Bio-orthogonal triazolinedione (TAD) crosslinked protein nanocapsules affect protein adsorption and cell interaction

Frey, Marie‐Luise; Simon, Johanna; Brückner, Maximilian; Mailänder, Volker; Morsbach, Svenja; Landfester, Katharina

doi:10.1039/d0py00087f

Cited by 11 publications

(11 citation statements)

References 48 publications

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“…This class of delivery vehicle provides excellent structural stability and a high degree of biodegradability, which can be exploited to control the release of payload. 21,22 The hollow nanocapsules are composed of crosslinked biopolymers and have a high loading capacity in their inner aqueous core. 23 They are highly degradable by intracellular proteinases under natural conditions but preserve their structural integrity in biological media during their delivery to the site of action.…”

Section: Introductionmentioning

confidence: 99%

Controlling the semi-permeability of protein nanocapsules influences the cellular response to macromolecular payloads

et al. 2021

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Section: Introductionmentioning

confidence: 99%

Controlling the semi-permeability of protein nanocapsules influences the cellular response to macromolecular payloads

et al. 2021

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“…In a similar approach, protein nanocarriers were formed via a Diels-Alder reaction of the tryptophan moieties of proteins with triazolinedione (TAD) in an inverse miniemulsion. [97] In this paper, the authors found that different crosslinking chemistries affected the protein conformation and hence carrierprotein and carrier-cell interaction. Other encapsulation strategies via inverse miniemulsion include carbohydrates as carrier Reproduced with permission.…”

Section: Nanocarriers By Chemical Reactionsmentioning

confidence: 95%

“…In a similar approach, protein nanocarriers were formed via a Diels‐Alder reaction of the tryptophan moieties of proteins with triazolinedione (TAD) in an inverse miniemulsion. [ 97 ] In this paper, the authors found that different crosslinking chemistries affected the protein conformation and hence carrier–protein and carrier–cell interaction. Other encapsulation strategies via inverse miniemulsion include carbohydrates as carrier materials, where for example azide‐modified hyaluronic acid [ 85 ] was crosslinked through a copper‐free azide–alkyne click chemistry with hexanediol dipropionate and dextran‐based polyaldehydes through polycondensation with polyhydrazides to pH‐responsive hydrazones.…”

Section: Encapsulation Of Hydrophilic Cargo Moleculesmentioning

confidence: 99%

Nanocarriers with Multiple Cargo Load—A Comprehensive Preparation Guideline Using Orthogonal Strategies

Hueppe

Wurm

Landfester

2022

Macromol. Rapid Commun.

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Multifunctional nanocarriers enhance the treatment efficacy for modern therapeutics and have gained increasing importance in biomedical research. Codelivery of multiple bioactive molecules enables synergistic therapies. Coencapsulation of cargo molecules into one nanocarrier system is challenging due to different physicochemical properties of the cargo molecules. Additionally, coencapsulation of multiple molecules simultaneously shall proceed with high control and efficiency. Orthogonal approaches for the preparation of nanocarriers are essential to encapsulate sensitive bioactive molecules while preserving their bioactivity. Preparation of nanocarriers by physical processes (i.e., self‐assembly or coacervation) and chemical reactions (i.e., click reactions, polymerizations, etc.) are considered as orthogonal methods to most cargo molecules. This review shall act as a guideline to allow the reader to select a suitable preparation protocol for a desired nanocarrier system. This article helps to select for combinations of cargo molecules (hydrophilic‐hydrophobic, small‐macro, organic–inorganic) with nanocarrier material and synthesis protocols. The focus of this article lies on the coencapsulation of multiple cargo molecules into biocompatible and biodegradable nanocarriers prepared by orthogonal strategies. With this toolbox, the selection of a preparation method for a known set of cargo molecules to prepare the desired biodegradable and loaded nanocarrier shall be provided.

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“…[3][4][5][6] Especially NCs made from proteins have many advantages, such as their biodegradability, high loading capacity with a combination of hydrophilic drugs and low toxicity. [7,8] Due to their size, nanocarriers (NCs) can permeate cells easily and therefore it is of great importance to elucidate how the uptake and the further fate of the nanocarrier in the cell occur. [9] Nanocarriers are usually processed along the endolysosomal pathway.…”

Section: Introductionmentioning

confidence: 99%

Nanocarriers Made of Proteins: Intracellular Visualization of a Smart Biodegradable Drug Delivery System

Frey

Han

Halim

et al. 2022

Small

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be observed by electron microscopy (EM). Correlative light and electron microscopy (CLEM) combine the strengths of both techniques and contribute to a precise localization of the nanocarriers in the cell. Using fluorescent nanodiamonds, for example, can serve as a fluorescent marker [11,12] These markers have the advantage of being biocompatible and can be easily modified to achieve a certain surface functionalization. [13] CLEM preparation ideally features a fluorophore with a stable inherent fluorescence suitable for confocal laser scanning microscopy (cLSM) which, in combination, has a contrasting component suitable for transmission electron microscopy (TEM). Another approach is using inorganic, fluorescent nanoparticles. Quantum dots are the commonly used fluorescent markers for intracellular tracking, but they are not as bright as NPLs for both one photon and two photon excitation. [19] Moreover, due to their small size and spherical shape it can be challenging to identify quantum dots-but also the larger, rectangular NPLs-in a cellular environment by TEM. [14,15] This might involve additional elemental analysis (e.g., energy dispersive x-ray spectroscopy [EDS] or electron energy loss spectroscopy [EELS]) to confirm the identity of the quantum dots to ultimately locate the nanocarrier. [16][17][18] Here, we develop a model system consisting of an organic nanocapsule (NC) labeled with a fluorescent labeling system. As fluorescent marker we utilize large (20-50 nm), rectangular CdSe-CdZnS nanoplatelets (NPLs). We encapsulated these NPLs into biocompatible NCs by a polyaddition reaction at the droplet interface in an inverse miniemulsion. We used NCs made of bovine serum albumin (BSA), crosslinked at the interface with toluene diisocyanate (TDI), forming a dense polymeric shell. [6,7] The NPLs were added to the aqueous dispersed phase during the miniemulsion process, leading to the encapsulation of the NPLs into the NCs. The key to success of the NPL markers hinged on the protective coating on the NPLs. [19] This coating makes NPLs both easy to disperse in aqueous medium and protects the NPLs' surface from major damage during the encapsulation process, thus leading to high fluorescence after encapsulation. The potential toxicity of CdSe nanoparticles is not an issue at this stage. The fluorescent marker can either be easily replaced or even omitted completely.To follow the intracellular pathway of the protein NCs, RAW264.7 macrophages were incubated with these NCs followed by different techniques like flow cytometry, cLSM, and This work analyzes the intracellular fate of protein-based nanocarriers along their endolysosomal pathway by means of correlative light and electron microscopy methods. To unambiguously identify the nanocarriers and their degradation remnants in the cellular environment, they are labeled with fluorescent, inorganic nanoplatelets. This allows tracking the nanocarriers on their intracellular pathway by means of electron microscopy imaging. From the present data, it is possible to identify d...

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Bio-orthogonal triazolinedione (TAD) crosslinked protein nanocapsules affect protein adsorption and cell interaction

Abstract: Albumin-based protein nanocarriers obtained by TAD click chemistry have been widely exploited as drug delivery systems, since they show excellent degradability, low toxicity, but at the same time provide high loading capacity and relevant uptake into cells.

Cited by 11 publications

References 48 publications

Controlling the semi-permeability of protein nanocapsules influences the cellular response to macromolecular payloads

Controlling the semi-permeability of protein nanocapsules influences the cellular response to macromolecular payloads

Nanocarriers with Multiple Cargo Load—A Comprehensive Preparation Guideline Using Orthogonal Strategies

Nanocarriers Made of Proteins: Intracellular Visualization of a Smart Biodegradable Drug Delivery System

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