Superstructures with cyclodextrins: Chemistry and applications IV
Superstructures are generally formed from molecules through noncovalent interactions, which can be either attractive or repulsive. The first examples of superstructures formed by attractive intermolecular forces were complexes of crown ethers, cryptands, and spherands. Inclusion compounds of cyclodextrins, cyclic oligomers of glucose, also belong to this category.
Since superstructures are accessible through rational design, supramolecular chemistry has a great influence on organic and macromolecular chemistry as well as pharmacology and materials sciences. Cyclodextrins in particular became the most important building blocks for superstructures because they are the only hosts that are nontoxic and available on an industrial scale.
This thematic issue provides insights into the synthesis and properties of cyclodextrin superstructures, covering many aspects, such as catalysis, molecular recognition, colloids, molecular engineering, polyrotaxanes, drug delivery, and more.
See related thematic issues:
Superstructures with cyclodextrins: Chemistry and applications III
Superstructures with cyclodextrins: Chemistry and applications II
Superstructures with cyclodextrins: Chemistry and applications
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- Published 12 Aug 2016
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Figure 1: Chemical structure of the non-activated polyBTCA-CD.
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Figure 2: Determination of the PZC for the non-activated and activated polyBTCA-CD polymers (pHi: initial pH ...
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Figure 3: XRD pattern of the two polymers: non-activated and activated polyBTCA-CD.
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Figure 4: CPMAS and MAS spectra of polyBTCA-CD.
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Figure 5: Adsorption capacity (%) of (a) the non-activated and (b) the activated (NaHCO3 treatment) polyBTCA-...
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Figure 6: Adsorption kinetics for two solutions containing five metals at two concentrations (solution at 10 ...
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Figure 7: Removal efficiency (%) after treatment with activated polyBTCA-CD (concentration = 2 g·L−1) for (a)...
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Figure 8: Removal efficiency (%) of inorganic elements after treatment of five DWs by polyBTCA-CD (concentrat...
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- Published 22 Nov 2016
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Figure 1: Preparation scheme of α-CD-CTA.
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Figure 2: Crystal structure of α-CD with N,N-dimethylacrylamide (DMA). (a) The structure of an 1:1 inclusion ...
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Figure 3: Time-conversion curves (a), kinetic plots (b) and plots of number-average molecular weight (Mn) ver...
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Figure 4: Proposed polymerization mechanism for a water-soluble vinyl monomer with α-CD-CTA as a chain transf...
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- Published 25 Nov 2016
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Figure 1: Schematic representation of adamantane-substituted squaraine (AdSq) binding as a divalent guest to ...
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Figure 2: Absorption spectra of AdSq in acetonitrile. [AdSq] = 7.5 µM. Top: Absorption at different time poin...
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Figure 3: Top: Emission spectra (ex: 630 nm) of AdSq immobilized at CDV. [CDV] = 0–100 µM; [AdSq] = 5 µM. Bot...
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Figure 4: Confocal fluorescence microscopy of giant unilamellar vesicles (GUVs) of amphiphilic cyclodextrins ...
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Figure 5: Top: Absorption spectra at different time points during irradiation of a CDV solution with AdSq imm...
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Figure 6: Synthesis of AdSq (I) NaH, DMF, 1,6-dibromohexane, 24 h, rt. (II) benzothiazole, acetonitrile, 12 h...
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- Published 07 Dec 2016
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Scheme 1: Structure and conventional representation of native CDs.
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Scheme 2: Proposed mechanism for morphological changes in erythrocytes induced by methylated CDs.
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Scheme 3: Proposed mechanism for the conformational change of egg white lysozyme with temperature elevating i...
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Scheme 4: Sugar hydrophobicity scale according to Janado and Yano and correlation with the binding constant v...
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Scheme 5: Principle of chemically switched DNA intercalators based on anthryl(alkylamino)-β-CD/1-adamantanol ...
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Scheme 6: Normal (left) and diseased artery (right).
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Scheme 7: Kinetics of [DiC10] insertion into the viral envelope without (left) or with γ-CD (right). Note tha...
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- Published 28 Dec 2016
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Figure 1: Adsorption of β-CD on the surface of nanoTiO2 [37].
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Figure 2: Turbidity of nanoTiO2 dispersion (0.02%) in the presence of 1% HPBCD-P (green diamond) and 1% CMBCD...
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Figure 3: Aggregation effect of 0.1% NaCl on 0.02% nanoTiO2 dispersion in the absence (green curve) and prese...
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Figure 4: Aggregation effect of tap water on 0.02% nanoTiO2 dispersion in the absence (green curve) and prese...
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Figure 5: Photodegradation of MB in aqueous solutions: distilled water (A), 0.1% NaCl solution (B) and tap wa...
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Figure 6: Photodegradation of IBR in distilled water examining the drug itself (blue circle), and in the pres...
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- Full Research Paper
- Published 28 Dec 2016
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Scheme 1: Scheme for the end-capping of the PEG-NH2 (1)/α-CD pseudopolyrotaxane with 4-(azidomethyl)benzoic a...
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Figure 1: SEC charts for crude products of reaction 1 (upper chart) and 2 (lower chart).
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Figure 2: (A) SEC charts of α-CD, PEG-Ph-NH2 (3), PRX-Bn-N3 (4a), PRX-Ph-N3 (4b), and PRX-Ph-Me (4c). (B) FTI...
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Scheme 2: End-group modification of 4a-c with model alkyne via copper-catalyzed click reaction.
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Figure 3: (A) 1H NMR spectra of the PRXs before (4a, 4b, 4c) and after copper-catalyzed click reactions with p...
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Scheme 3: Scheme of the synthesis of water-soluble PRX (6) and the following end group modification with copp...
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Figure 4: SEC charts of the HEE-PRX-Bn-N3 (6) (A, B) and the HEE-PRX-DF488 (7) (C, D) monitored with fluoresc...
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Figure 5: CLSM images of HeLa cells treated with HEE-PRX-DF488 (7) (500 μg/mL) for 26 h (scale bars: 20 μm). ...
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- Published 03 Jan 2017
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Figure 1: Schematic representation for synthesis of multi-Lac-β-CD (5), β-CD (1), per-chloro-β-CD (2), per-az...
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Figure 2: MALDI–TOFMS (A) and 1H NMR spectra (B) of multi-Lac-β-CD (DSL5.6)
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Figure 3: Cytotoxicity of multi-Lac-β-CD in NPC-like HepG2 cells after treatment for 24 h. NPC-like HepG2 cel...
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Figure 4: Binding curves of multi-Lac-β-CD (DSL5.6) (A) and β-CD (B) with peanut agglutinin (PNA). The bindin...
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Figure 5: Intracellular distribution of TRITC-multi-Lac-β-CD (DSL5.6) in NPC-like HepG2 cells. Cells were inc...
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Figure 6: Intracellular distribution of cholesterol in NPC-like HepG2 cells. (A) NPC-like HepG2 cells (1 × 105...
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- Full Research Paper
- Published 06 Jan 2017
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Figure 1: Structure of cyclodextrins (CD) and their carboxymethylated (CM-CD) and phosphated (P-CD) derivativ...
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Figure 2: Structures of substrates included in the study. All compounds were examined in their protonated for...
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Figure 3: The (a) C-methyl resonance of 3 (10 mM, enriched in the (R)-enantiomer) in the presence of (b) P-α-...
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Figure 4: The (a) methine resonance of the carbinol carbon (5.124 ppm) and N-methyl resonance (2.768 ppm) of 7...
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Figure 5: The N-methyl resonance of 7 (10 mM, enriched in (1S,2R)-enantiomer) with P-β-CD-LDS (20 mM) and con...
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- Published 27 Jan 2017
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Figure 1: Schematic thermodynamic description of the CP process and time constants. The I-S model (left), the ...
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Figure 2: 1H MAS NMR spectra of a) CDNS(1:8)-IbuNa and b) CDNS(1:8). The inset (top right) shows the expansio...
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Figure 3: The effect of the spinning speed on the spectral features. 1H MAS NMR spectra of a) CDNS(1:4)-IbuNa...
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Figure 4: 13C CP-MAS NMR spectra for samples of β-CD (top), CDNS(1:4) (middle) and CDNS(1:8) polymers (bottom...
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Figure 5: 13C CP-MAS NMR spectrum of: a) CDNS(1:4) polymer; b) CDNS(1:4)-IbuNa system; c) CDNS(1:8)-IbuNa sys...
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Figure 6: 13C CP-MAS NMR spectra of CDNS(1:4) acquired with CP variable contact time in the range 50 μs–7 ms.
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Figure 7: Time dependence of 13C magnetization for CDNS(1:4) (left) and CDNS(1:8) (right) polymers.
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Figure 8: 1H-13C CP oscillatory kinetics for the carbon C(1) and C(4) of CDNS(1:4)-IbuNa sample (left) and CD...
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Figure 9: 1H-13C CP oscillatory kinetics for the ibuprofen aromatic carbon atoms C(6,8) in samples CDNS(1:4)-...
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Figure 10: PXRD patterns of: a) CDNS(1:8), b) CDNS(1:4), c) CDNS(1:8)-IbuNa loaded, d) CDNS(1:4)-IbuNa loaded,...
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- Published 06 Mar 2017
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Figure 1: Structures of G agents.
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Figure 2: Scavenger based on a heterodifunctionalized β-cyclodextrin derivative.
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Figure 3: Structures of β-cyclodextrin derivatives 2–5.
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Figure 4: Structures of pesticides tested.
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Scheme 1: Synthetic pathway to derivatives 2 and 3 (Tr = trityl).
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Scheme 2: Synthesis of compound 4.
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Scheme 3: Synthesis of compound 5 (Tr = trityl).
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Figure 5: Hydrolysis of methyl paraoxon (0.5 mM) in the presence of compounds 1, 2, 3 or 2-iodosobenzoic acid...
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Figure 6: Hydrolysis of methyl paraoxon (0.5 mM) in the presence of compounds 1, 2, 3 or 2-iodosobenzoic acid...
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Figure 7: Hydrolysis of methyl paraoxon (0.5 mM) in the presence of compounds 2, 4, 5 or 2-iodosobenzoic acid...
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Figure 8: Hydrolysis of methyl paraoxon (0.5 mM) in the presence of mixtures of compounds 4, 5 with IBA or im...
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Figure 9: Influence of the pesticide structure on the hydrolytic efficiency of compound 2 (0.25 mM). Kinetic ...
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Figure 10: Influence of TRIMEB, IBA and imidazole on the hydrolysis of methyl parathion (0.5 mM). The final co...
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Figure 11: Ability of compounds 1–4 in preventing the inhibition of acetylcholinesterase by soman (GD).
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- Published 15 Mar 2017
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Figure 1: Reaction scheme for the synthesis of eosin Y (2) and eosin B (4).
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Figure 2: Reaction scheme for the synthesis of eosin-appended β-CDs, 2–β-CD and 4–β-CD (NMM: N-methylmorpholi...
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Figure 3: TLC analysis of the composition of the crude coupling reaction mixtures.
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Figure 4: 1H NMR spectrum of 2–β-CD with partial assignment (DMSO-d6, 600 MHz, 298 K).
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Figure 5: Size distributions of 1 mM aqueous solutions of conjugates 4–β-CD (a) and 2–β-CD (b) at 25.0 °C (pH...
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Figure 6: Normalized absorption spectra of aqueous solutions of (a) eosin Y (2) and (b) conjugate 2–β-CD and ...
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Figure 7: Time-resolved fluorescence observed for aqueous solutions of (a) eosin Y (2) and (b) the 2–β-CD con...
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Figure 8: 1O2 luminescence detected upon 528 nm light excitation of D2O solutions of (a) eosin Y (2) and (b) 2...
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- Published 13 Apr 2017
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Figure 1: Molecular formulae and atom numbering of cyclobenzaprine (1, left) and amitriptyline (2, right). E ...
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Figure 2: Left: Job’s plot for H3’ chemical shift variations of the complex β-CD/1. Right: Job’s plot for H11...
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Figure 3: Expansion of 2D-ROESY of 1/β-CD (left) and 2/β-CD (right) complexes. Atom numbering is referred to Figure 1...
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Figure 4: X-ray diffraction structures of 1/β-CD (top) and 2/β-CD (bottom) complexes.
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Figure 5: The distance between the center of mass (c.o.m.) of molecule 1 (at left) and of molecule 2 (at righ...
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Figure 6: The value of the C9–C10 dihedral angle as a function of time for the complexes of molecule 1 and 2 ...
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Figure 7: Snapshots of the conformational transition in 2/β-CD in water taken at a 1 ps interval.
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- Published 05 May 2017
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Figure 1: Chemical structure of β-CD (a) and β-CD derivatives (b).
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Figure 2: Phase solubility diagrams of CD/trans-Ner inclusion complexes.
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Figure 3: Phase solubility profile of cabreuva EO obtained by the TOC method.
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Figure 4: a) 2D ROESY spectrum of β-CD/trans-Ner inclusion complex in D2O and b) representation of the most s...
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Figure 5: Photodegradation kinetics of cis-Ner (a), trans-Ner (b), the isomer mixture Ner (c) in the absence ...
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- Published 09 Aug 2017
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Scheme 1: Numbering scheme of one glucopyranose residue (G) of β-CD and the NAcTrp molecule; specific atom la...
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Figure 1: 3D maps of the observed dipolar, through-space host–guest interactions depicted so as to (a) reflec...
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Figure 2: Two dimers of β-CD–L-NAcTrp, stacked along the a-axis, are shown. Each β-CD dimer (A, B) encloses a...
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Figure 3: β-CD–L-NAcTrp complex at the interface between two β-CD dimers along the a-axis (major orientation ...
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Figure 4: “β-CD–D-NAcTrp” structure. (a) The herring bone packing of β-CD along the c-axis; (b) The guest (cy...
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Figure 5: L-NAcTrp and L-NAcPhe in β-CD dimers (the lines indicate the levels of the O2 and O3 secondary hydr...
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- Published 07 Sep 2017
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Figure 1: β-Cyclodextrin- and adamantyl-substituted poly(acrylate)s PAAβ-CDen, PAAADen, PAAADhn, and PAAADddn...
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Figure 2: ITC data for the PAAβ-CDen/PAAADen, system obtained in aqueous Na2HPO4/KH2PO4 pH 7.0 buffer at I = ...
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Figure 3: ITC data for the PAAβ-CDen/PAAADddn system obtained in aqueous Na2HPO4/KH2PO4 pH 7.0 buffer at I = ...
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Figure 4: Representation of ditopic complexation of an ADddn substituent of PAAADddn, by two β-CDen substitue...
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Figure 5: 2D NOESY 1H NMR spectrum of 0.44 wt % PAAβ-CDen ([β-CDen] = 2.0 × 10−3 mol dm−3) and 0.60 wt % PAAA...
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Figure 6: (a) Molar absorbance variation of 1.5 cm3 of a EO solution ([EO] = 2.00 × 10−5 mol dm−3) with 20 se...
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Figure 7: (a) Molar absorbance variation of 1.5 cm3 of a EO solution ([EO] = 2.00 × 10−5 mol dm−3) with 20 se...
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Figure 8: Speciation plot with [β-CDen]total = 100% for the PAAβ-CDen/PAAADhn/EO system.
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Figure 9: 2D NOESY 1H NMR spectrum of MR ([MR] = 2.0 × 10−3 mol dm−3) in solution with PAAβ-CDen (0.78 wt %, ...
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Figure 10: Viscosity variations at a 0.03 s−1 shear rate of 1.14 wt % PAAβ-CDen/PAAADen, 1.18 wt % PAAβ-CDen/P...
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Figure 11: Representation of dye complexation in the PAAβ-CDen/PAAADen and PAAβ-CDen/PAAADhn networks.
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Figure 12: Release profiles for EO (i), MO (ii) and MR (iii) from aqueous (a) Na2HPO4/KH2PO4 buffer alone, (b)...
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- Published 27 Nov 2017
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Scheme 1: Preparation of 2I-O-, 3I-O- and 6I-O-naphthylallyl derivatives of γ-CD by cross-metathesis.
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Scheme 2: Preparation of 2-O-, 3-O- and 6-O-NA derivatives of γ-CD by direct alkylation (see Table 1 for the yields ...
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Figure 1: Volume-weighted distribution functions for water solutions of 2-O- (2a), 3-O- (2b), and 6-O- (2c) N...
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Figure 2: Distribution functions for 2-O- (2a), 3-O- (2b), and 6-O- (2c) NA-γ-CD regioisomers in 50% MeOH (v/...
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Figure 3: Volume-weighted distribution functions for the 3-O- (2b) and 6-O- (2c) NA-γ-CD regioisomer at diffe...
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Figure 4: Effect of increasing concentration and sonication on the morphology of the 3-O-derivative 2b. A to ...
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Figure 5: Effect of increasing concentration and sonication on the morphology of the 2-O-derivative 2a. A: 2 ...
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Figure 6: Effect of increasing concentration and sonication on the morphology of the 6-O-derivative 2c. A: 0....
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Figure 7: Heat change for injection per mole of NA-γ-CD added as a function of the total concentration of NA-...
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Figure 8: 1H NMR spectra of 2-O-derivative 2a in D2O at concentrations of 100, 10, and 1 mM.
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Figure 9: 1H NMR spectra of 3-O-derivative 2b in D2O at concentrations of 100, 10, and 1 mM.
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Figure 10: Putative objects and interactions in naphthylallyl-γ-CD solution, depicted schematically for 6I-O-n...
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