8-Pyrenylvinyl Adenine Controls Reversible Duplex Formation between Serinol Nucleic Acid and RNA by [2 + 2] Photocycloaddition

Murayama, Keiji; Yamano, Yuuhei; Asanuma, Hiroyuki

doi:10.1021/jacs.9b03267

Cited by 38 publications

(40 citation statements)

References 51 publications

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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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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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“…Amongst photochemical reactions, [2+2] cycloadditions have key advantages such as λ-orthogonal reversibility, wavelengthdependent reactivity and lack of any additives [30][31][32][33][34][35] . Combining these advantages with the ease of functionalizing photoreactive groups, several chromophores with redshifted reactivity (up to 470 nm) such as styrylpyrene 30,32 and acrylamidylpyrene 36 have been introduced by our group and their applications in soft matter design are being actively exploited 30,36,37 .…”

mentioning

confidence: 99%

Green light triggered [2+2] cycloaddition of halochromic styrylquinoxaline—controlling photoreactivity by pH

et al. 2020

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Photochemical reactions are a powerful tool in (bio)materials design due to the spatial and temporal control light can provide. To extend their applications in biological setting, the use of low-energy, long wavelength light with high penetration propertiesis required. Further regulation of the photochemical process by additional stimuli, such as pH, will open the door for construction of highly regulated systems in nanotechnology-and biology-driven applications. Here we report the green light induced [2+2] cycloaddition of a halochromic system based on a styrylquinoxaline moiety, which allows for its photo-reactivity to be switched on and off by adjusting the pH of the system. Critically, the [2+2] photocycloaddition can be activated by green light (λ up to 550 nm), which is the longest wavelength employed to date in catalyst-free photocycloadditions in solution. Importantly, the pH-dependence of the photoreactivity was mapped by constant photon action plots. The action plots further indicate that the choice of solvent strongly impacts the system's photo-reactivity. Indeed, higher conversion and longer activation wavelengths were observed in water compared to acetonitrile under identical reaction conditions. The wider applicability of the system was demonstrated in the crosslinking of an 8-arm PEG to form hydrogels (ca. 1 cm in thickness) with a range of mechanical properties and pH responsiveness, highlighting the potential of the system in materials science.

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“…In spite of the many advances achieved in the past decades, high controllability, high efficiency, and eligibility for physiological application still remain significant problems. This has inspired various groups to explore novel photoregulating approaches in the hope of mimicking the natural molecular motors observed in living organisms . Because most photoswitching molecules are hydrophobic, a main challenge for photoregulating the conformation and function of biomolecules under physiological conditions is the design of water‐soluble photoregulators …”

Section: Introductionmentioning

confidence: 99%

Sulfonated Pyrene as a Photoregulator for Single‐Stranded DNA Looping

Miyamoto

Tojo

et al. 2020

Chemistry A European J

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Controlling the conformationa nd functiono fb iomolecules through photoregulators holds great promise as a spatiotemporally controllable tool for disease control.I na ddition, introducing photoregulators into biomoleculesh as also found applicationsi nc onstructings martn anomaterials. In spite of the astonishing advances that have been made in the past few years, realizing highly controllable and efficient regulation over the conformation and functiono fb iomolecules under physiological conditionsi ss till challenging. Herein,s ulfonated pyrene SPy was synthesized and used as ap hotoregulator to control the looping of single-stranded DNAs (ssDNAs) in aqueous solution.Due to its water solubility, SPy merits use in the study of biomolecules in aqueous solution.T he looping of the doubly SPy-modified ssDNAs is stimulated by irradiation and regulated by SPy.P hotoionization generatest he radicalc ation of SPy (SPyC + ). The association of SPyC + + with its neutralc ounterpart, SPy,g ives rise to the dimer radicalc ation of SPy (SPy 2 C + + ). During the association process, the stabilization energy released to form SPy 2 C + + provides ad riving force for the looping of ssDNAs. Conversely,t he formed loop conformationsw ere trapped by the formation of SPy 2 C + + ,a nd this allowed the looping dynamics to be investigated. The results reported herein suggest potential of SPy as ap hotoregulator for controlling the conformationa nd function of biomolecules under physiological conditions.[a] J.[a] Immediately formed SPy 2 C + + component. P static = DOD t = 10 ns /DOD max .

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8-Pyrenylvinyl Adenine Controls Reversible Duplex Formation between Serinol Nucleic Acid and RNA by [2 + 2] Photocycloaddition

Cited by 38 publications

References 51 publications

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

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

Green light triggered [2+2] cycloaddition of halochromic styrylquinoxaline—controlling photoreactivity by pH

Sulfonated Pyrene as a Photoregulator for Single‐Stranded DNA Looping

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