Visible‐Light‐Triggered Cross‐Linking of DNA Duplexes by Reversible [2+2] Photocycloaddition of Styrylpyrene

Doi, Tetsuya; Kawai, Hayato; Murayama, Keiji; Kashida, Hiromu; Asanuma, Hiroyuki

doi:10.1002/chem.201602006

Cited by 73 publications

(74 citation statements)

References 78 publications

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“…As can be seen in Figure , PCA proceeded quantitatively until complete consumption of the starting dyad. In general, PCA is a reversible reaction, and complete transformation of one isomer to another is sometimes possible only if one of isomers does not absorb an incident light. However, it is not relevant to this case: 4 has low but noticeable absorbance at 370 nm (MAC=4300 M −1 cm −1 ).…”

Section: Methodsmentioning

confidence: 99%

Irreversible One‐Way [2+2] Photocycloaddition in Bis‐Styrylbenzo[f]quinoline Dyad: Photoactive and Photoinert Excimers in the Same System

et al. 2018

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Competitive photoprocesses were found in a novel biphotochromic dyad with 3‐styrylbenzo[f]quinoline (SBQ) photochromes ‐ fluorescence and unexpectedly irreversible [2+2] photocycloaddition (PCA) resulting in formation of a cyclobutane derivative with two benzo[f]quinoline (BQ) substituents. No SBQ trans‐cis photoisomerization was observed. Quantum‐chemical DFT calculations predict π‐stacking of the SBQ units in the dyad that hinders trans‐cis photoisomerization but favors a photoactive excimer formation with following PCA. Calculations predict also π‐stacking of the BQ units in the cyclobutane that explains experimentally observed exciton absorption and excimer emission of the latter. The unique property of the cyclobutane excimer is its photoinertness: cyclobutane does not undergo photocycloreversion with ring opening. The photoinert excimer is observed for the first time. Possible reasons of difference between chemical properties of photoactive and photoinert excimers are discussed.

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Section: Methodsmentioning

confidence: 99%

Irreversible One‐Way [2+2] Photocycloaddition in Bis‐Styrylbenzo[f]quinoline Dyad: Photoactive and Photoinert Excimers in the Same System

et al. 2018

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“…To develop long wavelength reactive photoreactions that can be operated in a sensitive biological environment without adverse effect on cells and tissues, recent studies have focused on the development of chromophores that can absorb light in the visible region 38–43. In particular, our group has reported the activation of [4+4] cycloadditions under visible light irradiation using an electron‐rich anthracene moiety38 by substitution of a triazole group at the 9‐position.…”

Section: Introductionmentioning

confidence: 99%

Wavelength‐Dependent Stiffening of Hydrogel Matrices via Redshifted [2+2] Photocycloadditions

Kalayci

Frisch

Barner‐Kowollik

et al. 2020

Adv Funct Materials

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Hydrogels with on-demand tunable mechanical properties within sensitive biological environments are of critical importance for examining cellular responses to cell culture platforms. Herein, the first bio-orthogonal hydrogel that can be formed and subsequently tuned in its mechanical properties by simply switching different wavelengths of visible light (i.e., 455 and 420 nm) is reported. Specifically, both the initial hydrogelation and the tuning of the mechanical properties can be fully decoupled and selectively initiated by different colors of light. Sparing the need for any catalysts, the development of such a dual wavelength selective hydrogel for biological applications spans four levels: First, the development of the until today most redshifted photocycloaddition to allow for the selective initiation of only one photoreaction; second, the investigation of its wavelength-dependent ligation efficiency; third, translation of the ligation chemistry into a hydrogelator, and fourth, establishing a biocompatible hydrogel platform for applications in biomaterials engineering including detachment of fibroblasts from 2D culture areas or primary 3D culture of human mesenchymal stem cells. The introduced platform technology enables the fabrication of a hydrogel of predefined mechanical properties exclusively with visible light.

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“…Recently, we developed a pair of stirylpyrenes that react upon visible light irradiation. 33 We also demonstrated that pairs of cyanostilbene improve the stability and enzymatic durability of siRNA. Fluorescent labeling of DNA or RNA has been widely used in biology and biotechnology, but most fluorophores are quenched by nucleobases through electronhole transfer.…”

Section: Cationic and Photocrosslinking Pairsmentioning

confidence: 74%

Development of Pseudo Base-Pairs on d-Threoninol which Exhibit Various Functions

Kashida

Asanuma

2016

Bulletin of the Chemical Society of Japan

Self Cite

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. Currently his research interests are focused on the development of functional artificial oligonucleotides with acyclic scaffolds, such as, 1) photoregulation of DNA and RNA functions, 2) design of new XNAs, 3) new fluorescent probes for practical applications, 4) design of nucleic acid-based drugs, and 5) assembled functional molecules. AbstractThe authors have developed various kinds of pseudo base pairs using a D-threoninol scaffold. Although the chemical structures of the pseudo base pairs are much different from natural nucleobases, they can mimic supramolecular properties of natural base pairs. Moreover, modified DNA can possess various functions that cannot be achieved by natural nucleic acids, such as fluorescent switchability, photocrosslinking, insulating and emission color change. These pseudo base pairs can be used to prepare various functional nanomaterials. In the present account, we summarize our recent work on pseudo base pairs, focusing on molecular designs and functions.

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Visible‐Light‐Triggered Cross‐Linking of DNA Duplexes by Reversible [2+2] Photocycloaddition of Styrylpyrene

Cited by 73 publications

References 78 publications

Irreversible One‐Way [2+2] Photocycloaddition in Bis‐Styrylbenzo[f]quinoline Dyad: Photoactive and Photoinert Excimers in the Same System

Irreversible One‐Way [2+2] Photocycloaddition in Bis‐Styrylbenzo[f]quinoline Dyad: Photoactive and Photoinert Excimers in the Same System

Wavelength‐Dependent Stiffening of Hydrogel Matrices via Redshifted [2+2] Photocycloadditions

Development of Pseudo Base-Pairs on d-Threoninol which Exhibit Various Functions

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