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Search for "micelles" in Full Text gives 75 result(s) in Beilstein Journal of Organic Chemistry.

Facile access to pyridinium-based bent aromatic amphiphiles: nonionic surface modification of nanocarbons in water

  • Lorenzo Catti,
  • Shinji Aoyama and
  • Michito Yoshizawa

Beilstein J. Org. Chem. 2024, 20, 32–40, doi:10.3762/bjoc.20.5

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  • )2–Y (Y = OCH3, OH, and imidazole)). The new amphiphiles quantitatively self-assemble into ≈2 nm-sized aromatic micelles in water independent of the side-chain. Importantly, efficient water-solubilization and nonionic surface modification of various nanocarbons (e.g., fullerene C60, carbon nanotubes
  • of the m-phenylene unit with an N-functionalized pyridinium core reduces the synthetic steps from 6 to 2–4, while at the same time enabling the use of various nonionic side-chains. Amphiphiles PA-R quantitatively self-assemble into aromatic micelles (PA-R)n, with outer diameters of ≈2 nm, independent
  • and structure of aromatic micelles Aromatic micelle (PA-CH3)n was facilely generated via dissolution of PA-CH3 (2.1 mg, 4.3 μmol) in water (8.6 mL). The 1H NMR spectrum of PA-CH3 in D2O showed significantly upfield-shifted signals (Δδ = −2.73 ppm for Hb) compared to the spectrum in CD3OD, in a manner
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Published 08 Jan 2024

Anion–π catalysis on carbon allotropes

  • M. Ángeles Gutiérrez López,
  • Mei-Ling Tan,
  • Giacomo Renno,
  • Augustina Jozeliūnaitė,
  • J. Jonathan Nué-Martinez,
  • Javier Lopez-Andarias,
  • Naomi Sakai and
  • Stefan Matile

Beilstein J. Org. Chem. 2023, 19, 1881–1894, doi:10.3762/bjoc.19.140

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  • than intrinsic anion–π interactions should provide access to really strong catalysts [3]. They have been predicted theoretically to occur on π-stacks [6], and confirmed recently to exist and apply to anion–π catalysis on π-stacked foldamers (Figure 1B) [7] and micelles [8]. However, due to their unique
  • -to-face π stacking because the delocalized π electrons move within the stack away from the charge, which induces a macrodipole along the stack that supports the binding of the anion (Figure 1B) [61]. What works for anion–(π)n–π catalysis on π-stacked foldamers [61] and micelles [8] should apply to
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Published 12 Dec 2023
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  • microscopy [36][37]. In nature, chemical gradients and phase separation are maintained by compartmentalization in liposomes, micelles, and vesicles rather than at interfaces such as ITIES. Artificial photosynthesis systems are being designed to mimic this behavior and recently the field of artificial
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Published 08 Aug 2023

Preparation of β-cyclodextrin/polysaccharide foams using saponin

  • Max Petitjean and
  • José Ramón Isasi

Beilstein J. Org. Chem. 2023, 19, 78–88, doi:10.3762/bjoc.19.7

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  • ]. Saponins, because of their amphiphilic nature, are known as natural surfactants [9]. They have been used as natural detergents, foaming agents, stabilizers, emulsifiers and wetting agents, for example [10]. The micelles produced will be different in size and shape as a function of the type of saponin
  • molecules into the cavity of the glycoside micelles should be taken into account. Our main goal in this part of the study is to guarantee that the prepared foams remain stable at least until the crosslinking reaction takes place. Once the six experimental synthetic paths were set (see Experimental section
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Published 24 Jan 2023

Inline purification in continuous flow synthesis – opportunities and challenges

  • Jorge García-Lacuna and
  • Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 1720–1740, doi:10.3762/bjoc.18.182

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  • dissolve the magnesium salts, and the organic mixture was the appropriate solvent for the next step. Recently, a regenerated cellulose membrane to purify micelles via inline dialysis was reported by Junkers and co-workers [63]. This semicontinuous closed-loop setup can remove the organic solvent (THF) to a
  • concentration of less than 1% within four hours, and water-soluble monomers. In addition, the integration of this setup into an inline synthesis step starting from block copolymer solutions, and rhodamine encapsulation produced micelles without affecting the particle size is also demonstrated. The growing
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Published 16 Dec 2022

Tetraphenylethylene-embedded pillar[5]arene-based orthogonal self-assembly for efficient photocatalysis in water

  • Zhihang Bai,
  • Krishnasamy Velmurugan,
  • Xueqi Tian,
  • Minzan Zuo,
  • Kaiya Wang and
  • Xiao-Yu Hu

Beilstein J. Org. Chem. 2022, 18, 429–437, doi:10.3762/bjoc.18.45

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  • tunable self-assembly, such as vesicles [14][15][16], micelles [17][18][19], nanocrystals [20], coordination-driven assemblies [9][21][22], host–guest interactions [15][23][24][25], etc. In the above systems, catalysts are encapsulated by supramolecular assemblies and thus provide a suitable environment
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Published 13 Apr 2022

Synthesis and bioactivity of pyrrole-conjugated phosphopeptides

  • Qiuxin Zhang,
  • Weiyi Tan and
  • Bing Xu

Beilstein J. Org. Chem. 2022, 18, 159–166, doi:10.3762/bjoc.18.17

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  • phosphatase (ALP) to convert the micelles made of phosphopeptides to the nanofibers of peptides via enzymatic dephosphorylation [20][60]. While ALP-catalyzed EISA has received considerable exploration, the structures of the peptide substrates mainly have centered on naphthylacetyl-capped phosphopeptides (e.g
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Published 31 Jan 2022

Cryogels: recent applications in 3D-bioprinting, injectable cryogels, drug delivery, and wound healing

  • Luke O. Jones,
  • Leah Williams,
  • Tasmin Boam,
  • Martin Kalmet,
  • Chidubem Oguike and
  • Fiona L. Hatton

Beilstein J. Org. Chem. 2021, 17, 2553–2569, doi:10.3762/bjoc.17.171

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  • the active ingredient is encapsulated within a particle, such as polymeric micelles [101] or microneedles [102], embedded within the cryogel. Therapeutic agents may not necessarily be represented solely by drug molecules. Recent examples of other types of therapeutic cargos used for delivery by
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Published 14 Oct 2021

Post-functionalization of drug-loaded nanoparticles prepared by polymerization-induced self-assembly (PISA) with mitochondria targeting ligands

  • Janina-Miriam Noy,
  • Fan Chen and
  • Martina Stenzel

Beilstein J. Org. Chem. 2021, 17, 2302–2314, doi:10.3762/bjoc.17.148

Graphical Abstract
  • efficiency. Micelles are ideal carriers when designing a nanoparticle with an abundance of functional groups on the surface, which could be conjugated with targeting ligands such as TPP. Moreover, they have already been used to successfully deliver arsenic drugs [28][29][30][31][32], highlighting their
  • suitability as a potential vehicle to deliver these drugs. Disadvantage is however the multistep procedure to generate micelles ranging from the synthesis of block copolymers to the self-assembly into micelles, often in low dilution, making the process inefficient. Micelles obtained by the PISA process can in
  • strategy, drug conjugated monomers can be directly used in the polymerization, eliminating the post-modification step [28][37][38][39]. In order to use micelles, prepared by PISA or traditional techniques, for targeting specific receptors, it is necessary that these materials are low-fouling, thus repel
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Published 03 Sep 2021

Constrained thermoresponsive polymers – new insights into fundamentals and applications

  • Patricia Flemming,
  • Alexander S. Münch,
  • Andreas Fery and
  • Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138

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  • , have been intensively studied in solution. For the application of such polymers in novel sensors, drug delivery systems or as multifunctional coatings, they typically have to be transferred into specific arrangements, such as micelles, polymer films or grafted nanoparticles. However, it turns out that
  • thermoresponsive polymers with limited mobility focusing on UCST behavior and the possibilities for influencing their thermoresponsive switching characteristics. It comprises star polymers, micelles as well as polymer chains grafted to flat substrates and particulate inorganic surfaces. The elaboration of the
  • arrange them into confined polymeric architectures, such as star polymers or micelles, in a defined way. All these arrangements have in common that the mobility, i.e., the degrees of freedom of movement of the polymer chains, is limited compared to free polymers in solution, which affects the
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Published 20 Aug 2021

Synthesis and physicochemical evaluation of fluorinated lipopeptide precursors of ligands for microbubble targeting

  • Masayori Hagimori,
  • Estefanía E. Mendoza-Ortega and
  • Marie Pierre Krafft

Beilstein J. Org. Chem. 2021, 17, 511–518, doi:10.3762/bjoc.17.45

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  • ; Introduction Various nano- and microsystems, including micelles, liposomes, and microbubbles, have been developed as imaging agents and to selectively deliver chemotherapeutics to tumor cells [1][2][3][4][5][6]. An increased specificity for tumor cells can be gained through ligand-mediated active targeting
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Published 19 Feb 2021

19F NMR as a tool in chemical biology

  • Diana Gimenez,
  • Aoife Phelan,
  • Cormac D. Murphy and
  • Steven L. Cobb

Beilstein J. Org. Chem. 2021, 17, 293–318, doi:10.3762/bjoc.17.28

Graphical Abstract
  • nuclei such as 1H or 15N PREs. 19F NMR has also been applied to study the conformational heterogeneity and dynamics of a broad range of proteins and peptides upon their interaction with model lipid vesicles [59], micelles [60] and bicelles [61]. It has enabled the quantification and mechanistic
  • several properties of a specifically 3-FTyr-labelled α-synuclein analogue, including its native conformation and the conformational changes induced by urea, spermine and sodium dodecyl sulfate (SDS) [75]. Subsequently, α-synuclein interaction with SDS micelles and model membranes have also been
  • accurate determination of inter-subunit distances in pentameric ligand-gated ion channels (pLGICs) by means of solution 19F PRE NMR experiments in micelles (Figure 13) [88]. To ensure a uniform 19F PRE signal from the adjacent paramagnetic labels, the 19F NMR TFET probe was tagged to a selected cysteine
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Published 28 Jan 2021

Dirhamnolipid ester – formation of reverse wormlike micelles in a binary (primerless) system

  • David Liese,
  • Hans Henning Wenk,
  • Xin Lu,
  • Jochen Kleinen and
  • Gebhard Haberhauer

Beilstein J. Org. Chem. 2020, 16, 2820–2830, doi:10.3762/bjoc.16.232

Graphical Abstract
  • We report new dirhamnolipid ester forming reverse wormlike micelles in nonpolar solvents without the addition of any primer. Therefore, these compounds represent a rare case of a binary system showing this gel-like behavior. In this study, the influence of the concentration of the rhamnolipid ester
  • and the ester alkyl chain length on the rheological properties of the reverse wormlike micelles in toluene was investigated in detail. Highly viscoelastic solutions were obtained even at a relatively low concentration of less than 1 wt %. The phase transition temperatures indicate that the formation
  • of reverse wormlike micelles is favored for dirhamnolipid esters with shorter alkyl chain lengths. Oscillatory shear measurements for the viscoelastic samples reveal that the storage modulus (G') and the loss modulus (G'') cross each other and fit the Maxwell model very well in the low-ω region. As
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Published 19 Nov 2020

Synthesis and investigation of quadruplex-DNA-binding, 9-O-substituted berberine derivatives

  • Jonas Becher,
  • Daria V. Berdnikova,
  • Heiko Ihmels and
  • Christopher Stremmel

Beilstein J. Org. Chem. 2020, 16, 2795–2806, doi:10.3762/bjoc.16.230

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  • , cyclodextrins or micelles [55][56][57][58]. Presumably the radiationless deactivation of the excited state by conformational changes, that leads to the low emission intensity in aqueous solution, is suppressed in the sterically restricted binding site. Therefore, it can be deduced that the increased emission of
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Published 18 Nov 2020

Easy access to a carbohydrate-based template for stimuli-responsive surfactants

  • Thomas Holmstrøm,
  • Daniel Raydan and
  • Christian Marcus Pedersen

Beilstein J. Org. Chem. 2020, 16, 2788–2794, doi:10.3762/bjoc.16.229

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  • hydrophilic and a lipophilic domain, thereby rendering them amphiphilic. This dual functionality gives surfactants unique properties such as being able to stabilize emulsions (emulsifiers) or forming large self-assembled aggregates that can take the shape of, for example, micelles or liposomes [1]. The latter
  • property has been of great interest during the recent decades as the self-assembled aggregates have found the way into many fields of research. Within the field of organic chemistry, the smaller aggregates, micelles, have been exploited as a new reaction medium, making it possible to perform organic
  • reactions in water, thereby giving rise to a greener approach to organic synthesis [2][3]. Furthermore, the micelles act as a mini-reactor in which the reagents exist in a very high concentration, giving cleaner and faster reactions [1]. The larger aggregates, liposomes, have shown great potential as drug
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Published 17 Nov 2020

Enzyme-instructed morphological transition of the supramolecular assemblies of branched peptides

  • Dongsik Yang,
  • Hongjian He and
  • Bing Xu

Beilstein J. Org. Chem. 2020, 16, 2709–2718, doi:10.3762/bjoc.16.221

Graphical Abstract
  • assemblies of the peptides. The attachment of DEDDDLLI sequences to the ε-amine of the lysine residue of a tetrapeptide produces branched peptides that form micelles. Upon the proteolytic cleavage of the branch, catalyzed by proteinase K, the micelles turn into nanofibers. We also found that the acetylation
  • serendipitously found that an enzyme-responsive branched peptide was able to deliver small molecules or proteins to mitochondria efficiently in a cell-specific manner [33]. The branched peptide, which bears FLAG-tag as the branch [32], forms micelles. Certain proteases on the mitochondria of certain cells cleave
  • the branch of the peptide, and such enzymatic proteolysis turns the micelles into nanofibers. This morphological transition (i.e., micelle to nanofiber) releases the cargos into the mitochondria of the cells [33]. These results imply that enzyme-responsive branched peptides can act as responsive
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Published 04 Nov 2020

Morphology-tunable and pH-responsive supramolecular self-assemblies based on AB2-type host–guest-conjugated amphiphilic molecules for controlled drug delivery

  • Yang Bai,
  • Cai-ping Liu,
  • Di Chen,
  • Long-hai Zhuo,
  • Huai-tian Bu and
  • Wei Tian

Beilstein J. Org. Chem. 2019, 15, 1925–1932, doi:10.3762/bjoc.15.188

Graphical Abstract
  • was adjusted to 5.0, accompanied with morphology transitions from FSSAs to spherical self-assemblies (SSAs) due to the pH-induced dissociation of β-CD/BM inclusion complexes (Scheme 1c,d), and the hydrophilic–hydrophobic interaction-induced formation of spherical micelles with BM units as inner
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Published 13 Aug 2019

Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside

  • Dimitri Fayolle,
  • Nathalie Berthet,
  • Bastien Doumeche,
  • Olivier Renaudet,
  • Peter Strazewski and
  • Michele Fiore

Beilstein J. Org. Chem. 2019, 15, 937–946, doi:10.3762/bjoc.15.90

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  • dissolution of compounds 5–8 in PBS (pH 7.4) produced a slightly turbid suspension, suggesting that those molecules formed a mixture of microscopically visible vesicles (diameter >0.5 µm), small vesicles (diameter <0.5 µm) and perhaps micelles (diameter in the nanometer range). However, due to our interest to
  • for all micrographs in this figure. A simplified (and not in scale) representation of the ELLA assay, to study the interaction between GVs or micelles of compound 8 or 5 and WGA. OPD: O-phenylenediamine dihydrochloride; PAA: poly[N-(2-hydroxyethyl)acrylamide]. Inhibition curves for the binding of WGA
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Published 17 Apr 2019

Ammonium-tagged ruthenium-based catalysts for olefin metathesis in aqueous media under ultrasound and microwave irradiation

  • Łukasz Gułajski,
  • Andrzej Tracz,
  • Katarzyna Urbaniak,
  • Stefan J. Czarnocki,
  • Michał Bieniek and
  • Tomasz K. Olszewski

Beilstein J. Org. Chem. 2019, 15, 160–166, doi:10.3762/bjoc.15.16

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  • in the flourishing field of micellar catalysis and the use of surfactants that self-aggregate in water into micelles in which the hydrophobic core provides an environment for effecting homogeneous reactions between organic molecules has been reviewed by Scarso et al. [40] and very recently by
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Published 17 Jan 2019

Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium

  • Nadia Bouzayani,
  • Jamil Kraїem,
  • Sylvain Marque,
  • Yakdhane Kacem,
  • Abel Carlin-Sinclair,
  • Jérôme Marrot and
  • Béchir Ben Hassine

Beilstein J. Org. Chem. 2018, 14, 2923–2930, doi:10.3762/bjoc.14.271

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  • surfactants that can form micelles with a hydrophobic core and a hydrophilic corona. (iii) This clean method afforded compounds 5a–m without the need of additional purification such as column chromatography or recrystallization. (iv) The use of a sealed tube [36][37][38][39][40][41][42][43] obeys to four out
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Published 26 Nov 2018

Synthesis of new p-tert-butylcalix[4]arene-based polyammonium triazolyl amphiphiles and their binding with nucleoside phosphates

  • Vladimir A. Burilov,
  • Guzaliya A. Fatikhova,
  • Mariya N. Dokuchaeva,
  • Ramil I. Nugmanov,
  • Diana A. Mironova,
  • Pavel V. Dorovatovskii,
  • Victor N. Khrustalev,
  • Svetlana E. Solovieva and
  • Igor S. Antipin

Beilstein J. Org. Chem. 2018, 14, 1980–1993, doi:10.3762/bjoc.14.173

Graphical Abstract
  • ratio of the intensities of the first and third bands (373 and 384 nm, respectively) in its emission spectrum [40]. EY, an anionic xanthene dye, also can be used for CAC determination as its absorption spectrum shows a shift of the maximum absorption wavelength (λmax) in the presence of micelles or
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Published 31 Jul 2018

A survey of chiral hypervalent iodine reagents in asymmetric synthesis

  • Soumen Ghosh,
  • Suman Pradhan and
  • Indranil Chatterjee

Beilstein J. Org. Chem. 2018, 14, 1244–1262, doi:10.3762/bjoc.14.107

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  • asymmetric oxidations were examined in 20 mol % cetyltrimethylammonium bromide (CTAB) reversed micelles [25]. Interestingly, Varvoglis et al. synthesized another new class of a chiral reagent 3 using (+)-camphor sulfonic acids as the source of chirality [26] which was used by Chen et al. for the oxidation of
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Published 30 May 2018

Crystal structure of the inclusion complex of cholesterol in β-cyclodextrin and molecular dynamics studies

  • Elias Christoforides,
  • Andreas Papaioannou and
  • Kostas Bethanis

Beilstein J. Org. Chem. 2018, 14, 838–848, doi:10.3762/bjoc.14.69

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  • increased safety in NPC animal models [12]. Moreover, superstructures of cyclodextrins like mono-lactose-appended β-CD [13] and biocleavable pluronic/β-CD-based polyrotaxanes [14] as well as PEG-lipid micelles (DSPE-PEG) in combination with HP-β-CD [15] have shown enhanced therapeutic effects and exhibit a
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Published 11 Apr 2018

Nanoreactors for green catalysis

  • M. Teresa De Martino,
  • Loai K. E. A. Abdelmohsen,
  • Floris P. J. T. Rutjes and
  • Jan C. M. van Hest

Beilstein J. Org. Chem. 2018, 14, 716–733, doi:10.3762/bjoc.14.61

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  • , namely: (polymer) vesicles, micelles, dendrimers and nanogels. The ability and efficiency of catalytic nanoreactors to carry out organic reactions in water, to perform cascade reaction and their ability to be recycled will be discussed. Keywords: catalysis; dendrimers; green chemistry; nanogels
  • ; nanoreactors; micelles; polymersomes; Introduction It is widely acknowledged that “the best solvent is no solvent”; however, running a reaction under neat conditions is very challenging from the points of view of mass transfer and temperature gradients [1][2]. Therefore, sustainable chemical technologies are
  • more achievable. Nanocompartments such as polymersomes [40], micelles [41], dendrimers [42], and nanogels [43][44] represent smart and compact devices to carry out reactions in aqueous media. Besides, their facile recyclability make them very suitable as nanoreactors for a multitude of applications in
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Published 29 Mar 2018

Latest development in the synthesis of ursodeoxycholic acid (UDCA): a critical review

  • Fabio Tonin and
  • Isabel W. C. E. Arends

Beilstein J. Org. Chem. 2018, 14, 470–483, doi:10.3762/bjoc.14.33

Graphical Abstract
  • plane, defining a structure in which the molecule has a polar and an apolar surface. For this reason, these molecules and their derivatives are defined as amphipathic. Bile acids are considered very important molecules for their ability to form micelles in an aqueous environment [22]. Bile acids
  • . In addition, at higher concentrations than the critical micelles concentration (CMC), bile acids tend to form micelles: this phenomenon, due to the amphipathic structure of these molecules, is limiting the availability of free hydroxysteroids in solution. The reported CMCs of bile acids are in the
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Published 20 Feb 2018
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