Synthesis, structure, and mechanical properties of silica nanocomposite polyrotaxane gels

• Kazuaki Kato,
• Daisuke Matsui,
• Koichi Mayumi and
• Kohzo Ito

Beilstein J. Org. Chem. 2015, 11, 2194–2201, doi:10.3762/bjoc.11.238

• by a novel network formed using cyclodextrin-based polyrotaxanes. Covalent bond formation between the cyclic components of polyrotaxanes and the surface of silica nanoparticles (15 nm diameter) resulted in an infinite network structure without direct bonds between the main chain polymer and the

• . These toughness and softness properties are attributable to both the characteristic sliding of polymer chains through the immobilized cyclodextrins on the silica nanoparticle and the entropic contribution of the cyclic components to the elasticity of the gels. Keywords: cyclodextrin; gel; mechanical

• progress. Experimental Materials Crude polyrotaxane consisting of polyethylene glycol (PEG, Mn = 32,000) and α-cyclodextrin (CD) were purchased from Advanced Softmaterials, Inc. The crude polyrotaxane was purified by repeated reprecipitation from its DMSO solution into deionized water. The obtained

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

• .11.224 Abstract The Niemann–Pick type C disease (NPC) is one of inherited lysosomal storage disorders, emerges the accumulation of unesterified cholesterol in endolysosomes. Currently, 2-hydroxypropyl-β-cyclodextrin (HP-β-CyD) has been applied for the treatment of NPC. HP-β-CyD improved

• cholesterol in NPC-like HepG2 cells. These results suggest that Lac-β-CyD may have the potential as a drug for the treatment of hepatosplenomegaly in NPC disease. Keywords: asialoglycoprotein receptor; cholesterol; cyclodextrin; lactose; Niemann–Pick disease type C; Introduction The Niemann–Pick type C

• , etc., through complex formation [5][6]. Recently, 2-hydroxypropyl-β-cyclodextrin (HP-β-CyD) has attracted considerable attention for the treatment of NPC disease [4][7][8][9]. The administration of HP-β-CyD to NPC1-knock out (Npc1−/−) mice has been reported to remarkably prolong the life span of the

Qualitative evaluation of regioselectivity in the formation of di- and tri-6-O-tritylates of α-cyclodextrin

• Keisuke Yoshikiyo,
• Yoshihisa Matsui and
• Tatsuyuki Yamamoto

Beilstein J. Org. Chem. 2015, 11, 1530–1540, doi:10.3762/bjoc.11.168

• -cyclodextrin (CD), AD-isomer, with trityl chloride in pyridine at 55 °C gave 6A,6B,6E-tri-O-trityl-α-CD, the amount of which was only 25% of that of simultaneously formed 6A,6B,6D-tri-O-trityl-α-CD. This indicates that the bulky trityl groups of glucopyranose-A and -D (Glu-A and -D, respectively) in the AD

• supramolecular chemistry, as they allow the preparation of sophisticated concave molecules such as multi- or hetero-functionalized CD derivatives that are important intermediates for the preparation of enzyme mimics [1][2][3][4][5]. The tritylation of cyclodextrin (CD) has attracted much attention, since the

Synthesis and spectroscopic properties of β-triazoloporphyrin–xanthone dyads

• Dileep Kumar Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2015, 11, 1434–1440, doi:10.3762/bjoc.11.155

• photoelectric materials [7][8]. In addition, porphyrins are potentially used as photosensitizers in photodynamic therapy to treat various types of tumors [9][10]. In recent years, many hybrid molecules including porphyrin–C60 [11], porphyrin–quinones [12] and porphyrin–cyclodextrin [13] conjugates were

Synthesis of tripodal catecholates and their immobilization on zinc oxide nanoparticles

• Franziska Klitsche,
• Julian Ramcke,
• Julia Migenda,
• Andreas Hensel,
• Tobias Vossmeyer,
• Horst Weller,
• Silvia Gross and
• Wolfgang Maison

Beilstein J. Org. Chem. 2015, 11, 678–686, doi:10.3762/bjoc.11.77

• an effector was prepared. This triscatecholate might be useful for the construction of diamandoid hydrophobic coatings [44] or for the reversible attachment of cyclodextrins to NPs by the formation of cyclodextrin/adamantane inclusion complexes [45]. Alternatively, acrylamide 4 and bromide 12 [42

• and sulfobetaine) or switchable hydrophobic/hydrophilic layers (reversible formation of adamantane/cyclodextrin inclusion complexes) on bulk metal surfaces or NPs. The potential of these conjugates has been demonstrated through the immobilization of the tripodal PEG-catecholate 3 on ZnO NPs and a

Design, synthesis and photochemical properties of the first examples of iminosugar clusters based on fluorescent cores

• Mathieu L. Lepage,
• Antoine Mirloup,
• Manon Ripoll,
• Fabien Stauffert,
• Anne Bodlenner,
• Raymond Ziessel and
• Philippe Compain

Beilstein J. Org. Chem. 2015, 11, 659–667, doi:10.3762/bjoc.11.74

• ][10]. From 2010, the field has however experienced a major take-off with the discovery of the first strong multivalent effects in glycosidase inhibition observed with DNJ clusters based on β-cyclodextrin or C60 cores showing strong affinity enhancements over the corresponding monomers (up to 610-fold

Synthesis and surface grafting of a β-cyclodextrin dimer facilitating cooperative inclusion of 2,6-ANS

• Lars W. Städe,
• Thorbjørn T. Nielsen,
• Laurent Duroux,
• Reinhard Wimmer,
• Kyoko Shimizu and
• Kim L. Larsen

Beilstein J. Org. Chem. 2015, 11, 514–523, doi:10.3762/bjoc.11.58

• 140, DK-8000 Aarhus, Denmark 10.3762/bjoc.11.58 Abstract A novel β-cyclodextrin (β-CD) dimer was synthesized and surface-grafted by click chemistry onto azide-functionalized quartz surfaces in order to introduce the cooperative features of the β-CD dimer to solid surfaces. Using NMR and fluorescence

• fluorescence spectroscopy that the inclusion of the fluorescent guest into both cavities of the β-CD dimer is maintained when grafted onto a solid surface. Keywords: 2,6-ANS; β-cyclodextrin dimer; silicon dioxide; surface grafting; total internal reflection fluorescence spectroscopy; Introduction Since the

• initial reports [1][2][3][4] of the cooperative effects exerted by β-cyclodextrin (β-CD) dimers, they have been suggested for a wide range of applications, for example, for catalysis [5][6] and photochemistry [7][8], as synthetic enzymes [5] and in general to obtain improved binding affinity (as compared

Electrochemical oxidation of cholesterol

• Jacek W. Morzycki and
• Andrzej Sobkowiak

Beilstein J. Org. Chem. 2015, 11, 392–402, doi:10.3762/bjoc.11.45

• inclusion complex with β-cyclodextrin functionalized graphene and emerged as a cholesterol sensing matrix. Methylene blue was then replaced by the cholesterol molecule and moved out in the buffer solution, where it was detected electrochemically by using the differential pulse voltammetric technique [71

Superstructures with cyclodextrins: Chemistry and applications II

• Gerhard Wenz

Beilstein J. Org. Chem. 2015, 11, 271–272, doi:10.3762/bjoc.11.30

• ]. Many other applications are certain to follow. The 17th International Cyclodextrin Symposium, held in May 2014 in Saarbrücken, Germany provided an overview of the various aspects of CD chemistry, such as organic synthesis, analysis of inclusion compounds, polymeric and colloidal systems, as well as

• smart materials and drug delivery. These contributions to Cyclodextrin Chemistry are collected in this Thematic Series of the Beilstein Journal of Organic Chemistry. Gerhard Wenz Saarbrücken, January 2015

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

• 10.3762/bjoc.11.22 Abstract Background: The aim of this study was to design and evaluate hybrid cyclodextrin (CD) nanocapsules intended for the oral delivery of the anticancer agent camptothecin (CPT) in order to maintain drug stability in the body and to improve its eventual bioavailability. For this

• 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

Properties of cationic monosubstituted tetraalkylammonium cyclodextrin derivatives – their stability, complexation ability in solution or when deposited on solid anionic surface

• Martin Popr,
• Sergey K. Filippov,
• Nikolai Matushkin,
• Juraj Dian and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2015, 11, 192–199, doi:10.3762/bjoc.11.20

• , Czech Republic Department of Chemical Physics and Optics, Faculty of Mathematics and Physics, Charles University in Prague, Ke Karlovu 3, 121 16, Prague 2, Czech Republic 10.3762/bjoc.11.20 Abstract The thermal stability of the monosubstituted cationic cyclodextrin (CD) derivatives PEMEDA-β-CD and

Synthesis and biological evaluation of a novel MUC1 glycopeptide conjugate vaccine candidate comprising a 4’-deoxy-4’-fluoro-Thomsen–Friedenreich epitope

• Manuel Johannes,
• Maximilian Reindl,
• Bastian Gerlitzki,
• Edgar Schmitt and
• Anja Hoffmann-Röder

Beilstein J. Org. Chem. 2015, 11, 155–161, doi:10.3762/bjoc.11.15

• , 12 was dissolved in an aqueous 2-(N-morpholine)ethanesulfonic acid (MES buffer) at pH 4.5 (enzyme activity optimum) and incubated with the enzyme in the presence of solubilizing 2,6-di-O-methyl-ß-cyclodextrin at 25 °C [51]. By virtue of analytical HPLC (UV detection based on Fmoc) and mass

• were quantified by HPLC and expressed as a percentage of the corresponding value observed before exposure to enzyme digestion (t = 0); (A): β-cyclodextrin, MES buffer pH 4.5, 25 °C. ELISA of the antiserum of mouse 2 induced by 4’F-TF-Thr6-MUC1(20)-TTox vaccine 18b; coat: 5 µg/mL 4’F-TF-Thr6-MUC1(20

Formation of nanoparticles by cooperative inclusion between (S)-camptothecin-modified dextrans and β-cyclodextrin polymers

• Thorbjørn Terndrup Nielsen,
• Catherine Amiel,
• Laurent Duroux,
• Kim Lambertsen Larsen,
• Lars Wagner Städe,
• Reinhard Wimmer and
• Véronique Wintgens

Beilstein J. Org. Chem. 2015, 11, 147–154, doi:10.3762/bjoc.11.14

• prepared with a degree of substitution of (S)-camptothecin between 3.1 and 10.2%. The binding properties with β-cyclodextrin and β-cyclodextrin polymers were measured by isothermal titration calorimetry and fluorescence spectroscopy, showing no binding with β-cyclodextrin but high binding with β

• -cyclodextrin polymers. In aqueous solution nanoparticles were formed from association between the (S)-camptothecin–dextran polymers and the β-cyclodextrin polymers. Keywords: (S)-camptothecin; cyclodextrins; fluorescence; nanoparticles; ITC; Introduction Cancer remains to be the major cause of mortality in

• size. Interaction with suitable correspondent polymers with pendent cyclodextrins may form nanoparticles with the target properties. In recent years cyclodextrin (CD) polymer-based drug-delivery systems have attracted much attention in this field [7][8]. CDs are cyclic sugar molecules constituted of

Effects of RAMEA-complexed polyunsaturated fatty acids on the response of human dendritic cells to inflammatory signals

• Éva Rajnavölgyi,
• Renáta Laczik,
• Viktor Kun,
• Lajos Szente and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2014, 10, 3152–3160, doi:10.3762/bjoc.10.332

• Eva Rajnavolgyi Renata Laczik Viktor Kun Lajos Szente Eva Fenyvesi Department of Immunology, University of Debrecen, Egyetem tér 1, Debrecen 4032, Hungary CycloLab Cyclodextrin Research & Development Laboratory Ltd., Illatos út 7, Budapest 1097, Hungary 10.3762/bjoc.10.332 Abstract The n−3 fatty

• study we monitored the effects of α-linoleic acid, eicosapentaenoic acid and docosahexaenoic acid solubilized in a dimethyl sulfoxide (DMSO)/ethanol 1:1 mixture or as complexed by randomly methylated α-cyclodextrin (RAMEA) on the inflammatory response of human monocyte-derived dendritic cells (moDC

• ). The use of RAMEA for enhancing aqueous solubility of n−3 fatty acids has the unambiguous advantage over applying RAMEB (the β-cyclodextrin analog), since there is no interaction with cell membrane cholesterol. In vitro differentiated moDC were left untreated or were stimulated by bacterial

Inclusion of trans-resveratrol in methylated cyclodextrins: synthesis and solid-state structures

• Lee Trollope,
• Dyanne L. Cruickshank,
• Terence Noonan,
• Susan A. Bourne,
• Milena Sorrenti,
• Laura Catenacci and
• Mino R. Caira

Beilstein J. Org. Chem. 2014, 10, 3136–3151, doi:10.3762/bjoc.10.331

• derivatised) to establish their effect on the aqueous solubility of trans-resveratrol and to estimate association constants for complex formation. Keywords: cyclodextrin; inclusion complexes; thermal analysis; trans-resveratrol; X-ray structures; Introduction The naturally occurring phytoalexin trans

Release of β-galactosidase from poloxamine/α-cyclodextrin hydrogels

• César A. Estévez,
• José Ramón Isasi,
• Eneko Larrañeta and
• Itziar Vélaz

Beilstein J. Org. Chem. 2014, 10, 3127–3135, doi:10.3762/bjoc.10.330

• available source of calcium and protein. In this work, gels obtained by complexation of Tetronic 90R4 with α-cyclodextrin loaded with β-galactosidase are proposed as a way to administer the enzyme immediately before or with the lactose-containing meal. Both molecules are biocompatible, can form gels in situ

• , and show sustained erosion kinetics in aqueous media. The complex was characterized by FTIR that evidenced an inclusion complex between the polyethylene oxide block and α-cyclodextrin. The release profiles of β-galactosidase from two different matrices (gels and tablets) of the in situ hydrogels have

• , which can be used as supramolecular drug delivery systems [11]. Thus, cyclodextrin-based physical hydrogels assembled through microcrystalline formation are based upon the aggregation of polypseudorotaxane structures [12]. In the case of reverse Tetronics, α-cyclodextrin (composed of six glucose units

Conjugates of methylated cyclodextrin derivatives and hydroxyethyl starch (HES): Synthesis, cytotoxicity and inclusion of anaesthetic actives

• Lisa Markenstein,
• Antje Appelt-Menzel,
• Marco Metzger and
• Gerhard Wenz

Beilstein J. Org. Chem. 2014, 10, 3087–3096, doi:10.3762/bjoc.10.325

• /bjoc.10.325 Abstract The mono-6-deoxy-6-azides of 2,6-di-O-methyl-β-cyclodextrin (DIMEB) and randomly methylated-β-cyclodextrin (RAMEB) were conjugated to propargylated hydroxyethyl starch (HES) by Cu+-catalysed [2 + 3] cycloaddition. The resulting water soluble polymers showed lower critical solution

• than the corresponding monomeric CD derivatives. Since the binding potentials of these CD conjugates were very high, they are promising candidates for new oral dosage forms of anaesthetic actives. Keywords: anaesthetics; complexation; cyclodextrin; LCST; lower critical solution temperature; midazolam

• solubilized in water to allow further use in oral or parenteral dosage forms as an analgesic drug. Also the uptake of midazolam could be improved by complexation in CD derivatives [37][38]. Results and Discussion Cyclodextrin polymers were synthesized by copper-catalyzed [2 + 3] cycloaddition of methylated

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

• Milo Malanga Mihaly Balint Istvan Puskas Kata Tuza Tamas Sohajda Laszlo Jicsinszky Lajos Szente Eva Fenyvesi CycloLab Cyclodextrin Research and Development Laboratory Ltd, Illatos 7, Budapest, H-1097 Hungary 10.3762/bjoc.10.319 Abstract The fluorescent tagging of cyclodextrin derivatives enlarges

• their spectroscopic properties thus generating chemosensors, biological tools for visualization and sophisticated photoresponsive devices. Cyclodextrin polymers, due to the cooperative interactions, exhibit additional properties compared to their monomeric counterpart. These macromolecules can be

• prepared either in well water-soluble form or as gels of high swelling. Two versatile synthetic strategies for introducing a fluorescent tag (rhodamine, fluorescein, nitrobenzofuran or coumarin) into the water-soluble epichlorohydrin branched cyclodextrin polymers were worked out and compared. The

Modification of physical properties of poly(L-lactic acid) by addition of methyl-β-cyclodextrin

• Toshiyuki Suzuki,
• Ayaka Ei,
• Yoshihisa Takada,
• Hiroki Uehara,
• Takeshi Yamanobe and
• Keiko Takahashi

Beilstein J. Org. Chem. 2014, 10, 2997–3006, doi:10.3762/bjoc.10.318

• PLLA and enhanced the drawability. Keywords: crystallinity; DSC; methyl-β-cyclodextrin; poly(L-lactic acid); Raman spectroscopy; Introduction Poly(L-lactic acid) (PLLA) has attracted attention because it is a biodegradable polymer derived from carbon-neutral resources. However, its melting point (Tm

• interactions, a modified CD may improve the mechanical properties of PLLA. Methyl-β-cyclodextrin (MeCD) is soluble in chloroform, as is PLLA, and the affinity of MeCD for PLLA may be sufficient to improve the mechanical properties of PLLA. In order to analyze the interchain interactions of polymers, it is

Synthesis of uniform cyclodextrin thioethers to transport hydrophobic drugs

• Lisa F. Becker,
• Dennis H. Schwarz and
• Gerhard Wenz

Beilstein J. Org. Chem. 2014, 10, 2920–2927, doi:10.3762/bjoc.10.310

• Lisa F. Becker Dennis H. Schwarz Gerhard Wenz Organic Macromolecular Chemistry, Saarland University, Campus C4.2, 66123 Saarbrücken, Germany 10.3762/bjoc.10.310 Abstract Methyl and ethyl thioether groups were introduced at all primary positions of α-, β-, and γ-cyclodextrin by nucleophilic

• the β-cyclodextrin derivatives exhibit very high binding potentials towards the anaesthetic drugs sevoflurane and halothane. Since the resulting inclusion compounds are highly soluble in water at temperatures ≤37 °C they are good candidates for new aqueous dosage forms which would avoid inhalation

• anaesthesia. Keywords: active pharmaceutical ingredient; binding constant; cyclodextrin; derivatization; gas chromatography; sevoflurane; substitution pattern; Introduction Cyclodextrins (CDs) are cyclic oligomers of α-1,4-linked glucose units. Those CDs consisting of 6, 7, and 8 glucose units are called α

Cyclodextrin–polysaccharide-based, in situ-gelled system for ocular antifungal delivery

• Anxo Fernández-Ferreiro,
• Noelia Fernández Bargiela,
• María Santiago Varela,
• Maria Gil Martínez,
• Maria Pardo,
• Antonio Piñeiro Ces,
• José Blanco Méndez,
• Miguel González Barcia,
• Maria Jesus Lamas and
• Francisco.J. Otero-Espinar

Beilstein J. Org. Chem. 2014, 10, 2903–2911, doi:10.3762/bjoc.10.308

• Pharmacy, University of Santiago de Compostela (USC), Praza Seminario de Estudos Galegos s/n, Santiago de Compostela, 15701, Spain 10.3762/bjoc.10.308 Abstract Fluconazole was studied with two different hydrophilic cyclodextrins (hydroxypropyl-β-cyclodextrin (HPBCD) and sulfobutyl ether-β-cyclodextrin

• polysaccharides gellan gum and κ-carrageenan. This system showed good bioadhesive properties and effective control of fluconazole release. Keywords: cyclodextrins; eye drops; fluconazole; hydroxypropyl-β-cyclodextrin; sulfobutylether-β-cyclodextrin; Introduction Fungal keratitis is a serious disease that can

• -Hydroxypropyl-β-cyclodextrin (HPBCD) and sulfobutyl ether-β-cyclodextrin (SBECD) are two chemically modified cyclodextrins frequently used as vehicles to improve drug solubility. The aim of this work is to obtain an ophthalmic drug delivery system for the release of fluconazole (FC) based on the use of ion

Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimer

• Florian Hamon,
• Claire Blaszkiewicz,
• Marie Buchotte,
• Estelle Banaszak-Léonard,
• Hervé Bricout,
• Sébastien Tilloy,
• Eric Monflier,
• Christine Cézard,
• Laurent Bouteiller,
• Christophe Len and
• Florence Djedaini-Pilard

Beilstein J. Org. Chem. 2014, 10, 2874–2885, doi:10.3762/bjoc.10.304

• -cyclodextrin (β-CD) is known to form supramolecular inclusion complexes with molecules, and such inclusion usually enhances the solubility of water-insoluble substances [1][2][3][4]. Pharmaceutical companies already use these cyclodextrins or their derivatives in their formulations [5][6]. In fact, they have a

• ]. As an exception, Vargas et al. [29] described the synthesis of 1,2,3-triazole-linked azobenzene-cyclodextrin derivatives producing rather good yields but the photoisomerization and inclusion complex properties were not investigated. Here, we report an efficient preparation of a new bis-β-CD with

• with a yield of 49% (Scheme 1) [30]. Then, the carboxylic groups were activated by N-hydroxysuccinimide (NHS) and condensed with mono-6-amino-6-deoxy-β-cyclodextrin (β-CD-NH2) [31] in anhydrous DMF at room temperature. Flash chromatography (C18 column, H2O/MeOH 90:10 to 10:90 v/v in 20 min) afforded

Synthesis of modified cyclic and acyclic dextrins and comparison of their complexation ability

• Kata Tuza,
• László Jicsinszky,
• Tamás Sohajda,
• István Puskás and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2014, 10, 2836–2843, doi:10.3762/bjoc.10.301

• Kata Tuza Laszlo Jicsinszky Tamas Sohajda Istvan Puskas Eva Fenyvesi CycloLab Cyclodextrin R&D Laboratory Ltd, Illatos út 7, Budapest, 1097, Hungary Dipartimento di Scienza e Tecnologia del Farmaco, Universitá di Torino, via P. Giuria 9, Turin, 10125, Italy 10.3762/bjoc.10.301 Abstract We

• ; cyclodextrin; ibuprofen; maltodextrin; maltoheptaose; maltohexaose; maltooctaose; Introduction The complexing ability of amylose to iodine and fatty acids is well known in the literature [1][2][3]. The question is raised whether the maltooligomers containing 6, 7, or 8 glucose units (G6, G7 and G8), derived

• applied for the native compounds. The guest candidates were chlorpheniramine, histidine, ibuprofen, camphoric acid, and chrysanthemic acid. Most of the guest compounds were racemates in order to detect enantiorecognition ability if there is any. In most cases the maltooligomers and the cyclodextrin

A study on the inhibitory mechanism for cholesterol absorption by α-cyclodextrin administration

• Takahiro Furune,
• Naoko Ikuta,
• Yoshiyuki Ishida,
• Hinako Okamoto,
• Daisuke Nakata,
• Keiji Terao and
• Norihiro Sakamoto

Beilstein J. Org. Chem. 2014, 10, 2827–2835, doi:10.3762/bjoc.10.300

• , α-cyclodextrin (α-CD) is reportedly one of the most powerful dietary fibers for decreasing blood cholesterol. However, it is difficult to believe that α-CD directly removes cholesterol because it has a very low affinity for cholesterol and its mechanism of action is less well understood than those

• dietary fibers. The decrease in micellar cholesterol solubility in the FeSSIF was the strongest with α-CD addition. Keywords: α-cyclodextrin; bile salt micelles; cholesterol; lecithin; micellar solubility; Introduction α-Cyclodextrin (α-CD) is a ring molecule composed of six glucose units that has an

Synthesis of an organic-soluble π-conjugated [3]rotaxane via rotation of glucopyranose units in permethylated β-cyclodextrin

• Jun Terao,
• Yohei Konoshima,
• Akitoshi Matono,
• Hiroshi Masai,
• Tetsuaki Fujihara and
• Yasushi Tsuji

Beilstein J. Org. Chem. 2014, 10, 2800–2808, doi:10.3762/bjoc.10.297

• -phenylene) and oligothiophene with a pseudo-linked [3]rotaxane structure by full rotation of glucopyranose units via a flipping (tumbling) mechanism in the π-conjugated guest having two permethylated β-cyclodextrin units at both ends. We also succeeded in the synthesis of an organic-soluble fixed [3

• ; permethylated cyclodextrin; [3]rotaxane; Introduction Insulated molecular wires (IMWs) [1][2], which feature π-conjugated polymer chains covered by protective sheaths, have attracted considerable attention as next-generation mono-molecular electronic devices because of their potential conductivity and

• luminescent properties [3][4][5]. Cyclodextrin (CD) derivatives are widely used as a protective sheath for the synthesis of IMWs because they are easily obtainable and efficient in the inclusion of various polymers into their cavity via hydrophobic interactions in water [6][7]. General methods for the