Thermotropic liquid crystalline glycolipids

Goodby, John W.; Görtz, Verena; Cowling, Stephen J.; Mackenzie, Grahame; Martin, Patrick; Plusquellec, Daniel; Benvegnu, Thierry; Boullanger, Paul; Lafont, Dominique; Queneau, Yves; Chambert, Stéphane; Fitremann, Juliette

doi:10.1039/b708458g

Cited by 195 publications

(114 citation statements)

References 236 publications

(150 reference statements)

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“…Water exhibits a high dielectric constant and has the ability to form hydrogen bonds, greatly influencing the structure and functions of biomacromolecules or compromising electronic properties such as charge transport (12)(13)(14)(15). Indeed, anhydrous TLC systems containing glycolipids (16)(17)(18)(19), ferritin (20), and polylysine have been reported (21)(22)(23). However, a general approach to fabricating TLCs based on nucleic acids, polypeptides, proteins, and protein assemblies of large molecular weights such as virus particles remains elusive.…”

mentioning

confidence: 99%

Thermotropic liquid crystals from biomacromolecules

Li¹,

Chen

Marcozzi³

et al. 2014

Proc. Natl. Acad. Sci. U.S.A.

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Complexation of biomacromolecules (e.g., nucleic acids, proteins, or viruses) with surfactants containing flexible alkyl tails, followed by dehydration, is shown to be a simple generic method for the production of thermotropic liquid crystals. The anhydrous smectic phases that result exhibit biomacromolecular sublayers intercalated between aliphatic hydrocarbon sublayers at or near room temperature. Both this and low transition temperatures to other phases enable the study and application of thermotropic liquid crystal phase behavior without thermal degradation of the biomolecular components.L iquid crystals (LCs) play an important role in biology because their essential characteristic, the combination of order and mobility, is a basic requirement for self-organization and structure formation in living systems (1-3). Thus, it is not surprising that the study of LCs emerged as a scientific discipline in part from biology and from the study of myelin figures, lipids, and cell membranes (4). These and the LC phases formed from many other biomolecules, including nucleic acids (5, 6), proteins (7,8), and viruses (9, 10), are classified as lyotropic, the general term applied to LC structures formed in water and stabilized by the distinctly biological theme of amphiphilic partitioning of hydrophilic and hydrophobic molecular components into separate domains. However, the principal thrust and achievement of the study of LCs has been in the science and application of thermotropic materials, structures, and phases in which molecules that are only weakly amphiphilic exhibit LC ordering by virtue of their steric molecular shape, flexibility, and/or weak intermolecular interactions [e.g., van der Waals and dipolar forces (11)]. These characteristics enable thermotropic LCs (TLCs) to adopt a wide variety of exotic phases and to exhibit dramatic and useful responses to external forces, including, for example, the electro-optic effects that have led to LC displays and the portable computing revolution. This general distinction between lyotropic LCs and TLCs suggests there may be interesting possibilities in the development of biomolecular or bioinspired LC systems in which the importance of amphiphilicity is reduced and the LC phases obtained are more thermotropic in nature. Such biological TLC materials are very appealing for several reasons. Most biomacromolecules were extensively characterized in aqueous environments, but in TLC phases, their solvent-free properties and functions could be investigated in a state in which no or only traces of water are present. Water exhibits a high dielectric constant and has the ability to form hydrogen bonds, greatly influencing the structure and functions of biomacromolecules or compromising electronic properties such as charge transport (12-15). Indeed, anhydrous TLC systems containing glycolipids (16-19), ferritin (20), and polylysine have been reported (21-23). However, a general approach to fabricating TLCs based on nucleic acids, polypeptides, proteins, and protein assemblies of larg...

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mentioning

confidence: 99%

Thermotropic liquid crystals from biomacromolecules

Li¹,

Chen

Marcozzi³

et al. 2014

Proc. Natl. Acad. Sci. U.S.A.

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“…Some amphiphilic liquid crystals have a structural affinity to various biological cellstructures such as cell membranes, phospholipids, and lysosomes. However, few studies thus far have addressed the biological and pharmacological characteristics of LCs, although there has been an increasing interest in these compounds [8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Suppressive effects of liquid crystal compounds on the growth of the A549 human lung cancer cell line

et al. 2010

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The aim of this study was to evaluate the biological activity and pharmacological activity of several amphiphilic liquid-crystalline compounds (LCs), i.e. phenylpyrimidine derivatives possessing D-glucamine and cyanobiphenyl derivatives with a terminal hydroxyl unit, to explore novel anti-cancer functions of the LCs. The anti-cancer properties of the LCs were investigated in A549 human lung cancer cells by assessing cell growth, cell cycle distribution, and cell signaling pathways using a flow cytometer and a Western blot analysis. In addition, the effect of LCs on the growth of WI-38 normal fibroblasts was examined. Consequently, the phenylpyrimidine derivatives and cyanobiphenyl derivatives showed cytostatic effects, causing the suppression of cell growth through G1 phase arrest in A549 cells. Further analyses using phenylpyrimidine derivatives and precursors of a cyanobiphenyl compound demonstrated the structure-activity relationships. One of the phenylpyrimidine derivatives inhibited A549 growth without any toxicity to normal fibroblasts. As a result, a novel pharmacological function was hypothesized to be inherent in the structure of the LCs themselves, and the dependence of the tumor-specific activity on the hydrophobic group of phenylpyrimidine derivatives therefore remains an interesting issue. Our results suggest the possibility that the LCs themselves may act as a novel type of chemotherapeutic agent.

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“…While the phase of thermotropic LC characteristic ordering depends only on temperature [11], thermotropic LC phases are: nematic, smectic, and cholesteric [12]. Cholesteric liquid crystals have many advanced technology applications [13] like liquid crystal displays [14], optical filters [15], imaging systems [16], chromatography techniques [17], optical storage systems [18], temperature sensors [19] and medical thermography [20].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, physical and biological properties of some cholesterol derivatives

2016

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A series of new cholesterol derivatives have been prepared via Mitsunobu reaction. The reaction was monitored by thin-layer chromatography (TLC) technique. All new compounds were characterized by melting points, elemental analysis, FT-IR, 1 H, 13 C and 2D-NMR spectroscopy. The antibacterial and antifungal activity of these derivatives was also determined. The phase transitions of the prepared derivatives were measured with the aid of differential scanning calorimetry. The textures of the mesophases have been determined with a hot stage equipped polarizing microscope, also the electrical conductivity of the solutions of these liquid crystals measured by electrical conductivity meter. The analysis showed that these prepared derivatives were liquid crystals.

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Thermotropic liquid crystalline glycolipids

Cited by 195 publications

References 236 publications

Thermotropic liquid crystals from biomacromolecules

Thermotropic liquid crystals from biomacromolecules

Suppressive effects of liquid crystal compounds on the growth of the A549 human lung cancer cell line

Synthesis, characterization, physical and biological properties of some cholesterol derivatives

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