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Aki, Hatsumi; Niiya, Tokihiro; Iwase, Yukiko; Yamamoto, Magobei

doi:10.1023/a:1011592327676

Journal of Thermal Analysis and Calorimetry

2001

DOI: 10.1023/a:1011592327676

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Hatsumi Aki

Tokihiro Niiya

Yukiko Iwase

et al.

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Cited by 12 publications

(20 citation statements)

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“…yclodextrins (CDs) have been widely used in the pharmaceutical industry to increase the aqueous solubility, stability, and bioavailability for drugs and in chemical analysis to determine a variety of compounds, from neutral and charged organic molecules to inorganic ions [1][2][3][4]. However, the application of naturally occurring CDs is hampered because of their low aqueous solubility.…”

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confidence: 99%

“…Unlike other coordination compounds, there are no covalent bonds between the host CD and the guest molecule. Although the dimensional fit between host cavity and guest molecule is important in the formation of the complex, hydrophobic desolvation, hydrogen bonding, and van der Waals interactions are among the most important driving forces for CD complexation [1,4]. Stable inclusion complexes of various drugs with SBE-␤-CDs that have 4 to 7 average degrees of substitution of SBE have been reported [5][6][7].…”

mentioning

confidence: 99%

“…Stable inclusion complexes of various drugs with SBE-␤-CDs that have 4 to 7 average degrees of substitution of SBE have been reported [5][6][7]. One way to evaluate the stability of the inclusion complex is to measure their association constants [4,7].…”

mentioning

confidence: 99%

“…1) [5]. The SBE-␤-CD used in the separation was a mixture of positional and regional isomers containing from 1 to 10 sulfobutyl ether groups with an average degree of substitution of 4 per cyclodextrin, SBE [4]-␤-CD. The CD used appeared to be well suited for the separation of neutral estrogens because of its negative charges.…”

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confidence: 99%

“…The separation was carried out in the normal electroosmotic flow (EOF) mode in which the cathode is at the detector end of the capillary and the electrolyte solution flows toward the detector. In the presence of an electric field, the negatively charged SBE [4]-␤-CD along with its estrogen inclusion complexes move in the opposite direction of the osmotic flow. But the EOF overcomes this opposite migration.…”

mentioning

confidence: 99%

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Capillary electrophoretic separation and theoretical study of inclusion complexes of sulfobutyl ether β‐cyclodextrin with estrogens

Deng

Huang

2004

Int J of Quantum Chemistry

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ABSTRACT:Five estrogens (2-hydroxyestrone, 2-methoxyestradiol, estrone, estriol, and 17␣-estradiol) and two stereoisomers (17␣-and 17␤-estradiol) have been successfully separated using capillary electrophoresis with anionic sulfobutyl ether ␤-cyclodextrin (SBE-␤-CD). The SBE-␤-CD used in the separation was a mixture of positional and regional isomers containing from 1 to 10 sulfobutyl ether groups with an average degree of substitution of four per cyclodextrin; thus, a tetra-SBE substituted CD, SBE[4]-␤-CD, has been chosen as the model host molecule in the present study. Relative to the position of the cavity, three initial arrangements of the 4 SBE groups, 0-, 2-, and 4-up, have been considered. In addition two types of inclusion complexes, cis and trans orientations, are also considered for each estrogen. In the cis structure the SBE group of the cyclodextrin and the phenol group of the estrogen are on the same side, while in the trans structure the two groups are on opposite sides. The objective of the present study is to perform PM3 (Parametric Method 3) semiempirical molecular orbital calculations on these six inclusion complexes (12 different orientations) for each SBE[4]-␤-CD to correlate the migration order with their relative stability. Theoretical calculations have shown that only when SBE groups are perpendicular to the axis of CD (0-up arrangement), the cavity is open on both sides for incoming guest molecules. A correlation was observed between the total heats of formation for the cis and trans estrogen-CD inclusion complexes of the same estrogen and the electrophoretic migration time although the relationship is not linear, suggesting that both orientations may occur simultaneously. In other two SBE[4]-␤-CDs, the narrower side of the cavity is partially capped due to the formation of intra-hydrogen bonds among three of the four SBE groups. Thus, a guest molecule can enter the cavity from the wide end of the cavity only. As a result, the estrogen molecules protrude from the cavity in most cases.

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confidence: 99%

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confidence: 99%

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confidence: 99%

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confidence: 99%

mentioning

confidence: 99%

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Capillary electrophoretic separation and theoretical study of inclusion complexes of sulfobutyl ether β‐cyclodextrin with estrogens

Deng

Huang

2004

Int J of Quantum Chemistry

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Synthesis and applications of adsorbents containing cyclodextrins

Crini¹,

2002

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Synthesis and applications of adsorbents containing cyclodextrinsCyclodextrins (CDs), which possess a hydrophobic cavity, have a remarkable capacity to form inclusion complexes with various molecules through host-guest interactions. It is well known that the usefulness of CDs is due to the combination of the inclusion properties and structural features of these molecules. CDs are used extensively in separation science because CD-complexation phenomena offer a procedure of choice for separation of compounds and extraction processes, and provide a useful and versatile tool for protecting the environment. The present review shows the advantages accruing from the use of adsorbents containing cyclodextrins, in particular in chromatographic separations and in waste water treatment. The main goal of this review is to provide a summary of the information concerning the synthesis of materials containing CDs and to give a general overview of the different possible applications of CDs as sorbents in the field of separation techniques. Recent and continuing interest in these adsorbents is evident from the number of papers that appear each year in the literature.

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Computational modeling of inclusion complexes of β‐cyclodextrin with enantiomers of salsolinol, N‐methyl‐salsolinol, and 1‐benzyl‐tetrahydroisoquinoline

Huang

Quan

Liu

2008

Int J of Quantum Chemistry

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Capillary electrophoresis with β-CD as a chiral selector has successfully separated the two enantiomers of salsolinol, N-methyl-salsolinol, and 1-benzyl-tetrahydroisoquinoline. The migration times of each enantiomer in capillary electrophoresis reflect the stability of their β-CD inclusion complexes. This paper reports a computational modeling study of the inclusion complexes of β-cyclodextrin (β-CD) with salsolinol, N-methyl-salsolinol, and 1-benzyltetrahydroisoquinoline by using PM3 (Parametric Method 3) semi-empirical molecular orbital calculations and the ONIOM hybrid method. Two types of the inclusion complexes, cis-and transorientations, are considered for each enantiomer of the guest molecules, salsolinol, N-methylsalsolinol, and 1-benzyl-tetrahydroisoquinoline. In the cis-orientation, the nitrogen in the salsolinol, N-methyl-salsolinol, and 1-benzyl-tetrahydroisoquinoline points toward the secondary hydroxyls of the β-CD, while in the trans-orientation, the nitrogen in salsolinol, N-methylsalsolinol, and 1-benzyl-tetrahydroisoquinoline points toward the primary hydroxyls of the β-CD. We found that the stabilization energies of these inclusion complexes from these PM3 and ONIOM different methods correlate very well with the migration order deduced from the study of capillary electrophoretic separation.

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Untitled

Cited by 12 publications

References 9 publications

Capillary electrophoretic separation and theoretical study of inclusion complexes of sulfobutyl ether β‐cyclodextrin with estrogens

Capillary electrophoretic separation and theoretical study of inclusion complexes of sulfobutyl ether β‐cyclodextrin with estrogens

Synthesis and applications of adsorbents containing cyclodextrins

Computational modeling of inclusion complexes of β‐cyclodextrin with enantiomers of salsolinol, N‐methyl‐salsolinol, and 1‐benzyl‐tetrahydroisoquinoline

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