Monovalent maleimide functionalization of gold nanoparticles<i>via</i>copper-free click chemistry

Nieves, Daniel J.; Azmi, Nina Suhaity; Xu, Ruoyan; Lévy, Raphaël; Yates, Edwin A.; Fernig, David G.

doi:10.1039/c4cc05909c

Cited by 25 publications

(20 citation statements)

References 34 publications

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“…These can be coupled flexible with various molecules carrying different targeted functionalities . Other modification studies using TEMA have been reported for different surfaces and particles including glass and polymer surfaces, salmon calcitonin (sCT), hydrogels, AuNPs, magnetic nanoparticles (Fe 3 O 4 ), porous cellulose nanocrystals/poly(vinyl alcohol) nanocomposite films on glass, porous polymeric monolith, and a mixed macrodiol polyurethane and tantalum …”

Section: Introductionmentioning

confidence: 99%

A Comparative Study of Thiol‐Terminated Surface Modification by Click Reactions: Thiol‐yne Coupling versus Thiol‐ene Michael Addition

Dadfar

Sekula-Neuner

Trouillet

et al. 2018

Adv Materials Inter

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Two quick and efficient, metal catalyst free conjugation routes for the covalent attachment of functional compounds to functionalized surfaces by scanning probe lithography methods are compared in the presented work. The studied methods are thiol‐yne coupling (TYC) and thiol‐ene Michael addition (TEMA). First, the surface of hydroxyl‐terminated glass is thiolated using (3‐mercaptopropyl)trimethoxysilane (MPTMS). Then, in the distinct experiments, the thiol‐terminated surface is spotted by microchannel cantilever spotting with different fluorescent and nonfluorescent inks containing cycloalkyne (dibenzocyclooctyne (DBCO)) or alkene (maleimide) groups. Experiments with different fluorophores show that both routes are successful in coupling functional moieties to the surface in a short time and low temperature. Comparing the protein binding experiments for biotin‐DBCO and biotin‐maleimide reveals a higher surface density of immobilized biotin via the TEMA route. The results from this study are applicable in design and fabricating of biosensors, appropriate for protein detection and other biomedical/biological applications.

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Section: Introductionmentioning

confidence: 99%

A Comparative Study of Thiol‐Terminated Surface Modification by Click Reactions: Thiol‐yne Coupling versus Thiol‐ene Michael Addition

Dadfar

Sekula-Neuner

Trouillet

et al. 2018

Adv Materials Inter

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“…At higher mole % the number of FluPep ligands per nanoparticle will increase. It is interesting to note that not all gold nanoparticles were observed to bind to the CM Sepharose resin at higher mole % of FluPep ligand, something that has been observed previously with other functional peptides (Nieves et al, 2014, Paramelle et al, 2015. Nonetheless, this straightforward purification of the functionalised gold nanoparticles means that the effects on influenza virus infectivity of mono-versus plurifunctionalisation can be determined.…”

Section: Purification Of Flupep Functionalised Gold Nanoparticlesmentioning

confidence: 71%

“…To functionalise the nanoparticles, the peptide FluPep ligand was included in the ligand mix, its mole % in relation to the matrix ligand reflects its grafting density on the gold nanoparticles (Levy et al, 2006, Duchesne et al, 2008a, Duchesne et al, 2012, Paramelle et al, 2015, Nieves et al, 2014. This can be determined by chromatography targeting specifically the grafted function, which also provides a means to purify the functionalised gold nanoparticles from those not Mix matrix gold nanoparticles did not to CM Sepharose nor to DEAE Sepharose ( Fig.…”

Section: Purification Of Flupep Functionalised Gold Nanoparticlesmentioning

confidence: 99%

Enhanced inhibition of influenza virus infection by peptide-noble metal nanoparticle conjugates

Alghrair

Fernig

Ebrahimi

2018

Preprint

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Influenza virus is a major medical and veterinary health concern and causes global pandemics. The peptide 'FluPep' is an established inhibitor of influenza virus infectivity in model systems. We have explored the potential for FluPep functionalised noble metal nanoparticle to enhance the antiviral activity of the peptide Flupep and determined their potential for the delivery of FluPep. The FluPep ligand designed here is FluPep extended at its N-terminus with the sequence CVVVTAAA-, to allow its incorporation into a mix matrix ligand shell of a peptidol and an alkanethiol ethyleneglycol comprising 70% H-CVVVTol and 30% HS(CH 2 ) 11 (ethyleneglycol) 4 (both mole/mole). Gold and silver nanoparticles (~10 nm diameter) prepared with up to 5% (mole/mole) FluPep ligand contained in the mixture of mix-matrix peptide ligands remained as stable as the control mix-matrix coated nanoparticles against ligand exchange with dithiothreitol. FluPep ligand was found to inhibit viral plaque formation in canine MDCK cells (IC 50 2.1 nM), but was less potent than FluPep itself (IC 50 140 pM). FluPep ligand functonalised nanoparticles retained antiviral activity in the plaque assay. Moreover, at low grafting densities (where nanoparticles incorporate ~1 FluPep ligand, the antiviral potency in terms of FluPep ligand concentration was enhanced significantly for gold and silver nanoparticles (IC 50 ~8-fold and ~3-fold lower, respectively). At higher grafting density the potency relative to free FluPep ligand concentration decreased. The data demonstrate that conjugation of FluPep to gold and silver nanoparticles enhances its antiviral potency; the antimicrobial activity of silver ions may enable the design of even more potent anti-microbial inhibitors.

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“…The liberated maleimide groups were subsequently used in a Michael addition reaction with cysteine. More recently, an elegant combination of metal‐free click reactions was reported by Fernig and co‐workers, who used the thiol‐Michael addition for the functionalization of maleimide‐functionalized Au NPs with dithiothreitol (DTT) . Initially, the maleimide‐functionalized Au NPs were prepared by a SPAAC reaction between DIBO‐terminated maleimides and azide‐functionalized Au NPs, and the subsequent thiol‐Michael addition with DTT yielded thiol‐functionalized nanoparticles, which were again used to react with maleimide‐functionalized heparin‐derived oligosaccharides through a second thiol‐Michael addition.…”

Section: Thiol‐michael Addition Reactionsmentioning

confidence: 99%

Metal‐Free Click Chemistry Reactions on Surfaces

Escorihuela

Marcelis

Zuilhof

2015

Adv Materials Inter

112

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In the last decade, interest in the functionalization of surfaces and materials has increased dramatically. In this regard, click chemistry deserves a central focus because of its mild reaction conditions, high efficiency, and easy post‐treatment. Among such novel click reactions, those that do not require any metal catalyst are of special interest, as metals may have undesirable effects in many fields. In this Review, the backgrounds and application of such metal‐free click reactions for the modification of surfaces are highlighted.

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Monovalent maleimide functionalization of gold nanoparticlesviacopper-free click chemistry

Abstract: A single maleimide was installed onto the self-assembled monolayer of gold nanoparticles by copper-free click chemistry. Simple covalent biofunctionalisation is demonstrated by coupling fibroblast growth factor 2 and an oligosaccharide in a 1 : 1 stoichiometry by thiol-Michael addition.

Cited by 25 publications

References 34 publications

A Comparative Study of Thiol‐Terminated Surface Modification by Click Reactions: Thiol‐yne Coupling versus Thiol‐ene Michael Addition

A Comparative Study of Thiol‐Terminated Surface Modification by Click Reactions: Thiol‐yne Coupling versus Thiol‐ene Michael Addition

Enhanced inhibition of influenza virus infection by peptide-noble metal nanoparticle conjugates

Metal‐Free Click Chemistry Reactions on Surfaces

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