Synthesis of Chiral Oligomer‐Grafted Biodegradable Polyurethanes and Their Chiral‐Dependent Influence on Bone Marrow Stem Cell Behaviors

Hu, Bin; Deng, Jun; Zheng, Honghao; Yu, Shan Ping; Gao, Changyou

doi:10.1002/marc.201600250

Cited by 13 publications

(6 citation statements)

References 40 publications

(50 reference statements)

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“…The N ‐acryloyl‐ l ( d )‐valine chiral monomers are produced and polymerized to get chiral ( l ( d )‐PAV‐SH) oligomers, and covalently immobilized on electron‐deficient poly(propylene fumarate)‐based polyurethane (PPFU). The PPFU‐ l ‐PAV associates strongly and effectively with bone marrow stem cells (BMSCs) than the PPFU‐ d ‐PAV, resulting in a larger area of cell distribution, a higher velocity of migration and a stronger propensity for osteo‐differentiation 10 . The interaction of l ‐poly(acryloyl‐valine) ( l ‐PAV) and d ‐poly(acryloyl‐valine) ( d ‐PAV) chiral brushes with gold nanoparticles (NPs), nanooctahedras (NOs) and nano cubes (NCs) have been studied to investigate the albumin protein adsorption, 11 mesenchymal cell differentiation, 12 cellular uptake and cytotoxicity in A549 and HepG2 cells 11 …”

Section: Introductionmentioning

confidence: 99%

“…The PPFU-L-PAV associates strongly and effectively with bone marrow stem cells (BMSCs) than the PPFU-D-PAV, resulting in a larger area of cell distribution, a higher velocity of migration and a stronger propensity for osteo-differentiation. 10 The interaction of L-poly(acryloylvaline) (L-PAV) and D-poly(acryloyl-valine) (D-PAV) chiral brushes with gold nanoparticles (NPs), nanooctahedras (NOs) and nano cubes (NCs) have been studied to investigate the albumin protein adsorption, 11 mesenchymal cell differentiation, 12 cellular uptake and cytotoxicity in A549 and HepG2 cells. 11 The immune system can differentiate between selfantigens and non-self-antigens to maintain the homeostasis in the body.…”

Section: Introductionmentioning

confidence: 99%

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Taking chiral polymers toward immune regulation

Ahmed

Karabaliev

Gao

2022

Journal of Polymer Science

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The implanted materials and devices can be recognized by the immune system, which in turn mediate the immune microenvironment of tissues. The immune system in mammals is composed of diverse components such as immune cells, cytokines, radicals and antibodies etc. Chiral polymers with good biocompatibility, tailorable ability and ease of fabrication are excellent candidates for diverse biomedical applications. Different chiral biomaterials have been investigated to study the interactions of immune cells and the resulted immune responses, but the effects of chiral polymers on immune regulation are less tackled. Tailoring the chemical and physical properties of chiral polymers can lead to beneficial immune responses. This review focuses on the different fabrication strategies of chiral polymers and interactions of chiral polymers with immune cells and other biological components. The adhesion and interaction patterns of chiral polymers with immune cells, changes in shapes and characteristics of cells, release or inhibition of cytokines, and resulting response are discussed in the review.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Taking chiral polymers toward immune regulation

Ahmed

Karabaliev

Gao

2022

Journal of Polymer Science

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“…The above results revealed that the amino type could influence the chiral effects on biological systems. Our previous works also prepared chiral surface based on the valine and studied stereoselective interactions between cells and chiral interface materials [ 13 , 20 , 23 , 56 ]. We observed that cancer cells (e.g., A549 cells and HepG2 cells) prefer to internalize the d -PAV-AuNPs through the possible preferable interaction between the l -phospholipid-based cell membrane and the d -enantiomers [ 42 ], while the bone marrow mesenchymal stem cells uptake more l -PAV-AuNPs than the d -PAV coated ones [ 20 ].…”

Section: Discussionmentioning

confidence: 99%

Chiral polymer modified nanoparticles selectively induce autophagy of cancer cells for tumor ablation

Yuan

Zhang

et al. 2018

J Nanobiotechnol

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BackgroundAutophagy regulation through exogenous materials has aroused intensive attention to develop treatment protocols according to diverse human diseases. However, to the best of our knowledge, few examples have been reported to selectively control autophagy process and ultimately achieve efficient therapeutic potential.ResultsIn this study, monolayers of poly (acryloyl-l, d and racemic valine) (l-PAV-AuNPs, d-PAV-AuNPs and l/d-PAV-AuNPs) chiral molecules were anchored on the surfaces of gold nanoparticles (PAV-AuNPs), and the subsequent chirality-selective effects on autophagy activation were thoroughly studied. The cytotoxicity induced by PAV-AuNPs towards MDA-MB-231 cells (Breast cancer cells) was achieved mainly through autophagy and showed chirality-dependent, with d-PAV-AuNPs exhibiting high autophagy-inducing activity in vitro and in vivo. In contrast, the PAV-AuNPs exhibited autophagy inactivation for normal cells, e.g., 3T3 fibroblasts and HBL-100 cells. The chirality-selective autophagy activation effect in MDA-MB-231 cells was likely attributed to the chirality-variant ROS generation, cellular uptake and their continuous autophagy stimulus. Furthermore, the intratumoral injection of d-PAV-AuNPs could largely suppress the tumor growth but exhibit negligible toxicity in vivo.ConclusionsAs the first exploration on stereospecific NPs for autophagy induction, this work not only substantiates that chiral polymer coated NPs can selective induce autophagy-specific in cancer cells and achieve a high tumor eradication efficiency in vivo, but also opens up a new direction in discovering unprecedented stereospecific nanoagents for autophagy-associated tumor treatment.Electronic supplementary materialThe online version of this article (10.1186/s12951-018-0383-9) contains supplementary material, which is available to authorized users.

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“…[29,30] Chiral supramolecular polyurethanes with ordered hard segments and helical conformation have been further fabricated, which combines the respective advantages of helical polymers and elastomers. [31][32][33][34] Nakano et al reported the synthesis of a chiral polyurethane from optically active (R)−1,1′-bi(2-naphthol) (R-BINOL) and 1,4 phenylene diisocyanate. [32] While Hayes et al synthesized a series of novel supramolecular polyurethanes elastomers that feature chiral polar end-groups and investigated how highly oriented stereochemistry enhanced the phase separated structures and the mechanical properties of polyurethane.…”

Section: Introductionmentioning

confidence: 99%

Flexible Anti‐Counterfeiting Circularly Polarized Luminescent Elastomer from Supramolecular Polyurethanes

Duan,

Zhao,

et al. 2024

Advanced Optical Materials

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Supramolecular polymers with circularly polarized luminescence (CPL) have promoted future intelligence development of polymer‐based materials for flexible display. However, preparing polymer‐based CPL materials with simultaneous enhanced luminescence dissymmetry factor (|glum|) and mechanical performance for industrial applications remains challenging. This work develops an eco‐friendly preparation method for preparing CPL elastomers from supramolecular polyurethanes bearing chiral fluorescent S (or R)‐1,1′‐Bi(2‐naphthol) (BINOL) groups in a solvent‐free system. Surprisingly, a polymer system containing 0.0028 mol% of chiral BINOL unit is sufficient to emit the significant CPL‐activity with a |glum| value of 2.30 × 10−2, appear a good mechanical toughness of 56.28 ± 3.9 MJ·m−3, thereby exhibit multiple flexible anti‐counterfeiting behaviors. The long‐range ordered microphase arrangement in polyurethanes is the key to improving both mechanical properties and |glum|. This is attributed to in‐situ additive polymerization of BINOL‐based isocyanate prepolymer and macromolecular polyols induced helical supramolecular structure, afforded solid‐state films with flexibility and chiral amplification. Furthermore, these results from Circular dichroism, CPL, Fourier transform infrared, X‐ray diffraction analyses, and atomic force microscope confirm the formation of long‐range ordered microphase arrangement through the synergistic effect of hydrogen bonding and π–π interactions. This work offers significant insights into the construction of CPL elastomers for developing novel flexible display materials.

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Synthesis of Chiral Oligomer‐Grafted Biodegradable Polyurethanes and Their Chiral‐Dependent Influence on Bone Marrow Stem Cell Behaviors

Cited by 13 publications

References 40 publications

Taking chiral polymers toward immune regulation

Taking chiral polymers toward immune regulation

Chiral polymer modified nanoparticles selectively induce autophagy of cancer cells for tumor ablation

Flexible Anti‐Counterfeiting Circularly Polarized Luminescent Elastomer from Supramolecular Polyurethanes

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