Superstructures with cyclodextrins: Chemistry and applications II

Editor: Prof. Gerhard Wenz
Universität des Saarlandes

Cyclodextrins are cyclic oligomeres of anhydroglucose. Since they can be produced through the enzymatic degradation of starch on an industrial scale with high purity, they are now considered to be the most interesting class of organic host molecules. Furthermore, α- and γ-cyclodextrins are known to be nontoxic and are approved as food additives. Since cyclodextrins are soluble in water and able to solubilize hydrophobic active ingredients, they are broadly used in biomedical applications. They are also well known to complex suitable monomeric and polymeric guest molecules, leading to supramolecular structures and topological compounds. The solubility and stability of cyclodextrin complexes are controllable through the derivatization of cyclodextrins. Remarkable progress has been achieved over the past ten years regarding their regioselective derivatization. Many other applications are certain to follow.

See also the Thematic Series:
Superstructures with cyclodextrins: Chemistry and applications IV
Superstructures with cyclodextrins: Chemistry and applications III
Superstructures with cyclodextrins: Chemistry and applications

Superstructures with cyclodextrins: Chemistry and applications II

Gerhard Wenz

Editorial
Published 18 Feb 2015

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

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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

Full Research Paper
Published 19 Mar 2014

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1. Graphical Abstract
2. Scheme 1: Synthetic route for the synthesis of thiol functionalized 4-alkylphenols.
  
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3. Scheme 2: Synthetic route for the chain transfer polymerization of N,N-diethylacrylamide (7) with CTA 6a and ...
  
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4. Figure 1: Section of the MALDI –TOF spectrum of polymer 8b, indicating the high degree of end-group functiona...
  
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5. Figure 2: ¹H NMR spectrum of polymer 9b in CDCl₃ (300 MHz, rt).
  
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6. Figure 3: Top left: Section of the FTIR-spectrum of polymer 8b (black line) in comparison to 8bOx (red line);...
  
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7. Figure 4: Dependency of the cloud point values on the degree of polymerization (calculated by end-group analy...
  
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8. Figure 5: Shifts of the cloud points after the oxidation of the polymers (8a–d, 9a–d) to its corresponding su...
  
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9. Figure 6: Turbidimetry measurements of polymer 8b (straight black line – heating curve; dotted black line – c...
  
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10. Figure 7: 2D NMR NOESY spectrum of polymer 8b with two equivalents RAMEB-CD in D₂O (600 MHz, rt).
  
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11. Figure 8: Left: Schematic illustration of the micellar-like structures and reversibility by addition of RAMEB...
  
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12. Figure 9: Schematic illustration of the micellar-like structures, its deformation upon addition of one equiva...
  
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Beilstein J. Org. Chem. 2014, 10, 680–691, doi:10.3762/bjoc.10.61

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Influence of cyclodextrin on the UCST- and LCST-behavior of poly(2-methacrylamido-caprolactam)-co-(N,N-dimethylacrylamide)

Alexander Burkhart and
Helmut Ritter

Full Research Paper
Published 21 Aug 2014

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1. Graphical Abstract
2. Scheme 1: Synthesis of monomer 2-methacrylamido-caprolactam (4) and copolymers 6a–i based on 4 and N,N-dimeth...
  
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3. Figure 1: Turbidity curves upon heating and corresponding curves upon cooling of 10 mg ml⁻¹ solution of polym...
  
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4. Figure 2: 2D NMR ROESY (300 MHz, D₂O) spectrum of monomer 4_CD (a), Job plot of 2 with RAMEB-CD (b).
  
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5. Figure 3: Turbidity curves upon cooling of 10 mg ml⁻¹ solution of copolymer 6a in various n-alcohols at a coo...
  
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6. Figure 4: Turbidity curves upon cooling of 10 mg ml⁻¹ solution of polymer 6a and 6a_CD at a cooling rate of 1 ...
  
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7. Figure 5: Glass-transition temperature as a function of the amount of N,N-dimethylacrylamide (5) in the copol...
  
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Beilstein J. Org. Chem. 2014, 10, 1951–1958, doi:10.3762/bjoc.10.203

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The effect of permodified cyclodextrins encapsulation on the photophysical properties of a polyfluorene with randomly distributed electron-donor and rotaxane electron-acceptor units

Aurica Farcas,
Ana-Maria Resmerita,
Pierre-Henri Aubert,
Flavian Farcas,
Iuliana Stoica and
Anton Airinei

Full Research Paper
Published 09 Sep 2014

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1. Graphical Abstract
2. Figure 1: Top: Chemical structures of the starting materials. Bottom: Synthetic route of the non-rotaxane 4, ...
  
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3. Figure 2: Changes in the absorption spectra of the monomer 1 upon the addition of increasing amounts of TMS-γ...
  
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4. Figure 3: ¹H NMR spectrum of the polyrotaxane 4a copolymer in toluene-d₈.
  
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5. Figure 4: Termogravimetric curves (TG) of the copolymers.
  
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6. Figure 5: DSC traces on second heating scan of 4 (a), 4a (b) and 4b (c).
  
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7. Figure 6: Optical absorption spectra of the copolymers in DCM solutions (c = 1.5∙10⁻⁶ mg∙mL⁻¹) (a) and thin f...
  
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8. Figure 7: Fluorescence emission spectra of the copolymers in DCM solutions (c = 1.5∙10⁻⁶ mg∙mL⁻¹) (a) and thi...
  
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9. Figure 8: Fluorescence lifetime decay traces of 4a polyrotaxane at 440 nm in DCM solution.
  
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10. Figure 9: CV of 4 (a), 4a (b) and 4b (c) in 0.1 M TBAP/ACN solution at scan rate 20 mV∙s⁻¹ copolymer films.
  
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11. Figure 10: Representative AFM images obtained over 20 × 20 and 5 × 5 µm² areas of the non-rotaxane 4, 4a and 4b...
  
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12. Figure 11: The roughness exponent α calculated as the slope of log(S_q) versus log(Lsc) for the reference 4, 4a...
  
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Beilstein J. Org. Chem. 2014, 10, 2145–2156, doi:10.3762/bjoc.10.222

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Effect of cyclodextrin complexation on phenylpropanoids’ solubility and antioxidant activity

Miriana Kfoury,
David Landy,
Lizette Auezova,
Hélène Greige-Gerges and
Sophie Fourmentin

Full Research Paper
Published 06 Oct 2014

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1. Graphical Abstract
2. Figure 1: Chemical structure of studied phenylpropanoids (PPs).
  
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3. Figure 2: Phase solubility profiles of (a) CD/trans-anethole and (b) CD/p-coumaric acid inclusion complexes.
  
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4. Figure 3: Solubility enhancement (log (S_t/S₀)) as a function of the solubility (log (S₀)) of studied phenylpr...
  
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5. Figure 4: Representation of the most stable CD/trans-anethole inclusion complex conformers resulting from the...
  
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6. Figure 5: DPPH radical scavenging activity (%) of studied PPs alone or in presence of CD.
  
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Beilstein J. Org. Chem. 2014, 10, 2322–2331, doi:10.3762/bjoc.10.241

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Phosphinocyclodextrins as confining units for catalytic metal centres. Applications to carbon–carbon bond forming reactions

Matthieu Jouffroy,
Rafael Gramage-Doria,
David Sémeril,
Dominique Armspach,
Dominique Matt,
Werner Oberhauser and
Loïc Toupet

Full Research Paper
Published 15 Oct 2014

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1. Graphical Abstract
2. Figure 1: CD-based mono- and diphosphines with inward-pointing phosphorus atoms.
  
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3. Scheme 1: Complexation of a "PdCl(dmba)" unit by HUGPHOS ligands.
  
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4. Scheme 2: Reaction of HUGPHOS-1 with [MCl₂(PhCN)₂] complexes (M = Pd, Pt). Only one isomer with a given MeO–M...
  
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5. Scheme 3: Synthesis of complexes 3–5.
  
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6. Figure 2: X-ray structure of aqua palladium complex 5 [44] (top: side view; bottom: view from the primary face). ...
  
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7. Scheme 4: Dehydration of Pd(II) complex 5.
  
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8. Figure 3: Ruthenium complexes 7 and 8 in Newman projection along the Ru–P bond.
  
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9. Figure 4: Titration of HUGPHOS-1 with [Rh(CO)₂Cl]₂ at 25 °C.
  
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10. Scheme 5: Synthesis of rhodium carbonyl complexes 9–11.
  
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11. Scheme 6: Synthesis of rhodium complexes 12 and 13.
  
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12. Scheme 7: Selective formation of complex 14 under 40 bar CO/H₂ at 80 °C.
  
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13. Figure 5: High pressure NMR spectra of 13 under CO/H₂ (1:1) recorded in toluene-d₈ (at various temperatures a...
  
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14. Figure 6: IR spectra of 14 recorded in CH₂Cl₂ at 50 °C under 40 bar of CO/H₂ 1:1.
  
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15. Figure 7: Calculated structures (Spartan 10) of trigonal bipyramidal [RhH(CO)₃(HUGPHOS-2)] with the phosphoru...
  
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16. Scheme 8: Possible mechanism for the hydroformylation of styrene when using monophosphine complexes 12 or 13 ...
  
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17. Scheme 9: Simplified Heck coupling mechanism when using HUGPHOS-1 or HUGPHOS-2 as ligands. Doted lines stand ...
  
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Beilstein J. Org. Chem. 2014, 10, 2388–2405, doi:10.3762/bjoc.10.249

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A versatile δ-aminolevulinic acid (ΑLA)-cyclodextrin bimodal conjugate-prodrug for PDT applications with the help of intracellular chemistry

Chrysie Aggelidou,
Theodossis A. Theodossiou,
Antonio Ricardo Gonçalves,
Mariza Lampropoulou and
Konstantina Yannakopoulou

Full Research Paper
Published 17 Oct 2014

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1. Graphical Abstract
2. Scheme 1: The structure of δ-aminolevulinic acid (1), a precursor in cellular biosynthesis of protoporphyrin ...
  
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3. Scheme 2: Synthesis of conjugate 2 i) Br₂, Ph₃P, DMF, 75–80 °C, 93% according to [16]; ii) 2-hydroxyethylamine, 8...
  
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4. Figure 1: ¹³C NMR spectrum of 2 (D₂O, 125 MHz) with assignment of the peaks.
  
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5. Figure 2: Representative confocal microscopy images of MCF7 cells incubated with 1 mM 2 (a, b and c), and 1 m...
  
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6. Figure 3: Representative confocal fluorescence microscopy images of MCF7 cells after incubation with a soluti...
  
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Beilstein J. Org. Chem. 2014, 10, 2414–2420, doi:10.3762/bjoc.10.251

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Towards the sequence-specific multivalent molecular recognition of cyclodextrin oligomers

Michael Kurlemann and
Bart Jan Ravoo

Full Research Paper
Published 20 Oct 2014

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1. Graphical Abstract
2. Figure 1: Chemical structures of the di- (A) and trivalent (B) CD sequences, the di- (C) and trivalent (D) gu...
  
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3. Figure 2: Synthesis of the di- and trivalent CD sequences 1–7 (for detailed reaction conditions see Supporting Information File 1).
  
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4. Figure 3: Solid phase peptide synthesis of the di- and trivalent guest strands 8 – 14 (for detailed reaction ...
  
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5. Figure 4: ¹H NMR spectra of 17 (B) and its inclusion complexes with β- (A) and α-CD (C), measured in D₂O (600...
  
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6. Figure 5: Schematic drawing of the complexation of the serine derivatives 17 (A) and 18 (B) with α- and β-CD....
  
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7. Figure 6: ¹H NMR spectra of 18 (B) and its inclusion complexes with β- (A) and α-CD (C), measured in D₂O (600...
  
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8. Figure 7: Selected binding models for the analysis of ITC data. (A) Monovalent receptor (R)-ligand (L) intera...
  
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9. Figure 8: Schematic drawing of the interactions of the divalent guest molecules 8 (A), 9 (B) and 10 (C) with ...
  
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10. Figure 9: Schematic drawing of the interactions of the trivalent guest molecules 11 (A), 12 (B), 13 (C) and 14...
  
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Beilstein J. Org. Chem. 2014, 10, 2428–2440, doi:10.3762/bjoc.10.253

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Loose-fit polypseudorotaxanes constructed from γ-CDs and PHEMA-PPG-PEG-PPG-PHEMA

Tao Kong,
Lin Ye,
Ai-ying Zhang and
Zeng-guo Feng

Full Research Paper
Published 23 Oct 2014

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1. Graphical Abstract
2. Scheme 1: Schematic description of self-assembly of γ-CDs with BrPPO-PEO-PPOBr and PHEMA-PPO-PEO-PPO-PHEMA in...
  
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3. Scheme 2: Synthetic pathway of a pentablock copolymer.
  
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4. Figure 1: Photographs of the turbidity evolution in PEP18CD (1) and PEP26MnCDs (2) (PEP26M9CD (left), PEP26H1...
  
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5. Figure 2: WXRD spectra of γ-CD, PHEMA, PEP26M, PEP18CD and PEP26MnCDs.
  
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6. Figure 3: ¹H NMR spectra of PEP26M9CD (A), PEP26M18CD (B) and PEP26M27CD (C).
  
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7. Figure 4: DSC curves of PHEMA, PEP26M, PEP26MnCDs, BrPEPBr and PEP18CD.
  
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8. Figure 5: TGA curves of γ-CD, PEP26M, PEP26MnCDs, BrPEPBr and PEP18CD.
  
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9. Figure 6: FTIR spectra of γ-CD, PEP26M, PEP18CD and PEP26MnCDs.
  
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10. Figure 7: ¹³C CP/MAS NMR spectra of PEP26M, γ-CD and PEP26M27CD.
  
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Beilstein J. Org. Chem. 2014, 10, 2461–2469, doi:10.3762/bjoc.10.257

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Host–guest-driven color change in water: influence of cyclodextrin on the structure of a copper complex of poly((4-hydroxy-3-(pyridin-3-yldiazenyl)phenethyl)methacrylamide-co-dimethylacrylamide)

Nils Retzmann,
Gero Maatz and
Helmut Ritter

Full Research Paper
Published 24 Oct 2014

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1. Graphical Abstract
2. Scheme 1: Synthesis of N-(4-hydroxy-3-(pyridin-3-yldiazenyl)phenethyl) methacrylamide (5) and preparation of ...
  
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3. Figure 1: Color-changing effects of polymer 7 upon addition of A) CuSO₄ and B) CuSO₄ and γ-CD in a 50:50 vol ...
  
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4. Figure 2: UV–vis absorption spectra of (orange) the solved copolymer 7 with the induced shifts by addition of...
  
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5. Figure 3: Number average particle size distribution of 7 obtained by DLS experiments.
  
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Beilstein J. Org. Chem. 2014, 10, 2480–2483, doi:10.3762/bjoc.10.259

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Synthesis of graft polyrotaxane by simultaneous capping of backbone and grafting from rings of pseudo-polyrotaxane

Kazuaki Kato,
Katsunari Inoue,
Masabumi Kudo and
Kohzo Ito

Full Research Paper
Published 04 Nov 2014

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1. Graphical Abstract
2. Scheme 1: General synthetic scheme of graft polyrotaxane (GPR) consisting of 1) functionalization of polymer ...
  
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3. Scheme 2: Simplified synthetic scheme of graft polyrotaxane (GPR).
  
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4. Figure 1: Partial ¹H NMR (400 MHz, CDCl₃, 298 K) spectra of PEG-GA (above) and PGE-amine (below).
  
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5. Figure 2: SEC traces of GPR (run 1 in Table 1) and PEG derivatives. Eluents: DMSO/LiBr; detection: differential refr...
  
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6. Figure 3: ¹H NMR spectra (400 MHz, DMSO-d₆, 298 K) of GPRs: (a) run 1 and (b) run 2.
  
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Beilstein J. Org. Chem. 2014, 10, 2573–2579, doi:10.3762/bjoc.10.269

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Synthesis and characterization of a hyper-branched water-soluble β-cyclodextrin polymer

Francesco Trotta,
Fabrizio Caldera,
Roberta Cavalli,
Andrea Mele,
Carlo Punta,
Lucio Melone,
Franca Castiglione,
Barbara Rossi,
Monica Ferro,
Vincenza Crupi,
Domenico Majolino,
Valentina Venuti and
Dominique Scalarone

Full Research Paper
Published 06 Nov 2014

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1. Graphical Abstract
2. Figure 1: FTIR spectra of branched β-CD polymer (a), cross-linked β-CD nanosponge (b) and pyromellitic dianhy...
  
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3. Figure 2: SEC curves of the β-CD-based polymer before (solid line) and after ultrafiltration with cut-off siz...
  
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4. Figure 3: Thermogravimetric curves of the β-CD-based polymer after ultrafiltration with cut-off size of 3000 ...
  
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5. Figure 4: Raman (a) and FTIR–ATR (b) spectra of the branched β-CD-based polymer in the wavenumber range of 15...
  
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6. Figure 5: Ratio between the intensity of the bands assigned to ester groups (I_CO1) and to the free carboxylic...
  
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7. Figure 6: NMR spectra of fluorescein in D₂O solution (a) and in the presence of the hyper-branched β-CD polym...
  
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8. Figure 7: UV–vis spectrum of fluorescein with increasing amounts of hyper-branched β-CD polymer. pH range: 8....
  
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Beilstein J. Org. Chem. 2014, 10, 2586–2593, doi:10.3762/bjoc.10.271

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Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens

Véronique Nardello-Rataj and
Loïc Leclercq

Review
Published 07 Nov 2014

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1. Graphical Abstract
2. Scheme 1: Principle of resistance mechanisms through selection of the most resistant micro-organism.
  
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3. Figure 1: Chemical structure of carbendazim.
  
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4. Scheme 2: Chemical structure of benomyl and its decomposition in aqueous solution.
  
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5. Figure 2: Chemical structure of enilconazole.
  
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6. Figure 3: Chemical structure of chloramidophos.
  
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7. Scheme 3: The complex problem of pentachlorophenol (PCP) degradation.
  
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8. Figure 4: Chemical structure of DCPE.
  
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9. Figure 5: Chemical structures of some biocides used in [59].
  
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10. Figure 6: Chemical structure of miconazole nitrate.
  
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11. Figure 7: Chemical structures of triclosan and butylparaben.
  
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12. Figure 8: Chemical structure of ciprofloxacin hydrochloride.
  
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13. Figure 9: Chemical structure of benzethonium chloride.
  
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14. Figure 10: Chemical structure of benzalkonium chlorides.
  
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15. Scheme 4: Multiple equilibria of CD with benzalkonium chloride (BZK) and fluorometholone.
  
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16. Scheme 5: Competition between co-micellization and biocidal activity observed for didecyldimethylammonium chl...
  
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17. Scheme 6: Proposed antimicrobial mechanism of encapsulated didecyldimethylammonium chloride by CDs: (1) diffu...
  
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18. Scheme 7: Inhibition of co-micellization process observed for didecyldimethylammonium chloride, octaethyleneg...
  
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19. Scheme 8: Schematic representation of biocide release from a chemically cross-linked CD network.
  
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20. Scheme 9: Proposed Trojan horse mechanism of silver nanoparticles capped by β-CD.
  
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21. Scheme 10: Proposed mechanism of copper nanoparticles immobilized on carbon nanotube and embedded in water-ins...
  
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22. Scheme 11: Advantages and drawback of the physicochemical and biopharmaceutical properties of CDs/biocides inc...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 2603–2622, doi:10.3762/bjoc.10.273

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

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

Full Research Paper
Published 10 Nov 2014

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1. Graphical Abstract
2. Scheme 1: Overall concept of the degradable PRX crosslinker.
  
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3. Scheme 2: Overall reaction scheme of the resin monomer-soluble PRX crosslinker with degradable end groups.
  
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4. Figure 1: ¹H NMR spectrum of C12-Bu12 PRX (DMSO-d₆).
  
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5. Figure 2: ¹H NMR spectrum of C12-Bu12-MA12 PRX (DMSO-d₆).
  
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6. Figure 3: SEC analysis of the prepared polymers a) PEG 10 k, b) C12-Bu12, c) C12-Bu12-MA12, d) C12-Bu12-MA12 ...
  
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7. Figure 4: a) Image of the photosetting plastic prepared by resin casting and b) the results of the Vickers ha...
  
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Beilstein J. Org. Chem. 2014, 10, 2623–2629, doi:10.3762/bjoc.10.274

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

Eléonore Bertaut and
David Landy

Full Research Paper
Published 11 Nov 2014

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1. Graphical Abstract
2. Figure 1: Non-competitive ITC isotherms for the β-CD-IBU complex at 298 K. Each protocol (from A to H) is def...
  
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3. Figure 2: Theoretical uncertainty on K (left) and ΔH (right) as a function of log K for titration (red curve)...
  
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4. Figure 3: Theoretical uncertainty on K (left) and ΔH (right) as a function of Log K for titration-titration (...
  
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5. Figure 4: Competitive ITC isotherms for the HPβ-CD-β-CD-IBU system at 283 K. Each protocol (from I to P) is d...
  
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Beilstein J. Org. Chem. 2014, 10, 2630–2641, doi:10.3762/bjoc.10.275

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Cyclodextrin-grafted polymers functionalized with phosphanes: a new tool for aqueous organometallic catalysis

Jonathan Potier,
Stéphane Menuel,
David Mathiron,
Véronique Bonnet,
Frédéric Hapiot and
Eric Monflier

Letter
Published 11 Nov 2014

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1. Graphical Abstract
2. Scheme 1: Synthesis of CD-substituted polymers 3a, 3b and 3c.
  
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3. Figure 1: ¹H NMR spectrum of 3c in D₂O at 25 °C.
  
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4. Figure 2: ³¹P NMR spectrum of 3b in a) DMF-d₇ at 25 °C and b) D₂O at 25 °C.
  
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5. Figure 3: ¹H NMR spectrum of 3b (10 mM) in D₂O at 25 °C (below) and 60 °C (above).
  
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6. Figure 4: Size-exclusion chromatography of polyNAS and polymers 3a, 3b and 3c.
  
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Beilstein J. Org. Chem. 2014, 10, 2642–2648, doi:10.3762/bjoc.10.276

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A green approach to the synthesis of novel phytosphingolipidyl β-cyclodextrin designed to interact with membranes

Yong Miao,
Florence Djedaïni-Pilard and
Véronique Bonnet

Letter
Published 12 Nov 2014

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1. Graphical Abstract
2. Figure 1: Targeted modified cyclodextrins.
  
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3. Scheme 1: Synthesis of bicatenar CDs 4, 5, 6 and 7; a) succinic anhydride, 135 °C, 10 min, 70%; b) phytosphin...
  
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Beilstein J. Org. Chem. 2014, 10, 2654–2657, doi:10.3762/bjoc.10.278

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

Yamei Zhao,
Wei Tian,
Guang Yang and
Xiaodong Fan

Full Research Paper
Published 18 Nov 2014

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1. Graphical Abstract
2. Scheme 1: Schematic representation of the details for the construction of a multifunctional nanocarrier used ...
  
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3. Figure 1: Particle size distributions of MP1, MP2, and MP3 at 25 °C as determined by DLS.
  
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4. Figure 2: TEM images of P1 (A), P2 (B) and P3 (C) micelles.
  
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5. Figure 3: UV–vis spectra of LND solutions in the presence of MP1, MP2 and MP3 in buffer solutions.
  
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6. Figure 4: Particle size distributions of DLMP1, DLMP2, and DLMP3 at 25 °C.
  
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7. Figure 5: Stability investigation of DLMP1, DLMP2, and DLMP3.
  
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8. Figure 6: Release profiles (a) and release kinetics (b–d) of LND from DLMP1, DLMP2 and DLMP3 in buffer soluti...
  
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Beilstein J. Org. Chem. 2014, 10, 2696–2703, doi:10.3762/bjoc.10.284

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Anomalous diffusion of Ibuprofen in cyclodextrin nanosponge hydrogels: an HRMAS NMR study

Monica Ferro,
Franca Castiglione,
Carlo Punta,
Lucio Melone,
Walter Panzeri,
Barbara Rossi,
Francesco Trotta and
Andrea Mele

Full Research Paper
Published 19 Nov 2014

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1. Graphical Abstract
2. Figure 1: a) ¹H high resolution NMR spectrum of IP dissolved in D₂O, b) ¹H HRMAS NMR spectrum of IP-CDNSEDTA ...
  
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3. Figure 2: Normalized NMR signal decay I(q,t_d) as function of q² for a) IP in D₂O solution, b) IP in CDNSEDTA ...
  
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4. Figure 3: log–log plot of MSD vs diffusion time t_d for: a) D₂O solution, b) CDNSEDTA (1:4) and CDNSEDTA (1:8)....
  
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5. Figure 4: TEM images of: a) CDNSEDTA (1:4) and b) CDNSEDTA (1:8).
  
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6. Figure 5: Effect of the increasing amount of crosslinker with respect to CD (expressed here as mol of crossli...
  
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7. Scheme 1: Schematic representation of the nanosponge synthesis. Acronyms: β-CD: β-cyclodextrin; EDTAn: anhydr...
  
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Beilstein J. Org. Chem. 2014, 10, 2715–2723, doi:10.3762/bjoc.10.286

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Removal of volatile organic compounds using amphiphilic cyclodextrin-coated polypropylene

Ludmilla Lumholdt,
Sophie Fourmentin,
Thorbjørn T. Nielsen and
Kim L. Larsen

Full Research Paper
Published 24 Nov 2014

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1. Graphical Abstract
2. Figure 1: Uptake selectivity (left) compared to weight gain of coated polypropylene (right) exemplified by a ...
  
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3. Figure 2: Results of titration experiment for 8 (left) and 10c (right). Standard deviation (n = 3) indicated ...
  
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Beilstein J. Org. Chem. 2014, 10, 2743–2750, doi:10.3762/bjoc.10.290

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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

Full Research Paper
Published 25 Nov 2014

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1. Graphical Abstract
2. Figure 1: (A) Photographs and (B) powder X-ray diffraction patterns of precipitates formed by mixing the CD s...
  
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3. Figure 2: (A) Chemical structures of DSPE and PEG-DSPE, (B) photographs of the γ-CD solutions after adding DO...
  
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4. Figure 3: (A) FTIR spectra, (B) powder X-ray diffraction patterns, (C) ¹H NMR spectrum and (D) proposed parti...
  
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5. Figure 4: (A) In vitro release profiles of the total DOX from γ-CD PPRX in various volumes of PBS, (B) releas...
  
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Beilstein J. Org. Chem. 2014, 10, 2756–2764, doi:10.3762/bjoc.10.292

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Binding mode and free energy prediction of fisetin/β-cyclodextrin inclusion complexes

Bodee Nutho,
Wasinee Khuntawee,
Chompoonut Rungnim,
Piamsook Pongsawasdi,
Peter Wolschann,
Alfred Karpfen,
Nawee Kungwan and
Thanyada Rungrotmongkol

Full Research Paper
Published 27 Nov 2014

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1. Graphical Abstract
2. Figure 1: Chemical structure of fisetin with the definition of the A- and B-rings (chromone and phenyl subuni...
  
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3. Figure 2: (A) Chemical structure of β-CD and (B) its truncated cone shape.
  
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4. Figure 3: Docked structures of the four possible inclusion complexes between fisetin and β-CD, where their pe...
  
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5. Figure 4: RMSD plots of all atoms in inclusion complex (black), β-CD (dark grey) and fisetin (light grey) for...
  
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6. Figure 5: Distance between the centers of gravity of each fisetin ring (A/B) and β-CD along the simulation ti...
  
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7. Figure 6: Radial distribution function (RDF) of oxygen atom of water molecules around the heteroatoms of fise...
  
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8. Figure 7: Comparison between QM and MM energies (∆E_QM and ∆E_MM) per the same set of 100 MD snapshots in the t...
  
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Beilstein J. Org. Chem. 2014, 10, 2789–2799, doi:10.3762/bjoc.10.296

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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

Letter
Published 28 Nov 2014

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1. Graphical Abstract
2. Figure 1: Synthesis of [1]rotaxane by self-inclusion of a host–guest-linked molecule: a) short molecular leng...
  
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3. Figure 2: Synthesis of an insulated molecule via flipping phenomenon.
  
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4. Scheme 1: The synthetic route to the PMβ-CD based linked [3]rotaxane with a 5,15-di([1,1'-biphenyl]-4-yl)porp...
  
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5. Figure 3: The aromatic region of the ¹H NMR spectra of 5 at 25 °C: 1) CDCl₃, 2) CD₃OD, and 3) CD₃OD:D₂O 1:1.
  
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6. Scheme 2: Selective synthesis of fixed [3]rotaxane by Suzuki cross-coupling reaction.
  
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7. Scheme 3: The synthetic routes to precursor of PM β-CD based insulated oligothiophene.
  
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8. Scheme 4: Synthesis of dibromohexa(para-phenylene) with two PMCDs 20.
  
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9. Scheme 5: Synthesis of pseudo-linked [3]rotaxanes via double self-inclusion through flipping.
  
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10. Figure 4: The aromatic region of the ¹H NMR spectra of 5 at 25 °C: 1) CDCl₃, 2) CD₃OD, and CD₃OD/D₂O 1:1.
  
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11. Figure 5: The aromatic region of the ¹H NMR spectra of 20 at 25 °C: 1) CDCl₃, 2) CD₃OD, and CD₃OD/D₂O 1:1.
  
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12. Scheme 6: Synthesis of fixed [3]rotaxane via complexation with rhodium porphyrin.
  
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13. Figure 6: Partial ROESY NMR spectrum of 26 (400 MHz, CDCl₃) showing the NOEs between aromatic protons of the ...
  
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Beilstein J. Org. Chem. 2014, 10, 2800–2808, doi:10.3762/bjoc.10.297

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Thermal and oxidative stability of the Ocimum basilicum L. essential oil/β-cyclodextrin supramolecular system

Daniel I. Hădărugă,
Nicoleta G. Hădărugă,
Corina I. Costescu,
Ioan David and
Alexandra T. Gruia

Full Research Paper
Published 28 Nov 2014

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1. Graphical Abstract
2. Figure 1: The main compounds identified in raw O. basilicum L. essential oils (a) and the degradation reactio...
  
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3. Figure 2: The score plot from the PCA analysis of the O. basilicum L. essential oil compounds nanoencapsulati...
  
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Beilstein J. Org. Chem. 2014, 10, 2809–2820, doi:10.3762/bjoc.10.298

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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

Full Research Paper
Published 02 Dec 2014

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1. Graphical Abstract
2. Figure 1: Image of the FeSSIF and other buffers with and without α-CD. α-CD was added into the FeSSIF or othe...
  
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3. Figure 2: Effect of α-CD on the concentration of lecithin and taurocholate in the FeSSIF. After adding each a...
  
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4. Figure 3: Concentration of α-CD in the FeSSIF. The experimental conditions were the same as those described i...
  
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5. Figure 4: Time-dependent relationship between decreases in lecithin and α-CD. The experimental conditions wer...
  
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6. Figure 5: Amounts of lecithin and α-CD precipitates. The amounts of lecithin and α-CD precipitated were calcu...
  
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7. Figure 6: Dose-dependent decrease of the micellar cholesterol solubility in the FeSSIF by α-CD. After additio...
  
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8. Figure 7: Effect of several dietary fibers on the micellar cholesterol solubility in FeSSIF. Various amounts ...
  
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9. Figure 8: Hypothetical scheme for the inhibitory action of α-CD on the micellar cholesterol solubility in int...
  
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Beilstein J. Org. Chem. 2014, 10, 2827–2835, doi:10.3762/bjoc.10.300

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

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

Letter
Published 02 Dec 2014

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1. Graphical Abstract
2. Figure 1: Aggregate size analysis of aqueous solutions of G8 and ibuprofen by PCS. a) G8 in 1% solution; b) s...
  
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3. Scheme 1: Schematic representation of the preparation of HP-substituted maltooligomers.
  
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4. Figure 2: Electropherograms of tested model drugs in the presence of 2-hydroxypropylated acyclic and cyclic d...
  
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Beilstein J. Org. Chem. 2014, 10, 2836–2843, doi:10.3762/bjoc.10.301

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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

Full Research Paper
Published 04 Dec 2014

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1. Graphical Abstract
2. Scheme 1: Synthesis pathway of the dimer AZO-CDim 1.
  
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3. Figure 1: Overlaid UV spectra of the irradiation of AZO-CDim 1 (a) from 0 to 120 min at 365 nm and then (b) f...
  
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4. Figure 2: HPLC quantification of the cis/trans ratio of AZO-CDim 1 before irradiation (left) and after irradi...
  
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5. Figure 3: Percentage of cis isomer of AZO-CDim 1 produced during photoisomerization cycles (c = 10⁻⁴ M, water...
  
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6. Figure 4: Representation of the most stable structures obtained for the azobenzene linker (a) for the trans c...
  
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7. Figure 5: Structure of the ditopic guest ADAdim 4.
  
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8. Figure 6: Titration of (a) β-CD (c = 0.8 mM) and (b) β-CD-NH₂ (c = 0.8 mM) by ADAdim 4 (c = 4 mM). (c) Diluti...
  
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9. Figure 7: (a) ¹H NMR spectra of AZO-CDim 1 (500 MHz, D₂O, 2.5 mM) in the absence (bottom) and presence of ADA...
  
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10. Figure 8: Proposed structures of inclusion complexes with the ditopic host AZO-CDim 1 and the ditopic guest A...
  
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Beilstein J. Org. Chem. 2014, 10, 2874–2885, doi:10.3762/bjoc.10.304

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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

Full Research Paper
Published 08 Dec 2014

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1. Graphical Abstract
2. Figure 1: Phase solubility diagrams for fluconazole obtained with β-cyclodextrin derivatives at 25 °C in wate...
  
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3. Figure 2: Solubility of fluconazole in aqueous solutions containing 5% of CD and 0.5% of the respective polys...
  
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4. Figure 3: Ocular cytotoxicity studies of HPBCD and SBECD in primary corneal human keratocytes, using real-tim...
  
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5. Figure 4: Ocular cytotoxicity studies of fluconazole in primary corneal human keratocytes obtained using real...
  
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6. Figure 5: HET-CAM assay: (a) positive Control (NaOH 0.1 N); (b) negative control (NaCl 0.9%); (c) HPBCD 10 mg...
  
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7. Figure 6: Bioadhesive properties (bioadhesion work and maximum force of detachment) of ion-sensitive hydrogel...
  
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8. Figure 7: Release profiles of fluconazole in simulated tear fluid from the gels with (closed symbols) or with...
  
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Graphical Abstract

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

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Synthesis of uniform cyclodextrin thioethers to transport hydrophobic drugs

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

Full Research Paper
Published 09 Dec 2014

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1. Graphical Abstract
2. Scheme 1: Synthetic route to neutral water-soluble CD thioethers.
  
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3. Figure 1: ESI MS spectra of CD derivatives 2b₁ (left) and 3b₁ (right).
  
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4. Figure 2: ¹H NMR spectra of a) the statistical CD derivatives 2b₁ and b) the corresponding uniform derivative ...
  
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5. Figure 3: Transmission (λ = 670 nm) of aqueous solutions (1.0 wt %) of 2b₁ (red) and 3b₁ (blue).
  
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6. Figure 4: Decay of the relative vapour pressure A/A₀ as function of the host concentration 3b₁ measured by GC...
  
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Beilstein J. Org. Chem. 2014, 10, 2920–2927, doi:10.3762/bjoc.10.310

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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

Full Research Paper
Published 16 Dec 2014

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1. Graphical Abstract
2. Figure 1: Thermo-gravitometry for PLLA, PL-MCD83, PL-MCD67, PL-MCD50 and MeCD.
  
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3. Figure 2: Observed weight loss and stoichiometric line.
  
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4. Figure 3: DSC curves for PLLA, PL-MCD83, PL-MCD67 and PL-MCD50.
  
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5. Figure 4: Stress-Strain curve for PLLA, PL-MCD50, 67 and 83 at a) 100 °C, b) 60˚C and c) 25 °C.
  
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6. Figure 5: Temperature dependence of tanδ for PLLA, PL-MCD50, PL-MCD67 and PL-MCD83.
  
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7. Figure 6: Raman spectra for PLLA, PL-MCD83, 67, 50 and MeCD at room temperature.
  
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8. Figure 7: Temperature dependence of Raman spectrum of PL-MCD83.
  
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9. Figure 8: Stacked line profiles of Raman spectra of PL-MCD83 for the characteristic peak of PLLA at 873 cm⁻¹.
  
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10. Figure 9: PCA results of PLLA at 2955 cm⁻¹, 1760 cm⁻¹, 1452 cm⁻¹, 1385 cm⁻¹, 1292 cm⁻¹, 1129 cm⁻¹, 873 cm⁻¹, ...
  
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11. Figure 10: PCA results of PL-MCD83 at 2955 cm⁻¹, 1768 cm⁻¹, 1452 cm⁻¹, 1385 cm⁻¹, 1294 cm⁻¹, 1128 cm⁻¹, 873 cm...
  
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Beilstein J. Org. Chem. 2014, 10, 2997–3006, doi:10.3762/bjoc.10.318

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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

Full Research Paper
Published 16 Dec 2014

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1. Graphical Abstract
2. Scheme 1: Schematic representation of the various synthetic routes for the introduction of an anchoring group...
  
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3. Scheme 2: Synthetic strategy for the rhodaminylation of β-CD polymer.
  
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4. Figure 1: TLC study of β-CD iodination showing the proceeding of 6-monoiodination with increasing reaction ti...
  
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5. Figure 2: HSQC-DEPT spectrum of compound 1 with partial assignment.
  
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6. Figure 3: IR spectra of compound 1 (black line) and compound 2 (red line) showing the disappearance of the az...
  
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7. Scheme 3: Schematic representation for the coumarinylation of methylated β-CD-polymer, n, m, p and q mean the...
  
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8. Figure 4: HSQC-DEPT spectra of compound 4 with partial assignment; in the upper part the full spectrum is sho...
  
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9. Scheme 4: Schematic representation for the introduction of NBF in a cationic β-CD-polymer.
  
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10. Scheme 5: Schematic representation for the introduction of fluorescein into a β-CD-polymer.
  
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Beilstein J. Org. Chem. 2014, 10, 3007–3018, doi:10.3762/bjoc.10.319

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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

Full Research Paper
Published 19 Dec 2014

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1. Graphical Abstract
2. Scheme 1: Synthesis of azido functionalized DIMEB 1a. a) Ba(OH)₂·8H₂O/BaO/Me₂SO₄
  
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3. Figure 1: ESI mass spectrum of azido functionalized DIMEB 1a.
  
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4. Figure 2: ¹H NMR spectra of a) 1a, b) 2, and c) 5a.
  
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5. Scheme 2: Synthesis of propargylated HES 2.
  
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6. Scheme 3: Synthesis of 5a by [2 + 3] cycloadditon, a) CuSO₄, ascorbate, 50 °C, 48 h.
  
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7. Figure 3: Viabilities of Caco-2 cells incubated with a) 5a after 2 h, b) 5a after 24 h, c) DIMEB after 2 h, d...
  
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8. Scheme 4: Structures of a) midazolam and b) sevoflurane.
  
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Beilstein J. Org. Chem. 2014, 10, 3087–3096, doi:10.3762/bjoc.10.325

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

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

Full Research Paper
Published 24 Dec 2014

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1. Graphical Abstract
2. Figure 1: Inclusion complex (polypseudorotaxane) between α-cyclodextrins and reverse Tetronics.
  
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3. Figure 2: 90R4/α-CD gels loaded with lactase. Octablock Tetronic molecules (grey) are threaded by CDs (red) f...
  
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4. Figure 3: FTIR spectra of Tetronic 90R4, α-CD, lactase and T25a10 complex.
  
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5. Figure 4: Release profiles of lactase from T25a10 (open circles) and T15a10 (filled circles) at pH 6 from a) ...
  
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6. Figure 5: Contribution of diffusion (open circles) and erosion (filled circles) mechanisms from polymers a) T...
  
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7. Figure 6: Chemical structure of a reverse Tetronic.
  
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Beilstein J. Org. Chem. 2014, 10, 3127–3135, doi:10.3762/bjoc.10.330

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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

Full Research Paper
Published 29 Dec 2014

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1. Graphical Abstract
2. Figure 1: Chemical structure of trans-resveratrol (1).
  
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3. Figure 2: DSC traces of RSV (a), TMA (b), TMA–RSV physical mixture (PM) (c), TMA–RSV preparation by kneading ...
  
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4. Figure 3: TG (red) and DSC (blue) traces for the hydrated TMA·RSV complex (top), and hot stage micrographs sh...
  
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5. Figure 4: The two symmetry-independent complex units of TMA·RSV·6.25H₂O (A and B), with only the major compon...
  
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6. Figure 5: Representative atomic labelling for the ordered RSV molecule A (blue) present in host A and the two...
  
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7. Figure 6: Space-filling representations of the two independent complex units A (a) and B (b) of the complex T...
  
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8. Figure 7: Crystal packing for the complex TMA·RSV·6.25H₂O projected down [010].
  
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9. Figure 8: The components of the disorder model for RSV in its inclusion complex with TMB (s.o.f. = 0.73 for t...
  
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10. Figure 9: The asymmetric unit in the crystal of TMB·RSV·5.6H₂O (a), and the non-H atom and methylglucose ring...
  
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11. Figure 10: Space-filling model of the inclusion complex TMB·RSV·5.6H₂O showing the inclusion of the RSV molecu...
  
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12. Figure 11: Packing arrangement in the crystal of TMB·RSV·5.6H₂O viewed down [010] (a) and [100] (b). Hydrogen ...
  
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13. Figure 12: Structure of the host–guest complex DMB·RSV·4.0H₂O (a), ring and atomic nomenclature for the host m...
  
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14. Figure 13: Space-filling model of the inclusion complex DMB·RSV·4.0H₂O showing the encapsulation of part of th...
  
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15. Figure 14: Stereoview of two DMB·RSV·4.0H₂O complex units related by a unit translation along the crystal a-ax...
  
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16. Figure 15: Projections of the crystal structure of the complex DMB·RSV·4H₂O along [100] (a) and [010] (b). Hyd...
  
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17. Figure 16: Solubility of RSV as a function of [β-CD] (blue) and [γ-CD] (red) at 25 °C.
  
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18. Figure 17: Solubility of RSV as a function of the concentrations of TMB (light blue), DMB (red), HP-β-CD (gree...
  
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Beilstein J. Org. Chem. 2014, 10, 3136–3151, doi:10.3762/bjoc.10.331

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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

Full Research Paper
Published 30 Dec 2014

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1. Graphical Abstract
2. Figure 1: Structure of RAMEA.
  
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3. Figure 2: Structures of ALA, EPA and DHA.
  
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4. Figure 3: Solubility of n−3 PUFAs and cholesterol in water solutions of 20% randomly methylated α-, β- and γ-...
  
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5. Figure 4: The effect of n−3 PUFAs on the expression of CD1a cell surface protein in resting (red), LPS-activa...
  
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6. Figure 5: Effect of n−3 PUFAs on the expression of the CD83 activation marker in resting (red), LPS-activated...
  
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7. Figure 6: Effect of n−3 PUFAs on the expression of the pro-inflammatory cytokine IL-6 in moDC activated by LP...
  
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8. Figure 7: The effect of n−3 PUFAs on the expression of GPR120 receptor in resting (red), LPS-activated (yello...
  
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Beilstein J. Org. Chem. 2014, 10, 3152–3160, doi:10.3762/bjoc.10.332

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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

Full Research Paper
Published 21 Jan 2015

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1. Graphical Abstract
2. Scheme 1: Reaction scheme for synthesis of azide-modified (S)-camptothecin.
  
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3. Scheme 2: Cu(I)-catalyzed grafting of azide-modified (S)-camptothecin onto alkyne-modified dextran.
  
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4. Figure 1: Titration of a) D70GP-CPT2 and b) D10GP-CPT1 by D70HPβ-CD at 298 K showing heat flow as a function ...
  
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5. Figure 2: Fluorescence emission spectra of a) D70GPCPT and b) D10GPCPT recorded at different concentrations (...
  
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Beilstein J. Org. Chem. 2015, 11, 147–154, doi:10.3762/bjoc.11.14

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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

Full Research Paper
Published 02 Feb 2015

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1. Graphical Abstract
2. Scheme 1: Thermal decomposition of PEMEDA- and PEMPDA-β-CD with the decomposition products as characterized b...
  
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3. Figure 1: Decomposition kinetics of PEMEDA- and PEMPDA-β-CD at 50 °C as determined by ¹H NMR thermal experime...
  
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4. Scheme 2: Host and guest molecules employed in K_s determination in solution at different pH.
  
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5. Figure 2: Stability constants for β-CD with SAL, MEQ and NIA obtained by ITC measurements.
  
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6. Figure 3: Stability constants for PEMPDA-β-CD with SAL, MEQ and NIA obtained by ITC measurements.
  
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7. Scheme 3: Deposition of PEMPDA-β-CD onto solid surface (Nafion^® 117).
  
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8. Figure 4: Deposition kinetics of PEMPDA-β-CD onto Nafion^® 117 as obtained from ELSD detection of the decreasi...
  
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9. Scheme 4: Deposition of three model guests into the cavities of immobilized PEMPDA-β-CD.
  
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Graphical Abstract

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

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

Hale Ünal,
Naile Öztürk and
Erem Bilensoy

Full Research Paper
Published 04 Feb 2015

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Album
1. Graphical Abstract
2. Figure 1: Scanning electron microphotographs of A) 6OCAPRO nanocapsules and B) CS-6OCAPRO nanocapsules.
  
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3. Figure 2: In vitro release profiles of CPT from anionic and cationic CD nanocapsules in pH 1.2 PBS A) in 2 ho...
  
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4. Figure 3: Cell viability of blank 6OCAPRO and CS-6OCAPRO nanocapsules against L929 cells after 48 h incubatio...
  
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5. Figure 4: Viability of MCF-7 cells cultured with CPT loaded 6OCAPRO and CS-6OCAPRO nanocapsules in comparison...
  
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6. Figure 5: Apparent permeability coefficient (P_aap) of different CPT formulations: CPT in DMSO solution, CPT l...
  
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Beilstein J. Org. Chem. 2015, 11, 204–212, doi:10.3762/bjoc.11.22

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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

Full Research Paper
Published 21 Apr 2015

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1. Graphical Abstract
2. Scheme 1: Synthetic route for the synthesis of the β-CD dimer with a free alkyne, allowing for subsequent sur...
  
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3. Figure 1: MS spectra (2440–2500 Da) of the purified β-CD dimer.
  
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4. Figure 2: Structure of fluorescent guest molecule, 2,6-ANS, used to probe host–guest interaction and two deri...
  
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5. Figure 3: Illustration of potential 1:1 inclusion complexes of the β-CD dimer and 2,6-ANS.
  
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6. Figure 4: (a) Steady-state fluorescence emission spectra of 50 µM 2,6-ANS in PBS (solid grey, smoothed), in t...
  
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7. Figure 5: Region of interest of a ROESY (250 ms mixing time) showing cross peaks between the β-CD-dimer and 2...
  
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8. Figure 6: Steady-state fluorescence titration of 2,6-ANS with β-CD dimer and parent β-CD in solution. 2,6-ANS...
  
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9. Scheme 2: Synthetic route for the activation of silicon dioxide surfaces and the grafting of the β-CD dimer t...
  
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10. Figure 7: (a) Steady-state TIRF emission spectra of 1 mM 2,6-ANS in PBS, recorded on a bare quartz slide (sol...
  
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Beilstein J. Org. Chem. 2015, 11, 514–523, doi:10.3762/bjoc.11.58

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