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Search for "amphiphilic" in Full Text gives 127 result(s) in Beilstein Journal of Organic Chemistry.
Potential of acylated peptides to target the influenza A virus
Beilstein J. Org. Chem. 2015, 11, 589–595, doi:10.3762/bjoc.11.65
- by infection inhibition assays, in which we achieved low micromolar inhibition constants against both viral strains. In addition, we compared C18-PeBGF to other published amphiphilic peptide inhibitors, such as the stearylated sugar receptor mimicking peptide (Matsubara et al. 2010), and the “Entry
- limitations of this type of self-assembling IAV inhibitors. Keywords: amphiphilic peptide; antiviral; influenza virus; multivalency; self-assembled structures; Introduction Annually influenza A virus infections cause up to 500.000 deaths worldwide, and are therefore a serious threat, and burden to humans [1
- )-N,N,N',N'-tetramethyluronium tetrafluoroborate (TBTU) as coupling reagent in the presence of diisopropylethylamine (DIPEA) in DMF. Peptides summarized in Table 1 were explored for influenza A virus inhibition. Acylated and other amphiphilic peptides are well known to self-assemble into
Chemoselective O-acylation of hydroxyamino acids and amino alcohols under acidic reaction conditions: History, scope and applications
Beilstein J. Org. Chem. 2015, 11, 446–468, doi:10.3762/bjoc.11.51
- cumbersome copper protective chemistry has continued to dominate in the literature for the preparation of side-chain acrylic derivatives of hydroxyamino acids [5][6][7][8]. Use of chemoselective O-acylation of hydroxyamino acids for preparation of amphiphilic organocatalysts Following the first 2009 report
- on the chemoselective O-acylation of hydroxyproline in CF3CO2H solutions [46], taken together with the potential for preparation of amphiphilic organocatalysts on large scale, in a protective group-free and non-chromatographic manner, the use of acidic O-acylation of hydroxyamino acids within
- asymmetric organocatalysis picked up momentum quite rapidly. Through a series of disclosures, during the time period from 2010 to 2012, Xiangkai Fu and co-workers detailed the preparation of amphiphilic organocatalysts from serine, threonine and cysteine by acidic O-acylation, as well as their use in
Formulation development, stability and anticancer efficacy of core-shell cyclodextrin nanocapsules for oral chemotherapy with camptothecin
Beilstein J. Org. Chem. 2015, 11, 204–212, doi:10.3762/bjoc.11.22
- reason, an amphiphilic cyclodextrin (CD) derivative per-modified on the primary face 6OCAPRO was used as core molecule to form nanocapsules with the nanoprecipitation technique. Nanocapsules were further coated with the cationic polymer chitosan to improve the cellular uptake and interaction with
- as CPT which may contribute to patient quality of life and drug efficacy in cancer therapy. Keywords: amphiphilic cyclodextrin; camptothecin; core-shell; nanocapsule; oral chemotherapy; Introduction Cancer is one of the major fatal diseases in the world and causes abnormal growth of cells spreading
- -(+)-glucopyranose units linked by α-(1,4) glucosidic bonds. The most common advantages of CDs in the pharmaceutical field are to enhance the stability, solubility, and bioavailability of drug molecules [24]. Amphiphilic CDs are derivatives of natural CDs which are chemically obtained and modified on the primary and
Formation of nanoparticles by cooperative inclusion between (S)-camptothecin-modified dextrans and β-cyclodextrin polymers
Beilstein J. Org. Chem. 2015, 11, 147–154, doi:10.3762/bjoc.11.14
- of nanoparticles. It has been shown that CD polymers can form nanoparticles when associated with various amphiphilic polymers such as dextran modified with fatty acid chains [15] or adamantane [16] in aqueous solution. Simply by mixing solutions of β-CD polymers and the hydrophobic-modified dextrans
Release of β-galactosidase from poloxamine/α-cyclodextrin hydrogels
Beilstein J. Org. Chem. 2014, 10, 3127–3135, doi:10.3762/bjoc.10.330
- relative to the initial amount loaded for α-CD, Tetronic 90R4, and pulverized T25a10 tablets were 98.7 ± 6.0, 94.5 ± 6.8 and 97.4 ± 8.8, respectively. Note that even in the case of a mixture of the lactase protein with an amphiphilic block copolymer (such as Tetronic 90R4), the activity is as high as 95
Conjugates of methylated cyclodextrin derivatives and hydroxyethyl starch (HES): Synthesis, cytotoxicity and inclusion of anaesthetic actives
Beilstein J. Org. Chem. 2014, 10, 3087–3096, doi:10.3762/bjoc.10.325
- ; occupancy; polymer; sevoflurane; solubility; starch; Introduction Cyclodextrins (CDs), α(1→4) linked cyclic oligomers of anhydroglucose, are produced nowadays in industrial scale [1]. CDs are able to complex hydrophobic or amphiphilic guest molecules in aqueous phase [2]. β-CD, the seven membered ring
Synthesis of uniform cyclodextrin thioethers to transport hydrophobic drugs
Beilstein J. Org. Chem. 2014, 10, 2920–2927, doi:10.3762/bjoc.10.310
- either nearly insoluble in water or the binding constants are rather low [32][33][34]. We focussed our effort on the design of hydrophilic and/or amphiphilic CD thioethers, because only amphiphilic molecules can form [35][36] or incorporate into bilayer membranes [37][38]. Amphiphilic CD carriers can
- hydrophobic β-CD derivatives [41][42]. Mazzaglia et al. reported on amphiphilic β-CD derivatives with alkyl chains (C2–C16) connected by the thioether linkages to the primary site and a statistical substitution with oligoethylene glycol at secondary sites [43]. Becker et al. describe similar hosts with 2,2,2
Removal of volatile organic compounds using amphiphilic cyclodextrin-coated polypropylene
Beilstein J. Org. Chem. 2014, 10, 2743–2750, doi:10.3762/bjoc.10.290
- , F-59140 Dunkerque, France 10.3762/bjoc.10.290 Abstract Polypropylene nonwovens were functionalised using a self-assembled, amphiphilic cyclodextrin coating and the potential for water purification by removal of pollutants was studied. As benzene is one of the problematic compounds in the Water
- organic compounds are known to form stable inclusion complexes with cyclodextrins. Six different amphiphilic cyclodextrin derivatives were synthesised in order to elucidate whether or not the uptake abilities of the coating depend on the structure of the derivative. Headspace gas chromatography was used
- for quantification of the uptake exploiting the volatile nature of benzene and its derivatives. The capacity was shown to increase beyond the expected stoichiometries of guest–host complexes with ratios of up to 16:1. Keywords: amphiphilic cyclodextrins; polypropylene; static headspace chromatography
Linear-g-hyperbranched and cyclodextrin-based amphiphilic block copolymer as a multifunctional nanocarrier
Beilstein J. Org. Chem. 2014, 10, 2696–2703, doi:10.3762/bjoc.10.284
- achieve controlled drug release. An amphiphilic, triblock polymer (ABC) with hyperbranched polycarbonsilane (HBPCSi) and β-cyclodextrin (β-CD) moieties were first synthesized by the combination of a two-step reversible addition-fragmentation transfer polymerization into a pseudo-one-step hydrosilylation
- exhibit controlled drug release based on the diffusion release mechanism. The novel multifunctional nanocarrier may be applicable to produce highly efficient and specialized delivery systems for drugs, genes, and diagnostic agents. Keywords: amphiphilic block copolymer; cyclodextrin polymer
- contrast properties, raising increasing attention [3][6][7][9][10][11][12][13][14]. Compared with other multifunctional nanocarriers reported in the literature, polymeric micelles formed by amphiphilic block copolymers (ABC) may possess many advantages including water-solubility, nontoxicity, selectivity
A green approach to the synthesis of novel phytosphingolipidyl β-cyclodextrin designed to interact with membranes
Beilstein J. Org. Chem. 2014, 10, 2654–2657, doi:10.3762/bjoc.10.278
- Yong Miao Florence Djedaini-Pilard Veronique Bonnet LG2A FRE-CNRS 3517 Institut de Chimie de Picardie FR CNRS 3085, SFR Condorcet, UPJV, 33 rue St Leu, 80039 Amiens, France 10.3762/bjoc.10.278 Abstract This work reports the synthesis of a new family of mono-substituted amphiphilic cyclodextrins
- with a promising yield. Keywords: fatty ester; green chemistry; lipase; mono-substituted amphiphilic cyclodextrins; peptide Coupling; solvent-free medium; transesterification; Introduction Cyclodextrins (CDs) are sustainable compounds which are particularly interesting in the frame of pharmaceutical
- and cosmetic applications and food industry thanks to their ability to encapsulate the hydrophobic molecules by forming inclusion complexes [1]. Moreover, the modified amphiphilic CDs are able to form nanoparticles without cosolvent or surfactant which could be ideal for drug delivery systems [2]. In
Cyclodextrin-grafted polymers functionalized with phosphanes: a new tool for aqueous organometallic catalysis
Beilstein J. Org. Chem. 2014, 10, 2642–2648, doi:10.3762/bjoc.10.276
- supercritical CO2, ionic liquids or fluorous phases have been used to immobilize the organometallic catalyst [3][4][5]. Co-solvents, surfactants, amphiphilic phosphanes, molecular receptors, polymers or dispersed particles have also been investigated to favour contacts between the aqueous and the organic
Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens
Beilstein J. Org. Chem. 2014, 10, 2603–2622, doi:10.3762/bjoc.10.273
- . Moreover, the concentration used has also a considerable influence on the mechanism. As examples at relatively low concentrations, the amphiphilic agents (surfactants) are membrane permeabilisers whereas at high concentrations, the penetration of these compounds in the cytoplasmic leads to protein
- environment [23]. The toxicity of some biocides has been particularly well described. As examples glutaraldehyde and amphiphilic ammonium have been associated with dermatitis [24][25]. Toxicity, hypersensitivity and irritation have also been reported with other biocides such as formaldehyde [26
- CDs. In this review, the advantages of using CDs in the presence of biocides will be discussed and illustrated throughout several examples from the literature. It is noteworthy that the review is divided in three parts devoted to three biocide families: organic, amphiphilic and heavy-metal biocides
Towards the sequence-specific multivalent molecular recognition of cyclodextrin oligomers
Beilstein J. Org. Chem. 2014, 10, 2428–2440, doi:10.3762/bjoc.10.253
- toxins or viruses and for imaging and targeted drug delivery [3]. Hydrogels which are built up by multivalent host–guest interactions and vesicles of amphiphilic host molecules have been intensively studied for their ability to function as drug delivery systems as well [4][5][6][7][8][9]. Additionally
Supercritical carbon dioxide: a solvent like no other
Beilstein J. Org. Chem. 2014, 10, 1878–1895, doi:10.3762/bjoc.10.196
- through the addition of amphiphilic molecules, such as surfactants or polymers. The domains created are on the nanometer scale leading to the dispersions being transparent or translucent in appearance. The microemulsion appearance does not alter over time. Following this discovery, a vast array of
- another with twin vinyl acetate oligomeric chains (AO-Vac, Table 1, compound 15). Polymers: Amphiphilic block-copolymers are classic examples of molecules which have an inherent ability to adsorb at interfaces and generate aggregation structures. Polymeric micelles may be generated in water and have been
- that have been previously reported due to the amphiphilic nature of their cores; ensuring that both non-polar and polar components could be dissolved in the micellar interiors. Conclusions – factors impacting solubility in CO2 Significant effort has gone into further understanding the origins and
Synthesis of rigid p-terphenyl-linked carbohydrate mimetics
Beilstein J. Org. Chem. 2014, 10, 1749–1758, doi:10.3762/bjoc.10.182
- soluble polyhydroxylated compound 26 (Scheme 11). Due to the amphiphilic character this compound was only soluble in pyridine that makes purification and subsequent reactions fairly difficult. The conversion of the deprotection step was high but the yield after purification was only 30%. The reduction
Influence of perylenediimide–pyrene supramolecular interactions on the stability of DNA-based hybrids: Importance of electrostatic complementarity
Beilstein J. Org. Chem. 2014, 10, 1589–1595, doi:10.3762/bjoc.10.164
- interaction of the two complementary strands is governed mainly by aromatic π–π stacking interactions, hydrogen bonds, and electrostatic repulsion from the negatively-charged sugar phosphate backbone [10][23][24][25][26][27][28]. DNA can be regarded as an amphiphilic polymer in which aromatic residues are
The search for new amphiphiles: synthesis of a modular, high-throughput library
Beilstein J. Org. Chem. 2014, 10, 1578–1588, doi:10.3762/bjoc.10.163
- 2476, Melbourne, VIC 3001, Australia 10.3762/bjoc.10.163 Abstract Amphiphilic compounds are used in a variety of applications due to their lyotropic liquid-crystalline phase formation, however only a limited number of compounds, in a potentially limitless field, are currently in use. A library of
- organic amphiphilic compounds was synthesised consisting of glucose, galactose, lactose, xylose and mannose head groups and double and triple-chain hydrophobic tails. A modular, high-throughput approach was developed, whereby head and tail components were conjugated using the copper-catalysed azide–alkyne
- throughput; library synthesis; Introduction Amphiphilic compounds contain a hydrophilic polar head group and a hydrophobic non-polar side chain. Upon addition of water, these amphiphiles may self-assemble into lyotropic phases that have a variety of uses, from simple household detergents and cleaning
Synthesis and solvodynamic diameter measurements of closely related mannodendrimers for the study of multivalent carbohydrate–protein interactions
Beilstein J. Org. Chem. 2014, 10, 1524–1535, doi:10.3762/bjoc.10.157
- , compared to the one generated in BTAs-centered structures 12 and 21, could explain this observation. Also, these discrepancies might result from the general amphiphilic behavior of this kind of macromolecules [39]. In fact, these glycoclusters shared common structural factors with hydrophilic peripheral
Postsynthetic functionalization of glycodendrons at the focal point
Beilstein J. Org. Chem. 2014, 10, 1482–1487, doi:10.3762/bjoc.10.152
- molecule. This allows for their postsynthetic elaboration to achieve amphiphilic glycolipid mimetics, for example, which eventually can be applied in biology, biophysics, or material science. Here, postsynthetic modification of di- and tetravalent polyether glycodendrons has been explored using
- etherification, thiol-ene reaction and in particular olefin cross metathesis. Keywords: amphiphilic glycomimetics; cross metathesis; glycodendrons; multivalent glycoconjugates; multivalent glycosystems; Introduction In addition to nucleic acids and proteins, molecular life is based on a third important class
- expected in case of the glycodendrons 3–9. However, the so-called “thiol-ene” reaction [10] gave reliable results with both bivalent and tetravalent glycodendrons. The radical addition of mercaptododecane to either 3 or 7, employing AIBN as radical starter, led to the amphiphilic thioethers 12 and 13
Carbohydrate PEGylation, an approach to improve pharmacological potency
Beilstein J. Org. Chem. 2014, 10, 1433–1444, doi:10.3762/bjoc.10.147
- multiarm PEGs, with the aim to increase the loading of the active sugar. Multivalent glycomolecules have proven to mediate or inhibit a variety of biological or pathological processes [17][23]. Review Polyethylene glycol (PEG) derivatives Polyethyleneglycol is an amphiphilic polymer consisting of repeating
An economical and safe procedure to synthesize 2-hydroxy-4-pentynoic acid: A precursor towards ‘clickable’ biodegradable polylactide
Beilstein J. Org. Chem. 2014, 10, 1365–1371, doi:10.3762/bjoc.10.139
- clinical application. More recently, Coumes and coworkers have prepared acetylene functionalized PLAs from precursor 1 and ‘click’ modification of the resulting PLAs with PEG azides provided amphiphilic graft copolymers which form nanorod aggregates in water [19]. The results discussed above indicate the
Glycosystems in nanotechnology: Gold glyconanoparticles as carrier for anti-HIV prodrugs
Beilstein J. Org. Chem. 2014, 10, 1339–1346, doi:10.3762/bjoc.10.136
- corresponding ABC-GNPs showed similar IC50 values of 5 μM and 8 μM, respectively (Figure 3 left and Table 1). Surprisingly, the abacavir derivative seems to induce viral replication. With the presented data we are not able to explain this result, but it may be due to the amphiphilic properties of the drug
Automated solid-phase peptide synthesis to obtain therapeutic peptides
Beilstein J. Org. Chem. 2014, 10, 1197–1212, doi:10.3762/bjoc.10.118
- known to be amphiphilic, non-toxic, little immunogenic, non-antigenic and highly soluble [108]. These beneficial attributes are conveyed to the peptide by covalent attachment leading to an increased size, which lowers renal ultrafiltration [109]. Moreover, the PEGylated peptide is surrounded by a large
Atherton–Todd reaction: mechanism, scope and applications
Beilstein J. Org. Chem. 2014, 10, 1166–1196, doi:10.3762/bjoc.10.117
- design of phosphorus-based amphiphilic compounds. 2. Mechanism of the Atherton–Todd reaction In their initial publication, Atherton and Todd have suggested two possible mechanisms to explain the formation of phosphoramidate [1]. The first one (Scheme 2-i) was based on a two-step sequence with the
The influence of intraannular templates on the liquid crystallinity of shape-persistent macrocycles
Beilstein J. Org. Chem. 2014, 10, 910–920, doi:10.3762/bjoc.10.89
- ]. Amphiphilic macrocycles in aqueous solution have been shown to be able to form vesicles [24][25]. In the bulk state, most of the macrocycles crystallize and some could be explored by single-crystal X-ray analysis [26][27][28]. Heating crystalline macrocycles above the melting point does not always lead
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