Spatial and temporal control of chemical processes

Aubert, Sidonie; Bézagu, Marine; Spivey, Alan C.; Arseniyadis, Stellios

doi:10.1038/s41570-019-0139-6

Cited by 78 publications

(81 citation statements)

References 135 publications

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“…However, in the field of soft matter materials, the majority of studies on photocycloadditions are carried out on stilbene,25,26 coumarin,27–29 thymine,30,31 and cinnamic acid32 derivatives, which require activation by short wavelength UV light (note that we are referring exclusively to the bond forming photocycloaddition of coumarin, in the context of bond cleavage short wavelength blue light has been successfully used for coumarin‐based photocages) 33. To overcome limitations of applicability in biology‐related systems from UV light exposure,34 and broaden the synthetic toolbox of orthogonally addressable photoligation reactions,21,35,36 the development of redshifted photocycloadditions is key 37…”

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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“…ight-gated reactions are important tools in soft matter materials design and the biological sciences due to their unique spatial and temporal control over the chemical processes [1][2][3][4][5] . Critically, by switching the wavelength of irradiation in photo-regulated processes, it is possible to trigger specific reactions in a sequence as well as establish true wavelength orthogonality [6][7][8][9][10][11][12][13][14] .…”

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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“…The tedious purification and low yields limit scale-up processes. It is necessary to develop highly efficient and readily operable organic reactions to quickly assemble the conjugates, such as azide-alkyne clickable reactions, sulfur fluoride exchange (SuFEx) [ 76 ] and other robust reactions [ 77 ]. The bioavailability of fluorophores should be considered as they could bring unexpected effects to drugs’ function in non-breakable versions and also cause side effects after release in breakable versions.…”

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Recent advances in construction of small molecule-based fluorophore-drug conjugates

Lang

Yuan

Zhu

et al. 2020

Journal of Pharmaceutical Analysis

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As a powerful tool to advance drug discovery, molecular imaging may provide new insights into the process of drug effect and therapy at cellular and molecular levels. When compared with other detection methods, fluorescence-based strategies are highly attractive and can be used to illuminate pathways of drugs’ transport, with multi-color capacity, high specificity and good sensitivity. The conjugates of fluorescent molecules and therapeutic agents create exciting avenues for real-time monitoring of drug delivery and distribution, both in vitro and in vivo. In this short review, we discuss recent developments of small molecule-based fluorophore-drug conjugates, including non-cleavable and cleavable ones, that are capable of visualizing drug delivery.

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Spatial and temporal control of chemical processes

Cited by 78 publications

References 135 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

Recent advances in construction of small molecule-based fluorophore-drug conjugates

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