Rapid Bioorthogonal Chemistry Turn-on through Enzymatic or Long Wavelength Photocatalytic Activation of Tetrazine Ligation
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- 作者：Han Zhang ; William S. Trout ; Shuang Liu ; Gabriel A. Andrade ; Devin A. Hudson ; Samuel L. Scinto ; Kevin T. Dicker ; Yi Li ; Nikifar Lazouski ; Joel Rosenthal ; Colin Thorpe ; Xinqiao Jia ; Joseph M. Fox
- 刊名：Journal of the American Chemical Society
- 出版年：2016
- 出版时间：May 11, 2016
- 年：2016
- 卷：138
- 期：18
- 页码：5978-5983
- 全文大小：495K
- 年卷期：0
- ISSN：1520-5126
文摘
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.