Micelles consisting of choline phosphate-bearing Calix[4]arene lipids

Fujii, Shota; Nishina, Koichi; Yamada, Shimpei; Mochizuki, Seibu; Ohta, Nobuhiro; Takahara, Atsushi; Sakurai, Kazuo

doi:10.1039/c4sm01355g

Cited by 30 publications

(19 citation statements)

References 41 publications

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“…Experiments with cancer cells also verified that the controlled release of doxorubicin does not affect the therapeutic properties of the drug. With the aim to increase the possibility of interactions with the phospholipid head groups of the cell membrane, Fujii et al 97 proposed the use of calix [4]arenes 33 in the cone structure that bear choline phosphate groups (CP) at the upper rim. These micellegenerating amphiphiles were demonstrated to interact quite favourably with the phosphoryl choline (PC) groups of phospholipids, the major component of cell membranes, via multiple CP-PC complementary interactions due to the formation of quadrupoles between the quaternary ammonium groups and the phosphate anions.…”

Section: Targeting Na and Polyphosphatesmentioning

confidence: 99%

Moulding calixarenes for biomacromolecule targeting

et al. 2015

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After their successful use as a preorganized platform for the preparation of receptors for metal ions and small neutral molecules over the last 15 years, calixarenes are enjoying a renaissance of popularity as scaffolds for ligands that are able to efficiently and selectively target macromolecules such as proteins/enzymes, nucleic acids and lipids. This feature article summarizes the peculiar factors characterizing the calixarene structure and properties, as well as outlines the main rules that can be used to turn such macrocycles into efficient and successful ligands for these classes of biomacromolecules. Factors that affect the multivalent properties of calixarenes, such as the size, conformation and stereochemical presentation of binding groups or their amphiphilicity and hybrid character, are described in detail with the use of a few selected examples from the literature. Perspectives and applications of these ligands in bionanotechnology and nanomedicine, such as protein sensing and inhibition, gene-delivery, targeted drug-delivery and cell imaging, are also discussed.

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Section: Targeting Na and Polyphosphatesmentioning

confidence: 99%

Moulding calixarenes for biomacromolecule targeting

et al. 2015

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“…We have synthesized several other calix[4]arene derivatives with sugar (GalCaL3), amino acid (CCaL3 and ECaL3)10, amine dendrimer (G1CaL3), choline phosphate (CPCaL3 and CPCaL6)11, and poly(ethylene oxide)(PEGnCaL5) headgroups as summarized in Table S1. Some examples exhibit similar monodispersity and discreteness of N agg .…”

Section: Resultsmentioning

confidence: 99%

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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“…However, in this case further transformations by CuAAC reactions are limited mainly due to the fact that low molecular weight organic azides, especially containing less than 3 carbon atoms are highly explosive [29]. Usually azide groups are installed in the upper rim of the macrocycle by a chloromethylation reaction and subsequent nucleophilic substitution by azide anions [30–31] forming rather flexible azidomethyl fragments. In this investigation more rigid arylazide calixarene derivatives were chosen as precursors for the synthesis of the targeted macrocycles having an enlarged cavity for the effective binding of large biomolecules (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of new p-tert-butylcalix[4]arene-based polyammonium triazolyl amphiphiles and their binding with nucleoside phosphates

Burilov¹,

Fatikhova²,

Dokuchaeva³

et al. 2018

Beilstein J. Org. Chem.

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The synthesis of new calix[4]arenes adopting a cone stereoisomeric form bearing two or four azide fragments on the upper rim and water-soluble triazolyl amphiphilic receptors with two or four polyammonium headgroups via copper-catalyzed azide–alkyne cycloaddition reaction has been performed for the first time. It was found that the synthesized macrocycles form stable aggregates with hydrodynamic diameters between 150–200 nm and electrokinetic potentials about +40 to +60 mV in water solutions. Critical aggregation concentration (CAC) values were measured using a micelle method with pyrene and eosin Y as dye probes. The CAC values of tetraalkyl-substituted macrocycles 12a,b (5 µM for both) are significantly lower than those for dialkyl-substituted macrocycles 10a,b (790 and 160 µM, respectively). Premicellar aggregates of macrocycles 10a,b and 12a,b with the dye eosin Y were used for nucleotides sensing through a dye replacement procedure. It is unusual that disubstituted macrocycles 10a,b bind more effectively a less charged adenosine 5'-diphosphate (ADP) than adenosine 5'-triphosphate (ATP). A simple colorimetric method based on polydiacetylene vesicles decorated with 10b was elaborated for the naked-eye detection of ADP with a detection limit of 0.5 mM.

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Micelles consisting of choline phosphate-bearing Calix[4]arene lipids

Cited by 30 publications

References 41 publications

Moulding calixarenes for biomacromolecule targeting

Moulding calixarenes for biomacromolecule targeting

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

Synthesis of new p-tert-butylcalix[4]arene-based polyammonium triazolyl amphiphiles and their binding with nucleoside phosphates

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