4 results on '"William S. Trout"'
Search Results
2. Enabling In Vivo Photocatalytic Activation of Rapid Bioorthogonal Chemistry by Repurposing Silicon-Rhodamine Fluorophores as Cytocompatible Far-Red Photocatalysts
- Author
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Luke D. Lavis, Joseph M. Fox, William S. Trout, He Zhang, Julia E. Rosenberger, Xiaoyu Zou, Jonathan B. Grimm, Raghu Vannam, Hui Wang, Chuanqi Wang, Zibo Li, Xinqiao Jia, Tao Zhang, and Colin Thorpe
- Subjects
Silicon ,Infrared Rays ,medicine.medical_treatment ,Tetrazoles ,Photodynamic therapy ,Conjugated system ,Photochemistry ,Biochemistry ,Article ,Catalysis ,Rhodamine ,Cyclooctanes ,Mice ,Tetrazine ,chemistry.chemical_compound ,Colloid and Surface Chemistry ,Tumor Cells, Cultured ,medicine ,Animals ,Humans ,Fluorescent Dyes ,Molecular Structure ,Rhodamines ,Singlet oxygen ,General Chemistry ,Photochemical Processes ,chemistry ,Photocatalysis ,Bioorthogonal chemistry ,Methylene blue - Abstract
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.
- Published
- 2021
3. Enabling in vivo Photocatalytic Activation of Rapid Bioorthogonal Chemistry by Repurposing Si-Rhodamine Fluorophores as Cytocompatible Far-Red Photocatalysts
- Author
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Hui Wang, William S. Trout, Zibo Li, He Zhang, Xinqiao Jia, Joseph M. Fox, Xiaoyu Zou, Raghu Vannam, Julia E. Rosenberger, Tao Zhang, and Chuanqi Wang
- Subjects
Rhodamine ,chemistry.chemical_compound ,Tetrazine ,Chemistry ,Singlet oxygen ,Photocatalysis ,Click chemistry ,Bioorthogonal chemistry ,Conjugated system ,Photochemistry ,Methylene blue - Abstract
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.
- Published
- 2021
4. Rapid Bioorthogonal Chemistry Turn-on through Enzymatic or Long Wavelength Photocatalytic Activation of Tetrazine Ligation
- Author
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Samuel L. Scinto, Joseph M. Fox, Han Zhang, Nikifar Lazouski, Colin Thorpe, Shuang Liu, Xinqiao Jia, Gabriel A. Andrade, Joel Rosenthal, Yi Li, William S. Trout, Devin A. Hudson, and Kevin T. Dicker
- Subjects
Light ,Conjugated system ,010402 general chemistry ,Photochemistry ,01 natural sciences ,Biochemistry ,Horseradish peroxidase ,Article ,Catalysis ,Heterocyclic Compounds, 1-Ring ,Tetrazine ,chemistry.chemical_compound ,Colloid and Surface Chemistry ,Adhesives ,Reactivity (chemistry) ,Horseradish Peroxidase ,biology ,010405 organic chemistry ,General Chemistry ,Photochemical Processes ,Small molecule ,Enzymes ,0104 chemical sciences ,Methylene Blue ,Kinetics ,chemistry ,Covalent bond ,biology.protein ,Photocatalysis ,Spectrophotometry, Ultraviolet ,Bioorthogonal chemistry ,Oxidation-Reduction - Abstract
Rapid bioorthogonal reactivity can be induced by controllable, catalytic stimuli using air as the oxidant. Methylene blue (4 μM) irradiated with red light (660 nm) catalyzes the rapid oxidation of a dihydrotetrazine to a tetrazine thereby turning on reactivity toward trans-cyclooctene dienophiles. Alternately, the aerial oxidation of dihydrotetrazines can be efficiently catalyzed by nanomolar levels of horseradish peroxidase under peroxide-free conditions. Selection of dihydrotetrazine/tetrazine pairs of sufficient kinetic stability in aerobic aqueous solutions is key to the success of these approaches. In this work, polymer fibers carrying latent dihydrotetrazines were catalytically activated and covalently modified by trans-cyclooctene conjugates of small molecules, peptides, and proteins. In addition to visualization with fluorophores, fibers conjugated to a cell adhesive peptide exhibited a dramatically increased ability to mediate contact guidance of cells.
- Published
- 2016
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