Abstract:Cyclodextrine werden gerne als Bau-molekule auf ein passendes Gastmole-higkeit zur molekularen Erkennung zur steine eingesetzt, da sie sich gezielt so-kul aufgefadelt werden. Solche supra-chromatographischen Trennung von wohl kovalent, als auch nichtkovalent molekularen Strukturen entstehen meist komplexen Stoffgemischen, insbesondeverknupfen lassen. So wurden an ein in Losung, so daD sie durch hochauflo-re von Racematen, genutzt. Auch kon-/I-Cyclodextrinmolekul regioselektiv ein, sende spektroskopische Method… Show more
“…They consist of 6(α), 7(β), 8(γ) or more units of 1,4-linked glucose and exhibit a truncated-conus-shaped structure with a hydrophobic cavity and hydrophilic rim. This structure is the key to enclose smaller hydrophobic molecules to form hostguest compounds, in which the host is entrapped in the cavity of the cyclodextrin torus [1][2][3][4]. Despite the fact that the guest molecule is water-insoluble like, e.g., styrene (1), the complex formed by treatment with an aqueous solution of cyclodextrin becomes water-soluble without any chemical modification done during the complexation.…”
Styrene was encapsulated by an equimolar amount of randomly methylated β-cyclodextrin (CD) in water resulting in a water-soluble CD complex. Polymerization of this complex was carried out at 50°C using different amounts of the water-soluble azo-initiator 2,2'-azobis[N,N'-dimethyleneisobutyramidine] dihydrochloride. Unthreading of CD during polymerization led to water-insoluble polystyrene. Analysis of the polymers obtained showed that the polymerization from homogenous aqueous solution can be described by an equation similar to the classical polymerization in solution (number-average degree of polymerization vs. initiator concentration: P n -1 ~ [I] 0.5 ).
“…They consist of 6(α), 7(β), 8(γ) or more units of 1,4-linked glucose and exhibit a truncated-conus-shaped structure with a hydrophobic cavity and hydrophilic rim. This structure is the key to enclose smaller hydrophobic molecules to form hostguest compounds, in which the host is entrapped in the cavity of the cyclodextrin torus [1][2][3][4]. Despite the fact that the guest molecule is water-insoluble like, e.g., styrene (1), the complex formed by treatment with an aqueous solution of cyclodextrin becomes water-soluble without any chemical modification done during the complexation.…”
Styrene was encapsulated by an equimolar amount of randomly methylated β-cyclodextrin (CD) in water resulting in a water-soluble CD complex. Polymerization of this complex was carried out at 50°C using different amounts of the water-soluble azo-initiator 2,2'-azobis[N,N'-dimethyleneisobutyramidine] dihydrochloride. Unthreading of CD during polymerization led to water-insoluble polystyrene. Analysis of the polymers obtained showed that the polymerization from homogenous aqueous solution can be described by an equation similar to the classical polymerization in solution (number-average degree of polymerization vs. initiator concentration: P n -1 ~ [I] 0.5 ).
“…Cyclodextrins are cyclic oligosaccharides known for their ability to include into their hydrophobic cavity via host-guest complexation a variety of hydrophobic compounds [1]. This property has been extensively exploited to change the physicopharmaceutical properties of lipophilic drugs such as water solubility, bioavailability, improved stability and effectiveness [2], and cyclodextrins at present are widely used as transportactive additives.…”
Mono(6-succinylamido-6-deoxy)-13-cyclodextrin was synthesized by classical carbohydrate chemistry and used as a template mono-functionalized with the linear, fully flexible 4C-spacer carboxylate for covalent linkage of the calpain inhibitor leucyl-leucyl-norleucinal. Spectroscopic analyses of the conjugate do not support a self-inclusion of part of the hydrophobic peptide tail, but confirm its intra-or intermolecular interaction with the template moiety that leads to full water solubility. The inhibitory potency of the ~-cyclodextrin/peptide aldehyde construct was compared with that of the parent Ac-Leu-Leu-Nle-H against cathepsin B and calpain. Despite the large size of the template the inhibition of cathepsin B was only slightly reduced in full agreement with the X-ray structure of this enzyme which shows full accessibility of the S-subsites. For this enzyme the 4C-spacer is apparently sufficient to guarantee optimal interaction of the peptide tail with the binding cleft. Conversely, for gcalpain a significantly decreased inhibitory potency was obtained with the conjugate suggesting steric interference of the template in the binding process. These results show that the beneficial properties of the cyclodextrin template can be retained in conjugates with bioactive peptides if attention is paid to optimize in each case the size and nature of the spacer for optimal recognition of the grafted biomolecule.
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