Inclusion Complex of 8-Anilinonaphthalene-1-sulfonate with β-Cyclodextrin

Nishijo, Juziro; Nagai, Mayumi

doi:10.1002/jps.2600800115

Cited by 42 publications

(12 citation statements)

References 7 publications

(2 reference statements)

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“…[130] High electron density inside the CyD cavity mobilizes the electrons of the entrapped guest molecule. [20] This phenomenon has been observed in literature for 8-anilinonaphthalene-1-sulfonate, [131] naphthalene [132] and naproxen. [108] …”

Section: Visible and Ultraviolet Spectroscopymentioning

confidence: 73%

A review on cyclodextrin encapsulation of essential oils and volatiles

Cabral-Marques

2010

Flavour & Fragrance J

578

383

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Cyclodextrins (CyDs) are cyclic carbohydrates derived from starch. The parent CyDs contain six, seven and eight glucopyranose units and are referred as a-, b-and g-CyD, respectively. The most important property of the CyDs is the ability to establish specific interactions -molecular encapsulation -with various types of molecules through the formation of noncovalently bonded entities, either in the solid phase or in aqueous solution. These nano-encapsulating agents may form inclusion complexes with essential oils and volatiles, or their components, in order to improve their characteristics, such as transformation of liquid compounds into crystalline form; masking unpleasant smells and tastes of some compounds; improving the physical and/or chemical stability; and stabilizing volatile compounds by reducing or eliminating any losses through evaporation. Complexation has been used to avoid the destruction of certain flavours by processing or, on storage, allowing the use of minor amounts of flavours. The guest molecule is released in the warm moisture of the mouth. Examples are spices, essential oils of vegetable origin and plant flavours, chamomile oil and extract, eucalyptus oil, fennel oil, lemon oil, onion and garlic oil, camphor, menthol, thymol, etc. There are several methods for the preparation of inclusion complexes; kneading, co-precipitation, freeze-drying and spray-drying the most commonly used. Evidence for a guest inclusion into the apolar CyD cavity may be proved by various analytical techniques, including NMR spectroscopy, UV-visible absorption spectroscopy, optical rotatory dispersion and circular dichroism, fluorescence, infrared/FT-IR spectroscopy, thermo-analysis, TLC, mass spectromety, and powder X-ray diffractometry.

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Section: Visible and Ultraviolet Spectroscopymentioning

confidence: 73%

A review on cyclodextrin encapsulation of essential oils and volatiles

Cabral-Marques

2010

Flavour & Fragrance J

578

383

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“…Most methods for determining the K values are based on titrating changes in the physicochemical properties of the guest molecule, i.e., the drug molecule, with the cyclodextrin and then analyzing the concentration dependencies. Additive properties that can be titrated in this way to provide information on the K values include 25 aqueous solubility, 19,[26][27][28] chemical reactivity, 10,29,30 molar absorptivity and other optical properties (CD, ORD), [31][32][33][34] phase solubility measurements, 35 NMR chemical shifts, 23,36 pH-metric methods, 37 calorimetric titration, 38 freezing point depression, 39 and LC chromato- graphic retention times. 40 While it is possible to use both guest or host changes to generate equilibrium constants, guest properties are usually most easily assessed.…”

Section: Cyclodextrin Complexesmentioning

confidence: 99%

Pharmaceutical Applications of Cyclodextrins. 1. Drug Solubilization and Stabilization

Loftsson

Brewster

1996

Journal of Pharmaceutical Sciences

1,990

1,035

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Cyclodextrins are cyclic oligosaccharides which have recently been recognized as useful pharmaceutical excipients. The molecular structure of these glucose derivatives, which approximates a truncated cone or torus, generates a hydrophilic exterior surface and a nonpolar cavity interior. As such, cyclodextrins can interact with appropriately sized molecules to result in the formation of inclusion complexes. These noncovalent complexes offer a variety of physicochemical advantages over the unmanipulated drugs including the possibility for increased water solubility and solution stability. Further, chemical modification to the parent cyclodextrin can result in an increase in the extent of drug complexation and interaction. In this short review, the effects of substitution on various cyclodextrin properties and the forces involved in the drug-cyclodextrin complex formation are discussed. Some general observations are made predicting drug solubilization by cyclodextrins. In addition, methods which are useful in the optimization of complexation efficacy are reviewed. Finally, the stabilizing/destabilizing effects of cyclodextrins on chemically labile drugs are evaluated.

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“…The driving forces for the complex formation have been attributed to the release of entropy-rich water molecules from the cavity [5], van der Waals interactions [6,7], hydrogen bonding [8 -10], hydrophobic interactions [7,11], release of ring strain in the CD molecule [9], and changes in solvent-surface tension [12].…”

Section: Introductionmentioning

confidence: 99%

Theoretical AM1 studies of inclusion complexes of heptakis(2‐O‐hydroxypropyl)‐β‐cyclodextrins with alkylated phenols

Huang

2004

Int J of Quantum Chemistry

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Semiempirical Austin model I (AM1) calculations have been performed on a family of inclusion complexes of heptakis(2-O-hydroxypropyl)-␤-cyclodextrin isomers derived from the 2-hydroxyl position (2HP␤CD) and from the 6-hydroxyl position (6HP␤CD) with alkylated phenol derivatives. From the stabilization energies and hydrogen bonding studies of the inclusion complexes of 2HP␤CD and 6HP␤CD with substituted phenols in head-first and tail-first positions, we found that the main driving forces for the formation of the inclusion complexes are from the van der Waals interactions.

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Inclusion Complex of 8-Anilinonaphthalene-1-sulfonate with β-Cyclodextrin

Cited by 42 publications

References 7 publications

A review on cyclodextrin encapsulation of essential oils and volatiles

A review on cyclodextrin encapsulation of essential oils and volatiles

Pharmaceutical Applications of Cyclodextrins. 1. Drug Solubilization and Stabilization

Theoretical AM1 studies of inclusion complexes of heptakis(2‐O‐hydroxypropyl)‐β‐cyclodextrins with alkylated phenols

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