derivatives belong to the cis-trans isomerization category and are composed of 2 phenyl rings linked by a NAN double bond (Fig. 1) (9). The 2 isomers can be switched with particular wavelengths of light: UV light at 365 nm, corresponding to the trans-to-cis conversion, and visible light at 465 nm, corresponding to the cis-to-trans isomerization. There are reports that demonstrate the possible applications of su...

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“…In just 30 minutes, a detection limit of 0.0128 HA unit could be achieved. Another approach was used by the Zhong and Tan groups to produce a hydrogel that contracted in the presence of visible light, but swelled under UV [71,72]. This was achieved by using an azobenzene modified DNA.…”

Section: Sensors Based On Gel Volume Changementioning

confidence: 99%