Dual-Bioorthogonal Molecular Tool: "Click-to-Release" and "Double-Click" Reactivity on Small Molecules and Material Surfaces

Bioconjugate Chemistry
Wilson LuoMark S Workentin

Abstract

The development of reactive moieties that enable molecular control of bond-forming and bond-breaking reactions within complex media is highly important in materials and biomaterials research as it provides opportunities to carefully manipulate small molecules and material surfaces in a reliable manner. Despite recent advances in the realization of new ligation strategies and "click-and-release" systems, there has been little development of multifunctional moieties that feature a broad range of chemical capabilities. To address this challenge, we designed a molecular tool that can utilize four well-defined bioorthogonal chemistries interchangeably for the attachment, replacement, and release of molecules within a system: the Staudinger-Bertozzi ligation (SBL), perfluoroaryl azide Staudinger reaction (PFAA-SR), strain-promoted alkyne-azide cycloaddition (SPAAC), and strain-promoted alkyne-nitrone cycloaddition (SPANC). We demonstrate "click-to-release" and "double-click" reactivity on small molecules and gold nanoparticles (AuNPs) as a model material substrate. As a proof of concept for material derivatization, we employed 5 nm AuNPs-functionalized with a Rhodamine B derivative and biotin through the double-click strategy-and sho...Continue Reading

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Citations

Aug 21, 2020·ChemistryOpen·Youshan Li, Hua Fu
Oct 24, 2020·Chemical Communications : Chem Comm·Norikazu TerashimaSuguru Yoshida
Nov 6, 2020·Current Opinion in Chemical Biology·Mike L W J SmeenkKimberly M Bonger
Jun 9, 2021·Chemical Reviews·Tyler K HeissJennifer A Prescher
Sep 6, 2019·Organic Letters·Jannick Meinecke, Ulrich Koert
May 2, 2020·Chemical Reviews·Christin BednarekStefan Bräse
Jan 11, 2020·Langmuir : the ACS Journal of Surfaces and Colloids·Wilson LuoMark S Workentin

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