Size-controlled and redox-responsive supramolecular nanoparticles

• Raquel Mejia-Ariza,
• Gavin A. Kronig and
• Jurriaan Huskens

Beilstein J. Org. Chem. 2015, 11, 2388–2399, doi:10.3762/bjoc.11.260

• according to earlier reports with slight modifications [25][26]. A reaction between 6-monotosyl-β-cyclodextrin (TsCD) and PEI in DMSO was performed using an excess of triethylamine as a base, followed by purification by dialysis. In order to control the stoichiometry of the host and guest moieties, the

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

• crosslinker/DM-β-CD feed ratio = 3/1). The resulting crosslinked DM-β-CD/PDI polymer is water soluble. The polymer product was purified by dialysis (molecular weight cut off = 10,000) against water. A powder of the DM-β-CD/PDI polymer obtained by freeze-drying was easily redispersed in water with the aid of

• . (Japan). The dialysis membrane with a cellulose tube (molecular weight cut-off of 10 kDa) was purchased from the Japan Medical Science Co. Ltd. (Japan) and stored in a moist environment prior to use. Distilled water was used for the purification process. Ultra pure water (Milli-Q) was used for the

• anhydrous DMF (10 mL) for 12 h at 70 °C under an argon atmosphere. The reaction mixture was dropped into water under ice bath cooling to terminate the reaction. The resulting polymer solution was purified by dialysis for three days using a dialysis membrane to remove unreacted DM-β-CD and PDI. The dialysis

Cholesterol lowering effects of mono-lactose-appended β-cyclodextrin in Niemann–Pick type C disease-like HepG2 cells

• Keiichi Motoyama,
• Yumi Hirai,
• Rena Nishiyama,
• Yuki Maeda,
• Taishi Higashi,
• Yoichi Ishitsuka,
• Yuki Kondo,
• Tetsumi Irie,
• Takumi Era and
• Hidetoshi Arima

Beilstein J. Org. Chem. 2015, 11, 2079–2086, doi:10.3762/bjoc.11.224

• ) were dissolved in 3.4 L of 0.2 M borate buffer (pH 7.5) and mixed at room temperature for 24 h. After dialysis using a dialysis membrane, Spectra/pore (MWCO = 1,000), in water at room temperature for 72 h, the sample was concentrated with a rotary evaporator (EYELA N-1000S, Tokyo Rikakikai, Tokyo

Mechanical stability of bivalent transition metal complexes analyzed by single-molecule force spectroscopy

• Manuel Gensler,
• Christian Eidamshaus,
• Maurice Taszarek,
• Hans-Ulrich Reissig and
• Jürgen P. Rabe

Beilstein J. Org. Chem. 2015, 11, 817–827, doi:10.3762/bjoc.11.91

• rupture. Results and Discussion Regarding the synthesis, pyridine nanorod 3, which was also precursor for the synthesis of complex 2a [27], was hydrogenated to receive intermediate 4 (Scheme 1). Subsequent coupling with bifunctional poly(ethylene glycol) (PEG) and purification by dialysis gave compound 5

• purified by dialysis (MW cut-off: 1000 g/mol) against MeOH to provide the pyridine-PEG conjugate 5 (33 mg, 41%) as a colorless solid. Mp 127 °C; 1H NMR (700 MHz, CDCl3) δ 1.54–1.62, 1.64–1.72 (2 m, 2H each, C-2/C-3), 2.62 (m, 2H, 4-H), 3.06 (s, 4H, 1’-H/2’-H), 3.64 (s, OCH2CH2O), 6.94 (t, J = 8.0 Hz, 1H

• , 0.035 mmol) and the resulting mixture was stirred at room temperature under an atmosphere of argon for 9 days. The solvent was evaporated and the residue was purified by dialysis (MW cut-off: 1000 g/mol) against MeOH to provide the pyridine-PEG conjugate 10 (69 mg, 59%) as a colorless solid (mp. 55–58

Multivalent dendritic polyglycerolamine with arginine and histidine end groups for efficient siRNA transfection

• Fatemeh Sheikhi Mehrabadi,
• Hanxiang Zeng,
• Mark Johnson,
• Cathleen Schlesener,
• Zhibin Guan and
• Rainer Haag

Beilstein J. Org. Chem. 2015, 11, 763–772, doi:10.3762/bjoc.11.86

• in specific molar ratios. 1.2 Equivalents of BOP and DIPEA with respect to the amino groups were added to the reaction subsequently. The reaction mixture was stirred at room temperature overnight. This mixture was then transferred directly into a dialysis tube of 1000 MWCO and dialyzed in methanol

• for 2 days. After removing methanol on a rotary evaporator completely, the reaction mixture was treated with a mixture of TFA/DCM/TIPS. The reaction was left running overnight to complete the deprotection. After the deprotection step, dialysis in 0.2 N solution of HCl for two days resulted in the

Multivalent polyglycerol supported imidazolidin-4-one organocatalysts for enantioselective Friedel–Crafts alkylations

• Tommaso Pecchioli,
• Manoj Kumar Muthyala,
• Rainer Haag and
• Mathias Christmann

Beilstein J. Org. Chem. 2015, 11, 730–738, doi:10.3762/bjoc.11.83

• described. A modified tyrosine-based imidazolidin-4-one was grafted to a soluble high-loading hyperbranched polyglycerol via a copper-catalyzed alkyne–azide cycloaddition (CuAAC) reaction and readily purified by dialysis. The efficiency of differently functionalized multivalent organocatalysts 4a–c was

• such as high loading capacity combined with the solubility characteristics of the respective dendrimers [20][21]. As a macromolecule, the supported catalyst can be recovered from the reaction media by selective precipitation, dialysis or filtration techniques, depending on its particular physical

• reaction was monitored by IR spectroscopy and TLC. Purification of the products 4a–c was carried out by washing with aqueous saturated EDTA solution followed by dialysis in methanol/chloroform mixture for 24 h, and then in methanol and chloroform, respectively, for additional 12 h each. The catalyst

Synthesis of multivalent carbohydrate mimetics with aminopolyol end groups and their evaluation as L-selectin inhibitors

• Joana Salta,
• Jens Dernedde and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2015, 11, 638–646, doi:10.3762/bjoc.11.72

• the corresponding sodium salts using a 1 M solution of sodium hydroxide. Subsequent purification by dialysis against water should afford the desired pure polysulfated compounds. We performed the sulfation reactions in deuterated DMF as solvent in order to allow the direct reaction control by 1H NMR

• spectroscopy. In this case no additional equivalents of the sulfating agent were added to the mixture and after dialysis the desired product 33 was isolated in very good yield. The examples depicted in Scheme 5 and Scheme 6 were selected from quite a number of experiments. Often these transformations were not

• exchange DOWEX® Na+ (50WX8-200) column to assure that all sulfuric acid monoesters as well as the excess of the sulfating agent were converted into the corresponding sodium salts. After this filtration a dialysis of the mixture generally afforded pure products. The modified procedure was applied to the O

Formulation development, stability and anticancer efficacy of core-shell cyclodextrin nanocapsules for oral chemotherapy with camptothecin

• Hale Ünal,
• Naile Öztürk and
• Erem Bilensoy

Beilstein J. Org. Chem. 2015, 11, 204–212, doi:10.3762/bjoc.11.22

• permeability. The CD nanocapsules were imaged by scanning electron microscopy (SEM). The concentration of CPT entrapped in nanocapsules was determined by reversed phase HPLC. The in vitro release study of CPT was performed with a dialysis bag method under sink conditions mimicking the gastric and intestinal pH

Synthetic strategies for the fluorescent labeling of epichlorohydrin-branched cyclodextrin polymers

• Milo Malanga,
• Mihály Bálint,
• István Puskás,
• Kata Tuza,
• Tamás Sohajda,
• László Jicsinszky,
• Lajos Szente and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2014, 10, 3007–3018, doi:10.3762/bjoc.10.319

• hydrazine-Pd/C is fast and exhaustive (based on the evaluation of the IR spectra, Figure 3), but because of the laborious work-up (filtration, centrifugation, membrane filtration) and the partial inefficacy of the dialysis purification, this method needed further development. The overall progress of the

• technique due to the strong interaction between the stationary phase and the polymer. In this case liquid/liquid extraction is necessary to remove the bulk of the dye-related byproducts, the hot charcoal treatment can decrease their amounts and the final dialysis step (or ultrafiltration) can further reduce

• -coumarin a series of liquid–liquid extraction steps together with a dialysis cycle must be applied. The CD content of compound 6 determined by 1H NMR is around 70% w/w and the molar ratio between the methyl groups and the CD units is 4.8 (Supporting Information File 1,Figure S19). The substitution of tosyl

Linear-g-hyperbranched and cyclodextrin-based amphiphilic block copolymer as a multifunctional nanocarrier

• Yamei Zhao,
• Wei Tian,
• Guang Yang and
• Xiaodong Fan

Beilstein J. Org. Chem. 2014, 10, 2696–2703, doi:10.3762/bjoc.10.284

• micelles, the release experiments were carried out by dialysis. Figure 6a shows the release profiles of LND from LND-loaded micelles at 37 ºC. Compared with pure LND (without micelles), no significant burst release was observed from LND-loaded micelles. This result indicates that the function of controlled

Synthesis of a resin monomer-soluble polyrotaxane crosslinker containing cleavable end groups

• Ji-Hun Seo,
• Shino Nakagawa,
• Koichiro Hirata and
• Nobuhiko Yui

Beilstein J. Org. Chem. 2014, 10, 2623–2629, doi:10.3762/bjoc.10.274

• mixture was then transferred to a dialysis tube (MWCO 8k) and dialyzed in methanol for 2 d. The methanol solution was then dropped into 50 mL of water, and the white, heterogeneous water suspension was centrifuged at 2000 rpm for 10 min. The obtained precipitate was dispersed in 5 mL of water and freeze

• rt for 3 h. Then, 248 mg of 2-aminoethyl methacrylate hydrochloride (at a molar ratio of 1:12 with respect to α-CD) were added and stirred at rt for 3 d. The reaction mixture was then transferred to a dialysis tube (MWCO 8k), and dialyzed in methanol for 2 d. The methanol solution was then dropped

Multivalent scaffolds induce galectin-3 aggregation into nanoparticles

• Candace K. Goodman,
• Mark L. Wolfenden,
• Pratima Nangia-Makker,
• Anna K. Michel,
• Avraham Raz and
• Mary J. Cloninger

Beilstein J. Org. Chem. 2014, 10, 1570–1577, doi:10.3762/bjoc.10.162

• neutralized solution was placed in a dialysis membrane (MW cutoff 3500 Da) and dialyzed in 1 L of deionized water for 8 h. The water was changed and let stand for a further 8 h twice more. The remaining liquid in the membrane was frozen and lyophilized to give a white fluffy solid. This procedure for

A promising cellulose-based polyzwitterion with pH-sensitive charges

• Thomas Elschner and
• Thomas Heinze

Beilstein J. Org. Chem. 2014, 10, 1549–1556, doi:10.3762/bjoc.10.159

• solvents, like dioxane and CH2Cl2, is decreased and the deprotection has to be carried out in trifluoroacetic acid (TFA), followed by a subsequent anion exchange by dialysis of the polymer solution against aqueous sodium chloride and water. 7b was prepared from the polycation 6 by alkaline treatment, but

Synthesis and solvodynamic diameter measurements of closely related mannodendrimers for the study of multivalent carbohydrate–protein interactions

• Yoann M. Chabre,
• Alex Papadopoulos,
• Alexandre A. Arnold and
• René Roy

Beilstein J. Org. Chem. 2014, 10, 1524–1535, doi:10.3762/bjoc.10.157

• spectrum supported complete conversion. Note that working with peracetylated sugar precursors allows less tedious purification practices as opposed to working with unprotected sugars which often necessitate purification by cumbersome dialysis followed by HPLC treatment. Here again, the complete structural

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

• dimethyl sulfoxide (2 mL), and the solution was poured into a dialysis tube (Cellulose Dialyzer Tubing VT351, molecular weight cut-off: 3500, Nacalai Tesque, Inc., Japan) suffused with distilled water (20 mL). After 2 days of dialysis, the solution was subjected to ultrafiltration at 3,000g for 15 min by

Polyglycerol-functionalized nanodiamond as a platform for gene delivery: Derivatization, characterization, and hybridization with DNA

• Li Zhao,
• Yuki Nakae,
• Hongmei Qin,
• Tadamasa Ito,
• Takahide Kimura,
• Hideto Kojima,
• Lawrence Chan and
• Naoki Komatsu

Beilstein J. Org. Chem. 2014, 10, 707–713, doi:10.3762/bjoc.10.64

• synthesized by the central research laboratory of Shiga University of Medical Science and G*Arg8 was purchased from GL Biochem Ltd. in Shanghai, China. The pBluescript II KS (Agilent Technologies, Inc., Tokyo, Japan) was used as a test pDNA for the hybridization with ND-PG-BPP. Dialysis was carried out by use

• of Spectra/Pro® dialysis membrane, MWCO: 12–14 kDa. FTIR spectral measurements were conducted using IR Prestige-21 (Shimadzu Co.). Samples were prepared by drop-coating of suspension to form a thin film on a stainless alloy plate, and then dried at 70 °C. Hydrodynamic diameters in solution were

End-group-functionalized poly(N,N-diethylacrylamide) via free-radical chain transfer polymerization: Influence of sulfur oxidation and cyclodextrin on self-organization and cloud points in water

• Sebastian Reinelt,
• Daniel Steinke and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 680–691, doi:10.3762/bjoc.10.61

• length on the solubility in water. The molar ratio of [CTA] to [2,2’-azobis(2-methylpropionnitrile) (AIBN)] was kept thereby constant at a ratio of 20 to 1. The final polymers (8a–d and 9a–d) were obtained as colorless solids after dialysis for 7 days. The analytical data of 8a–d and 9a–d are listed in

Aqueous reductive amination using a dendritic metal catalyst in a dialysis bag

• Jorgen S. Willemsen,
• Jan C. M. van Hest and
• Floris P. J. T. Rutjes

Beilstein J. Org. Chem. 2013, 9, 960–965, doi:10.3762/bjoc.9.110

• metal complex to DAB-Am dendrimers via an adapted asymmetric bipyridine ligand. These dendritic catalysts were applied in the aqueous reductive amination of valine while contained in a dialysis bag. Comparable conversions were observed as for the noncompartmentalized counterparts, albeit with somewhat

• ; dialysis; Introduction Cascade catalysis, a bioinspired strategy to conduct multiple consecutive catalytic steps in one pot, is attracting the attention of an increasing number of chemists [1][2][3][4][5][6][7][8][9]. Advantages of cascade processes include a reduction in the number of workup and

• utilized for purification purposes after the reaction [22] and in continuous-flow reactors during the reaction [23]. Dendritic catalysts have also been applied while enclosed in commercially available dialysis bags [24][25][26]. The latter examples, however, were conducted in organic, environmentally

Influence of cyclodextrin on the solubility and the polymerization of (meth)acrylated Triton^® X-100

• Melanie Kemnitz and
• Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 2176–2183, doi:10.3762/bjoc.8.245

• complexed with RAMEB-CD, similar hydrodynamic diameters were observed (Supporting Information File 1, Table S1). To determine the molecular weight of the polymers RAMEB-CD had to be removed first. This was achieved by a dialysis at 45 °C (Table 3). The molecular weights of the polymers 11 and 13 derived

• radical initiator for 24 h. The polymerization reactions were carried out under an oxygen-free N2 atmosphere. The polymers were purified by dialysis for two days. Methacrylic polymer with 1 equiv of RAMEB-CD (10) and 2 equiv of RAMEB-CD (11) Yield 10: 37%; yield 11: 89%; FTIR (diamond, cm−1): ν 3404 (-OH

• polymers 10–13 after dialysis at 45 °C. Supporting Information Supporting Information File 344: Additional ITC results, 2D NMR ROESY and hydrodynamic diameters.

Cyclodextrin-based nanosponges as drug carriers

• Francesco Trotta,
• Marco Zanetti and
• Roberta Cavalli

Beilstein J. Org. Chem. 2012, 8, 2091–2099, doi:10.3762/bjoc.8.235

• protection application, 5-fluorouracile was used as a light-sensitive model drug. β-CD nanosponges were able to incorporate up to 30% of 5-fluorouracile [40]. The in vitro release of 5-fluorouracile, determined by using the dialysis-bag technique at pH 7.4, was about 60% of the encapsulated amount after 2 h

Supramolecular hydrogels formed from poly(viologen) cross-linked with cyclodextrin dimers and their physical properties

• Yoshinori Takashima,
• Yang Yuting,
• Miyuki Otsubo,
• Hiroyasu Yamaguchi and
• Akira Harada

Beilstein J. Org. Chem. 2012, 8, 1594–1600, doi:10.3762/bjoc.8.182

• (40 mL). After being stirred at 100 °C for 2 d, the solution became turbid. The precipitate was collected and washed with acetone three times. The product was purified by dialysis for 4 d to give VP in 20% yield as a brown solid. 1H NMR (D2O, 500 MHz) δ 9.25 (m, 92H, 2-position of bipyridyl in the

Cyanoethylation of the glucans dextran and pullulan: Substitution pattern and formation of nanostructures and entrapment of magnetic nanoparticles

• Kathrin Fiege,
• Heinrich Lünsdorf,
• Sevil Atarijabarzadeh and
• Petra Mischnick

Beilstein J. Org. Chem. 2012, 8, 551–566, doi:10.3762/bjoc.8.63

• monosaccharide derivatives. Nanostructuring of the highly substituted cyanoethylpolysaccharides was performed by dialysis against a non-solvent. In the presence of ferromagnetic iron-oxide nanoparticles, multicore cyanoethylglucan-coated ferromagnetic nanoparticles were formed by selective entrapment. The

• solubility mediator in some reactions. Reaction conditions were varied to obtain scarcely, moderately and highly substituted cyanoethylglucans. Products were isolated and purified by dialysis. Reaction parameters are shown in Table 1. DS values ranging from 0.74 to 2.40 (dextran, CED-1–CED-3) and 0.84 to

• investigated [12][13][14][39]. DMSO solutions of the cyanoethylpolysaccharides CEP-3 (DSGC = 2.42) and CED-3 (DSGC = 2.40) were submitted to dialysis against water. Only the derivatives with a DS value >2 formed regular particles that were stable in water for several weeks without precipitation [13

Chiral recognition of macromolecules with cyclodextrins: pH- and thermosensitive copolymers from N-isopropylacrylamide and N-acryloyl-D/L-phenylalanine and their inclusion complexes with cyclodextrins

• Sabrina Gingter,
• Ella Bezdushna and
• Helmut Ritter

Beilstein J. Org. Chem. 2011, 7, 204–209, doi:10.3762/bjoc.7.27

• bath for 23 h at a constant temperature of 80 °C, the reactions stopped and the products obtained by addition of diethyl ether and washed with diethyl ether. The products were purified by dialysis in a micropore 1000. Yield: 70%, 1H NMR (500 MHz, DMSO-d6) δ (ppm) 8.06–6.49 (m, 1H), 3.84 (s, 10H), 2.14

Miniemulsion polymerization as a versatile tool for the synthesis of functionalized polymers

• Daniel Crespy and
• Katharina Landfester

Beilstein J. Org. Chem. 2010, 6, 1132–1148, doi:10.3762/bjoc.6.130

• miniemulsion [57]. Although the polymerizable moiety was not fixed at the end of the fluorinated chain (the hydrophobe part), the authors claimed that the surfactant was copolymerized with the styrene monomer. They compared the IR spectra (vibration of –CF2 and –CF3) before and after dialysis and estimated

• that 92% of the surfactant remained grafted after dialysis. Nanoparticles and nanocapsules from polymerization of styrene and/or divinylbenzene in miniemulsion could be produced in the presence of a polymerizable derivative of polyethylene oxide/polypropylene oxide which was used to stabilize the

• vesicle or liposome formation or solvent evaporation, the solvent used initially can be removed by dialysis or evaporation and exchanged with water to build the new dispersion medium. The capsules could be obtained with different wall thicknesses depending on the concentration of monomers and with a large

Functionalized polymers: synthesis and properties

• Helmut Ritter

Beilstein J. Org. Chem. 2010, 6, No. 55, doi:10.3762/bjoc.6.55

• fillings, wound dressings, bone cements or hollow fibers for dialysis. Typical examples of such materials include hydrogels and stimulus-responsive polymers which are also the basis of ophthalmic surgery. Thus, our aim in this Thematic Series is to bring together a broad spectrum of reports in the field of