Fabrication of nanostructures through self-assembly of non-ionic amphiphiles for biomedical applications

Prasad, Suchita; Achazi, Katharina; Böttcher, Christoph; Haag, Rainer; Sharma, Sunil K.

doi:10.1039/c6ra28654b

Cited by 31 publications

(28 citation statements)

References 58 publications

(82 reference statements)

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“…After the lyophilization process, the solid had a pink color, and this implies that NR interacted with the non-polar environment of the polyelectrolyte complex. The results agree with previous studies, such as the encapsulation of the NR in PLA/Pluronic nanoparticles [ 26 ], in nanostructures of non-ionic amphiphiles using 2,2-di(prop-2-yn-1-yl)propane-1,3-dio [ 44 ] and a sensor based on fluorescent dye-doped [ 45 ].…”

Section: Resultssupporting

confidence: 91%

Polyelectrolyte Nanoparticles of Amphiphilic Chitosan/Pectin from Banana Peel as Potential Carrier System of Hydrophobic Molecules

Méndez

López

2020

Polymers

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In this study, pectins were extracted from banana wastes Musa paradisiaca under different acidic conditions, obtaining pectins with different degrees of esterification (DE) depending on the acid type and pH. The formation of the polyelectrolyte nanoparticles was evaluated according to the DE of the pectin, the mass ratio of the polymers of pectin to amphiphilic chitosan (AmCh), and their concentration. The properties of the polyelectrolyte nanoparticles were evaluated at different pH and temperatures. The pectin with 24.3% DE formed polyelectrolyte nanoparticles through the electrostatic interaction with AmCh, which was evidenced by changes in the zeta potential and particle size. The study of mass ratio AmCh:Pectin, to get a stable system, showed that it must be at least equal (1:1), or AmCh must be in higher proportion (6:1, 50:1, 100:1), and the polymers concentration must be 1 mg/mL. The study of the temperature effect showed that, when the temperature increases, the particle size decreases, and the pH study showed a stable particle size for the polyelectrolyte nanoparticles in the range of pH 5–6. Nile Red (NR), a hydrophobic molecule, was encapsulated in the polyelectrolyte nanoparticles with a loading capacity of 1.8% and an encapsulation efficiency of 80%.

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Section: Resultssupporting

confidence: 91%

Polyelectrolyte Nanoparticles of Amphiphilic Chitosan/Pectin from Banana Peel as Potential Carrier System of Hydrophobic Molecules

Méndez

López

2020

Polymers

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“…However, in case of Nile red, a relatively hydrophobic compound than curcumin, d ‐lactose‐based nanocarrier 17 exhibits higher transport and encapsulation efficiency as compared to amphiphilic systems 12 and 13 , which might be because of greater interactions between the dye and supramolecular aggregate of amphiphile 17 . 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%

“…2,2‐Di(prop‐2‐yn‐1‐yl)propane‐1,3‐diol ( 1 ), the core unit of the amphiphiles was synthesized by following the procedure reported earlier by our group . The hydrophobic moieties ( 2 – 5 ) were developed employing the core 1 by following Scheme .…”

Section: Resultsmentioning

confidence: 99%

“…The hydrophobic moieties ( 2 – 5 ) were developed employing the core 1 by following Scheme . The compounds 4 and 5 have been reported earlier by our group . The hydrophobic unit bearing ether linkage ( 2 ) was synthesized by O ‐alkylation of the diol 1 using 1‐bromooctadecane in the presence of potassium hydroxide as a base and dimethyl sulfoxide (DMSO) as a solvent.…”

Section: Resultsmentioning

confidence: 99%

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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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“…Self‐assembly of amphiphilic macromolecules provide a unique and newer opportunity for designing novel material for advanced applications in biomedicine and bionanotechnology . Among the diverse and various promising applications of amphiphilic macromolecules, the area of drug delivery is challenging because of the limited aqueous‐solubility and short circulation half‐life of most clinically used drugs .…”

Section: Introductionmentioning

confidence: 99%

Fabrication of oligo‐glycerol based hydrolase responsive amphiphilic nanocarriers

Mittal

Singh

Kumar

et al. 2020

Polymers for Advanced Techs

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Herein, we report on the synthesis of a new class of novel non-ionic amphiphiles using triglycerol as a core, which is further functionalized with hydrophilic units poly(ethylene glycol) monomethyl ether (M n : 350 and 550) and a pair of hydrophobic alkyl chains (C 18 or C 15 ) via chemo-enzymatic approach. Fluorescence measurements and dynamic light scattering studies showed that all of the synthesized amphiphilic systems spontaneously self-assemble in aqueous solution, which is further confirmed by the transmission electron microscopy. Encapsulation of hydrophobic moieties like Nile red and nimodipine was studied using ultraviolet-visible (UV-vis) and fluorescence spectrometer techniques. A cytotoxicity study of the amphiphiles using A549, HeLa, and MCF7 cell, which showed that all of the synthesized nanocarriers are well tolerated at the concentrations studied. The release profile of encapsulated Nile red in synthesized amphiphilic system was studied in the presence of the immobilized enzyme (Novozym 435).amphiphile, cytotoxicity, encapsulation, self-assembly 1 | INTRODUCTION Molecular self-assembly, the spontaneous process of forming ordered aggregates without external intervention is gaining attention by researchers from different disciplines because of its widespread applications. The phenomenon is derived mostly by various noncovalent interactions such as hydrophobic, ionic, π-π stacking, and electrostatic interaction adopting the minimal Gibbs free energy and thermodynamic stability. 1-4 The natural self-assembly phenomenon, for example, polypeptide chains folding into proteins or conformational changes of nucleic acids into their different functional forms etc, have inspired the scientific community to mimic the process using newly designed molecules. 5,6 Self-assembly of amphiphilic macromolecules provide a unique and newer opportunity for designing novel material for advanced applications in biomedicine and bionanotechnology. 7-11 Among the diverse and various promising applications of amphiphilic macromolecules, the area of drug delivery is challenging because of the limited aqueous-solubility and short circulation half-life of most clinically used drugs. [12][13][14] Carrier-mediated drug delivery not only can maximize the bioavailability but also allow targeting the active site in the body while minimizing the side effects.Amphiphiles can self-assemble into a variety of nano and microscale structures in the aqueous medium, where the majorly known 3-D structures include vesicles, micelles, and molecular gels. [15][16][17] Micelles vary in diameter in the range of 5 to 100 nm and may consist of spheres, discs, and wormlike assemblies, 18 whereas vesicles are found in hollow, spherical, and lamellar type morphologies within the diameter range of 20 nm to micrometer. 19 Since micelles formed by small molecules have simple synthesis, high loading capacity, and low toxicity, they may be able to target many cancer tissues and ensure the accumulation within the small vasculatures of tumors. 20,21 However, o...

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Fabrication of nanostructures through self-assembly of non-ionic amphiphiles for biomedical applications

Abstract: Non-cytotoxic and non-ionic amphiphiles having supramolecular aggregation behavior were synthesized from biocompatible starting materials using a “greener” chemo-enzymatic method.

Cited by 31 publications

References 58 publications

Polyelectrolyte Nanoparticles of Amphiphilic Chitosan/Pectin from Banana Peel as Potential Carrier System of Hydrophobic Molecules

Polyelectrolyte Nanoparticles of Amphiphilic Chitosan/Pectin from Banana Peel as Potential Carrier System of Hydrophobic Molecules

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

Fabrication of oligo‐glycerol based hydrolase responsive amphiphilic nanocarriers

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