Designing fluoroprobes through Förster resonance energy transfer: surface modification of nanoparticles through “click” chemistry

Rungta, Parul; Bandera, Yuriy; Tsyalkovsky, Volodymyr; Foulger, Stephen H.

doi:10.1039/c0sm00470g

Cited by 14 publications

(14 citation statements)

References 74 publications

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“…1 H and C NMR spectra were recorded on a JEOL Lambda 500 MHz Fourier transform NMR spectrometer. ESI‐MS spectra were measured by a Thermo Scientific Exactive mass spectrometer.…”

Section: Methodsmentioning

confidence: 99%

“…A variety of functional materials including fluorescent dyes, proteins, polyelectrolyte, and inorganic materials have been introduced for further surface functionalization of polymer particles. In order to functionalize solid substrates including polymer particles, various surface modification techniques such as layer‐by‐layer self‐assembly, click chemistry, grafting‐to, and grafting‐from polymerization have been energetically developed. Recently, click chemistry, especially azide‐alkyne cycloaddition (Huisgen cycloaddition), has been attracting much attention because of its high selectivity, chemical orthogonality, adaptability in aqueous media.…”

Section: Introductionmentioning

confidence: 99%

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Quantification of ATRP initiator density on polymer latex particles by fluorescence labeling technique using copper-catalyzed azide-alkyne cycloaddition

Kasuya

Taniguchi

Motokawa

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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We developed a novel fluorescence labeling technique for quantification of surface densities of atom transfer radical polymerization (ATRP) initiators on polymer particles. The cationic P(St-CPEM-C 4 DMAEMA) and anionic P(St-CPEM) polymer latex particles carrying ATRP-initiating chlorine groups were prepared by emulsifier-free emulsion polymerization of styrene (St), 2-(2-chloropropionyloxy)ethyl methacrylate (CPEM), and N-n-butyl-N,N-dimethyl-N-(2-methacryloyloxy)ethylammonium bromide (C 4 DMAEMA). ATRP initiators on the surface of polymer particles were converted into azide groups by sodium azide, followed by fluorescent labeling with 5-(N,Ndimethylamino)-N 0 -(prop-2-yn-1-yl)naphthalene-1-sulfonamide (Dansyl-alkyne) by copper-catalyzed azide-alkyne cycloaddition (CuAAC). The reaction time required for both azidation of ATRP-initiating groups and successive fluorescence labeling of azide groups with Dansyl-alkyne by CuAAC were investigated in detail by FTIR and fluorescence spectral measurement, respectively. The ATRP initiator densities on the cationic P(St-CPEM-C 4 DMAEMA) and anionic P(St-CPEM) particle surfaces were estimated to be 0.21 and 0.15 molecules nm 22 , respectively, which gave close agreement with values previously determined by a conductometric titration method. The fluorescence labeling through click chemistry proposed herein is a versatile technique to quantify the surface ATRP initiator density both on anionic and cationic polymer particles.

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“…1 H and C NMR spectra were recorded on a JEOL Lambda 500 MHz Fourier transform NMR spectrometer. ESI‐MS spectra were measured by a Thermo Scientific Exactive mass spectrometer.…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Quantification of ATRP initiator density on polymer latex particles by fluorescence labeling technique using copper-catalyzed azide-alkyne cycloaddition

Kasuya

Taniguchi

Motokawa

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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“…In the current effort, an azide‐modified carbazole was attached to crosslinked and inert poly(propargyl acrylate) (PA) particles following a previously presented procedure 26. Briefly, the preparation of aqueous‐phase nanoparticles that are surface‐functionalized with a carbazole substrate was achieved through a “click” chemistry approach 27–29.…”

Section: Introductionmentioning

confidence: 99%

Substrate‐Baited Nanoparticles: A Catch and Release Strategy for Enzyme Recognition and Harvesting

Daniele

Bandera

Sharma

et al. 2012

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The isolation of a single type of protein from a complex mixture is vital for the characterization of the function, structure, and interactions of the protein of interest and is typically the most laborious aspect of the protein purification process. In this effort, a model system was utilized to show the efficacy of synthesizing a “baited” nanoparticle to capture and recycle enzymes (proteins that catalyze chemical reactions) from crude cell lysate. Enzyme trapping and recycling was illustrated with the CARDO system, an enzyme important in bioremediation and natural product synthesis. The enzymes were baited with azide modified carbazolyl moieties attached to poly (propargyl acrylate) nanoparticles through a click transformation. MALDI-TOF and SDS-PAGE analysis indicated the single step procedure to immobilize the enzymes on the particles was capable of significantly concentrating the protein from raw lysate and sequestering all required components of the protein to maintain bioactivity. These results establish a universal model applicable to concentrating and extracting known substrate protein pairs, but it can be an invaluable tool in recognizing unknown protein-ligand affinities.

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“…The method has been previously used to react particles with small azides. [29,30] Here we use the approach to link particles to nanogels.…”

Section: Introductionmentioning

confidence: 99%

Soft poly(N-vinylcaprolactam) nanogels surface-decorated with AuNPs. Response to temperature, light, and RF-field

Siirilä

Karesoja

Pulkkinen

et al. 2019

European Polymer Journal

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Soft poly(N-vinylcaprolactam) (PNVCL) based nanogels were prepared and surface-decorated with gold nanoparticles (AuNPs). The applicability of the hybrid nanogels (PNVCL-AuNPs) as carriers for low molar mass substances was of special interest. AuNPs protected with a mixture of 11azidoundecanothiol and 11-mercaptoundecanoic acid were bound to propargyl functionalized PNVCL based nanogels. Acidic groups on the surfaces of AuNPs and PNVCL based nanogels stabilize the particle dispersions against precipitation above the phase transition temperature of PNVCL. Both the neat PNVCL nanogels and the PVCL-AuNPs shrink upon heating the dispersions. Even though the AuNPs are mainly located in the soft surface layer of the nanogels, the PNVCL-AuNPs respond to visible light as well as to radio-frequency (RF) irradiation by shrinking due to the AuNPs acting as nanoheaters. Interactions of linear PNVCL, PNVCL nanogels and PNVCL-AuNPs with two fluorescent probes were studied as function of increasing temperature. Once bound to the polymer the fluorescent probe may or may not be released from it, depending on its polarity and water solubility. Presence of AuNPs changed the release behavior of the water soluble charged fluorescent probe from the nanogels.

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Designing fluoroprobes through Förster resonance energy transfer: surface modification of nanoparticles through “click” chemistry

Cited by 14 publications

References 74 publications

Quantification of ATRP initiator density on polymer latex particles by fluorescence labeling technique using copper-catalyzed azide-alkyne cycloaddition

Quantification of ATRP initiator density on polymer latex particles by fluorescence labeling technique using copper-catalyzed azide-alkyne cycloaddition

Substrate‐Baited Nanoparticles: A Catch and Release Strategy for Enzyme Recognition and Harvesting

Soft poly(N-vinylcaprolactam) nanogels surface-decorated with AuNPs. Response to temperature, light, and RF-field

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