Host-guest complexation of oligosaccharides: Interaction of maltodextrins with hydrophobic fluorescence probes in water

Aoyama, Yasuhiro; Otsuki, Jun-ichi; Nagai, Y.; Kobayashi, Kenji; Toi, Hiroo

doi:10.1016/0040-4039(92)80022-c

Cited by 34 publications

(14 citation statements)

References 13 publications

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“…An NMR study indicated that the triazole and triazolone rings of the drug molecule could be involved in the 1:2 complex formation. 34 Because of the very low aqueous drug solubility, the NMR study of the itraconazole/cyclodextrin complex was done in pure dimethyl sulfoxide-d 6 . The authors argue that because the dielectric constants of dimethyl sulfoxide and water are similar (e ¼ 46.8 and 80, respectively), the stoichiometry of the complex should be similar.…”

Section: Methods Used To Determine Stability Constants Of Cyclodextrimentioning

confidence: 99%

“…[4][5][6][7] It has also been shown that cyclodextrins are, like noncyclic oligosaccharides, able to form non-inclusion complexes. [8][9][10][11][12][13] For example, Gabelica et al 8,9 have reported that a-cyclodextrin forms both inclusion and noninclusion complexes with a,o-dicarboxylic acids and that the two types of complexes coexist in aqueous solutions.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Self-Association of Cyclodextrins and Cyclodextrin Complexes

Loftsson

Másson

Brewster

2004

Journal of Pharmaceutical Sciences

393

230

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Section: Methods Used To Determine Stability Constants Of Cyclodextrimentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Self-Association of Cyclodextrins and Cyclodextrin Complexes

Loftsson

Másson

Brewster

2004

Journal of Pharmaceutical Sciences

393

230

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“…in solution, and in all cases the equilibrium association constants were found to be about 2-3 orders of magnitude lower than for the corresponding inclusion complexes with cyclodextrins [31,32]. Maltohexaose cannot form inclusion complexes in solution, and hydrogen bonds between the OH groups of the sugar and the guest are thought to be responsible for the weak binding (hydrogen bonding interactions are disfavored in water) [33].…”

Section: Influence Of Chain Length On the Relative Abundance Of Complexmentioning

confidence: 99%

On the specificity of cyclodextrin complexes detected by electrospray mass spectrometry

Gabelica

Galić

Pauw

2002

J. Am. Soc. Mass Spectrom.

123

116

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␣-cyclodextrin complexes with linear ␣, -dicarboxylic acids were investigated by electrospray mass spectrometry. These hydrophobic complexes are known to have an equilibrium binding constant that increases with the diacid chain length. However, the electrospray mass spectrometry (ES-MS) spectra showed that the relative intensity of the complex did not vary significantly with chain length. This contradiction is caused by a contribution of nonspecific adducts to the signal of the complex in ES-MS. In order to estimate the contribution of nonspecific adducts to the total intensity of the complexes with ␣-cyclodextrin, the comparison was made between ␣-cyclodextrin and maltohexaose, the latter being incapable of making inclusion complexes in solution. The signal observed for complexes between diacids and maltohexaose can only result from nonspecific electrostatic aggregation, and is found to be more favorable with the shorter diacids. This is also supported by MS/MS experiments. A procedure is described which allows estimation of the contribution of the nonspecific complex in the spectra of the complexes with ␣-cyclodextrin by using the relative intensity of the complex with maltohexaose. The contribution of the specific complex to the total signal intensity is found to increase with the diacid chain length, which is in agreement with solution behavior. (J Am Soc Mass Spectrom 2002, 13, 946 -953)

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“…However, the binding affinities of succinoglycan dimers with ANS and TNS are similar as based on the value of K aANS /K aTNS , whereas β-CD binds TNS 18 fold more strongly than ANS. 12 The notable aspect of this result is that the succinoglycan dimer is an acyclic hexadecasaccharide containing 14 glucoses and 2 galactoses substituted with succinyl, acetyl, and pyruvyl moieties and, the dimer has no distinct cavity in its structure. This result might be possible in that linear oligosaccharides can exhibit amphiphilicity caused by hydrophilic and hydrophobic surfaces in sugar chains.…”

Section: Notesmentioning

confidence: 96%

“…10 As representative fluorescent probes, 8-anilino-1-naphthalene sulfonate (ANS) and 6-ptoluidino-2-naphthalenesulfonate (TNS) have been used to explore the hydrophobicity of biomolecules. [11][12][13] The chemical structures of both fluorescent probes are shown in Figure 1(b) and 1(c). In the present study, the fluorescence of ANS and TNS, respectively, in an aqueous solution was investigated under the presence of succinoglycan dimers (D1, D2, D3, and D4), and the hydrophobic character of the dimers was analyzed.…”

Section: -7mentioning

confidence: 99%