Shining a Light on Bioorthogonal Photochemistry for Polymer Science

Boase, Nathan R. B.

doi:10.1002/marc.202000305

Cited by 9 publications

(12 citation statements)

References 199 publications

(271 reference statements)

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“…Many photoactivatable polymeric materials, micelles, and vesicles have been developed for drug/species delivery in recent decades. ,,− Photocleavable polymer nanostructures are particularly interesting platforms for targeted drug delivery . Several release mechanisms are available: these systems can serve as photoresponsive/degradable nanocarriers for drug delivery, polymeric films can facilitate photochemical species detachment or patterning, and hydrogels can alter the properties of biomaterials and affect the microenvironment. , …”

Section: Photoactivatable Polymers Micelles and Vesiclesmentioning

confidence: 99%

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

et al. 2020

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Photoactivatable (alternatively, photoremovable, photoreleasable, or photocleavable) protecting groups (PPGs), also known as caged or photocaged compounds, are used to enable non-invasive spatiotemporal photochemical control over the release of species of interest. Recent years have seen the development of PPGs activatable by biologically and chemically benign visible and near-infrared (NIR) light. These long-wavelength-absorbing moieties expand the applicability of this powerful method and its accessibility to non-specialist users. This review comprehensively covers organic and transition metal-containing photoactivatable compounds (complexes) that absorb in the visible- and NIR-range to release various leaving groups and gasotransmitters (carbon monoxide, nitric oxide, and hydrogen sulfide). The text also covers visible- and NIR-light-induced photosensitized release using molecular sensitizers, quantum dots, and upconversion and second-harmonic nanoparticles, as well as release via photodynamic (photooxygenation by singlet oxygen) and photothermal effects. Release from photoactivatable polymers, micelles, vesicles, and photoswitches, along with the related emerging field of photopharmacology, is discussed at the end of the review.

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Section: Photoactivatable Polymers Micelles and Vesiclesmentioning

confidence: 99%

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

et al. 2020

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“…However, the very small focal volumes of two-photon techniques can limit their biomedical applications, and the development of chemical methods that directly utilize far-red/NIR light would be desirable. 73 Previously, our group described a method for catalytic turn-on of the tetrazine ligation, where rapid bioorthogonal reactivity can be induced by controllable, catalytic stimuli. 47 Either visible light and a photosensitizer or very low loadings of horseradish peroxidase can be used to catalyze the oxidation of a dihydrotetrazine to a tetrazine with oxygen as the terminal oxidant (Figure 1).…”

Section: ■ Introductionmentioning

confidence: 99%

“…For example, LNCaP prostate cancer cells are poorly tumorigenic and generally require other types of cells or Matrigel to support tumor model generation. , Two-photon methods provide an approach for hydrogel patterning with high spatial resolution using far-red/NIR light. However, the very small focal volumes of two-photon techniques can limit their biomedical applications, and the development of chemical methods that directly utilize far-red/NIR light would be desirable …”

Section: Introductionmentioning

confidence: 99%

Enabling In Vivo Photocatalytic Activation of Rapid Bioorthogonal Chemistry by Repurposing Silicon-Rhodamine Fluorophores as Cytocompatible Far-Red Photocatalysts

Wang

Zhang

et al. 2021

J. Am. Chem. Soc.

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Chromophores that absorb in the tissue-penetrant far-red/near-infrared window have long served as photocatalysts to generate 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. Herein, silicon-Rhodamine compounds (SiRs) are described 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 bioimaging but have not been applied to catalyze chemical reactions. A series of SiR derivatives were evaluated, and the Janelia Fluor-SiR dyes were found to be especially effective in catalyzing photooxidation (typically 3%). A dihydrotetrazine/tetrazine pair is described that displays high stability in both oxidation states. A protein that was site-selectively modified by trans-cyclooctene was quantitatively 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 cross-link hyaluronic acid derivatives functionalized by dihydrotetrazine and trans-cyclooctenes, enabling 3D culture of human prostate cancer cells. Photoinducible hydrogel formation could also be carried out in live mice through subcutaneous injection of a Cy7-labeled hydrogel precursor solution, followed by brief irradiation to produce a stable hydrogel. This cytocompatible method for using red light photocatalysis to activate bioorthogonal chemistry is anticipated to find broad applications where spatiotemporal control is needed in biological environments.

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“…The renewal of photochemistry based on lower energy light sources and more biocompatible compounds opens huge opportunities for biomedical applications [48][49][50][51][52] , including for antibacterial applications as detailed below.…”

Section: Introductionmentioning

confidence: 99%