Uptake of Well‐Defined, Highly Glycosylated, Pentafluorostyrene‐Based Polymers and Nanoparticles by Human Hepatocellular Carcinoma Cells

Babiuch, Krzysztof; Pretzel, David; Tolstik, T.; Vollrath, Antje; Stanca, Sarmiza Elena; Foertsch, Franziska; Becer, C. Remzi; Gottschaldt, Michael; Biskup, Christoph; Schubert, Ulrich S.

doi:10.1002/mabi.201200024

Cited by 14 publications

(9 citation statements)

References 37 publications

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“…However, a specific effect of the type of conjugated sugar on the cytotoxicity could not be observed, since for both, glucose and galactose functionalized polymers, the viability rates of the particular cell types were in most cases on similar levels. The absence of an enhanced effectiveness of galactose functionalized polymers in HepG2 cells is unexpected since literature reports a galactose‐mediated targeting of polymeric substances to liver cells via the asialoglycoprotein receptors . Possibly, the uptake of the platinum containing glycopolymers was accomplished preferentially via non‐receptor–mediated endocytosis.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and in vitro activity of platinum containing 2-oxazoline-based glycopolymers

Tauhardt

Pretzel

Bode

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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We report the synthesis of glyco(poly(2‐oxazoline)s) functionalized with Pt(II) units for targeted tumor applications. To this end, poly(2‐ethyl‐2‐oxazoline‐block‐2‐(3‐butenyl)‐2‐oxazoline) is modified with thiol‐modified acetyl protected glucose and galactose, respectively, and terpyridine (tpy) units using thiol‐ene photoaddition. Deprotection of the sugars with sodium methoxide and treatment with Pt(COD)Cl2 applying a mild synthesis route yields polymers with monosaccharide targeting moieties and cytotoxic Pt(II) units. The polymers and intermediates are characterized by 1H nuclear magnetic resonance spectroscopy and size exclusion chromatography. Subsequently, the hemolytic activity, induction of erythrocyte aggregation as well as the cytotoxicity against mouse fibroblast L929 cells, human embryonic kidney cells HEK 293, and human hepatocytes HepG2 are studied. The comparison to cisplatin, the standard for cancer therapy, demonstrates the potential of the presented system. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 2703–2714

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Section: Resultsmentioning

confidence: 99%

Synthesis and in vitro activity of platinum containing 2-oxazoline-based glycopolymers

Tauhardt

Pretzel

Bode

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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“…ASGPR, abundantly and predominantly expressed at the surface of hepatic (liver) cells, is a hetero-oligomer consisting of two homologous transmembrane proteins with a Ca 2+ -dependent CRD that interacts with Gal, GalNAc, and related galactosides. , Once ASGPR binds the targeted ligands, the complexes can be internalized by ASGPR-mediated endocytosis; thus, Gal moieties can be used as targeted ligands for diagnosis and therapy with, e.g., hepatocellular carcinoma (HepG2), hepatitis, and malaria. − To regulate the delivery system, parameters such as nanocarrier size, surface carbohydrate density, patterning, and material flexibility were systematically explored …”

Section: Therapeutic and Diagnostic Delivery Systemsmentioning

confidence: 99%

Carbohydrate-Based Macromolecular Biomaterials

et al. 2021

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Carbohydrates are the most abundant and one of the most important biomacromolecules in Nature. Except for energy-related compounds, carbohydrates can be roughly divided into two categories: Carbohydrates as matter and carbohydrates as information. As matter, carbohydrates are abundantly present in the extracellular matrix of animals and cell walls of various plants, bacteria, fungi, etc., serving as scaffolds. Some commonly found polysaccharides are featured as biocompatible materials with controllable rigidity and functionality, forming polymeric biomaterials which are widely used in drug delivery, tissue engineering, etc. As information, carbohydrates are usually referred to the glycans from glycoproteins, glycolipids, and proteoglycans, which bind to proteins or other carbohydrates, thereby meditating the cell–cell and cell–matrix interactions. These glycans could be simplified as synthetic glycopolymers, glycolipids, and glycoproteins, which could be afforded through polymerization, multistep synthesis, or a semisynthetic strategy. The information role of carbohydrates can be demonstrated not only as targeting reagents but also as immune antigens and adjuvants. The latter are also included in this review as they are always in a macromolecular formulation. In this review, we intend to provide a relatively comprehensive summary of carbohydrate-based macromolecular biomaterials since 2010 while emphasizing the fundamental understanding to guide the rational design of biomaterials. Carbohydrate-based macromolecules on the basis of their resources and chemical structures will be discussed, including naturally occurring polysaccharides, naturally derived synthetic polysaccharides, glycopolymers/glycodendrimers, supramolecular glycopolymers, and synthetic glycolipids/glycoproteins. Multiscale structure–function relationships in several major application areas, including delivery systems, tissue engineering, and immunology, will be detailed. We hope this review will provide valuable information for the development of carbohydrate-based macromolecular biomaterials and build a bridge between the carbohydrates as matter and the carbohydrates as information to promote new biomaterial design in the near future.

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“…[ 5,8,9 ] Fluorine‐based monomers, such as pentafluorostyrene (PFS), have also been used on the manufacture of functionalized polymer materials. [ 20–24 ] However, most studies perform the polymer synthesis and functionalization in solution, which is not ideal regarding the production of nanoparticles and enzyme supports.…”

Section: Introductionmentioning

confidence: 99%

Production of New Functionalized Polymer Nanoparticles and Use for Manufacture of Novel Nanobiocatalysts

Pinto

Cipolatti

Manoel

et al. 2020

Macro Materials & Eng

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New nanoparticles are synthesized through emulsion polymerization, using distinct comonomers (styrene, divinylbenzene, glycidyl methacrylate and pentafluorostyrene). Then, for the first time, two strategies are adopted to functionalize such nanoparticles using benzylamine and thiophenol: (i) after the manufacture of the nanoparticles; and (ii) in situ during the polymerization reaction. Afterwards, the functionalized nanoparticles are used as nanosupports for immobilization of lipase B from Candida antarctica and the performance of the novel nanobiocatalysts are evaluated. It is shown that the nanoparticles exhibit different properties (specific areas ranging from 34 m2 g−1 to 324 m2 g−1; and contact angles ranging from 29° to 126°), indicating that both procedures can be used to adjust the properties of the polymer supports. Moreover, the nanobiocatalysts are applied successfully in hydrolysis and esterification reactions, exhibiting higher activities than the non‐functionalized biocatalysts. It is also observed that more hydrophilic supports result in more active biocatalysts in hydrolysis (27 ± 1 U g−1) and intermediate hydrophobic matrices conduct to more active biocatalysts in esterification reactions (1564 ± 50 U g−1). It is shown that highly hydrophobic surfaces may cause a significant decrease in the activity of such biocatalysts, probably due to distortions on the enzyme active center and to more intense chemical partitioning effects.

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Uptake of Well‐Defined, Highly Glycosylated, Pentafluorostyrene‐Based Polymers and Nanoparticles by Human Hepatocellular Carcinoma Cells

Cited by 14 publications

References 37 publications

Synthesis and in vitro activity of platinum containing 2-oxazoline-based glycopolymers

Synthesis and in vitro activity of platinum containing 2-oxazoline-based glycopolymers

Carbohydrate-Based Macromolecular Biomaterials

Production of New Functionalized Polymer Nanoparticles and Use for Manufacture of Novel Nanobiocatalysts

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