Towards engineering of self-assembled nanostructures using non-ionic dendritic amphiphiles

Thota, Bala N. S.; Berlepsch, Hans von; Böttcher, Christoph; Haag, Rainer

doi:10.1039/c4cc09513h

Cited by 36 publications

(58 citation statements)

References 38 publications

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“…The guest encapsulation experiments were carried out as reported in the literature . A detailed description of the procedure as well as the mode of calculation of the encapsulation capacity are provided in the Experimental Section/Supporting Information.…”

Section: Resultssupporting

confidence: 70%

“…The transport capacity of different amphiphiles with identical mPEG and alkyl chains showed similar trends for the two different guest molecules, indicating a strong relation between transport capacity and structure of the hosting amphiphile. The transport capacity of Nile Red is found to be in line with our previous report on nonionic dendritic amphiphiles displaying unexpected parameters in micellar assemblies, while for Nimodipinie these systems were found to be better than our previous reported system . For amphiphiles 2 and 4 having a short C 11 alkyl chain, it was observed that increasing the length of the mPEG head group from M n 350 ( 2 ) to 1000 ( 4 ) leads to a considerably decreased transport capacity for either of the guest molecules.…”

Section: Resultsmentioning

confidence: 66%

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Aggregation Behavior of Non‐ionic Twinned Amphiphiles and Their Application as Biomedical Nanocarriers

Singh

Thota

Schade

et al. 2017

Chemistry An Asian Journal

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A new class of twinned amphiphiles was developed by conjugating a pair of hydrophilic head groups from mPEG chains (M : 350 or 1000) and a pair of hydrophobic segments from linear alkyl chains (C or C ) through a novel spacer synthesized from glycerol and p-hydroxybenzoic acid. The aggregation phenomena of the amphiphiles were proven by DLS and fluorescence experiments, whereas size and morphology of the aggregates were evaluated by cryo-TEM. The measurements proved the formation of globular, thread-like or rod-like micelles as well as planar double-layer assemblies, depending on the amphiphile's molecular structure. The applicability of these non-ionic amphiphilic systems as nanocarriers for hydrophobic guest molecules was demonstrated by encapsulating a hydrophobic dye, Nile Red, and a hydrophobic drug, Nimodipine. The transport capacity results for both Nimodipine and Nile Red prove them as a promising candidate for drug delivery.

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Section: Resultssupporting

confidence: 70%

Section: Resultsmentioning

confidence: 66%

Aggregation Behavior of Non‐ionic Twinned Amphiphiles and Their Application as Biomedical Nanocarriers

Singh

Thota

Schade

et al. 2017

Chemistry An Asian Journal

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“…( 27 ) were prepared pursuant to reported literature procedures. [39][40][41] LA-NHS , 1-Azidooctadecane ( 26 ), and compound LA-G1-OH ( 14 ) were synthesized according to published protocols. [42][43][44] Synthetic details for the preparation of the noncrosslinkable control molecule Alkyl-Glycine ( 5 ) can be found in Figure S1, pp.…”

Section: Methodsmentioning

confidence: 99%

Crosslinked Redox‐Responsive Micelles Based on Lipoic Acid‐Derived Amphiphiles for Enhanced siRNA Delivery

Tschiche

Thota

Neumann

et al. 2016

Macromolecular Bioscience

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Successful application of gene silencing approaches critically depends on systems that are able to safely and efficiently deliver genetic material such as small interfering RNA (siRNA). Due to their beneficial well-defined dendritic nanostructure, self-assembling dendrimers are emerging as promising nanovectors for siRNA delivery. However, these kinds of vectors are plagued with stability issues, especially when considered for in vivo applications. Therefore, in the present study, disulfide-based temporarily fixed micelles are developed that can degrade upon reductive conditions, and thus lead to efficient cargo release. In detail, lipoic acid-derived crosslinked micelles are synthesized based on small polymerizable dendritic amphiphiles. Particularly, one candidate out of this series is able to efficiently release siRNA due to its redox-responsive biodegradable profile when exposed to simulated intracellular environments. As a result, the reduction-triggered disassembly leads to potent gene silencing. In contrast, noncrosslinkable, structurally related constructs fails under the tested assay conditions, thereby confirming the applied rational design approach and demonstrating its large potential for future in vivo applications.

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“…Further, it is inferred from the results that PG [G2.0] based nanocarriers 12 and 13 are more efficient drug/dye transporters (exception: Nile red encapsulation by amphiphile 13 ) in comparison to their analogous PEGylated amphiphiles reported earlier by our group . In addition, amphiphile 13 is found to be a better solubilizer for Nile red and nimodipine than the dendritic amphiphiles involving PG [G2.0] and [G3.0] dendrons as head groups and lipophilic tail segments having two alkyl chains (C 12 and C 18 ) reported in literature …”

Section: Resultsmentioning

confidence: 75%

Nonionic Dendritic and Carbohydrate Based Amphiphiles: Self‐Assembly and Transport Behavior

Prasad

Achazi

Schade

et al. 2018

Macromolecular Bioscience

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Herein, a new series of non-ionic dendritic and carbohydrate based amphiphiles is synthesized employing biocompatible starting materials and studied for supramolecular aggregate formation in aqueous solution. The dendritic amphiphiles 12 and 13 possessing poly(glycerol) [G2.0] as hydrophilic unit and C-10 and C-18 hydrophobic alkyl chains, respectively, exhibit low critical aggregation concentration (CAC) in the order of 10 m and hydrodynamic diameters in the 8-10 nm range and supplemented by cryogenic transmission electron microscopy. Ultraviolet-visible (UV-Vis) and fluorescence spectroscopy suggests the effective solubilization of hydrophobic guests by the self-assembled architectures, with the nanotransporters 12 and 13 possessing the highest encapsulation efficiency of 80.74 and 98.03% for curcumin. Efficient uptake of encapsulated curcumin in adenocarcinomic human alveolar basal epithelial (A549) cells is observed by confocal laser scanning microscopy. Amphiphiles 12 and 13 are non-cytotoxic at the concentrations studied, however, curcumin encapsulated samples efficiently reduce the viability of A549 cells in vitro. Experimental studies indicate the ability of amphiphile 13 to encapsulate 1-anilinonaphthalene-8-sulfonic acid (ANS) and curcumin with binding constant of 1.16 × 105 m and 1.43 × 10 m , respectively. Overall, our findings demonstrate the potential of these dendritic amphiphiles for the development of prospective nanocarriers for the solubilization of hydrophobic drugs.

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Towards engineering of self-assembled nanostructures using non-ionic dendritic amphiphiles

Abstract: We have reported on the formation of different self-assembled nanostructures by subtle changes in the structure of non-ionic dendritic amphiphiles.

Cited by 36 publications

References 38 publications

Aggregation Behavior of Non‐ionic Twinned Amphiphiles and Their Application as Biomedical Nanocarriers

Aggregation Behavior of Non‐ionic Twinned Amphiphiles and Their Application as Biomedical Nanocarriers

Crosslinked Redox‐Responsive Micelles Based on Lipoic Acid‐Derived Amphiphiles for Enhanced siRNA Delivery

Nonionic Dendritic and Carbohydrate Based Amphiphiles: Self‐Assembly and Transport Behavior

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