Review: A History of Cyclodextrins

Crini, Grégorio

doi:10.1021/cr500081p

Cited by 1,516 publications

(1,136 citation statements)

References 418 publications

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“…The corresponding mean areas per single lipid chain were 0.204, 0.213, and 0.200 nm 2 for 10, 11 and 12, respectively. These values are independent of the size of the cyclodextrin and close to the calculated hydrocarbon cross-sectional area of 0.200 nm 2 . This result indicates that the hydrophobic chains of SO 3 -CDC 16 are well-packed and form dense monolayers.…”

Section: Monolayer Behaviors Of So3-cdc16 At the Air-water Interfacesupporting

confidence: 84%

Synthesis of Sulfated Cyclodextrin Amphiphiles with Liposomal Encapsulation Properties

Furuike¹,

Nasu²,

Tamura³

2015

JEAS

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A novel class of amphiphiles with sulfate groups at the C-6 position and palmitoyl groups at the C-2, 3 positions of α-, β-, and γ-cyclodextrin (CD) were efficiently synthesized. These compounds formed stable monolayers with high collapse pressures at the air-water interface. The mixed monolayer behaviors of the 6-O-sulfated CD amphiphiles (SO3-CDC16) in the presence of dipalmitoyl phosphatidylcholine (DPPC) and cholesterol were discussed using the surface pressure-molecular area (π-A) isotherms. The collapse pressures showed maxima at molar ratios of SO3-CDC16 lower than 10 mol%. A morphological analysis of the liposomes containing DPPC and 4 mol% SO3-CDC16 formed in PBS was carried out using transmission electron microscopy with negative staining, and vesicles with maximum diameters of 350 -500 nm were observed. Moreover, the releasing ability of these liposomes was examined using a fluorescent compound, calcein. It was clearly shown that liposomes containing SO3-CDC16 could release encapsulated calcein more easily than liposomes consisting only of DPPC, and that the release rate depended on the phase transition temperature of the SO3-CDC16 included in the liposome membrane.

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Section: Monolayer Behaviors Of So3-cdc16 At the Air-water Interfacesupporting

confidence: 84%

Synthesis of Sulfated Cyclodextrin Amphiphiles with Liposomal Encapsulation Properties

Furuike¹,

Nasu²,

Tamura³

2015

JEAS

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“…The list of available water-soluble hosts includes (but is not limited to): cyclodextrins, 33 cucurbiturils 34 and bambusurils, 35 cyclophanes 36,37 such as pillarenes, 38 and cavitands, the related calixarenes, and cyclotriveratrylenes ( Figure 2). 39 In addition, there are several classes of host that utilize self-assembly to form water-soluble hosts, [40][41][42] as well as 'foldamers' that, like proteins, are predisposed to fold into a conformation possessing a site for guest recognition.…”

Section: Host Molecules As Tools For Probing Aqueous Solutionsmentioning

confidence: 99%

Collaborative routes to clarifying the murky waters of aqueous supramolecular chemistry

et al. 2017

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Collaborative routes to clarifying the murky waters of aqueous supramolecular chemistry. AbstractOn planet Earth, water is everywhere: the majority of the surface is covered with it; it is a key component of all life; its vapor and droplets fill the lower atmosphere; even rocks contain it and undergo geomorphological changes because of it. A community of physical scientists largely drives studies of the chemistry of water and aqueous solutions, with expertise in biochemistry, spectroscopy, and computer modeling. More recently however, supramolecular chemistry -with its expertise in macrocyclic synthesis and measuring supramolecular interactions -have renewed their interest in water-mediated non-covalent interactions. These two groups offer complementary expertise that, if harnessed, offers to accelerate our understanding of aqueous supramolecular chemistry and water writ large. This review summarizes the state-of-the-art of the two fields, and highlights where there is latent chemical space for collaborative exploration by the two groups. 4Water is ubiquitous and essential to life on planet Earth. A full understanding of aqueous solutions is therefore of significance to a wide range of fields within the atmospheric, environmental, biological and geological sciences. Within the chemical sciences, a deeper appreciation of how non-covalent interactions and chemical transformations are influenced by water would benefit a variety of fields. However, as we highlight here, there are many open questions regarding the chemical and physical properties of aqueous solutions.The aqueous realm is frequently bifurcated into the Hofmeister and hydrophobic effects, phenomena that respectively deal with the properties of solutions of salts and relatively nonpolar molecules. However, it is becoming increasingly evident that these areas do in fact frequently overlap; two prime examples being the accumulation of large polarizable anions at the air-water interface, 1-5 and the favorable interactions of polarizable anions with non-polar surfaces. [6][7][8][9][10][11][12][13][14][15] Thus the hydrophobic and Hofmeister effects are but part of a greater continuum of aqueous supramolecular chemistry, with many important and outstanding questions regarding the influence of the different kinds of non-covalent interactions involved.Studies of water and aqueous solutions have mostly been driven by the physical sciences community, a broad range of scientists whose expertise in spectroscopy, computer modeling, and biochemistry (to name just three areas) has generally not involved macrocycles or host molecules in general. However, for some time now, supramolecular chemists -with their expertise in macrocyclic synthesis and measuring weak non-covalent interactions -have been travelling a parallel course of exploration. This Review, inspired by discussions between sixteen members of each community at a recent workshop, 16 is an attempt to summarize what we know about aqueous solutions, what we do not know about them, and where the two communit...

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“…Cyclodextrins, CD, are cyclic oligosaccharides formed through (1-4) ether linkages of glucopyranoside units [1,2]. The most common CDs, -, -, and -CD, are composed of six, seven and eight glucose units, respectively.…”

Section: Introductionmentioning

confidence: 99%

Host-guest interactions between cyclodextrins and surfactants with functional groups at the end of the hydrophobic tail

Martı́n

Ostos

Angulo

et al. 2017

Journal of Colloid and Interface Science

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Graphical abstractIn this work the influence of the incorporation of aromatic substituents at the end of the hydrophobic tail on the binding of cationic surfactants to cyclodextrins was studied. 2 HOST-GUEST INTERACTIONS BETWEEN CYCLODEXTRINS AND SURFACTANTS WITH FUNCTIONAL GROUPS AT THE END AbstractThe aim of this work was to investigate the influence of the incorporation of substituents at the end of the hydrophobic tail on the binding of cationic surfactants to α-, β-, and -cyclodextrins. The equilibrium binding constants of the 1:1 inclusion complexes formed follow the trend K 1 (α-CD)>K 1 (β-CD)>>K 1 (-CD), which can be explained by considering the influence of the CD cavity volume on the host-guest interactions. From the comparison of the K 1 values obtained for dodecyltriethylammonium bromide, DTEAB, to those estimated for the surfactants with the substituents, it was found that the incorporation of a phenoxy group at the end of the hydrocarbon tail does not affect K 1 , and the inclusion of a naphthoxy group has some influence on the association process, slightly diminishing K 1 . This makes evident the importance of the contribution of hydrophobic interactions to the binding, the length of the hydrophobic chain being the key factor determining K 1 . However, the presence of the aromatic rings does influence the location of the host and the guest in the inclusion complexes. The observed NOE interactions between the aromatic protons and the CD protons indicate that the aromatic rings are partially inserted within the host cavity, with the cyclodextrin remaining close to the aromatic rings, which could be partially intercalated in the host cavity. To the authors´ knowledge this is the first study on the association of cyclodextrins with monomeric surfactants incorporating substituents at the end of the hydrophobic tail.

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Review: A History of Cyclodextrins

Cited by 1,516 publications

References 418 publications

Synthesis of Sulfated Cyclodextrin Amphiphiles with Liposomal Encapsulation Properties

Synthesis of Sulfated Cyclodextrin Amphiphiles with Liposomal Encapsulation Properties

Collaborative routes to clarifying the murky waters of aqueous supramolecular chemistry

Host-guest interactions between cyclodextrins and surfactants with functional groups at the end of the hydrophobic tail

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