Surface Modification of Magnetic Nanoparticle via Cu(I)-Catalyzed Alkyne-azide [2 + 3] Cycloaddition

Lin, Po‐Chiao; Ueng, Shau‐Hua; Yu, Sheng-Chieh; Jan, Mi-Dan; Adak, Asok; Yu, Ching‐Ching; Lin, Chun‐Cheng

doi:10.1021/ol070588f

Cited by 105 publications

(54 citation statements)

References 33 publications

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“…Similarly low efficiency was reported for CuAAC reactions on other alkynyl-presenting surfaces,30,31,44 and was attributed to steric hindrance 30. During optimization of the reaction conditions, we found that O 2 substantially decreased the yields, likely due to the facile oxidation of Cu + to the catalytically inactive Cu 2+ that may also promote the homocoupling of the adjacent alkynes 45.…”

Section: Resultssupporting

confidence: 77%

Biofunctionalization on Alkylated Silicon Substrate Surfaces via “Click” Chemistry

et al. 2010

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Biofunctionalization of silicon substrates is important to the development of silicon-based biosensors and devices. Compared to conventional organosiloxane films on silicon oxide intermediate layers, organic monolayers directly bound to the non-oxidized silicon substrates via Si-C bonds enhance the sensitivity of detection and the stability against hydrolytic cleavage. Such monolayers presenting a high density of terminal alkynyl groups for bioconjugation via coppercatalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC, a "click" reaction) were reported. However, yields of the CuAAC reactions on these monolayer platforms were low. Also, the nonspecific adsorption of proteins on the resultant surfaces remained a major obstacle for many potential biological applications. Herein, we report a new type of "clickable" monolayers grown by selective, photo-activated surface hydrosilylation of α,ω-alkenynes, where the alkynyl terminal is protected with a trimethylgermanyl (TMG) group, on hydrogen-terminated silicon substrates. The TMG groups on the film are readily removed in aqueous solutions in the presence of Cu(I). Significantly, the degermanylation and the subsequent CuAAC reaction with various azides could be combined into a single step in good yields. Thus, oligo(ethylene glycol) (OEG) with an azidotag was attached to the TMG-alkyne surfaces, leading to OEG-terminated surfaces that reduced the non-specific adsorption of protein (fibrinogen) by >98%. The CuAAC reaction could be performed in microarray format to generate arrays of mannose and biotin with varied densities on the protein-resistant OEG background. We also demonstrated that the monolayer platform could be functionalized with mannose for highly specific capturing of living targets (Escherichia coli expressing fimbriae) onto the silicon substrates.

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Section: Resultssupporting

confidence: 77%

Biofunctionalization on Alkylated Silicon Substrate Surfaces via “Click” Chemistry

et al. 2010

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“…A more biocompatible CuAAC protocol avoiding the need of organic solvents for effective functionalization of MNP (silica oxide-coated Fe 3 O 4 ) with biologically relevant ligands was described by Lin and coworkers (109). Under reported conditions (CuSO 4 , tris(carboxyethyl)phosphine (TCEP), TBTA, pH 8), mannose, biotin, the FLAG peptide, Tn antigen, and various proteins (EGFP and maltose binding protein (MBP)) were incorporated on the MNP surface and detected using fluorescently labeled antibodies/proteins.…”

Section: Magnetic Nanoparticlesmentioning

confidence: 99%

Click Chemistry for Drug Delivery Nanosystems

et al. 2011

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The purpose of this Expert Review is to discuss the impact of click chemistry in nanosized drug delivery systems. Since the introduction of the click concept by Sharpless and coworkers in 2001, numerous examples of click reactions have been reported for the preparation and functionalization of polymeric micelles and nanoparticles, liposomes and polymersomes, capsules, microspheres, metal and silica nanoparticles, carbon nanotubes and fullerenes, or bionanoparticles. Among these click processes, Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) has attracted most attention based on its high orthogonality, reliability, and experimental simplicity for non-specialists. A renewed interest in the use of efficient classical transformations has been also observed (e.g., thiol-ene coupling, Michael addition, Diels-Alder). Special emphasis is also devoted to critically discuss the click concept, as well as practical aspects of application of CuAAC to ensure efficient and harmless bioconjugation.

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“…Carbohydrates can also be attached using the highly selective [3+2] Huisgen cycloaddition reaction (Fig. 2c) [72][73][74]. It was reported that the alkyne derivatized carbohydrate reacting with azide functionalized NPs gave better conjugate efficiency compared to that using alkynated NPs with azide bearing molecules [74].…”

Section: Immobilization Of Carbohydrates Onto Magnetic Npsmentioning

confidence: 99%

“…2c) [72][73][74]. It was reported that the alkyne derivatized carbohydrate reacting with azide functionalized NPs gave better conjugate efficiency compared to that using alkynated NPs with azide bearing molecules [74]. In addition, the high affinity binding between strepavidin and biotin can be utilized by incubating biotinated carbohydrates with strepavidin coated NPs [75,76].…”

Section: Immobilization Of Carbohydrates Onto Magnetic Npsmentioning

confidence: 99%

Glyco-Nanomaterials: Translating Insights from the “Sugar-Code” to Biomedical Applications

El‐Boubbou¹,

Huang²

2011

CMC

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Over the past decade, diagnostics and therapeutics have changed gradually towards the use of more specific and targeted approaches. The most profound impact has been in the nanotechnology sectors, where an explosion in directing biomolecules to specific biomarkers has illustrated great potentials not only in detection but also in targeted therapy. Increased knowledge of the diseases at the molecular level catalyzed a shift towards identifying new biological indicators. In particular, carbohydrate-mediated molecular recognitions using nano-vehicles are likely to increasingly affect medicine opening a new area of biomedical applications. This article provides an overview of the recent progress made in recruiting the "sugar code" functionalized on various nano-platforms to decipher cellular information for both in vitro and in vivo applications. Today's glyco-technologies are enabling better detection with great therapeutic potentials. Tomorrow they are likely to bring a full understanding of the "cell-glyconanomaterial bio-conversation" where major biomedical problems will be overcome translating insights from the "glyco-nanoworld" into clinical practice.

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Surface Modification of Magnetic Nanoparticle via Cu(I)-Catalyzed Alkyne-azide [2 + 3] Cycloaddition

Cited by 105 publications

References 33 publications

Biofunctionalization on Alkylated Silicon Substrate Surfaces via “Click” Chemistry

Biofunctionalization on Alkylated Silicon Substrate Surfaces via “Click” Chemistry

Click Chemistry for Drug Delivery Nanosystems

Glyco-Nanomaterials: Translating Insights from the “Sugar-Code” to Biomedical Applications

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Surface Modification of Magnetic Nanoparticle via Cu(I)-Catalyzed Alkyne-azide [2 + 3] Cycloaddition

Cited by 105 publications

References 33 publications

Biofunctionalization on Alkylated Silicon Substrate Surfaces via “Click” Chemistry

Biofunctionalization on Alkylated Silicon Substrate Surfaces via “Click” Chemistry

Click Chemistry for Drug Delivery Nanosystems

Glyco-Nanomaterials: Translating Insights from the &#x201C;Sugar-Code&#x201D; to Biomedical Applications

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Product

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Glyco-Nanomaterials: Translating Insights from the “Sugar-Code” to Biomedical Applications