Alcohol size as a factor in the ternary complexes formed with pyrene and .beta.-cyclodextrin

Peña, Arsenio Muñoz de la; Ndou, Thilivhali T.; Zung, Jonathan B.; Greene, Karen L.; Live, David; Warner, Isiah M.

doi:10.1021/ja00005a019

Cited by 186 publications

(120 citation statements)

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“…Fluorescence intensity changes have been widely used for the determination of formation constants for CD and guest molecules, although the fluorescence intensity is sometimes replaced by fluorescence intensity ratio such as I/III vibronic band ratio for pyrene [21][22][23][24]. Fluorescence intensity ratio R is given by…”

Section: Resultsmentioning

confidence: 99%

Spectral Narrowing of UV-Visible Absorption and Emission Spectra of Anthracene-Derivatives in β-Cyclodextrin Nanocavity: Effects of Host/Guest Stoichiometry

Sato

Yoshizumi

Kiba

et al. 2012

Molecular Crystals and Liquid Crystals

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Cyclodextrins (CD) are cyclic oligosaccharides consisting of six or more D-glucopyranose units, the interior of which forms a hydrophobic cavity. In the present study, we employed the CD confinement effects as a tool to suppress an electronic decoherence of guest wavefunction by reducing intermolecular interactions between a guest molecule and the surrounding environment.Effects of host/guest stoichiometry on the decoherence suppresion were investigated by comparing native -CD with trimethyl--CD that should form only a 1:1 complex. Both fluorecence and fluorecence-excitation spectra of inclusion complexes exhibited spectral narrowings only for the -CD host, suggesting that the formation of barrel-type -CD dimer plays a key role for the pronounced spectral narrowings.

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Section: Resultsmentioning

confidence: 99%

Spectral Narrowing of UV-Visible Absorption and Emission Spectra of Anthracene-Derivatives in β-Cyclodextrin Nanocavity: Effects of Host/Guest Stoichiometry

Sato

Yoshizumi

Kiba

et al. 2012

Molecular Crystals and Liquid Crystals

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“…The stability of ternary complexes formed by the Py/b-CD complex, in the presence of alcohols 21 and amino acids 19 has been previously reported. Data obtained in the present work, in buffer solution, show that the stability of the complexes is higher than that previously reported, underlining the importance of the solvent medium.…”

Section: Ternary Agent Structurementioning

confidence: 90%

A spectrofluorimetric study of binary fluorophore–cyclodextrin complexes used as chiral selectors

et al. 2005

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Abstract-Six binary complexes between three fluorophores (pyrene, xanthone and anthraquinone) and b-cyclodextrin (b-CD) or heptakis-(6-amino)-(6-deoxy)-b-cyclodextrin (am-b-CD) were tested at two pH values (8.0 and 9.0) as chiral selectors for three a-amino acids chosen as model. The conditional constant (b 2T ) values for ternary complexes (fluorophore-CD-amino acid), determined by means of fluorescence spectroscopy, showed that the binary complexes are suitable receptors for chiral recognition. The effect of a-amino acids on stability and stoichiometric ratio of the binary complexes has also been studied. The binary complexes were in most cases stabilized by adding the ternary agent. The trend of stoichiometric ratios found is supported by variations in fluorescence spectra. Those relative to pyrene (Py) show little changes going from binary to ternary complexes, while those recorded in the presence of xanthone (Xan) give the most significant variations underlining a deep reorganization of guest. Anthraquinone (Aq) shows an intermediate behavior.

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“…This implies that at high water content alcohols can exist more stably in the water phase than in the CD's cavity. Pena et al 3 ) and Zung et at. 4) suggeted that a ternary complex between CD, pyrene, and alcohol was formed stably in their system.…”

Section: The Effects Oj Addition Oj Linear Alcohols On the Jormation mentioning

confidence: 95%

“…Particularly, at a water content of less than 10, the addition of methanol and ethanol increased the formation of the inclusion complex of d-limonene. This implies that all linear alcohols, particularly methanol and ethanol, would behave Pena et al 3 ) and Zung et al 4 ) have suggested that the apparent formation constants of the inclusion complex between fJ-or y-CD and pyrene were large due to the decrease in the alcohol polarity. Our results are in direct contrast to theirs.…”

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confidence: 99%

“…There have been several studies upon the effects of the presence of organic solvents such as alcohols on the formation of inclusion complexes between guest molecules and CDs in solution. Pena et al 3) and Zung et al 4) have extensively examined the role of several alcohols in the formation of an inclusion complex between pyrene and fJ-or y-CD in aqueous solution. They reported that the apparent formation constant of the complex between the fJ-or y-CD and pyrene increased dramatically in the presence of alcohols.…”

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confidence: 99%

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Enhancement and Inhibition by Linear Alcohol of the Formation of Inclusion Complexes betweend-Limonene and Cyclodextrins at Low Water Content

Furuta

Yoshii

Miyamoto

et al. 1994

Bioscience, Biotechnology, and Biochemistry

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The influence of linear alcohols on the formation of inclusion complexes between d-limonene and IX-, fJ-, or y-cyclodextrin has been examined at a low water content using a micro-aqueous method. In the presence of alcohols, particularly methanol and ethanol, the formation of inclusion complexes between d-limonene and fJ-or y-cyclodextrin is enhanced. The alcohol included in the cyclodextrin at the low water content was replaced with d-limonene as the water content increased. This implies that these alcohols would behave like water and activate the inclusion reaction between d-limonene and fJ-or y-cyclodextrin. On the contrary, the formation of d-limonene complexes with IX-cyclodextrin is inhibited by the presence of alcohols except for methanol. By means of the apparent water content, the amount of d-limonene complex in fJ-and y-cyclodextrin correlated well with a single sigmoid curve.Cyclodextrins (CDs) are homogeneous cyclic oligosaccharides, which can include various guest molecules in their hydrophobic cavity. Many kinds of volatile and unstable materials have been formed into stable complexes with CDs by maximizing this capability, thus enhancing their stability to oxygen, heat, or light. The most important application of CDs in the food industry is the powder encapsulation of volatile food ingredients to prevent the loss of flavors and essences. Since the inclusion complex can stabilize unstable and/or volatile substances against oxidation or exposure to heat or light, CDs are used to put many food flavors and fragrances in a powder state. They are also useful for improving the solubility of medicines.There are several ways of preparing powdered complexes of guest ingredients with CDs.1) Furuta et al. 2) proposed an efficient method for encapsulating d-limonene, in which liquid d-limonene was kneaded directly with fJ-CD in a twin screw kneader at a very low moisture content (between 10 and 20% on a dry basis). However, the influence of the water content on the formation of inclusion complexes should be examined. Furthermore, from a practical perspective, it is also useful to understand the influence of third components such as alcohols on the formation of inclusion complexes, because the use of organic solvents is often inevitable during the complexing of compounds that are very insoluble in water. There have been several studies upon the effects of the presence of organic solvents such as alcohols on the formation of inclusion complexes between guest molecules and CDs in solution. Pena et al. 3) and Zung et al. 4) have extensively examined the role of several alcohols in the formation of an inclusion complex between pyrene and fJ-or y-CD in aqueous solution. They reported that the apparent formation constant of the complex between the fJ-or y-CD and pyrene increased dramatically in the presence of alcohols. Similar phenomena were reported by Schuette t To whom correspondence should be sent. et al. 5) for the binding strength between fJ-CD and acridine.Masui 6 ) reported that in the presence of methanol,...

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Alcohol size as a factor in the ternary complexes formed with pyrene and .beta.-cyclodextrin

Cited by 186 publications

References 2 publications

Spectral Narrowing of UV-Visible Absorption and Emission Spectra of Anthracene-Derivatives in β-Cyclodextrin Nanocavity: Effects of Host/Guest Stoichiometry

Spectral Narrowing of UV-Visible Absorption and Emission Spectra of Anthracene-Derivatives in β-Cyclodextrin Nanocavity: Effects of Host/Guest Stoichiometry

A spectrofluorimetric study of binary fluorophore–cyclodextrin complexes used as chiral selectors

Enhancement and Inhibition by Linear Alcohol of the Formation of Inclusion Complexes betweend-Limonene and Cyclodextrins at Low Water Content

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