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

2021 ◽  
Author(s):  
Chuanqi Wang ◽  
He Zhang ◽  
Tao Zhang ◽  
Xiaoyu Zou ◽  
Hui Wang ◽  
...  
Keyword(s):  
Bioorthogonal Chemistry

7 Tetrazine-Based Cycloadditions in Click Chemistry

2022 ◽  
Author(s):  
W. Kuba ◽  
M. Wilkovitsch ◽  
J. C. T. Carlson ◽  
H. Mikula
Keyword(s):  
Reaction Mechanisms ◽  
Chemical Biology ◽  
Bond Cleavage ◽  
Therapeutic Strategies ◽  
Complex Environments ◽  
Bioorthogonal Chemistry ◽  
Bioorthogonal Reaction ◽  
Low Concentrations ◽  
Time Critical

AbstractThe spontaneous cycloaddition of tetrazines with a number of different dienophiles has become a powerful tool in chemical biology, in particular for the biocompatible conjugation and modification of (bio)molecules. The exceptional reaction kinetics made these bioorthogonal ligations the methods of choice for time-critical processes at very low concentrations, facilitating controlled molecular transformations in complex environments and even in vivo. The emerging concept of bond-cleavage reactions triggered by tetrazine-based cycloadditions enabled the design of diagnostic and therapeutic strategies. The tetrazine-triggered activation of prodrugs represents the first bioorthogonal reaction performed in humans, marking the beginning of the era of clinical translation of bioorthogonal chemistry. This chapter provides an overview of the synthesis and reactivity of tetrazines, their cycloadditions with various dienophiles, and transformations triggered by these reactions, focusing on reaction mechanisms, kinetics and efficiency, and selected applications.

Near-Infrared Light Dual-Promoted Heterogeneous Copper Nanocatalyst for Highly Efficient Bioorthogonal Chemistry in Vivo

ACS Nano ◽  
2020 ◽  
Vol 14 (4) ◽  
pp. 4178-4187 ◽  
Author(s):  
Yawen You ◽  
Fangfang Cao ◽  
Yajie Zhao ◽  
Qingqing Deng ◽  
Yanjuan Sang ◽  
...  
Keyword(s):  
Near Infrared ◽  
Infrared Light ◽  
Bioorthogonal Chemistry ◽  
Near Infrared Light ◽  
Highly Efficient

scholarly journals Targeted and modular architectural polymers employing bioorthogonal chemistry for quantitative therapeutic delivery

2020 ◽  
Vol 11 (12) ◽  
pp. 3268-3280 ◽  
Author(s):  
Gayathri R. Ediriweera ◽  
Joshua D. Simpson ◽  
Adrian V. Fuchs ◽  
Taracad K. Venkatachalam ◽  
Matthias Van De Walle ◽  
...  
Keyword(s):  
Side Effects ◽  
Cancer Therapy ◽  
Drug Release ◽  
Standard Of Care ◽  
Release Profile ◽  
Specific Drug ◽  
Bioorthogonal Chemistry ◽  
Drug Release Profile ◽  
Therapeutic Delivery

There remain several key challenges to existing therapeutic systems for cancer therapy, such as quantitatively determining the true, tissue-specific drug release profile in vivo, as well as reducing side-effects for an increased standard of care.

Preparation of tetrazine-containing [2 + 1] complexes of 99mTc and in vivo targeting using bioorthogonal inverse electron demand Diels–Alder chemistry

2017 ◽  
Vol 46 (42) ◽  
pp. 14691-14699 ◽  
Author(s):  
Abdolreza Yazdani ◽  
Nancy Janzen ◽  
Shannon Czorny ◽  
Robert G. Ungard ◽  
Tanya Miladinovic ◽  
...  
Keyword(s):  
Bone Turnover ◽  
Diels Alder ◽  
Bone Lesions ◽  
Targeted Imaging ◽  
Bioorthogonal Chemistry ◽  
High Bone Turnover ◽  
Inverse Electron Demand ◽  
High Bone ◽  
Electron Demand

A new 99mTc-labelled tetrazine for targeted imaging using bioorthogonal chemistry was developed and evaluated in vivo using a trans-cyclooctene derived bisphosphonate targeting regions of high bone turnover and bone lesions.

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

2021 ◽  
Author(s):  
Chuanqi Wang ◽  
He Zhang ◽  
Tao Zhang ◽  
Xiaoyu Zou ◽  
Hui Wang ◽  
...  
Keyword(s):  
Singlet Oxygen ◽  
Chemical Reactions ◽  
Near Infrared ◽  
Red Light ◽  
3D Culture ◽  
Side Reactions ◽  
Bioorthogonal Chemistry ◽  
Long Wavelength ◽  
Spatiotemporal Control

<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>

Bioorthogonal chemistry in metal clusters: a general strategy for the construction of multifunctional probe for bioimaging in living cells and in vivo

2021 ◽  
Author(s):  
Xueqian Chen ◽  
Yong Zhang ◽  
Qing Yuan ◽  
Mingrui Li ◽  
Yongning Bian ◽  
...  
Keyword(s):  
Biomedical Imaging ◽  
Metal Clusters ◽  
Living Cells ◽  
General Strategy ◽  
Bioorthogonal Chemistry ◽  
Broad Application ◽  
Multiple Characteristics ◽  
Application Prospects

Multifunctional bioimaging probes based on metal clusters have multiple characteristics of metal clusters and functional conjugates, and their development has broad application prospects in the fields of biomedical imaging and...

scholarly journals Reactive polymer enables efficient in vivo bioorthogonal chemistry

2012 ◽  
Vol 109 (13) ◽  
pp. 4762-4767 ◽  
Author(s):  
N. K. Devaraj ◽  
G. M. Thurber ◽  
E. J. Keliher ◽  
B. Marinelli ◽  
R. Weissleder
Keyword(s):  
Bioorthogonal Chemistry ◽  
Reactive Polymer

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

2021 ◽  
Author(s):  
Chuanqi Wang ◽  
He Zhang ◽  
Tao Zhang ◽  
Xiaoyu Zou ◽  
Hui Wang ◽  
...  
Keyword(s):  
Singlet Oxygen ◽  
Chemical Reactions ◽  
Near Infrared ◽  
Red Light ◽  
3D Culture ◽  
Side Reactions ◽  
Bioorthogonal Chemistry ◽  
Long Wavelength ◽  
Spatiotemporal Control

<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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