Photo-controllable bioorthogonal chemistry for spatiotemporal control of bio-targets in living systems

Li, Jinbo; Kong, Hao; Zhu, Chenghong; Zhang, Yan

doi:10.1039/c9sc06540g

Cited by 53 publications

(47 citation statements)

References 70 publications

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“…The higher wavelength allows for reduced phototoxicity and deeper penetration compared to conventional light sources, while the non-linear excitation enables 3D spatial control. [7][8][9][10] Several groups have developed systems combining photoreactions with fast bioconjugation reactions [11][12][13][14][15][16][17] in hydrogels using photocaged hydroxylamines, [18] thiols [19][20][21] or cyclooctynes [22] that undergo deprotection and bioconjugation upon irradi-ation. This photocaging approach has been much rarer for other bioconjugation reactions such as tetrazine Diels-Alder or Staudinger reaction due to the lack of suitable photocaging methods.…”

Section: Introductionmentioning

confidence: 99%

Post‐Assembly Photomasking of Potassium Acyltrifluoroborates (KATs) for Two‐Photon 3D Patterning of PEG‐Hydrogels

Song

Mazunin

et al. 2020

Helvetica Chimica Acta

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In memory of our colleague and friend Professor François Diederich Chemical ligation reactions of functional groups that can be masked with two-photon labile protecting groups provide a powerful technology for the three-dimensional patterning of molecules-including proteinsonto hydrogel scaffolds. In order to utilize readily prepared hydrogels constructed by the potassium acyltrifluoroborate (KAT)-hydroxylamine amide formation ligation for two-photon patterning, we have developed a unique post-polymerization protecting group strategy through the reaction of KATs and dithiols in water and deprotection by two-photon excitation. After precise 3D spatially confined light irradiation, the unprotected KATs undergo ligations with hydroxylamine-functionalized superfolder GFP and sulforhodamine B for the composition of three-dimensional patterns.

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Section: Introductionmentioning

confidence: 99%

Post‐Assembly Photomasking of Potassium Acyltrifluoroborates (KATs) for Two‐Photon 3D Patterning of PEG‐Hydrogels

Song

Mazunin

et al. 2020

Helvetica Chimica Acta

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“…Thermally stable and unreactive species can be converted to highly reactive intermediates by irradiation with light, allowing for tissue and cellular level localization of the chemical reaction. [10,18] This has the potential to reduce unwanted, and dose limiting, off-target side effects of a therapeutic intervention. While photochemistry can improve selectivity to a region of interest, the highly reactive species generated can still be affected by non-specific interactions with biomolecules, such as nucleophiles or reducing agents, leading to reduced molecular level specificity.…”

Section: Design Parameters For Bioorthogonal Polymer Photochemistrymentioning

confidence: 99%

“…The reaction proceeds via a biradical intermediate, and PQ is the first example of a photoinduced electron transfer mechanism being used for bioorthogonal conjugation chemistry. [ 10 ] This system is still in its infancy, and there are no reported values for the second‐order rate constant to compare to other systems. The approach has been recently exploited for the post‐polymerization modification of a conjugated polymer, generally regarded as a synthetic challenge owing to the stability of the conjugated π‐electron system.…”

Section: Opportunities For Bioorthogonal Photochemistry In Polymer Scmentioning

confidence: 99%

“…While both classes have demonstrated significant benefit in the fields of biological chemistry, the additional spatial and temporal control afforded by photochemical reactions offers unique opportunities in this space. [ 10 ] This review will introduce the contributions of photochemically driven bioorthogonal reactions and the opportunities they present to polymer science.…”

Section: Introductionmentioning

confidence: 99%

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Shining a Light on Bioorthogonal Photochemistry for Polymer Science

Boase

2020

Macromol. Rapid Commun.

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Bioorthogonal chemistry is revolutionizing the fields of biological chemistry and nanomedicine, providing tools to actively probe and perturb native biochemical processes. Photochemistry provides the opportunity to actively and non‐invasively control bioorthogonal reactions, providing sophisticated optochemical tools. Despite the opportunities in bioorthogonal photochemistry, there remain many significant challenges to the clinical translation of current research. This review aims to provide an overview of these challenges and highlight recent examples from the literature that are providing revolutionary solutions to overcoming these barriers. It will highlight new photochemical systems that can be triggered by near infrared light in aqueous solutions and have been demonstrated to function in complex biological systems, including in living animals. It will cover diverse classes of photochemical reactions including photopolymerization, uncaging, conjugation, and photoswitching. The discussion will detail how new approaches are being integrated into polymers or highlight unexploited opportunities. This review intends to showcase how the unique synergy of bioorthogonal photochemistry and polymer science provides vast opportunities in the fields of biomaterials, nanomedicine, and theranostics. This will hopefully provide inspiration to material scientists to integrate bioorthogonal photochemistry into new adaptable materials and ensure translation to solve clinical challenges.

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“…23,24 Important advances include photochemical reactions of tetrazoles [25][26][27] and cyclopropenone [28][29][30][31] derivatives to produce reactive nitrile imines and cyclooctyne derivatives, respectively. Other advances include photo-induced versions of the Staudinger 32 and CuAAC 33 reactions as well as cycloadditions involving azirines, 34 benzyne 35 , diarylsydnones, 36,37 quinones, [38][39][40][41] o-napthaquinone methides 42 , o-quinodimethanes 43,44 and trans-cycloheptene. 45 While several methods for initiating bioorthogonal chemistry using NIR light with two-photon excitation have been described, 29,46 prior to our work, the direct use of red/NIR light to induce bioorthogonal reactivity had not been described.…”

Section: Introductionmentioning

confidence: 99%

Enabling in vivo Photocatalytic Activation of Rapid Bioorthogonal Chemistry by Repurposing Si-Rhodamine Fluorophores as Cytocompatible Far-Red Photocatalysts

Wang¹,

Zhang²,

Zhang³

et al. 2021

Preprint

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<p><a></a>Chromophores that absorb in the tissue-penetrant far-red/near-infrared window have long served as photocatalysts for the generation of singlet oxygen for photodynamic therapy. However, the cytotoxicity and side-reactions associated with singlet oxygen sensitization have posed a problem for using long wavelength photocatalysis to initiate other types of chemical reactions in biological environments. Described here is the use of Si-Rhodamine (SiR) dyes as photocatalysts for inducing rapid bioorthogonal chemistry using 660 nm light through the oxidation of a dihydrotetrazine to a tetrazine in the presence of trans-cyclooctene dienophiles. SiRs have been commonly used as fluorophores for applications in biology, but have not previously been applied to catalyze chemical reactions. A dihydrotetrazine/tetrazine pair is described that displays high stability in both oxidation states. A series of SiR derivatives were evaluated, and the Janelia-SiR dyes were found to be especially effective in catalyzing rapid photooxidation at low catalyst loadings (typically 1 µM). A protein that was site-selectively modified by trans-cyclooctene was quantitively conjugated upon exposure to 660 nm light and a dihydrotetrazine. By contrast, a previously described methylene blue catalyst was found to rapidly degrade the protein. SiR-red light photocatalysis was used to crosslink hyaluronic acid derivatives that were functionalized by dihydrotetrazine and trans-cyclooctenes, enabling 3D culture of human prostate cancer cells. This photoinducible hydrogel formation could also be carried out in vivo in live mice through subcutaneous injection of a solution containing SiR photocatalyst and a Cy7-labeled hydrogel precursor, followed by brief in vivo irradiation with 660 nm light to produce a stable hydrogel material. This cytocompatible method for using red light photocatalysis to activate bioorthogonal chemistry is anticipated to find broad applications where spatiotemporal control is needed in the in vivo environment. <br></p>

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Photo-controllable bioorthogonal chemistry for spatiotemporal control of bio-targets in living systems

Cited by 53 publications

References 70 publications

Post‐Assembly Photomasking of Potassium Acyltrifluoroborates (KATs) for Two‐Photon 3D Patterning of PEG‐Hydrogels

Post‐Assembly Photomasking of Potassium Acyltrifluoroborates (KATs) for Two‐Photon 3D Patterning of PEG‐Hydrogels

Shining a Light on Bioorthogonal Photochemistry for Polymer Science

Enabling in vivo Photocatalytic Activation of Rapid Bioorthogonal Chemistry by Repurposing Si-Rhodamine Fluorophores as Cytocompatible Far-Red Photocatalysts

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