A bimolecular micelle constructed from amphiphilic pillar[5]arene molecules

Nishimura, Tomoki; Sanada, Yusuke; Matsuo, Takuma; Okobira, Tadashi; Mylonas, Efstratios; Yagi, Naoto; Sakurai, Kazuo

doi:10.1039/c3cc41186a

Cited by 35 publications

(12 citation statements)

References 37 publications

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“…The molecular configuration cannot be identical to hemispheres, but we have two examples for N agg = 2. One is a dimer of bile acids22, and the other is a pillar[5]arene based amphiphilic molecule23. We have several examples at N agg = 8, but the coverage D(N ) at N = 8 is not so large.…”

Section: Resultsmentioning

confidence: 97%

Platonic Micelles: Monodisperse Micelles with Discrete Aggregation Numbers Corresponding to Regular Polyhedra

Fujii

Yamada

Matsumoto

et al. 2017

Sci Rep

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The concept of micelles was first proposed in 1913 by McBain and has rationalized numerous experimental results of the self-aggregation of surfactants. It is generally agreed that the aggregation number (Nagg) for spherical micelles has no exact value and a certain distribution. However, our studies of calix[4]arene surfactants showed that they were monodisperse with a defined Nagg whose values are chosen from 6, 8, 12, 20, and 32. Interestingly, some of these numbers coincide with the face numbers of Platonic solids, thus we named them “Platonic micelles”. The preferred Nagg values were explained in relation to the mathematical Tammes problem: how to obtain the best coverage of a sphere surface with multiple identical circles. The coverage ratio D(N) can be calculated and produces maxima at N = 6, 12, 20, and 32, coinciding with the observed Nagg values. We presume that this “Platonic nature” may hold for any spherical micelles when Nagg is sufficiently small.

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Section: Resultsmentioning

confidence: 97%

Platonic Micelles: Monodisperse Micelles with Discrete Aggregation Numbers Corresponding to Regular Polyhedra

Fujii

Yamada

Matsumoto

et al. 2017

Sci Rep

Self Cite

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“…Asymmetric pillar[ n ]arenes, in which the substituents in the para positions are non‐identical, are predisposed to form structures such as bilayers, vesicles and micelles. In one of the earliest examples of micelle formation Sakurai and colleagues designed a pillar[5]arene with n ‐butyl and propargyl substituents . Isolation of the D 5 conformer and subsequent click reaction introduced N ‐propylaminolysine groups to give 35 which formed 4.5 nm micelles in water at pH 3.…”

Section: Medical Applicationsmentioning

confidence: 99%

Pillar[n]arenes at the Chemistry‐Biology Interface

Cragg

2018

Israel Journal of Chemistry

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Macrocyclic chemistry has provided chemists with a wealth of molecular 'hosts'. Ever since resurgence in the field during the 1970s and 1980s these hosts' similarities to natural structures, such the active sites of enzymes, have been noted. Latterly there has been great interest in the recently reported pillar[n]arenes. As if to underline the importance of these compounds, exciting applications are starting to emerge, from electrochemical sensors to antimicrobial agents. Novel uses appear destined to have an impact on clinical conditions from Alzheimer's disease to cancer treatment. In order to demonstrate the impact of pillar[n]arenes across the chemistry-biology interface this review will cover the current state of the art from biomimicry and analyte-specific detection to emerging clinical applications. Examples include pillar[n]arene-based ion channels, enzyme-responsive compounds, imaging agents, biofilm inhibiting derivatives, drug complexing and drug releasing systems.

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“…119 Sakurai's group also synthesized a pillar [5]arene-based amphiphile with polar lysine head groups as the hydrophilic part, which spontaneously self-assembled into bimolecular micelles in water. 120 In order to explore the application of amphiphilic pillar [5]arenes in biologically relevant fields, Huang et al designed and synthesized a novel sugar-functionalized amphiphilic pillar [5]arene 20 with galactose groups as the hydrophilic portion and alkyl chains as the hydrophobic part (Fig. 22a).…”

Section: Macrocyclic Amphiphiles Based On Pillararenesmentioning

confidence: 99%

Macrocyclic amphiphiles

et al. 2015

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In this critical review, we summarize recent results in the investigation of macrocyclic amphiphiles, amphiphiles based on macrocyclic frameworks. These interesting molecules have drawn a lot of attention over the past decades due to their unique superiority in self-assembly processes and other advantages. Compared with traditional linear amphiphiles, macrocyclic amphiphiles can be tailored to promote their self-assembly into various well-defined architectures by locating hydrophilic and hydrophobic chains on the respective sides. Since macrocyclic amphiphiles can be regarded as "surfactants" with host-guest recognition sites, they may be highly beneficial for applications where guest molecules must be stabilized, transported or protected in aqueous media. Considering the abundant research results on the host-guest chemistry of macrocycles, the use of macrocyclic amphiphiles in the fabrication of multidimensional and hierarchical self-assemblies may also provide interesting new topological structures. Moreover, the interactions of their self-assemblies can be mediated by molecular recognition, which may further our understanding of biological processes.

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A bimolecular micelle constructed from amphiphilic pillar[5]arene molecules

Cited by 35 publications

References 37 publications

Platonic Micelles: Monodisperse Micelles with Discrete Aggregation Numbers Corresponding to Regular Polyhedra

Platonic Micelles: Monodisperse Micelles with Discrete Aggregation Numbers Corresponding to Regular Polyhedra

Pillar[n]arenes at the Chemistry‐Biology Interface

Macrocyclic amphiphiles

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