Molecular Properties Related to the Anomalous Solubility of β-Cyclodextrin

Naidoo, Kevin J.; Chen, Jeff Yu-Jen; Jansson, Jennie L. M.; Widmalm, Göran; Maliniak, Arnold

doi:10.1021/jp037704q

Cited by 100 publications

(110 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Due to their amphiphilicity, CDs are expected to be applied in many areas such as drug delivery, chromatography, selective removal and solubility enhancement (Araki and Ito 2007;Del Valle 2004;Giuffrida et al 2006;Hedges 1998;Naidoo et al 2004;Szejtli 1998).…”

Section: Introductionmentioning

confidence: 99%

“…The strong hydrogen boding induced by many -OH groups in β-CD make the molecules possible to form networking structure similarly to phospholipid and gemini surfactant. However, comparing to α-and γ-CDs, β-CD has very poor solubility in conventional solvents due to the local water held in the cavity and around the molecules (Naidoo et al 2004). The local water makes β-CD rigid macro-cyclic compound, which is not easily accommodated into conventional solvent system (Naidoo et al 2004).…”

Section: Introductionmentioning

confidence: 99%

“…However, comparing to α-and γ-CDs, β-CD has very poor solubility in conventional solvents due to the local water held in the cavity and around the molecules (Naidoo et al 2004). The local water makes β-CD rigid macro-cyclic compound, which is not easily accommodated into conventional solvent system (Naidoo et al 2004). This poor solubility of β-CD did not allow the direct dissolution for electrospinning.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Preparation of anti-bacterial cellulose fiber via electrospinning and crosslinking with β-cyclodextrin

Kang

Choi

Kim

et al. 2015

Fashion and Textiles

View full text Add to dashboard Cite

In the study, we successfully produced electrospun cellulose fibers crosslinked with β-CD. For electrospinning, cellulose was dissolve in 1-ethyl-3-methylimidazolium acetate and DMF was added to the prepared solution for better spinnability. The prepared cellulose fiber was immersed in the solution containing β-CD, crosslinking agent and sodium hypophosphite. In order to understand the effect of a crosslinking agent, two different types of the agents, BTCA (1,2,3,4-butanetetracarboxylic acid) and citric acid with various concentrations were used for cross-linking. The crosslinking degree was increased with the concentration of the crosslinking agents, for the both agents. The cross-linked web changed into membrane like morphology when the concentration of the cross-linking agent was higher than 5 wt%. The concentration of crosslinking agent also gave influence on the crystallinity, the thermal property and the antibacterial activity of fibers. Due to the cross-linking the crystallinity was decreased. The cross-linked fiber showed selective bacterial behavior according to the bacterial strain and the cross-linking agent.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Preparation of anti-bacterial cellulose fiber via electrospinning and crosslinking with β-cyclodextrin

Kang

Choi

Kim

et al. 2015

Fashion and Textiles

View full text Add to dashboard Cite

show abstract

“…Because of its cavity size, cost and relative ease of chemical modification, the derivatives of α-CD and β-CD have been used commercially as drug carriers. An inhibiting property of β-CD has been its relatively low solubility in water compared with those of α-and γ-CDs that are nine and eleven times more soluble, respectively [1][2][3][4][5]. Therefore, a detailed understanding, based on molecular mechanisms, of the anomalous behavior of β-CD is important for catalytic, industrial, and pharmaceutical applications of CDs [4,5].…”

Section: Introductionmentioning

confidence: 99%

Quantifying the Possible Short- and Long-term Impacts of Superoxide Redox Chemistry on Seawater pH

2016

Can Chem Trans

View full text Add to dashboard Cite

Absorption, steady state and time resolved fluorescence spectra of 4,4′-sulfonyldiphenol (SDP), 3,3'-dimethyl 4,4′-sulfonyldiphenol (DMSP), 4,4′-sulfonyldibenzoic acid (SDBA) were studied in the presence of α-and β-cyclodextrins. Both in water and CD, SDP and SDBA exhibit two emission maxima while DMSP exhibit three emission maxima. In β-CD, the rate of enhancement of longer wavelength (LW) emission is higher than that of shorter wavelength (SW) band, where as in α-CD the enhancement of SW is larger than that of LW. The normal Stokes shifted band was originated from the locally excited state and the large Stokes shifted band was due to the emission form a TICT state. In these molecules, the presence of OH or COOH groups at para position of the aromatic rings increase the coplanar geometry in the excited state. Semi-empirical quantum-mechanical calculations were also carried out to assign the encapsulation of the SDP, DMSP and SDBA. PM3 calculations show that most of the SDBA values are different from SDP and DMSP because the values are dependent on the size of the CD cavities and nature of the functional group of the guest.

show abstract

“…14 It is, however, the three-dimensional (3D) structure including charge, hydrogen bonding and hydrophobic interactions as well as flexibility that is of importance in resolving the way in which a molecule function and interacts with other molecules. We have utilized X-ray crystallography, solid 15 and solution state NMR spectroscopy and a number of different molecular simulation 16 approaches to address 3D structure.…”

mentioning

confidence: 99%

A perspective on the primary and three-dimensional structures of carbohydrates

Widmalm

2013

Carbohydrate Research

Self Cite

View full text Add to dashboard Cite

Carbohydrates, in more biologically oriented areas referred to as glycans, constitute one of the four groups of biomolecules. The glycans, often present as glycoproteins or glycolipids, form highly complex structures. In mammals ten monosaccharides are utilized in building glycoconjugates in the form of oligo-(up to about a dozen monomers) and polysaccharides. Subsequent modifications and additions create a large number of different compounds. In bacteria, more than a hundred monosaccharides have been reported to be constituents of lipopolysaccharides, capsular polysaccharides, and exopolysaccharides. Thus, the number of polysaccharide structures possible to create is huge. NMR spectroscopy plays an essential part in elucidating the primary structure, i.e., monosaccharide identity and ring size, anomeric configuration, linkage position, and sequence, of the sugar residues. The structural studies may also employ computational approaches for NMR chemical shift predictions (CASPER program).Once the components and sequence of sugar residues have been unraveled, the threedimensional arrangement of the sugar residues relative to each other (conformation), their flexibility (transitions between and populations of conformational states), together with the dynamics (timescales) should be addressed. To shed light on these aspects we have utilized a combination of experimental liquid state NMR techniques together with molecular dynamics simulations. For the latter a molecular mechanics force field such as our CHARMM-based PARM22/SU01 has been used. linkage two torsion angles φ and ψ are defined and for 6-substituted residues also the ω torsion angle is required. Major conformers can be identified for which highly populated states are present. Thus, in 2 many cases a well-defined albeit not rigid structure can be identified. However, on longer timescales, oligosaccharides must be considered as highly flexible molecules since also anti-conformations have been shown to exist with H-C-O-C torsion angles of ~180°, compared to syn-conformations in which the protons at the carbon atoms forming the glycosidic linkage are in close proximity.The accessible conformational space governs possible interactions with proteins and both minor changes and significant alterations occur for the oligosaccharides in these interaction processes.Transferred NOE NMR experiments give information on the conformation of the glycan ligand when bound to the proteins whereas saturation transfer difference NMR experiments report on the carbohydrate part in contact with the protein. It is anticipated that the subtle differences in conformational preferences for glycan structures facilitate a means to regulate biochemical processes in different environments. Further developments in analysis of glycan structure and in particular its role in interactions with other molecules, will lead to clarifications of the importance of structure in biochemical regulation processes essential to health and disease.

show abstract

Molecular Properties Related to the Anomalous Solubility of β-Cyclodextrin

Cited by 100 publications

References 19 publications

Preparation of anti-bacterial cellulose fiber via electrospinning and crosslinking with β-cyclodextrin

Preparation of anti-bacterial cellulose fiber via electrospinning and crosslinking with β-cyclodextrin

Quantifying the Possible Short- and Long-term Impacts of Superoxide Redox Chemistry on Seawater pH

A perspective on the primary and three-dimensional structures of carbohydrates

Contact Info

Product

Resources

About