Click-chemistry for nanoparticle-modification

Li, Nanwen; Binder, Wolfgang H.

doi:10.1039/c1jm11558h

Cited by 171 publications

(96 citation statements)

References 200 publications

(311 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The coupling of Curc molecules to the surface of NL by 'click chemistry' proceeded easily and almost quantitatively at 25°C in our experimental conditions. Among different nanoparticles suitable for click chemistry [44], or already utilized for coupling with Curc [30,41], we decided to use nanoliposomes, due to their known non-toxic and non-immunogenic features, fully biodegradable and structurally versatile nature [45].…”

Section: Discussionmentioning

confidence: 99%

Functionalization with TAT-Peptide Enhances Blood-Brain Barrier Crossing In vitro of Nanoliposomes Carrying a Curcumin-Derivative to Bind Amyloid-Β Peptide

Sancini

Gregori

Salvati

et al. 2013

J Nanomedic Nanotechnol

View full text Add to dashboard Cite

# These authors contributed equally to this work preventing high-molecular weight molecules from passing through [25]. Indeed, the design and engineering of NP with high specificity for brain capillary endothelial cells have been proposed as promising strategy for AD diagnosis and treatment [26][27][28][29].The aim of the present investigation was to design NP able to bind Aβ peptide and to cross the BBB. To reach this goal we developed nanoliposomes (NL) double-functionalized with a curcuminderivative and with a modified HIV Transactivating Transcriptional Activator (TAT) peptide. Preparation of NL covalently decorated with curcumin-derivative was previously carried out, starting from a curcumin alkyne-derivative showing a very high affinity for Aβ peptide [30], suitable for NL decoration by click chemistry and with improved features of stability with respect to curcumin itself [31]. On the other side, TAT-peptide could enhance NP BBB crossing [32,33] based on the evidence that its coupling to NP may facilitate their efficient translocation through the cell membrane, bypassing the endocytic pathway [34][35][36]. TAT-peptide was covalently attached to NL surface via a thiol-maleimide reaction. The ability of NL to bind Aβ after AbstractProduction of abnormally high amounts of amyloid-β peptide in the brain plays a central role in the onset and development of Alzheimer's disease, a neurodegenerative disorder affecting millions of individuals worldwide. Nanoparticles have been proposed as promising tools to treat the disease by delivering drugs and contrast agents to the brain. Here, nanoliposomes decorated with a curcumin-derivative, displaying high affinity for amyloid-β, were functionalized with a modified cell-penetrating TAT-peptide, with the aim of conferring on such nanoliposomes the ability to cross the blood-brain barrier. Functionalization with TAT-peptide did not modify the ability of curcumindecorated nanoliposomes to bind amyloid-β fibrils, as assessed by surface plasmon resonance. Confocal microscopy, mass spectrometry and radioactivity experiments with [3 H]-sphingomyelin showed about 3-fold increase in the uptake of nanoliposomes by human brain capillary endothelial cells (hCMEC/D3) after the functionalization with TATpeptide, with no alterations in cell viability. Moreover, TAT functionalization increased the permeability of curcuminnanoliposomes across a blood-brain barrier model made with the same cells. The similar permeabilities of curcuminderivative and [3 H]-sphingomyelin suggested that nanoliposomes were transported intact. Considering these results, nanoliposomes functionalized with the curcumin-derivative and TAT-peptide represent a promising tool for targeting amyloid-β directly in the brain parenchyma.

show abstract

Section: Discussionmentioning

confidence: 99%

Functionalization with TAT-Peptide Enhances Blood-Brain Barrier Crossing In vitro of Nanoliposomes Carrying a Curcumin-Derivative to Bind Amyloid-Β Peptide

Sancini

Gregori

Salvati

et al. 2013

J Nanomedic Nanotechnol

View full text Add to dashboard Cite

show abstract

“…[174] Boisselier et al [122] (2008) have shown that it is possible to perform this reaction on the surface of AuNPs, which are decorated with ligands bearing azide groups. [175] Using specific conditions (a 1:1-mixture of water and THF as solvent, stoichiometric copper sulfate and sodium ascorbate in an inert atmosphere at 20°C), the problems caused by the presence of copper in performing this reaction on colloidal gold [176,177] can be overcome. As a potential coupling partner for azide-decorated surfaces, RAFT agent ρ − − − -6 , bearing the complementary alkyne group at its R-group, was designed.…”

Section: Synthesis Of a "Clickable" Raft Agentmentioning

confidence: 99%

Building-block design

Ebeling

2015

Springer Theses

View full text Add to dashboard Cite

In order to study AuNPs, they first have to be synthesized. As already described in Section 1.2.3.2, "gold nanoparticles" is just the umbrella term for particles with fundamentally different properties, which in particular depend on their size and the kind of stabilization and thus directly on the synthesis method. Several liquid-chemical synthesis methods were performed and surveyed regarding the suitability of the products for the envisaged functionalization experiments and the experimental ease of implementation with the accessible equipment. In this section, the results from these experiments, the characteristic properties of the produced nanoparticles and feasible analysis methods for them are discussed. In Chapter 8 "Nanohybrids of gold particles", the functionalization reactions of the synthesized AuNPs using coupling reactions on their surface, the study of their interactions with trithiocarbonate groups, and the employment in grafting-to reactions with different classes of polymers will be presented. General remarks on AuNP synthesis strategiesBecause of the high curvature, the gold atoms on the surface of AuNPs are unsaturated and especially reactive. In order to obtain a stable colloid in a AuNP synthesis, particle aggregation must be prevented. This can be achieved in three fundamentally different ways:Electrostatic stabilization: The nanoparticles carry a (remaining) charge, so that they (or the oppositely charged ligand layers) repel each other. Gold colloids stabilized in this manner are very sensitive to salts. * The list only refers to the stability of AuNPs. In order to form a colloidal solution, also a good solubility is required, which is a different matter concerning the interactions with the solvent.

show abstract

“…Novel aspects involve application of click chemistry (Li and Binder 2011 ), which becomes a universal method to link reaction partners in high effi ciency, solvent insensitivity and at moderate reaction conditions.…”

Section: Interactions At Surfacesmentioning

confidence: 99%

Nanoscale Fluorescence Emitters

Demchenko

2015

Introduction to Fluorescence Sensing

View full text Add to dashboard Cite

This chapter provides comparative analysis of properties of different nanoscale materials to absorb and emit visual and near-IR light with the focus on their applications in sensing and imaging technologies. Nowadays we observe that in these applications the novel nanoscale fl uorescent materials appear in strong competition with traditional organic dyes. They demonstrate diverse photophysical behavior and allow obtaining diverse information when they are incorporated into sensor composites or form the images in biological systems. Among these nanoscale emitters are the structures formed of organic dyes or by these dyes incorporated into different types of polymers with the resulting dramatically increased brightness. Collective excitonic effects appear when the aromatic units are coupled in conjugated polymers. Nanoscale structures formed of inorganic carbon in the form of nanodiamonds, graphene and graphene oxide pieces and the so-called carbon dots joined quite recently the family of fl uorophores. Semiconductor quantum dots present a range of bright emitters covering whole visible and near-IR spectral range. Finally, the up-converting nanocrystals make possible visible emission with near-IR excitation. Here we overview the most important features of these nanoscale materials. The following Chap. 6 will be focused on functional nanocomposites that allow extending the useful properties of these basic components.

show abstract

Click-chemistry for nanoparticle-modification

Cited by 171 publications

References 200 publications

Functionalization with TAT-Peptide Enhances Blood-Brain Barrier Crossing In vitro of Nanoliposomes Carrying a Curcumin-Derivative to Bind Amyloid-Β Peptide

Functionalization with TAT-Peptide Enhances Blood-Brain Barrier Crossing In vitro of Nanoliposomes Carrying a Curcumin-Derivative to Bind Amyloid-Β Peptide

Building-block design

Nanoscale Fluorescence Emitters

Contact Info

Product

Resources

About