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Search for "amphiphilic" in Full Text gives 133 result(s) in Beilstein Journal of Organic Chemistry.

Binding abilities of a chiral calix[4]resorcinarene: a polarimetric investigation on a complex case of study

  • Marco Russo and
  • Paolo Lo Meo

Beilstein J. Org. Chem. 2017, 13, 2698–2709, doi:10.3762/bjoc.13.268

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  • occurring in host–guest complex formation processes involving calixarenes in general. This can be particularly useful, even because CAP and structurally related ligands might find various interesting applications, due to their amphiphilic character, chirality and coordination ability towards metal cations
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Published 15 Dec 2017

Phosphonic acid: preparation and applications

  • Charlotte M. Sevrain,
  • Mathieu Berchel,
  • Hélène Couthon and
  • Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2017, 13, 2186–2213, doi:10.3762/bjoc.13.219

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  • phosphonic acid function and its ability to be ionized in water render this group attractive to design the polar head group of anionic amphiphilic compounds [25][26] or polymeric-based amphiphilic derivatives [27]. This type of compound was used as surfactant to stabilize colloidal solutions of nanocrystals
  • using bromotrimethylsilane followed by methanolysis. This two-step methodology (1. BrSiMe3; 2. MeOH or H2O) was also applied to prepare macromolecules functionalized with phosphonic acid functional groups. For instance, a cyclodextrine derivative (compound 60 [177], Figure 19), amphiphilic compounds
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Published 20 Oct 2017

Superstructures with cyclodextrins: Chemistry and applications IV

  • Gerhard Wenz

Beilstein J. Org. Chem. 2017, 13, 2157–2159, doi:10.3762/bjoc.13.215

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  • , buckminsterfullerene C60 was covalently linked to two γ-CD rings [14]. This conjugate is highly soluble in water because it forms a sandwich-like self-complex, which makes it particularly useful as a sensitizer for singlet oxygen 1O2 generation [14]. Amphiphilic CD derivatives with oligoethylene oxide side chains form
  • ]. The group of Ravoo also conjugated arylazopyrazoles to amphiphilic cyclodextrin derivatives that form vesicles triggered by light [17]. A star-shaped polycationic CD derivative with many breakable, intrinsic, disulfide linkages forms nanoparticles with messenger RNA and drugs and is particularly
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Editorial
Published 18 Oct 2017

Chemical systems, chemical contiguity and the emergence of life

  • Terrence P. Kee and
  • Pierre-Alain Monnard

Beilstein J. Org. Chem. 2017, 13, 1551–1563, doi:10.3762/bjoc.13.155

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  • association with the interface of chemical systems. For instance, the activity of an RNA polymerase ribozyme was improved when the various RNA compounds of the system (the ribozyme, the template/primer) were derivatized with amphiphilic moieties and co-associated within micelle structures [69]. Although no
  • ]. Such vesicles with associated ribozymes could eventually prove to be novel functional chemical systems. The production of fatty acids from non-amphiphilic picolylesters performed using a photochemical reaction involving a ruthenium tris(bipyridine), functioning as photosensitizer and redox catalyst
  • -existing structures [94][95] has been experimentally exploited either by adding more amphiphiles at a pace that prevents the de novo formation of novel structures [17] or by adding amphiphile precursors that had to be converted within the structures into amphiphilic molecules themselves [83][96][97
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Published 07 Aug 2017

2-Methyl-2,4-pentanediol (MPD) boosts as detergent-substitute the performance of ß-barrel hybrid catalyst for phenylacetylene polymerization

  • Julia Kinzel,
  • Daniel F. Sauer,
  • Marco Bocola,
  • Marcus Arlt,
  • Tayebeh Mirzaei Garakani,
  • Andreas Thiel,
  • Klaus Beckerle,
  • Tino Polen,
  • Jun Okuda and
  • Ulrich Schwaneberg

Beilstein J. Org. Chem. 2017, 13, 1498–1506, doi:10.3762/bjoc.13.148

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  • rhodium-based biohybrid catalyst. Unlike commonly used detergents such as sodium dodecyl sulfate or polyethylene polyethyleneglycol, MPD does not form micelles in solution. Molecular dynamics simulations revealed the effect and position of stabilizing MPD molecules. The advantage of the amphiphilic MPD
  • over micelle-forming detergents is demonstrated in the polymerization of phenylacetylene, showing a ten-fold increase in yield and increased molecular weights. Keywords: amphiphilic molecule 2-methyl-2,4-pentanediol; hybrid catalyst; phenylacetylene polymerization; refolding agents; transmembrane
  • hydrophobic micelle core. Recently, the small amphiphilic alcohol 2-methyl-2,4-pentanediol (MPD) was shown to successfully stabilize membrane proteins and enable characterization of protein modifications [33][34]. Polymerization of phenylacetylene in the presence of MPD molecules as refolding agent was
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Published 31 Jul 2017

Glycoscience@Synchrotron: Synchrotron radiation applied to structural glycoscience

  • Serge Pérez and
  • Daniele de Sanctis

Beilstein J. Org. Chem. 2017, 13, 1145–1167, doi:10.3762/bjoc.13.114

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  • offers another example of difficulty in terms of single crystal growth. Glycolipids (or lipo-oligosaccharides) comprise a carbohydrate moiety covalently linked to a lipid that confers on them an amphiphilic character, which makes them reluctant to crystallize. One member of the family is tricolorin A (L
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Published 14 Jun 2017

From chemical metabolism to life: the origin of the genetic coding process

  • Antoine Danchin

Beilstein J. Org. Chem. 2017, 13, 1119–1135, doi:10.3762/bjoc.13.111

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  • function associated to this view is that the cell separates between an inside and an outside. In 1935, James Danielli proposed with Hugh Davson that this embodiment was achieved by formation of a bilayer made of amphiphilic lipid molecules [11]. This process is entropy-driven (life belongs to physics, it
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Published 12 Jun 2017

Correlation of surface pressure and hue of planarizable push–pull chromophores at the air/water interface

  • Frederik Neuhaus,
  • Fabio Zobi,
  • Gerald Brezesinski,
  • Marta Dal Molin,
  • Stefan Matile and
  • Andreas Zumbuehl

Beilstein J. Org. Chem. 2017, 13, 1099–1105, doi:10.3762/bjoc.13.109

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  • is a structural similarity between the flipper probes and cholesterol with both molecules being amphiphilic and flat. This called for a closer look at the influence of both molecules on phospholipid membrane organization (see Figure 4). For DPPC, the first-order phase transition between the
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Published 08 Jun 2017

Glyco-gold nanoparticles: synthesis and applications

  • Federica Compostella,
  • Olimpia Pitirollo,
  • Alessandro Silvestri and
  • Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

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  • thio-amphiphilic linker to impart improved solubility and flexibility to the glycosyl-ligand. UV–vis spectroscopy and dynamic light scattering measurements have been exploited to detect at low picomolar concentrations lactose-AuNP, mannose-AuNP and GlcNAc-AuNP interactions with their cognate lectins
  • peanut agglutinin [25]. In this case, the glycosyl residue is not coated on the gold surface by means of a thiol moiety but exploiting the strain-promoted azide–alkyne cycloaddition (SPAAC) to covalently link an azido galactoside on a lipid cyclooctyne. In this manner, the amphiphilic glyco-lipid can be
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Published 24 May 2017

Aggregation behaviour of a single-chain, phenylene-modified bolalipid and its miscibility with classical phospholipids

  • Simon Drescher,
  • Vasil M. Garamus,
  • Christopher J. Garvey,
  • Annette Meister and
  • Alfred Blume

Beilstein J. Org. Chem. 2017, 13, 995–1007, doi:10.3762/bjoc.13.99

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  • behaviour; nanofibres; self-assembly; Introduction Bolalipids are amphiphilic molecules consisting of two hydrophilic headgroups attached to both ends of a long hydrocarbon spacer [1]. The hydrophobic spacer is composed of either a single alkyl chain or two chains connected via a glycerol moiety. These
  • DPPC/DHPC systems [49], or for mixtures of phospholipids with other amphiphilic substances, e.g., in PEG-stabilized bilayer systems [50][51], for phospholipids with membrane scaffold proteins [52][53] or in combination with copolymers [54][55], or for DPPC in mixture with a T-shaped amphiphile [56
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Published 23 May 2017

Lipids: fatty acids and derivatives, polyketides and isoprenoids

  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2017, 13, 793–794, doi:10.3762/bjoc.13.78

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  • , sphingolipids and glycolipids. Lipids also constitute important post-translational protein modifications in lipoproteins. The amphiphilic nature of compounds such as phospholipids with a polar headgroup and a long apolar chain results in the spontaneous formation of lipid bilayers in aqueous environments. This
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Editorial
Published 27 Apr 2017

Conjecture and hypothesis: The importance of reality checks

  • David Deamer

Beilstein J. Org. Chem. 2017, 13, 620–624, doi:10.3762/bjoc.13.60

Graphical Abstract
  • ]. There are several advantages to using evaporation in this regard. First, simply concentrating potential reactants adds significant free energy to a system that can be used to drive condensation reactions [23]. Furthermore, if amphiphilic compounds are present they can organize and concentrate reactants
  • metabolism and polymerization. Products of reactions should accumulate within the site rather than dispersing into the bulk phase environment. Biologically relevant polymers are synthesized with chain lengths sufficient to act as catalysts or incorporate genetic information. If amphiphilic compounds are
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Published 28 Mar 2017

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

  • Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

Graphical Abstract
  • complexes with various biomolecules including lipids, carbohydrates, proteins and nucleic acids. In this section, some biomolecule/CD inclusion complexes are presented. i) Complexation of lipids and consequences Lipids are hydrophobic or amphiphilic molecules very diverse, including, among other fats, waxes
  • , sterols, fat-soluble vitamins, phospholipids, mono-, di- and triglycerides, etc. Their amphiphilic nature causes the molecules of certain lipids to organize into liposomes when they are in aqueous medium. This property allows the formation of biological membranes. Indeed, cells and organelles membranes
  • prenols, which are produced from condensation of isoprene units [54]. These compounds can be easily included inside the CDs because they are hydrophobic or amphiphilic molecules. As mentioned earlier, and as it will become exceeding clear throughout the following sections, the majority of research
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Published 07 Dec 2016

A self-assembled cyclodextrin nanocarrier for photoreactive squaraine

  • Ulrike Kauscher and
  • Bart Jan Ravoo

Beilstein J. Org. Chem. 2016, 12, 2535–2542, doi:10.3762/bjoc.12.248

Graphical Abstract
  • significant potential for photodynamic therapy. Herein we report that squaraines can be immobilized on a self-assembled nanocarrier composed of amphiphilic cyclodextrins to enhance their photochemical activity. To this end, a squaraine was equipped with two adamantane moieties that act as anchors for the
  • -assembled from amphiphilic cyclodextrin [27]. Given their negligible toxicity cyclodextrins have been utilized as carriers in a number of studies [28][29]. Amphiphilic cyclodextrins substituted with hydrophobic alkyl groups on the primary side and hydrophilic oligo(ethylene glycol) units on the secondary
  • . Amphiphilic β-cyclodextrins substituted with 7 dodecylsulfide groups on the primary side and 7 oligo(ethylene glycol) units on the secondary side were obtained via a straightforward three step synthesis as described [27][30]. A thin film of these amphiphiles was obtained by evaporation of a chloroform
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Published 25 Nov 2016

Efficient mechanochemical synthesis of regioselective persubstituted cyclodextrins

  • Laszlo Jicsinszky,
  • Marina Caporaso,
  • Katia Martina,
  • Emanuela Calcio Gaudino and
  • Giancarlo Cravotto

Beilstein J. Org. Chem. 2016, 12, 2364–2371, doi:10.3762/bjoc.12.230

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  • -CD derivatives are used in siRNA delivery and gene therapy [6]. The alkyl chain, usually C10–C16, makes the product very amphiphilic, which means that it is difficult to purify not only from possible byproducts but also from the reagents. Additionally, sulfur-containing organic compounds can form
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Published 10 Nov 2016

Mutagenic activity of quaternary ammonium salt derivatives of carbohydrates

  • Barbara Dmochowska,
  • Karol Sikora,
  • Anna Woziwodzka,
  • Jacek Piosik and
  • Beata Podgórska

Beilstein J. Org. Chem. 2016, 12, 1434–1439, doi:10.3762/bjoc.12.138

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  • or aromatic). Mostly, one of the aliphatic or aromatic residues possesses hydrophobic properties, whereas the nitrogen group is hydrophilic. The QAS molecules have a typical head/tail structure determining their amphiphilic character [5]. QASs find application in many fields of everyday life, and
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Published 12 Jul 2016

From N-vinylpyrrolidone anions to modified paraffin-like oligomers via double alkylation with 1,8-dibromooctane: access to covalent networks and oligomeric amines for dye attachment

  • Daniela Obels,
  • Melanie Lievenbrück and
  • Helmut Ritter

Beilstein J. Org. Chem. 2016, 12, 1395–1400, doi:10.3762/bjoc.12.133

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  • thermo- [18] or/and pH [19] responsive polymers. Besides classical alkylation reactions, Reinecke et al. performed ring-opening reactions to insert functional groups and aromatic side chains [20][21]. Furthermore, they investigated the formation of homogeneous [22] and amphiphilic [23] N-VP networks
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Published 06 Jul 2016

Synthesis of a deuterated probe for the confocal Raman microscopy imaging of squalenoyl nanomedicines

  • Eric Buchy,
  • Branko Vukosavljevic,
  • Maike Windbergs,
  • Dunja Sobot,
  • Camille Dejean,
  • Simona Mura,
  • Patrick Couvreur and
  • Didier Desmaële

Beilstein J. Org. Chem. 2016, 12, 1127–1135, doi:10.3762/bjoc.12.109

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  • , the use of fluorescent probes requires the covalent binding of large dye molecules (bodipy, cyanine, rhodamine etc, ...) to the drug conjugate, thus potentially modifying its physicochemical profile as well as the in vivo fate and the pharmacological activity. A simple encapsulation of an amphiphilic
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Published 06 Jun 2016

Stimuli-responsive HBPS-g-PDMAEMA and its application as nanocarrier in loading hydrophobic molecules

  • Yongsheng Chen,
  • Li Wang,
  • Haojie Yu,
  • Zain-Ul-Abdin,
  • Ruoli Sun,
  • Guanghui Jing,
  • Rongbai Tong and
  • Zheng Deng

Beilstein J. Org. Chem. 2016, 12, 939–949, doi:10.3762/bjoc.12.92

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  • aggregates were capable to encapsulate small hydrophobic molecules. These newly prepared HBPS-g-PDMAEMA nanocarriers might be used in, e.g., medicine or catalysis. Keywords: amphiphilic polymer; hyperbranched polystyrene; phase transition; poly[2-(dimethylamino)ethyl methacrylate] (PDMAEMA); stimuli
  • -responsive nanocarriers; Introduction Stimuli-responsive polymers have attracted much attention due to their broad applications including drug controlled release [1][2][3][4][5], sensing [6][7] and 4D printing [8][9]. Nanocarriers prepared from amphiphilic stimuli-responsive polymers are promising
  • blocking hydrophilic PDMAEMA chains on a hydrophobic chain. These amphiphilic polymers may aggregate in water to form nanoparticles having stimuli-responsive properties. Different hydrophobic segments with different microstructures give the aggregates adjustable properties that can be used for various
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Published 10 May 2016

Aggregation behavior of amphiphilic cyclodextrins in a nonpolar solvent: evidence of large-scale structures by atomistic molecular dynamics simulations and solution studies

  • Giuseppina Raffaini,
  • Fabio Ganazzoli and
  • Antonino Mazzaglia

Beilstein J. Org. Chem. 2016, 12, 73–80, doi:10.3762/bjoc.12.8

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  • nanoaggregates even in apolar solvents. Keywords: aggregation; amphiphilic cyclodextrins; molecular dynamics; nanoparticles; self-assembly; simulations; Introduction Amphiphilic cyclodextrins (aCD) are a class of molecules highly investigated for their self-assembly properties and inherent potential
  • . Furthermore, as the technique is highly sensitive to the aggregates presence, it was not possible to exclude the presence of even nanometric-sized clusters apart from the bigger aggregates [13]. Conclusion Amphiphilic cyclodextrins (aCD) are almost invariably investigated in a water environment for their
  • scattering investigations show that, indeed also in a nonpolar solvent such as dichloromethane, these amphiphilic cyclodextrins give rise to quite well defined aggregates, or nanostructures, having a hydrodynamic radius of about 80 nm and a relatively modest polydispersity. This result obtained with a
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Published 14 Jan 2016

Supramolecular polymer assembly in aqueous solution arising from cyclodextrin host–guest complexation

  • Jie Wang,
  • Zhiqiang Qiu,
  • Yiming Wang,
  • Li Li,
  • Xuhong Guo,
  • Duc-Truc Pham,
  • Stephen F. Lincoln and
  • Robert K. Prud’homme

Beilstein J. Org. Chem. 2016, 12, 50–72, doi:10.3762/bjoc.12.7

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  • carboxylate on average. This was attributed to aggregation of the dimers as a consequence of their amphiphilic nature, complexation of the octamethylene linker in the β-CD dimer annuli, and hydrogen bonding interactions between their β-CD annuli. The 1:1 complexation constants, 10−4K11 = 7.96, 2.32 and 26.42
  • chain such that the uncomplexed portions of the PEG chains are too short for significant interchain interaction to form a water soluble network [82][86][88]. However, when a hydrophobic adamantyl group is substituted onto one end of a low molecular weight PEG chain to form amphiphilic AD-PEG, it is
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Published 12 Jan 2016

Recent advances in metathesis-derived polymers containing transition metals in the side chain

  • Ileana Dragutan,
  • Valerian Dragutan,
  • Bogdan C. Simionescu,
  • Albert Demonceau and
  • Helmut Fischer

Beilstein J. Org. Chem. 2015, 11, 2747–2762, doi:10.3762/bjoc.11.296

Graphical Abstract
  • , amphiphilic Ru-modified triblock copolymers have been produced from biocompatible and bioconjugatable oxanorbornene monomers. By extending the above ROMP methodology, Sleiman et al. managed to synthesize the Ru triblock copolymers 25 and 26 (Scheme 11), and examined their self-assembling into micelles in
  • norbornene monomers substituted with rhodocenium units and their controlled polymerization, by two parallel routes (ROMP and RAFT), to rhodocenium-containing metallopolymers. ROMP of both triazolyl-rhodocenium monomers, 40 and 42, proceeded productively and in a living fashion to yield amphiphilic
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Published 28 Dec 2015

Smart molecules for imaging, sensing and health (SMITH)

  • Bradley D. Smith

Beilstein J. Org. Chem. 2015, 11, 2540–2548, doi:10.3762/bjoc.11.274

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  • ”. In 2003, Houk and coworkers published a survey of all known natural and synthetic host/guest binding systems and concluded that the best predictor of strong affinity is the amount of solvent accessible surface area that is buried upon binding [48]. Typically, this surface area is amphiphilic; that is
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Published 10 Dec 2015

Aggregation behaviour of amphiphilic cyclodextrins: the nucleation stage by atomistic molecular dynamics simulations

  • Giuseppina Raffaini,
  • Antonino Mazzaglia and
  • Fabio Ganazzoli

Beilstein J. Org. Chem. 2015, 11, 2459–2473, doi:10.3762/bjoc.11.267

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  • report a theoretical study of the aggregation of a few amphiphilic cyclodextrins carrying hydrophobic thioalkyl groups and hydrophilic ethylene glycol moieties at opposite rims, focusing on the initial nucleation stage in an apolar solvent and in water. The study is based on atomistic molecular dynamics
  • methods with a “bottom up” approach that can provide important information about the initial aggregates of few molecules. The focus is on the interaction pattern of amphiphilic cyclodextrin (aCD), which may interact by mutual inclusion of the substituent groups in the hydrophobic cavity of neighbouring
  • correlating their structures with the pharmaceutical properties. Keywords: aggregation; amphiphilic cyclodextrins; micelles; molecular dynamics simulations; nanoparticles; self-assembly; Introduction Inclusion complexes with supramolecular structures formed by native or modified cyclodextrins (CDs) are
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Published 07 Dec 2015

Preparation of Pickering emulsions through interfacial adsorption by soft cyclodextrin nanogels

  • Shintaro Kawano,
  • Toshiyuki Kida,
  • Mitsuru Akashi,
  • Hirofumi Sato,
  • Motohiro Shizuma and
  • Daisuke Ono

Beilstein J. Org. Chem. 2015, 11, 2355–2364, doi:10.3762/bjoc.11.257

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  • DM-β-CD polymers bearing a [MDI or PDI]/[DM-β-CD] feed ratio of more than three has a lipophilic nature, they show a poor hydrophilicity. Controlling the degree of crosslinking should provide an appropriate balance between the hydrophilicity and hydrophobicity, generating an amphiphilic crosslinked
  • CD polymer, which can be dispersed in water as well as in nonpolar solvents. This amphiphilic polymer should realize water-swellable hydrogel nanoparticles containing CDs (CD nanogels). In this paper, we describe the preparation of Pickering emulsions using CD nanogels composed of crosslinked DM-β-CD
  • the oil droplets from coalescence. Conclusion Amphiphilic CD nanogels, which are a new class of soft hydrogel nanoparticles, were prepared by crosslinking DM-β-CDs with PDI followed by the immersion in water. The DLS study shows that the primary CD nanogels (30–50 nm in diameter) assemble into larger
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Published 30 Nov 2015
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