Cyclodextrin Inclusion Complexes

Szejtli, J.

doi:10.1007/978-94-015-7797-7_2

Cited by 133 publications

(148 citation statements)

References 425 publications

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“…The CD environment is characterized by a hydrophobic cavity and a hydrophilic rim. In solution, the cavity of CD provides a receptive host for the incorporation of hydrophobic compounds to form a host/guest complex [3][4][5]. The use of electrospray ionization, a soft ionization technique, allows the transfer of these intact complexes as charged species into the gas-phase.…”

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confidence: 99%

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Structural relationships in small molecule interactions governing gas-phase enantioselectivity and zwitterionic formation

Cong

Czerwieniec

McJimpsey

et al. 2006

J. Am. Soc. Mass Spectrom.

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Gas-phase zwitterionic amino acids were formed in complexes of underivatized ␤-cyclodextrin through reactions with a neutral base, n-propylamine. The reaction was performed in the analyzer cell of an electrospray ionization-Fourier transform mass spectrometer. Most of the natural amino acids were studied with three cyclodextrin hosts including ␣-, ␤-, and ␥-cyclodextrin to understand better the structural features that lead to the stabilization of the zwitterionic complexes. Molecular dynamics calculations were performed to provide insight into the structural features of the complexes. The rate constants of the reactions were obtained through kinetic plots. Examination of both L-and D-enantiomers of the amino acid showed that the reaction was enantioselective. The reaction was then employed to analyze mixtures of Glu enantiomers naturally occurring in the bacteria Bacillus licheniformis. (J Am Soc Mass Spectrom 2006, 17, 442-452)

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confidence: 99%

“…For these reasons, they have been used as models for enzyme-substrate interactions as well as solvation shells for the stabilization of highly energetic structures [13]. CDs have also been proposed as potential drug delivery devices [3][4][5].…”

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confidence: 99%

Structural relationships in small molecule interactions governing gas-phase enantioselectivity and zwitterionic formation

Cong

Czerwieniec

McJimpsey

et al. 2006

J. Am. Soc. Mass Spectrom.

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“…'Guest' molecules of a suitable size can fit into the central cavity, and the inclusion complex thus formed can increase the aqueous solubility of lipophilic compounds (Szejtli, 1982 …”

Section: Discussionmentioning

confidence: 99%

“…'Guest' molecules of a suitable size can fit into the central cavity, and the inclusion complex thus formed can increase the aqueous solubility of lipophilic compounds (Szejtli, 1982). Although P-cyclodextrin is not very water-soluble, chemically modified derivatives are available with greatly increased water solubility.…”

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confidence: 99%

Pharmacokinetics and binding of the bioreductive probe for hypoxia, NITP: effect of route of administration

Hodgkiss

Stratford²,

Dennis³

et al. 1995

Br J Cancer

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SummaryThe novel compound 7-[4'-(2-nitroimidazol-l-yl)-butyl]-theophylline (NITP) can be used as an immunologically detectable probe for hypoxic cells. Because of the limited water solubility of NITP, it has been administered dissolved in peanut oil with 10% dimethylsulphoxide (DMSO). A new aqueous formulation has been devised, based on a 50% solution of a modified P-cyclodextrin (Molecusol HPB), which increases the water solubility of NITP 10-fold. The To circumvent this problem, NITP has been administered in vivo as a solution in peanut oil + 10% DMSO . While this formulation has given satisfactory results in the tumour models used, it is clearly unsuitable for clinical administration, and an aqueous preparation of the drug would be preferable.,-Cyclodextrin consists of seven glucose units joined into a ring, taking up the shape of a three-dimensional torus with a hydrophobic cavity. 'Guest' molecules of a suitable size can fit into the central cavity, and the inclusion complex thus formed can increase the aqueous solubility of lipophilic compounds (Szejtli, 1982 ChemicalsThe novel compound 7-[4'-(2-nitroimidazol-1-yl)-butyl]-theophylline (NITP) was custom synthesised by Lancaster Synthesis using similar methods to those previously described

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“…The most common forms of cyclodextrin are ␣-, ␤-, and ␥-cyclodextrin (cyclomaltohexa-, hepta-, and octaoses), which contain six, seven, and eight glucose units, respectively. The structures of these molecules are toroidal, containing an apolar cavity with primary hydroxyl groups lying on the outside and the secondary hydroxyl groups being located inside [6,7]. The guest molecules that have a suitable size and shape can be incorporated into the cyclodextrin cavity to form inclusion complexes.…”

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Using molecular recognition of β-cyclodextrin to determine molecular weights of low-molecular-weight explosives by MALDI-TOF mass spectrometry

Zhang

Shi

Bai

et al. 2006

J. Am. Soc. Mass Spectrom.

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This study presents a novel method for determining the molecular weights of low molecular weight (MW) energetic compounds through their complexes of ␤-cyclodextrin (␤-CD) and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) in a mass range of 500 to 1700 Da, avoiding matrix interference. The MWs of one composite explosive composed of 2,6-DNT, TNT, and RDX, one propellant with unknown components, and 14 single-compound explosives (RDX, HMX, 3,4-DNT, 2,6-DNT, 2,5-DNT, 2,4,6-TNT, TNAZ, DNI, BTTN, NG, TO, NTO, NP, and 662) were measured. The molecular recognition and inclusion behavior of ␤-CD to energetic materials (EMs) were investigated. The results show that (1) the established method is sensitive, simple, accurate, and suitable for determining the MWs of low-MW single-compound explosives and energetic components in composite explosives and propellants; and (2) ␤-CD has good inclusion and modular recognition abilities to the above EMs. has become a powerful instrument for analyzing large synthetic polymers and biomacromolecules. However, for low-mass analytes-especially compounds that have a mass-to-charge of less than 500 Da-it has been a challenge. Because most of the molecular weights (MWs) of the currently used matrixes are less than 500 Da and because, during laser irradiation, they also act as their own matrixes, a variety of matrix-related ions are produced. Therefore, the use of MALDI-TOF-MS has been limited to the analysis of low-mass analytes. As a consequence, many analysts and experts of MALDI-TOF-MS have made considerable efforts and approaches to overcome this problem [1][2][3][4][5].Cyclodextrins are cyclic oligosaccharides that have ␣-d-glucose units that are connected through (1¡4) linkages. The most common forms of cyclodextrin are ␣-, ␤-, and ␥-cyclodextrin (cyclomaltohexa-, hepta-, and octaoses), which contain six, seven, and eight glucose units, respectively. The structures of these molecules are toroidal, containing an apolar cavity with primary hydroxyl groups lying on the outside and the secondary hydroxyl groups being located inside [6,7]. The guest molecules that have a suitable size and shape can be incorporated into the cyclodextrin cavity to form inclusion complexes. The formation of these complexes has been attributed to weak interactions, including van der Waals interactions, hydrophobic effects, and hydrogen bonding. The ability of cyclodextrins to form inclusion complexes with a variety of guest molecules has attracted widespread interest in academic research and industrial applications. Cyclodextrin complexes have been studied by using different physical methods and spectroscopic methods. However, the analysis of low-mass analytes by MALDI-TOF-MS, especially those in the mass range below 500 Da, has been a major challenge [8 -15].In this paper, a novel method of using the molecular recognition of ␤-cyclodextrin (␤-CD) to determine the mass of low-MW explosives by MALDI-TOF-MS is established.

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Cyclodextrin Inclusion Complexes

Cited by 133 publications

References 425 publications

Structural relationships in small molecule interactions governing gas-phase enantioselectivity and zwitterionic formation

Structural relationships in small molecule interactions governing gas-phase enantioselectivity and zwitterionic formation

Pharmacokinetics and binding of the bioreductive probe for hypoxia, NITP: effect of route of administration

Using molecular recognition of β-cyclodextrin to determine molecular weights of low-molecular-weight explosives by MALDI-TOF mass spectrometry

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