Journal
MOLECULAR PHARMACEUTICS
Volume 10, Issue 1, Pages 43-50Publisher
AMER CHEMICAL SOC
DOI: 10.1021/mp3002528
Keywords
bionanoparticles; Cowpea mosaic virus; strain-promoted alkyne-azide cycloaddition (SPAAC) reaction; click chemistry; fluorogenic dye; bioconjugation
Funding
- NSF [CHE-0748690]
- Alfred P. Sloan Scholarship
- Camille Dreyfus Teacher Scholar Award
- NIH PREP program
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Chemical addressability of viral particles has played a pivotal role in adapting these biogenic macromolecules for various applications ranging from medicine to inorganic catalysis. Cowpea mosaic virus possesses multiple features that are advantageous for the next generation of virus-based nanotechnology: consistent multimeric assemblies dictated by its genetic code, facile large scale production, and lack of observable toxicity in humans. Herein, the chemistry of the viral particles is extended with the use of Cu-free strain-promoted azide-alkyne cycloaddition reaction, or SPAAC reaction. The elimination of Cu, its cocatalyst and reducing agent, simplifies the reaction scheme to a more straightforward approach, which can be directly applied to living systems. As a proof of concept, the viral particles modified with the azadibenzylcyclooctyne functional groups are utilized to trigger and amplify a weak fluorescent signal (azidocoumarin) in live cell cultures to visualize the non-natural sugars. Future adaptations of this platform may be developed to enhance biosensing applications.
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