Peptide-decorated gold nanoparticles via strain-promoted azide–alkyne cycloaddition and post assembly deprotection

Wang, Xiaoxiao; Gobbo, Pierangelo; Suchý, Mojmı́r; Workentin, Mark S.; Hudson, Robert

doi:10.1039/c4ra07574a

Cited by 25 publications

(40 citation statements)

References 21 publications

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“…Details of their synthesisc an be found in the Supporting Information. The MeO-EG 3 -AuNP substrate selected has ag old core diameter of 3 AE 1nma nd features excellent organic solventa nd water solubility.I na ddition, these AuNPs are resistant to both strongly acidic [43] and basic conditions, [32] they can be heated to over 100 8C, [44] and can be repeatedly dried and re-dissolved in different solvents with little to no aggregation, thus making themv ery resilients ubstrates for further modification as well as interfacial organic chemistry.A fter 15 min of place-exchange under vigorous stirring in the dark, the solvent was evaporated and the modified-AuNPs were purified from excess thiols by re-dissolving in CH 2 Cl 2 (4 mL) and precipitating them by adding hexanes (22 mL), in which the AuNPs are not soluble. The supernatant( containing excess thiols and disulfides) was removeda nd the entire washing procedure was repeated four times overall to afford clean photo-DIBO-AuNPs.…”

Section: Resultsmentioning

confidence: 99%

“Shine & Click” Photo‐Induced Interfacial Unmasking of Strained Alkynes on Small Water‐Soluble Gold Nanoparticles

Luo

Gobbo

McNitt

et al. 2016

Chemistry A European J

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In this study, we report the design, synthesis, and characterization of small 3 nm water soluble gold nanoparticles (AuNPs) that feature cyclopropenone-masked strained alkyne moieties capable of undergoing interfacial strain-promoted cycloaddition (i-SPAAC) with azides after exposure to UV-A light. A strained alkyne precursor was incorporated onto AuNPs by direct ligand exchange of a thiol-modified cyclopropenone-masked dibenzocyclooctyne (photoDIBO) ligand. These photoDIBO-AuNPs were characterized by H NMR, IR, and UV/Vis spectroscopy, as well as transmission electron microscopy (TEM) and thermogravimetric analysis (TGA), and the extent of modification was quantified. Upon irradiation with UV-A light, photoDIBO-AuNPs underwent efficient and quantitative regeneration of the parent strained alkyne by photochemical decarbonylation to afford DIBO-derivatized AuNPs. DIBO-AuNPs were found to react cleanly and rapidly (k=5.3×10 m s ) by an interfacial strain-promoted alkyne-azide cycloadditon (i-SPAAC) with benzyl azide, which served as a simple model system. Furthermore, DIBO-AuNPs were reacted with various azides and a nitrone (interfacial strain-promoted alkyne-nitrone cycloaddition, i-SPANC) to showcase the generality of this approach for the facile modification of AuNP surfaces and their properties. The cyclopropenone-based photo-triggered click chemistry at the interface of water-soluble AuNPs offers exciting opportunities for the atom-by-atom control and assembly of functional materials for applications in materials and biomaterials science as well as in chemical biology.

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Section: Resultsmentioning

confidence: 99%

“Shine & Click” Photo‐Induced Interfacial Unmasking of Strained Alkynes on Small Water‐Soluble Gold Nanoparticles

Luo

Gobbo

McNitt

et al. 2016

Chemistry A European J

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“…For PEG3, STOTDA's (N-Fmoc-N″-succinyl-4,7,10trioxa-1,13-tridecanediamine) succinic acid is coupled to the lysine's ε amine and the DBCO-acid to STOTDA's terminal amine after Fmoc deprotection. Special care needs to be taken when cleaving the final product from the resin, since DBCO is sensitive to high concentrations of TFA and can be converted into unreactive side-products (Wang et al, 2014). Therefore, a cleavage cocktail with only 5% TFA was used (DCM:TFA:TIS = 92.2:5:2.5).…”

Section: Oligomer Synthesismentioning

confidence: 99%

A microfluidic approach for sequential assembly of siRNA polyplexes with a defined structure-activity relationship

Loy

Klein

Krzysztoń

et al. 2019

PeerJ Materials Science

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Therapeutic nucleic acids provide versatile treatment options for hereditary or acquired diseases. Ionic complexes with basic polymers are frequently used to facilitate nucleic acid's transport to intracellular target sites. Usually, these polyplexes are prepared manually by mixing two components: polyanionic nucleic acids and polycations. However, parameters such as internal structure, size, polydispersity and surface charge of the complexes sensitively affect pharmaceutical efficiency. Hence a controlled assembly is of paramount importance in order to ensure high product quality. In the current study, we present a microfluidic platform for controlled, sequential formulation of polyplexes. We use oligo-amidoamines (termed "oligomers") with precise molecular weight and defined structure due to their solid phase supported synthesis. The assembly of the polyplexes was performed in a microfluidic chip in two steps employing a design of two successive Y junctions: first, siRNA and core oligomers were assembled into core polyplexes. These core oligomers possess compacting, stabilizing, and endosomal escape mediating motifs. Second, new functional motifs were mixed to the core particles and integrated into the core polyplex. The iterative assembly formed multi-component polyplexes in a highly controlled manner and enabled us to investigate structure-function relationships. We chose nanoparticle shielding polyethylene glycol (PEG) and cell targeting folic acid (termed "PEG-ligands") as functional components. The PEG-ligands were coupled to lipid anchor oligomers via strain promoted azidealkyne click chemistry. The lipid anchors feature four cholanic acids for inserting various PEG-ligands into the core polyplex by non-covalent hydrophobic interactions. These core-lipid anchor-PEG-ligand polyplexes containing folate as cell binding ligand were used to determine the optimal PEG-ligand length for transfecting folate receptor-expressing KB cells in vitro. We found that polyplexes with 20 mol % PEG-ligands (relative to n core oligomer ) showed optimal siRNA mediated gene knock-down when containing defined PEG domains of in sum 24 and 36 ethylene oxide repetitions, 12 EOs each from the lipid anchor and 12 or 24 EOs from the PEG-ligand, respectively. These results confirm that transfection efficiency depends on the linker length and stoichiometry and are consistent with previous findings using core-PEG-ligand polyplexes formed by click modification of How to cite this article Loy DM, Klein PM, Krzysztoń R, Lächelt U, Rädler JO, Wagner E. 2019. A microfluidic approach for sequential assembly of siRNA polyplexes with a defined structure-activity relationship.

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“…Using this same strategy, they also reported the synthesis of a Au NP‐CNT hybrid by a coupling reaction between ADIBO‐modified single‐walled carbon nanotubes (SWCNT) and azide‐modified Au NPs (1 h, rt) ( Figure ) . In a recent work, they reported the synthesis of peptide‐decorated gold nanoparticles via SPAAC reaction of azide‐AuNPs and an ADIBO moiety connected via a PEG linker to a protected tripeptide . As a final step, the peptide protecting groups were removed with 90% TFA/DCM.…”

Section: Strain‐promoted Azide‐alkyne and Other [2+3] Cycloadditionsmentioning

confidence: 99%

Metal‐Free Click Chemistry Reactions on Surfaces

Escorihuela

Marcelis

Zuilhof

2015

Adv Materials Inter

111

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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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Peptide-decorated gold nanoparticles via strain-promoted azide–alkyne cycloaddition and post assembly deprotection

Abstract: A new method combining an interfacial strain-promoted azide-alkyne cycloaddition and post assembly deprotection (SPAAC-PAD) has been developed for the well-defined functionalization of small, watersoluble gold nanoparticles with oligopeptides.

Cited by 25 publications

References 21 publications

“Shine & Click” Photo‐Induced Interfacial Unmasking of Strained Alkynes on Small Water‐Soluble Gold Nanoparticles

“Shine & Click” Photo‐Induced Interfacial Unmasking of Strained Alkynes on Small Water‐Soluble Gold Nanoparticles

A microfluidic approach for sequential assembly of siRNA polyplexes with a defined structure-activity relationship

Metal‐Free Click Chemistry Reactions on Surfaces

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