Solution-to-Surface Molecular-Delivery System Using a Macrocyclic Sugar Cluster. Sugar-Directed Adsorption of Guests in Water on Polar Solid Surfaces

Fujimoto, Takako; Shimizu, Chikao; Hayashida, Osamu; Aoyama, Yasuhiro

doi:10.1021/ja9709536

Cited by 88 publications

(37 citation statements)

References 20 publications

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“…[12] Subsequent work reveals that 1 a and, in a more pronounced manner, its higher (longer saccharide) homologue are co-precipitated with sodium phosphate in water. [13] Sugar and salt are two typical classes of highly water-soluble materials.…”

Section: Sticky Saccharides: Marriage Of Sugar and Salt Tomentioning

confidence: 99%

“…Escape from Otherwise Favorable Hydration Prisons [1,12,13] An important yet largely unexplored area of molecular recognition is effective complexation driven by hydrogen bonding in highly competitive water as a medium. Owing to their highly hydrophilic nature, saccharides may be regarded as one of the least potential hydrogen-bond makers in water.…”

Section: Sticky Saccharides: Marriage Of Sugar and Salt Tomentioning

confidence: 99%

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Macrocyclic Glycoclusters: From Amphiphiles through Nanoparticles to Glycoviruses

Aoyama

2004

Chemistry A European J

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Macrocyclic glycocluster amphiphiles are intended to be a covalent-bundle mimic of clustering glycolipid motifs on the cell membrane. They are irreversibly micellized to give glycocluster nanoparticles (GNPs); their masked hydrophobicity endows them with remarkable saccharide specificities in the interactions with biological saccharide receptors. The GNPs also exhibit unprecedented hydrogen-bond capacities; they are agglutinated with Na(2)HPO(4) and assembled on plasmid DNA in a number-, size-, and shape-controlled manner to give artificial glycoviral particles capable of transfection. Thus, the intrinsic function of viruses, that is, cell invasion followed by gene expression, is also intrinsic to size-regulated (approximately 50 nm) glycoviruses. The growth of glycocluster amphiphiles through nanoparticles to glycoviruses reveals a hierarchical adhesion control of the saccharide clusters.

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Section: Sticky Saccharides: Marriage Of Sugar and Salt Tomentioning

confidence: 99%

Section: Sticky Saccharides: Marriage Of Sugar and Salt Tomentioning

confidence: 99%

Macrocyclic Glycoclusters: From Amphiphiles through Nanoparticles to Glycoviruses

Aoyama

2004

Chemistry A European J

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“…The strength of the interaction may be enhanced by addition of specific functional groups enhancing hydrogen bonding in the upper or lower rim, crown ether linkages or metal-specific moieties. Calixarenes have been used in metal ion recognition 95 and complexation 96 , interaction with low molar mass guests 97 , film forming 98 , biomolecular recognition 99 , catalysis 100 , and drug delivery 101 . In terms of polymer science, calixarenes have been immobilized on polymer supports 102 , introduced as side groups 103 or into the main chain 104 .…”

Section: Figmentioning

confidence: 99%

Multi‐stimuli‐responsive Polymers Based on Calix[4]arenes and Dibenzo‐18‐crown‐6‐ethers

Wiktorowicz

Tenhu

Aseyev

2018

Temperature‐Responsive Polymers

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“…Nevertheless, it is highly adhesive in water and is readily adsorbed on polar solid surfaces such as quartz (silica) conceivably via polar (hydrogen bonding) interactions between sugar OH groups and quartz silanol (SiOH) moieties. 29 Glycocluster 28 is also easily bound to lectin (sugar binding protein) in a specific manner. 30 Thus, glucose-cluster compound Mal8 is bound to glucose/mannose binding concanavalin A but not to galactose binding peanut lectin.…”

Section: Huge But Finite Nano Systems Basedmentioning

confidence: 99%

Structure and Function of Molecular Assembly. A Personal Reminiscence

Aoyama¹

2009

Bulletin of the Chemical Society of Japan

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In this account is described an outline of research the author has conducted over the last 35 years. Depending on the type of molecular assemblies dealt with, the whole work is divided into four parts, i.e., small hostguest systems in organic media, infinite solid systems, huge but finite nano systems in aqueous media, and manipulated biological systems. The essence of the hostguest systems (Section 2) is molecular recognition based on convergent multiple interactions involving OH£O hydrogen bonds, where sugar binding and detailed thermodynamic analysis of multipoint recognition may be taken as highlights. A couple of new fields arise from the hostguest chemistry by paradigm shift. One is in the direction of multiple interactions, from convergent to divergent. Section 3 thus concerns molecular alignment control in crystals using orthogonal aromatic triad and diad building blocks. Catalysis by microporous metallo-organic frameworks as organic zeolites is also described. The other shift in paradigm is in the media, from organic to aqueous, and also in the significance of sugar binding, from sugars as a guest to sugars as a probe. Section 4 is devoted to the highly adhesive (hydrogen bonding) nature of glycocluster compounds and their micelle-like aggregates, focusing on the formation of glycoviruses and glycoviral gene delivery. With DNA and RNA manipulation techniques in hand, we became interested in in-cell gene sensing and transcription monitoring. The latest activity in this area is shown in Section 5. The entire work is design-based. The author, who is soon retiring from Kyoto University, now has mixed feelings about this apparently natural approach, as briefly referred to in the Closing Remark (Section 6).

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Solution-to-Surface Molecular-Delivery System Using a Macrocyclic Sugar Cluster. Sugar-Directed Adsorption of Guests in Water on Polar Solid Surfaces

Cited by 88 publications

References 20 publications

Macrocyclic Glycoclusters: From Amphiphiles through Nanoparticles to Glycoviruses

Macrocyclic Glycoclusters: From Amphiphiles through Nanoparticles to Glycoviruses

Multi‐stimuli‐responsive Polymers Based on Calix[4]arenes and Dibenzo‐18‐crown‐6‐ethers

Structure and Function of Molecular Assembly. A Personal Reminiscence

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