Synthesis and Self-Assembled Behavior of pH-Responsive Chiral Liquid Crystal Amphiphilic Copolymers Based on Diosgenyl-Functionalized Aliphatic Polycarbonate

Guo, Zhihao; Liu, Xiaofeng; Hu, Jianshe; Yang, Liqun; Chen, Zhang-Pei

doi:10.3390/nano7070169

Cited by 18 publications

(5 citation statements)

References 47 publications

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“…Depending on the percentage of the LC content, the disks displayed a unique ability to stack perpendicular to the major axis in a process driven by the narrow polydispersity (PD) of the copolymer chains, combined with the liquid crystalline order as a driving force. The morphology of BCP nano-objects as a function of pH was investigated by Guo et al [41]. for a diosgenyl functionalised block copolymer, mPEG 43 -PMCC 25 -P(MCC-DHO) 1 .…”

Section: Applications Of Sterol-based Liquid Crystalline Block Copoly...mentioning

confidence: 99%

Steroid-Based Liquid Crystalline Polymers: Responsive and Biocompatible Materials of the Future

2022

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Steroid-based liquid crystal polymers and co-polymers have come a long way, with new and significant advances being made every year. This paper reviews some of the recent key developments in steroid-based liquid crystal polymers and co-polymers. It covers the structure–property relationship between cholesterol and sterol-based compounds and their corresponding polymers, and the influence of chemical structure and synthesis conditions on the liquid crystalline behaviour. An overview of the nature of self-assembly of these materials in solvents and through polymerisation is given. The role of liquid crystalline properties in the applications of these materials, in the creation of nano-objects, drug delivery and biomedicine and photonic and electronic devices, is discussed.

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Section: Applications Of Sterol-based Liquid Crystalline Block Copoly...mentioning

confidence: 99%

Steroid-Based Liquid Crystalline Polymers: Responsive and Biocompatible Materials of the Future

2022

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“…For the synthesis, different bases and solvents were tested at different temperatures (Table 1). Cholesterol and cholestanol moieties were selected as molecular targets because of the thermodynamic affinity of cholesterol for cell membranes and its ability to change its properties, for example by improving their mechanical durability and reducing passive permeability [35][36][37][38][39][40]; another advantage for cholestanes is their rigidity, a useful characteristic in nanoarchitecture. The short-branched hydrocarbon tail confers to cholesterol a high hydrophobic structure, while the polar 3β-hydroxyl group provides a slight amphiphilic nature.…”

Section: Synthesis and Purification Of Bisteroidal Estersmentioning

confidence: 99%

Mesoscale Assembly of Bisteroidal Esters from Terephthalic Acid

et al. 2020

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A new series of bisteroidal esters was synthesized using a spacer group, sterols and sapogenins as substrates. Steroidal dimers were prepared in high yields employing diesters of terephthalic acid as linkages at the 3β, 3′β steroidal positions. In all attempts to crystallize bisteroids, it was observed that the compounds tended to self-organize in solution, which was detected when employing various solvent systems. The non-covalent interactions (van der Waals) of the steroidal moieties of this series of symmetrical bisteroids, the polarity of the solvents systems, and the different solubilities of the bisteroid aggregates, indeed induce the molecules to self-assemble into supramolecular structures with well-defined organization. Our results show that the self-assembled structures for the bisteroidal derivatives depend on the solvent system used: with hexane/EtOAc, membrane-shaped structures were obtained, while pure EtOAc afforded strand-shaped arrangements. In the CHCl3/CH3OH system, thin strands were formed, since van der Waals interactions are lowered in this system, as a consequence of the increased solubility of the bisteroids in CHCl3. Based on the characterization by SEM and XRD, we show evidence that the phenomenon of self-assembly of bisteroids occurs presenting different morphologies depending on the solvent used. The new steroidal dimer derivatives were characterized by NMR, TGA, DSC, SEM, and XRD. Finally, the molecular structure of one bisteroid was confirmed by single-crystal X-ray analysis.

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“…For instance, chiral liquid crystals can arrange themselves in highly ordered helical structures because of the twisting power of chiral molecules . In particular, chiral LCPs are promising candidates for stimuli-responsive materials because they undergo sharp changes in their highly ordered helical structures under external stimuli, such as changes in temperature, , pH, − and biomolecules, − similar to biological membranes. However, few studies have reported the use of thermotropic LCPs for medical applications such as drug delivery systems (DDSs) and biosensors.…”

Section: Introductionmentioning

confidence: 99%

Reversible Regulation of Drug Release from Chiral Liquid Crystalline Polymer Micelles without Leakage

Inoue,

Hirano,

Kawamura

et al. 2023

Macromolecules

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Liquid crystalline polymers (LCPs) exhibit abrupt changes in their organized structures and mobilities at phase transition temperatures, which is reminiscent of the unique structures and properties of biological membranes. Despite the numerous potential applications of LCPs, no study of their medical use has been reported. In this study, we synthesized amphiphilic LCPs with chiral mesogens by introducing hydrophilic oligo-(ethylene glycol) (OEG), hydrophobic mesogens, and chiral mesogens into polysiloxane main chains. The resulting chiral LCP-g-OEG formed micelles with a highly ordered hydrophobic core and a hydrophilic OEG shell. While the release of a model drug from chiral LCP-g-OEG micelles was effectively suppressed at temperatures below the nematic−isotropic phase transition temperature (T NI ), it was enhanced by an increase in the temperature above T NI . The reversible thermoresponsive ON−OFF regulation of drug release without leakage was achieved by using chiral LCP-g-OEG micelles. Interestingly, the chiral LCP-g-OEG micelles were preferentially internalized by cancer cells compared with normal cells.

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Synthesis and Self-Assembled Behavior of pH-Responsive Chiral Liquid Crystal Amphiphilic Copolymers Based on Diosgenyl-Functionalized Aliphatic Polycarbonate

Cited by 18 publications

References 47 publications

Steroid-Based Liquid Crystalline Polymers: Responsive and Biocompatible Materials of the Future

Steroid-Based Liquid Crystalline Polymers: Responsive and Biocompatible Materials of the Future

Mesoscale Assembly of Bisteroidal Esters from Terephthalic Acid

Reversible Regulation of Drug Release from Chiral Liquid Crystalline Polymer Micelles without Leakage

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