Supramolecular chemistry: from aromatic foldamers to solution-phase supramolecular organic frameworks

• Zhan-Ting Li

Beilstein J. Org. Chem. 2015, 11, 2057–2071, doi:10.3762/bjoc.11.222

• shape of the backbones can be readily tuned. The large cavity tolerates the existence of the methoxy groups for the backbones to stack efficiently. Thus, the backbones can stack to form vesicles or gelate organic solvents depending on the appended side chains [42]. Jiang and co-workers prepared methoxy

Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners

• Mohamed Ramadan El Sayed Aly,
• Hosam Ali Saad and
• Shams Hashim Abdel-Hafez

Beilstein J. Org. Chem. 2015, 11, 1922–1932, doi:10.3762/bjoc.11.208

• (V), were used to prepare nontoxic unilamellar vesicles as nanocarriers for gene delivery into Neuro2A cells, which are involved in neurodegenerative diseases [19]. Also, the involvement of cholesterol metal ion complexes in Alzheimer’s disease was reviewed [20]. Cholesterol glycosides are known for

Potential of acylated peptides to target the influenza A virus

• Daniel Lauster,
• Damian Pawolski,
• Julian Storm,
• Kai Ludwig,
• Rudolf Volkmer,
• Henry Memczak,
• Andreas Herrmann and
• Sumati Bhatia

Beilstein J. Org. Chem. 2015, 11, 589–595, doi:10.3762/bjoc.11.65

• unilamellar vesicles (LUV) containing 6.25 nmol DOPC for 30 minutes before virus and erythrocytes were added. In that case the KiHAI increased by a factor of 2–4 (data not shown; notably, a similar increase was found for KiA). This suggests that the potential of inhibitors to prevent hemagglutination must

• synthesized the s2s construct with a terminal rhodamine fluorophore. This compound was mixed with DOPC giant unilamellar vesicles (GUV) or human erythrocytes. In both cases clear membrane labeling could be detected (Figure 6). To assess how strong membrane incorporation of these peptides can perturb membranes

Articulated rods – a novel class of molecular rods based on oligospiroketals (OSK)

• Pablo Wessig,
• Roswitha Merkel and
• Peter Müller

Beilstein J. Org. Chem. 2015, 11, 74–84, doi:10.3762/bjoc.11.11

• ). A similar behaviour is observed in the presence of the double-stranded lipid DOPC, which typically forms vesicles with membrane double layers. To determine the orientation of 32a in the membranes quenching experiments with KI were undertaken (for details see Supporting Information File 1). We found

• be a versatile tool to investigate the STR/FOL equilibrium. We systematically investigated this phenomenon as a function of solvent viscosity, cyclodextrine addition and in the presence of lipids forming micelles and vesicles. In contrast to these noncovalent STR–FOL transitions we also reported on

Preparation and evaluation of cyclodextrin polypseudorotaxane with PEGylated liposome as a sustained release drug carrier

• Kayoko Hayashida,
• Taishi Higashi,
• Daichi Kono,
• Keiichi Motoyama,
• Koki Wada and
• Hidetoshi Arima

Beilstein J. Org. Chem. 2014, 10, 2756–2764, doi:10.3762/bjoc.10.292

• useful as sustained gene transfer carriers [26][27]. Liposomes (LPs) are microscopic phospholipid vesicles with a bilayered membrane structure and are used as a promising drug carrier [28]. When conventional LPs are administrated intravenously, they are coated with plasma proteins, which results in a

Improving ITC studies of cyclodextrin inclusion compounds by global analysis of conventional and non-conventional experiments

• Eléonore Bertaut and
• David Landy

Beilstein J. Org. Chem. 2014, 10, 2630–2641, doi:10.3762/bjoc.10.275

• as the release protocol; it has been introduced by Heerklotz [14] for vesicles and then applied to cyclodextrins [30][31]. Protocol D (called “dilution”) corresponds to the reverse of protocol C: buffer injections within the host–guest mixture induce weak dilutions, thus dissociating a weak part of

Towards the sequence-specific multivalent molecular recognition of cyclodextrin oligomers

• Michael Kurlemann and
• Bart Jan Ravoo

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

• , such vesicles can be modified with bio-active ligands and serve as model systems to mimic biological processes on cell membranes [10][11]. In the field of materials science multivalency has been used to create functional polymers [12][13][14] and self-assembled electronic [15][16][17][18][19][20] or

Specific DNA duplex formation at an artificial lipid bilayer: fluorescence microscopy after Sybr Green I staining

• Emma Werz and
• Helmut Rosemeyer

Beilstein J. Org. Chem. 2014, 10, 2307–2321, doi:10.3762/bjoc.10.240

• ability to form complex nano-architectures [5][6] as well as self-assembling aggregates such as micelles, vesicles [3] and bilayer formation of nucleolipids [7] offers numerous possibilities, e.g., for drug delivery [3]. Simultaneously, the interaction of such nanostructures with lipid membranes becomes

Photo, thermal and chemical degradation of riboflavin

• Muhammad Ali Sheraz,
• Sadia Hafeez Kazi,
• Sofia Ahmed,
• Zubair Anwar and
• Iqbal Ahmad

Beilstein J. Org. Chem. 2014, 10, 1999–2012, doi:10.3762/bjoc.10.208

• reducing the patient compliance [73]. Incorporation into liposomes Entrapment of RF within lipid bilayered vesicles (liposomes) is another approach to improve the photostability of the vitamin and various studies related to such preparations have been conducted [111][137][138][139][140][141][142][143]. The

Supercritical carbon dioxide: a solvent like no other

• Jocelyn Peach and
• Julian Eastoe

Beilstein J. Org. Chem. 2014, 10, 1878–1895, doi:10.3762/bjoc.10.196

• , Na-F7H4 formed rods (CPP = 0.40) and Rb-F7H4 formed vesicles (CPP = 0.52) at w = 12.5 systems. An increase of the w value lead to micellar elongation in the Li+, Na+ and K+ systems and no change in the Rb+ systems. The area of counterion exchange and its impact on surfactant packing in CO2 has been

• -assembly of the surfactant into multilamellar vesicles was observed. Multi-lamellar vesicles consequently transform into ultra-long fibres when [BnNH2∙HCl] ≥ [SBDS]. These ultra-long fibres are visible through optical microscopy and can entangle which would lead to an increase in viscosity. The one

Bis(β-lactosyl)-[60]fullerene as novel class of glycolipids useful for the detection and the decontamination of biological toxins of the Ricinus communis family

• Hirofumi Dohi,
• Takeru Kanazawa,
• Akihiro Saito,
• Keita Sato,
• Hirotaka Uzawa,
• Yasuo Seto and
• Yoshihiro Nishida

Beilstein J. Org. Chem. 2014, 10, 1504–1512, doi:10.3762/bjoc.10.155

• mono- and bis(α-D-mannopyranosyl)-[60]fullerenes in both AFM (atomic force microscopy) and DLS analyses. Probably, the smaller particles are bilayer vesicles that are stable in DMSO and pyridine while they can be destructed in parts by treatment with surfactants such as Triton-X [25]. These nano-sized

• sedimentation. Also upon the addition of ricin, a similar phenomenon could be observed, even though the precipitation took a prolonged time (ca. 15 min) in comparison with the case of RCA120 (ca. 2 min). Apparently, the proteotoxin possesses a lower ability to crosslink the [60]fullerene vesicles into larger

• ). These observations allowed us to expect that the sedimentary phenomenon might arise from species-specific interactions of the Ricinus communis proteins with the lactose cluster arrayed on the surface of the [60]fullerene vesicles. In nature, there are a lot of β-lactose-binding proteins. Not only to the

The influence of intraannular templates on the liquid crystallinity of shape-persistent macrocycles

• Joscha Vollmeyer,
• Ute Baumeister and
• Sigurd Höger

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

Chemical modification allows phallotoxins and amatoxins to be used as tools in cell biology

• Jan Anderl,
• Hartmut Echner and
• Heinz Faulstich

Beilstein J. Org. Chem. 2012, 8, 2072–2084, doi:10.3762/bjoc.8.233

• increasing amounts of the toxin were found in endocytotic vesicles. After 24 h most of the rhodamine-labeled toxin was still in endosomes, while some of it had found its target, as concluded from the decoration of filaments. Phalloidin causes apoptosis of cells Under the microscope, cells treated with

• fibroblasts after 1 h, while after 6 h most of the fluorescent material resides in endocytotic vesicles. This finding confirms the earlier observation [6] that TRITC-phalloidin 3 enters isolated mouse hepatocytes by endocytosis and not through a phalloidin-transporting protein, such as the OATP1B1 present on

Mannose-decorated cyclodextrin vesicles: The interplay of multivalency and surface density in lectin–carbohydrate recognition

• Ulrike Kauscher and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2012, 8, 1543–1551, doi:10.3762/bjoc.8.175

• Ulrike Kauscher Bart Jan Ravoo Organic Chemistry Institute, Westfälische Wilhelms-Universität Münster, Correnstraße 40, 48149 Münster, Germany 10.3762/bjoc.8.175 Abstract Cyclodextrin vesicles are versatile models for biological cell membranes since they provide a bilayer membrane that can easily

• be modified by host–guest interactions with functional guest molecules. In this article, we investigate the multivalent interaction of the lectin concanavalin A (ConA) with cyclodextrin vesicles decorated with mannose–adamantane conjugates with one, two or three adamantane units as well as one or two

• ; cyclodextrins; lectins; molecular recognition; multivalency; vesicles; Introduction The surface modification of materials with carbohydrates has attracted much attention due to the fact that such materials can be compared to and compatible with the cell surface [1]. The “glycocalyx” is a dense layer on the

Design of a novel tryptophan-rich membrane-active antimicrobial peptide from the membrane-proximal region of the HIV glycoprotein, gp41

• Evan F. Haney,
• Leonard T. Nguyen,
• David J. Schibli and
• Hans J. Vogel

Beilstein J. Org. Chem. 2012, 8, 1172–1184, doi:10.3762/bjoc.8.130

• wavelength of the emission maximum. A shift towards lower wavelengths is usually interpreted as the Trp residue residing in a more hydrophobic environment, which may be due to the gp41w peptides oligomerizing in solution. The addition of detergent micelles and large unilamellar vesicles (LUVs) to the peptide

• of the charged and hydrophobic sides of the helix (see below). Therefore, Trp8 likely does not penetrate as deeply into the acyl chains of the vesicles. The blue shifts seen in the gp41w samples were also comparatively small, but this is likely due to the unusual emission maximum measured for this

• evaporated under a stream of nitrogen gas and the resulting lipid cake was placed under vacuum for ~2 h then stored at −20 °C until ready for use. Large unilamellar vesicles (LUVs) were prepared by warming the lipid film to room temperature followed by resuspension in buffer (10 mM Tris, 150 mM NaCl, 1 mM

Partial thioamide scan on the lipopeptaibiotic trichogin GA IV. Effects on folding and bioactivity

• Marta De Zotti,
• Barbara Biondi,
• Cristina Peggion,
• Matteo De Poli,
• Haleh Fathi,
• Simona Oancea,
• Claudio Toniolo and
• Fernando Formaggio

Beilstein J. Org. Chem. 2012, 8, 1161–1171, doi:10.3762/bjoc.8.129

• [Leu11-OMe] trichogin GA IV and its monothionated analogues were tested by measuring the induced leakage of 5(6)-carboxyfluorescein (CF) entrapped in small unilamellar vesicles (SUVs) [65]. For this investigation, the overall negatively charged 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE)/1,2

• cycles of energy minimization by using a NOE force constant of 50 kcal/mol. The generated structures were visualized with the MOLMOL [74] (version 2K.2) program. Small unilamellar vesicles (SUVs) preparation DOPE and DOPG were purchased from Avanti Polar Lipids, Inc. (Alabaster, AL). The preparation of

• SUVs was performed in a similar way as described in reference [59]. Leakage from lipid vesicles The peptide-induced leakage from SUVs was measured at 293 K by using the CF-entrapped vesicle technique [65] and a Perkin Elmer model MPF-66 spectrofluorimeter. SUVs were prepared as described above. The

Planar-bilayer activities of linear oligoester bolaamphiphiles

• Jonathan K. W. Chui,
• Thomas M. Fyles and
• Horace Luong

Beilstein J. Org. Chem. 2011, 7, 1562–1569, doi:10.3762/bjoc.7.184

• alkyl compounds. These were expected to be active in voltage-clamp experiments, as close analogues to the phthalate compounds were found to be active in vesicles and planar bilayers [12], and the activities of the solid-phase compounds in vesicle experiments were previously established [13]. Results and

Oxalyl retro-peptide gelators. Synthesis, gelation properties and stereochemical effects

• Janja Makarević,
• Milan Jokić,
• Leo Frkanec,
• Vesna Čaplar,
• Nataša Šijaković Vujičić and
• Mladen Žinić

Beilstein J. Org. Chem. 2010, 6, 945–959, doi:10.3762/bjoc.6.106

• revealed that gelator assemblies of various morphologies, including fibers and fiber bundles of diverse diameters, helical fibers or ribbons, tapes and nano-tubules, sometimes simultaneously present with micelles or vesicles, could be found [17][18][19][20][21][22][23]. For many gel systems evidence for

Molecular recognition of organic ammonium ions in solution using synthetic receptors

• Andreas Späth and
• Burkhard König

Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32

Self-association of an indole based guanidinium-carboxylate-zwitterion: formation of stable dimers in solution and the solid state

• Carolin Rether,
• Wilhelm Sicking,
• Roland Boese and
• Carsten Schmuck

Beilstein J. Org. Chem. 2010, 6, No. 3, doi:10.3762/bjoc.6.3

• aromatic scaffolds such as benzene or furan instead of pyrrole or with an amidinium cation instead of a guanidinium cation was also confirmed by DFT calculations [14]. Zwitterion 1 has thus found widespread application in the formation of self-assembled nanostructures such as vesicles or supramolecular

New diarylmethanofullerene derivatives and their properties for organic thin- film solar cells

• Daisuke Sukeguchi,
• Surya Prakash Singh,
• Mamidi Ramesh Reddy,
• Hideyuki Yoshiyama,
• Rakesh A. Afre,
• Yasuhiko Hayashi,
• Hiroki Inukai,
• Tetsuo Soga,
• Shuichi Nakamura,
• Norio Shibata and
• Takeshi Toru

Beilstein J. Org. Chem. 2009, 5, No. 7, doi:10.3762/bjoc.5.7

• properties as acceptors, but it is still important to study the structure-efficiency relationship of the fullerene structure in order to develop highly efficient OPVs. The design of highly soluble derivatives of PCBM has also attracted much attention because 3D architectures such as vesicles and fibers are