Synthesis of lipo-glycopolymers for cell surface engineering

Liu, Qi; Xue, Hui; Gao, Jinbo; Cao, Limin; Chen, Gaojian

doi:10.1039/c6py01788f

Cited by 16 publications

(18 citation statements)

References 50 publications

(55 reference statements)

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“…These authors demonstrated that a lipid anchor leads to membrane insertion, whereas a GAG mimicking polymer was internalized by cells . Similarly, a terpolymer of sodium 4-vinylbenzenesulfonate, 2-methacrylamido glucopyranose, and fluorescein o -methacrylate was bound to the cell membrane when coupled to the lipid 1,2-dipalmytol- sn-glycero -3-phosphoethanolamine, but the terpolymer alone was internalized by cells …”

Section: Resultsmentioning

confidence: 99%

“…20 Similarly, a terpolymer of sodium 4vinylbenzenesulfonate, 2-methacrylamido glucopyranose, and fluorescein o-methacrylate was bound to the cell membrane when coupled to the lipid 1,2-dipalmytol-sn-glycero-3-phosphoethanolamine, but the terpolymer alone was internalized by cells. 21 To study possible effects of the selectin-binding polymers on immune cell activation mediated by binding to the selectin receptors, we incubated human primary macrophages for 60 min with the binders at three different concentrations (0.03, 0.3, or 3 μM), with or without additional stimulation by lipopolysaccharides (LPS) for another 24 h. We observed that the binders had no effects on macrophage activation at the two lowest concentrations. However, at the highest concentration of 3 μM, multivalent SLe X (P1) induced low levels of IL1β expression, while all binders slightly increased TNF.…”

Section: T H Imentioning

confidence: 98%

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Immunomodulatory Therapy of Inflammatory Liver Disease Using Selectin-Binding Glycopolymers

Bartneck¹,

Schlößer²,

Barz

et al. 2017

ACS Nano

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Immunotherapies have the potential to significantly advance treatment of inflammatory disease and cancer, which are in large part driven by immune cells. Selectins control the first step in immune cell adhesion and extravasation, thereby guiding leukocyte trafficking to tissue lesions. We analyzed four different highly specific selectin-binding glycopolymers, based on linear poly(2-hydroxypropyl)-methacrylamide (PHPMA) polymers. These glycopolymers contain either the tetrasaccharide sialyl-Lewis (SLe) or the individual carbohydrates fucose, galactose, and sialic acids mimicking the complex SLe binding motive. The glycopolymers strongly bind to primary human macrophages, without activating them, and also to primary human blood leukocytes, but poorly to fibroblasts and endothelial cells in vitro. After intravenous injection in mice, all glycopolymers accumulated in the liver without causing hepatotoxicity. The glycosylated binder most potently targeted resident hepatic macrophages (Kupffer cells) and protected mice from acute toxic liver injury in the two different experimental models, carbon tetrachloride (CCl) or Concanavalin A (ConA)-based hepatitis. Its sulfated counterpart, on the other hand, induced a decrease in infiltrating and resident macrophages, increased T helper cells, and aggravated immune-mediated liver injury. We demonstrate that, in the context of selectin-binding glycopolymers, minor modifications strongly impact leukocyte influx and macrophage activation, thereby ameliorating or aggravating liver inflammation depending on the underlying immunopathology. The nonsulfated random glycopolymer is a promising candidate for the treatment of inflammatory disease. The modulation of hepatic immune cells by selectin-binding glycopolymers might breach the immunosuppressive hepatic microenvironment and could improve efficacy of immunotherapies for inflammatory disease and cancer.

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Section: Resultsmentioning

confidence: 99%

Section: T H Imentioning

confidence: 98%

Immunomodulatory Therapy of Inflammatory Liver Disease Using Selectin-Binding Glycopolymers

Bartneck¹,

Schlößer²,

Barz

et al. 2017

ACS Nano

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“…The ζ potential and chemical modifications based on the phenol group accessibility suggested that phenol groups shifted inward into the nanofibers while the carboxylic groups migrated to the outer regions of the fibers following β-sheet structure formation. EDC/NHS chemistry based on carboxylic groups − was therefore used to modify the two solutions (Scheme S3). The modified solutions were termed BSS-flu and ASS-flu (Table S1), respectively, and their FT-IR spectra were assessed (Figure S6).…”

Section: Resultsmentioning

confidence: 99%

Structure–Chemical Modification Relationships with Silk Materials

Liu

Zhang

et al. 2019

ACS Biomater. Sci. Eng.

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Chemical modifications used with silk materials can be challenging due to heterogeneous reactions, in part due to the assembly state of the protein chains. Here, we assess factors that determine the efficiency of chemical modifications with silk materials. Unlike other natural macromolecules, silk presents changeable self-assembled or aggregation states in aqueous solution, which affect the chemical reactions based on reactive group distribution or accessibility. To confirm this hypothesis, silk nanofibers in various conformation and aggregation states in solution were exposed to the same reaction conditions. Amorphous silk nanofibers provided improved control for consistent chemical modification outcomes, while silk nanofibers with control of structure could be utilized to generate bifunctional materials through multiple chemical modifications. The results of the chemical modifications demonstrated that control of the conformational transitions of silk nanofibers provided a feasible strategy for developing multifunctional silk materials with improved chemical outcomes.

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“…Currently, RAFT is one of the most widely utilized metal-free polymerization methods for the synthesis of well-defined glycopolymers. 75,115–118 It offers the polymerization of both protected and unprotected glycomonomers in organic and as well as in aqueous media. The main components of RAFT are a dithio- or trithio-based chain transfer agent (CTA) and a free radical initiator.…”

Section: Synthesis Of Glycopolymers Via Reversible-deactivation Radic...mentioning

confidence: 99%

Tailor-made glycopolymersviareversible deactivation radical polymerization: design, properties and applications

2022

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Synthesis of lipo-glycopolymers for cell surface engineering

Abstract: A novel synthetic lipo-glycopolymer was inserted into cell membranes for cell surface engineering.

Cited by 16 publications

References 50 publications

Immunomodulatory Therapy of Inflammatory Liver Disease Using Selectin-Binding Glycopolymers

Immunomodulatory Therapy of Inflammatory Liver Disease Using Selectin-Binding Glycopolymers

Structure–Chemical Modification Relationships with Silk Materials

Tailor-made glycopolymersviareversible deactivation radical polymerization: design, properties and applications

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