Formation and Deposition of Monolayers of Amphiphilic β-Cyclodextrin Derivatives

Kawabata, Yasujiro; Matsumoto, Mutsuyoshi; Tanaka, Mieko; Takahashi, Hisao; Irinatsu, Yuichi; Tamura, Shoji; Tagaki, Waichiro; Nakahara, Hiroyuki; Fukuda, Kiyoshige

doi:10.1246/cl.1986.1933

Cited by 73 publications

(32 citation statements)

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“…[12,13] Either of these precursors can be used to obtain the alkyl thioethers 4 a-c and 5 a-c by nucleophilic substitution, although compounds 2 a-c are less reactive than 3 a-c and usually require longer reaction times to afford complete substitution in a good yield. While b-cyclodextrins 4 b and 5 b have been described, [14][15][16] a-and g-cyclodextrins 4 a, 4 c, 5 a, and 5 c are new. The most effective purification of these alkyl thioethers is a Soxhlet extraction with hexane to remove excess alkyl thiols.…”

Section: Resultsmentioning

confidence: 99%

“…For the analogues of 4 a-c and 5 ac described in the literature, [14][15][16] the molecular area is hardly different from unmodified cyclodextrin (170 2 for 1 a, 210 2 for 1 b, and 240 2 for 1 c). However, the presence of ethylene glycol residues clearly increases the molecular surface area.…”

mentioning

confidence: 89%

“…[14][15][16] The area per molecule at zero compression (A 0 ) and also at maximum compression (A C ) scales with the cyclodextrin ring size (Table 1), but it is similar for cyclodextrins with n-dodecyl and n-hexadecyl substituents.…”

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confidence: 99%

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Bilayer Vesicles of Amphiphilic Cyclodextrins: Host Membranes That Recognize Guest Molecules

Falvey

Lim

Darcy

et al. 2005

Chemistry A European J

183

212

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A family of amphiphilic cyclodextrins (6, 7) has been prepared through 6-S-alkylation (alkyl=n-dodecyl and n-hexadecyl) of the primary side and 2-O-PEGylation of the secondary side of alpha-, beta-, and gamma-cyclodextrins (PEG=poly(ethylene glycol)). These cyclodextrins form nonionic bilayer vesicles in aqueous solution. The bilayer vesicles were characterized by transmission electron microscopy, dynamic light scattering, dye encapsulation, and capillary electrophoresis. The molecular packing of the amphiphilic cyclodextrins was investigated by using small-angle X-ray diffraction of bilayers deposited on glass and pressure-area isotherms obtained from Langmuir monolayers on the air-water interface. The bilayer thickness is dependent on the chain length, whereas the average molecular surface area scales with the cyclodextrin ring size. The alkyl chains of the cyclodextrins in the bilayer are deeply interdigitated. Molecular recognition of a hydrophobic anion (adamantane carboxylate) by the cyclodextrin vesicles was investigated by using capillary electrophoresis, thereby exploiting the increase in electrophoretic mobility that occurs when the hydrophobic anions bind to the nonionic cyclodextrin vesicles. It was found that in spite of the presence of oligo(ethylene glycol) substituents, the beta-cyclodextrin vesicles retain their characteristic affinity for adamantane carboxylate (association constant K(a)=7.1 x 10(3) M(-1)), whereas gamma-cyclodextrin vesicles have less affinity (K(a)=3.2 x 10(3) M(-1)), and alpha-cyclodextrin or non-cyclodextrin, nonionic vesicles have very little affinity (K(a) approximately 100 M(-1)). Specific binding of the adamantane carboxylate to beta-cyclodextrin vesicles was also evident in competition experiments with beta-cyclodextrin in solution. Hence, the cyclodextrin vesicles can function as host bilayer membranes that recognize small guest molecules by specific noncovalent interaction.

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Section: Resultsmentioning

confidence: 99%

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confidence: 89%

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Bilayer Vesicles of Amphiphilic Cyclodextrins: Host Membranes That Recognize Guest Molecules

Falvey

Lim

Darcy

et al. 2005

Chemistry A European J

183

212

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“…Obtained by grafting aliphatic chains (length C10-C16) to all the primary hydroxyls of the CD molecule [117,118] Skirt-shaped cyclodextrins They consist of ,  and -cyclodextrins permodified with aliphatic esters (C2 to C14) on the secondary face.…”

Section: Non-ionic Amphiphilic Cyclodextrins Lollipop Cyclodextrinsmentioning

confidence: 99%

Molecular Buckets: Cyclodextrins for Oral Cancer Therapy

Calleja

Huarte

Agüeros

et al. 2011

Therapeutic Delivery

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The oral route is preferred by patients for drug administration due to its convenience, resulting in improved compliance. Unfortunately, for a number of drugs (e.g., anticancer drugs), this route of administration remains a challenge. Oral chemotherapy may be an attractive option and especially appropriate for chronic treatment of cancer. However, this route of administration is particularly complicated for the administration of anticancer drugs ascribed to Class IV of the Biopharmaceutical Classification System. This group of compounds is characterized by low aqueous solubility and low intestinal permeability. This review focuses on the use of cyclodextrins alone or in combination with bioadhesive nanoparticles for oral delivery of drugs. The state-of-the-art technology and challenges in this area is also discussed.

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“…terathiafulvalene (TTF) moieties [74], were transferred as L-B films from the water surface with a transfer ratio of 1 to the solid substrate. Charge-transfer interactions in the L-B films were then studied and new sensing devices were proposed [75][76][77][78][79].…”

Section: Langmuir-blodgett (L-b) Techniquementioning

confidence: 99%

Electrochemistry of Cyclodextrin Inclusion Complexes of Pharmaceutical Compounds

Radi¹

2010

TOCBMJ

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Electrochemistry of cyclodextrins (CDs) and cyclodextrin inclusion complexes with different pharmaceutical compounds is reviewed. The article highlights some electrochemical investigations of the CD-drugs interactions in solution. Cyclodextrin modified electrodes and their applications as electrochemical sensors in pharmaceutical analysis based on the self-assembly of CD derivatives on metal electrodes and nanoparticles, and cyclodextrin-modified multiwalled carbon nanotubes are also discussed.

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Formation and Deposition of Monolayers of Amphiphilic β-Cyclodextrin Derivatives

Abstract: Stable condensed monolayers of four different amphiphilic derivatives of β-cyclodextrin were formed on a water subphase. The base of the cylindrical cyclodextrin residue was found to be parallel to the water surface. Langmuir–Blodgett films were obtained for three derivatives.

Cited by 73 publications

References 1 publication

Bilayer Vesicles of Amphiphilic Cyclodextrins: Host Membranes That Recognize Guest Molecules

Bilayer Vesicles of Amphiphilic Cyclodextrins: Host Membranes That Recognize Guest Molecules

Molecular Buckets: Cyclodextrins for Oral Cancer Therapy

Electrochemistry of Cyclodextrin Inclusion Complexes of Pharmaceutical Compounds

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