Visible Light‐Responsive Dynamic Biomaterials: Going Deeper and Triggering More

Rapp, Teresa L.; DeForest, Cole A.

doi:10.1002/adhm.201901553

Cited by 93 publications

(89 citation statements)

References 107 publications

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“…178.80 (11) C9 C10 C11 C12 0.30 (19) F19 C6 C5 C4 178.18 (11) C14 C9 C10 C11 0.38 (18) N8 N7 C1 C2 -172.67 (10) C14 C13 C12 C11 -0.35 (19) N8 N7 C1 C6 6.46(18) C1 C2 C3 C4 -0.2 (2) N8 C9 C14 C13 179.08 (9) C1 C6 C5 C4 -1. 10(19) N8 C9 C14 B15 -2.43 (17) C2 C1 C6 F19…”

Section: A B C D Angle/˚ a B C D Angle/˚ F18 C2 C3 C4unclassified

“…-0.72 (16) C6 C1 C2 C3 -0.96 (18) N7 C1 C2 C3 178.30 (11) C6 C5 C4 C3 -0.2 (2) N7 C1 C6 F19 3.22(19) C10 C9 C14 C13…”

Section: A B C D Angle/˚ a B C D Angle/˚ F18 C2 C3 C4mentioning

confidence: 99%

“…177.51 (11) C9 N8 N7 C1 178.75 (9) C13 C14 B15 O17 -3.07 (17) C9 C14 C13 C12 0.98 (17) C13 C14 B15 O16…”

Section: A B C D Angle/˚ a B C D Angle/˚ F18 C2 C3 C4mentioning

confidence: 99%

“…175.15 (11) C9 C14 B15 O17 178.46 (11) C13 C12 C11 C10 -0.31 (19) C9 C14 B15 O16 -3.32 (19) Table 6 Hydrogen Bonds for cx1670. (14) 171.9…”

Section: A B C D Angle/˚ a B C D Angle/˚ F18 C2 C3 C4mentioning

confidence: 99%

“…Next, we investigated the generality of photoswitchable binding to boronic acid 3 with different diols. Using 3, we observed Krel values between 6 and 20 for a variety of diols, including a 1,3-diol (8), simple cyclic diols (9-10), nitro-catechol (11), and a variety of complex and biologically relevant diols, including glucose (14), adenosine (15), and the chemotherapeutic drug capecitabine (16) (Figure 9). Phenylboronic acid-containing polycarbonates have previously been used for the pH-dependent release of diols including capecitabine.…”

Section: Photoswitching Modulates Boronic Ester Equilibria With Diffementioning

confidence: 99%

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Using Visible Light to Tune Boronic Acid–ester Equilibria

Accardo

McClure

Mosquera

et al. 2020

Preprint

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We report a series of azobenzene boronic acids that reversibly control the extent of diol binding via photochemical isomerization. When the boronic acid is ortho to the azo group, the thermodynamically-favored E isomer binds weakly with diols to form boronic esters. Isomerization of the E azobenzene to its Z isomer enhances diol binding, and the magnitude of this enhancement is affected by the azobenzene structure. 2,6-Dimethoxy azobenzene boronic acids show over 20-fold enhancement in binding upon E–Z isomerization, which can be triggered with red light. Competition experiments and computational studies suggest that the changes in binding affinity originate from stabilization of the E boronic acids and destabilization of the E boronic esters. We demonstrate a correlation between diol binding and photostationary state: different wavelengths of irradiation yield different quantities of bound diol. Higher binding constants for the Z isomer relative to the E isomer was observed with all diols investigated, including cyclic diols, nitrocatechol, biologically relevant compounds, and polyols. This photoswitch was employed to “catch and release” a fluorescently tagged diol in buffered water. By tethering this photoswitch to a poly(ethylene glycol) star polymer, we can tune the stiffness of covalent adaptable hydrogels using different wavelengths of visible light. This work establishes photoswitchable equilibria as a tool for the reversible ligation of molecular and macromolecular species.

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Section: A B C D Angle/˚ a B C D Angle/˚ F18 C2 C3 C4unclassified

“…-0.72 (16) C6 C1 C2 C3 -0.96 (18) N7 C1 C2 C3 178.30 (11) C6 C5 C4 C3 -0.2 (2) N7 C1 C6 F19 3.22(19) C10 C9 C14 C13…”

Section: A B C D Angle/˚ a B C D Angle/˚ F18 C2 C3 C4mentioning

confidence: 99%

“…177.51 (11) C9 N8 N7 C1 178.75 (9) C13 C14 B15 O17 -3.07 (17) C9 C14 C13 C12 0.98 (17) C13 C14 B15 O16…”

Section: A B C D Angle/˚ a B C D Angle/˚ F18 C2 C3 C4mentioning

confidence: 99%

“…175.15 (11) C9 C14 B15 O17 178.46 (11) C13 C12 C11 C10 -0.31 (19) C9 C14 B15 O16 -3.32 (19) Table 6 Hydrogen Bonds for cx1670. (14) 171.9…”

Section: A B C D Angle/˚ a B C D Angle/˚ F18 C2 C3 C4mentioning

confidence: 99%

Section: Photoswitching Modulates Boronic Ester Equilibria With Diffementioning

confidence: 99%

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Using Visible Light to Tune Boronic Acid–ester Equilibria

Accardo

McClure

Mosquera

et al. 2020

Preprint

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Stimuli‐Responsive Nanocomposite Hydrogels for Biomedical Applications

Lavrador

Esteves

Gaspar

et al. 2020

Adv Funct Materials

308

201

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The complex tissue‐specific physiology that is orchestrated from the nano‐ to the macroscale, in conjugation with the dynamic biophysical/biochemical stimuli underlying biological processes, has inspired the design of sophisticated hydrogels and nanoparticle systems exhibiting stimuli‐responsive features. Recently, hydrogels and nanoparticles have been combined in advanced nanocomposite hybrid platforms expanding their range of biomedical applications. The ease and flexibility of attaining modular nanocomposite hydrogel constructs by selecting different classes of nanomaterials/hydrogels, or tuning nanoparticle‐hydrogel physicochemical interactions widely expands the range of attainable properties to levels beyond those of traditional platforms. This review showcases the intrinsic ability of hybrid constructs to react to external or internal/physiological stimuli in the scope of developing sophisticated and intelligent systems with application‐oriented features. Moreover, nanoparticle‐hydrogel platforms are overviewed in the context of encoding stimuli‐responsive cascades that recapitulate signaling interplays present in native biosystems. Collectively, recent breakthroughs in the design of stimuli‐responsive nanocomposite hydrogels improve their potential for operating as advanced systems in different biomedical applications that benefit from tailored single or multi‐responsiveness.

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Photon Upconversion Hydrogels for 3D Optogenetics

Meir

Hirschhorn

Kim

et al. 2021

Adv Funct Materials

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The ability to optically induce biological responses in 3D has been dwarfed by the physical limitations of visible light penetration to trigger photochemical processes. However, many biological systems are relatively transparent to low‐energy light, which does not provide sufficient energy to induce photochemistry in 3D. To overcome this challenge, hydrogels that are capable of converting red or near‐IR (NIR) light into blue light within the cell‐laden 3D scaffolds are developed. The upconverted light can then excite optically active proteins in cells to trigger a photochemical response. The hydrogels operate by triplet–triplet annihilation upconversion. As proof‐of‐principle, it is found that the hydrogels trigger an optogenetic response by red/NIR irradiation of HeLa cells that have been engineered to express the blue‐light sensitive protein Cry2olig. While it is remarkable to photoinduce the clustering of Cry2olig with blanket NIR irradiation in 3D, it is also demonstrated how the hydrogels trigger clustering within a single cell with great specificity and spatiotemporal control. In principle, these hydrogels may allow for photochemical control of cell function within 3D scaffolds, which can lead to a wealth of fundamental studies and biochemical applications.

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Visible Light‐Responsive Dynamic Biomaterials: Going Deeper and Triggering More

Cited by 93 publications

References 107 publications

Using Visible Light to Tune Boronic Acid–ester Equilibria

Using Visible Light to Tune Boronic Acid–ester Equilibria

Stimuli‐Responsive Nanocomposite Hydrogels for Biomedical Applications

Photon Upconversion Hydrogels for 3D Optogenetics

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