New amphiphilic polycarbonates with side functionalized cholesteryl groups as biomesogenic units: synthesis, structure and liquid crystal behavior

Xu, Xiaoxu; Liu, Xiaofeng; Li, Qun; Hu, Jianshe; Chen, Qifan; Yang, Liqun; Lü, Yanhua

doi:10.1039/c7ra00360a

Cited by 13 publications

(7 citation statements)

References 38 publications

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“…ROP of six-membered cyclic carbonates derived from glycerol was often performed in bulk using Sn(Oct) 2 with heating over 100 °C. ,,,, In addition, the use of enzymes or some organic catalysts was reported. ,,, In most cases, ROP proceeded with a moderate control, and high-molecular-weight polymers were rarely obtained. To achieve the ROP of MDO in a controlled manner, different organobasic catalysts were employed as previously reported to mediate the controlled ROP for a variety of functional cyclic carbonates. , While for ROP of TMC, a binary catalyst system of DBU and an equimolar of the cocatalyst TU is required, , most of the substituted TMC monomers can be ring-opened by milder catalyst systems because the substituent often contributes to an increase in the polymerizability .…”

Section: Resultsmentioning

confidence: 99%

“…15,30 ROP of six-membered cyclic carbonates derived from glycerol was often performed in bulk using Sn(Oct) 2 with heating over 100 °C. 16,17,19,31,32 In addition, the use of enzymes or some organic catalysts was reported. 18,27,28,33 In most cases, ROP proceeded with a moderate control, and highmolecular-weight polymers were rarely obtained.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Methoxy-Functionalized Glycerol-Based Aliphatic Polycarbonate: Organocatalytic Synthesis, Blood Compatibility, and Hydrolytic Property

Montagna

Takahashi

Tsai

et al. 2021

ACS Biomater. Sci. Eng.

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Polymers that are biocompatible and degradable are desired for tissue engineering approaches in the treatment of vascular diseases, especially for those involving small-diameter blood vessels. Herein, we report the compatibility of a newly developed glycerol-based aliphatic polycarbonate possessing simple methoxy side groups, named poly(5-methoxy-1,3-dioxan-2one) (PMDO), with blood cells and plasma proteins as well as its susceptibility to hydrolysis. As a consequence of the organocatalytic ringopening polymerization (ROP) of a methoxy-functionalized cyclic carbonate derived from glycerol, PMDO with a sufficiently high molecular weight (M n 14 kg/mol) and a narrow distribution (D̵ M 1.12) was obtained for evaluation as a bulk biomaterial. This study demonstrates for the first time the organocatalytic ROP of a glycerol-based cyclic carbonate in a controlled manner. Compared with the clinically applied aliphatic polycarbonate poly(trimethylene carbonate) (PTMC), PMDO inhibits platelet adhesion by 33% and denaturation of fibrinogen by 23%. Although the wettability of PMDO based on water contact angle was almost comparable to those of PTMC and poly(ethylene terephthalate), the reason for the inhibited platelet adhesion and protein denaturation appeared to be related to the presence of specific hydrated water formed in the hydrated polymer. The improved hydration of PMDO also enhanced the susceptibility to hydrolysis, with PMDO demonstrating a slightly higher hydrolytic property than PTMC. This simple glycerol-based aliphatic polycarbonate has the following benefits: bio-based characteristics of glycerol and improved blood compatibility and hydrolytic biodegradability stemming from moderate hydration of the methoxy side groups.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Methoxy-Functionalized Glycerol-Based Aliphatic Polycarbonate: Organocatalytic Synthesis, Blood Compatibility, and Hydrolytic Property

Montagna

Takahashi

Tsai

et al. 2021

ACS Biomater. Sci. Eng.

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“…POM showed that all the LC copolymers exhibited the fan-shaped texture of a smectic A (SmA) phase in heating and cooling processes. According to the results reported by Hu et al [ 29 ], the corresponding chiral monomer C showed a cholesteric phase. The result indicated that the macromolecular chain might hinder the formation of a cholesteric helical supermolecular structure and an ordered organization into the mesophase.…”

Section: Resultsmentioning

confidence: 73%

“…The synthetic route of the block copolymers is outlined in Scheme 1 . The cyclic monomer BTMC and the chiral LC monomer 6-cholesteroxy-6-oxocaproic acid (C) were synthesized according to our previous works [ 6 , 29 ].…”

Section: Experimental Methodsmentioning

confidence: 99%

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Synthesis, Self-Assembly, and Drug-Release Properties of New Amphipathic Liquid Crystal Polycarbonates

Xie

Liu

et al. 2018

Nanomaterials

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New amphiphilic liquid crystal (LC) polycarbonate block copolymers containing side-chain cholesteryl units were synthesized. Their structure, thermal stability, and LC phase behavior were characterized with Fourier transform infrared (FT-IR) spectrum, 1H NMR, gel permeation chromatographic (GPC), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), polarizing optical microscope (POM), and XRD methods. The results demonstrated that the LC copolymers showed a double molecular arrangement of a smectic A phase at room temperature. With the elevating of LC unit content in such LC copolymers, the corresponding properties including decomposition temperature (Td), glass temperature (Tg), and isotropic temperature (Ti) increased. The LC copolymers showed pH-responsive self-assembly behavior under the weakly acidic condition, and with more side-chain LC units, the self-assembly process was faster, and the formed particle size was smaller. It indicated that the self-assembly driving force was derived from the orientational ability of LC. The particle size and morphologies of self-assembled microspheres loaded with doxorubicin (DOX), together with drug release tracking, were evaluated by dynamic light scattering (DLS), SEM, and UV–vis spectroscopy. The results showed that DOX could be quickly released in a weakly acidic environment due to the pH response of the self-assembled microspheres. This would offer a new strategy for drug delivery in clinic applications.

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Development and characterization of a superabsorbing hydrogel film containing Ulmus davidiana var. Japonica root bark and pullulan for skin wound healing

Park

Lee

Amatya

et al. 2020

Saudi Pharmaceutical Journal

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New amphiphilic polycarbonates with side functionalized cholesteryl groups as biomesogenic units: synthesis, structure and liquid crystal behavior

Abstract: In this study, a series of new side cholesterol-functionalized amphipathic copolymers based on an aliphatic polycarbonate backbone were synthesized and characterized.

Cited by 13 publications

References 38 publications

Methoxy-Functionalized Glycerol-Based Aliphatic Polycarbonate: Organocatalytic Synthesis, Blood Compatibility, and Hydrolytic Property

Methoxy-Functionalized Glycerol-Based Aliphatic Polycarbonate: Organocatalytic Synthesis, Blood Compatibility, and Hydrolytic Property

Synthesis, Self-Assembly, and Drug-Release Properties of New Amphipathic Liquid Crystal Polycarbonates

Development and characterization of a superabsorbing hydrogel film containing Ulmus davidiana var. Japonica root bark and pullulan for skin wound healing

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