Lectin-vermitteltes Drug-Targeting: Diskriminierung zwischen der Kohlenhydrat-vermittelten Aufnahme von Neoglycokonjugaten, die in 3-Position modifizierte Fucose-Epitope tragen, in Tumor- oder Leberzellen

Lerchen, Hans‐Georg; Baumgarten, Joerg; Piel, Norbert; Kolb-Bachofen, Victoria

doi:10.1002/(sici)1521-3757(19991216)111:24<3884::aid-ange3884>3.0.co;2-z

Angewandte Chemie

1999

DOI: 10.1002/(sici)1521-3757(19991216)111:24<3884::aid-ange3884>3.0.co;2-z

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Lectin-vermitteltes Drug-Targeting: Diskriminierung zwischen der Kohlenhydrat-vermittelten Aufnahme von Neoglycokonjugaten, die in 3-Position modifizierte Fucose-Epitope tragen, in Tumor- oder Leberzellen

Hans‐Georg Lerchen

Joerg Baumgarten

Norbert Piel

et al.

Abstract: Die Umgehung der effizienten „Kohlenhydratfallen”︁ in der Leber ist für die Adressierung von Glycokonjugaten an Tumorzellen von entscheidender Bedeutung. Wie am Modellsystem der abgebildeten Rinderserumalbumin(BSA)‐Glycokonjugate gezeigt wird, spielt die Art der Substituenten R1–R3 am Fucose‐Epitop eine wichtige Rolle für die Diskriminierung zwischen der zellulären Aufnahme in Tumor‐ oder Leberzellen sowie für die Cytotoxizität.

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Cited by 4 publications

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Glycopeptide Synthesis and the Effects of Glycosylation on Protein Structure and Activity

Seitz

2000

ChemBioChem

197

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Despite the omnipresence of protein glycosylation in nature, little is known about how the attachment of carbohydrates affects peptide and protein activity. One reason is the lack of a straightforward method to access biologically relevant glycopeptides and glycoproteins. The isolation of homogeneous glycopeptides from natural sources is complicated by the heterogeneity of naturally occuring glycoproteins. It is chemical and chemoenzymatic synthesis that is meeting the challenge to solve this availability problem, thus playing a key role for the advancement of glycobiology. The current art of glycopeptide synthesis, albeit far from being routine, has reached a level of maturity that allows for the access to homogeneous and pure material for biological and medicinal research. Even the ambitious goal of the total synthesis of an entire glycoprotein is within reach. It is demonstrated that with the help of synthetic glycopeptides the effects of glycosylation on protein structure and function can be studied in molecular detail. For example, in immunology, synthetic (tumour-specific) glycopeptides can be used as immunogens to elicit a tumour-cell-specific immune response. Again, synthetic glycopeptides are an invaluable tool to determine the fine specificity of the immune response that can be mediated by both carbohydrate-specific B and T cells. Furthermore, selected examples for the use of synthetic glycopeptides as ligands of carbohydrate-binding proteins and as enzyme substrates or inhibitors are presented.

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Glycopeptide Synthesis and the Effects of Glycosylation on Protein Structure and Activity

Seitz

2000

ChemBioChem

197

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Oligosaccharide Mimics Containing Galactose and Fucose Specifically Label Tumour Cell Surfaces and Inhibit Cell Adhesion to Fibronectin

Kim¹,

Gronewold²,

Chatterjee³

et al. 2005

ChemBioChem

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With the aim of establishing a versatile and easy synthesis of branched saccharides for biological applications, we used molecular-dynamics simulations to model Lewis(y) to two classes of di- or triantennary saccharide mimetics. One set of mimetics was based on 1,3,5-tris(hydroxymethyl)cyclohexane (TMC) as the core, the other on furan, and both were derivatised with galactose and/or fucose. The TMC-based saccharides were biotinylated, while the furan disaccharides were treated with maleimide-activated biotin in a Diels-Alder fashion to yield oxazatricyclodecanes (OTDs). These were then assayed as cell-surface labels in human colon (SW480 and CaCo-2), liver (PLC), Glia (U333 CG 343) and ovary (SKOV-3) tumour cell lines. Discrete staining patterns were observed in all cells, usually at one or two poles of the cells, particularly with the asymmetric 3-beta-L-fucopyranosyloxymethyl-4-beta-D-galactopyranosyloxymethyl-OTD. Normal SV40-transformed fibroblasts (SV80) showed no staining. Adhesion of the highly metastatic mouse melanoma line B16 F10 to fibronectin was inhibited by 80 % by the TMC-digalactoside and by 30 % by 3,4-bis-(beta-D-galactopyranosyloxymethyl)furan. None of the saccharide mimetics inhibited the adhesion of the less metastatic B16 F1 line. Migration of B16 F10 cells through Matrigel was greatly inhibited by the TMC-digalactoside and weakly inhibited by the TMC-trigalactoside. The saccharide mimetics that had shown the best structural agreements with the terminal saccharides of Lewis(y) in the molecular dynamics simulation were also the most biologically potent compounds; this underlines the predictive nature of molecular dynamics simulations. The use of the non-saccharide cores enabled us to adapt spacer lengths and terminal saccharides to optimise the structures to bind more avidly to cell-surface lectins.

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In Situ RBL Receptor Visualization and Its Mediated Anticancer Activity for Solasodine Rhamnosides

Wang

Gao

et al. 2011

ChemBioChem

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Lectin-vermitteltes Drug-Targeting: Diskriminierung zwischen der Kohlenhydrat-vermittelten Aufnahme von Neoglycokonjugaten, die in 3-Position modifizierte Fucose-Epitope tragen, in Tumor- oder Leberzellen

Cited by 4 publications

References 23 publications

Glycopeptide Synthesis and the Effects of Glycosylation on Protein Structure and Activity

Glycopeptide Synthesis and the Effects of Glycosylation on Protein Structure and Activity

Oligosaccharide Mimics Containing Galactose and Fucose Specifically Label Tumour Cell Surfaces and Inhibit Cell Adhesion to Fibronectin

In Situ RBL Receptor Visualization and Its Mediated Anticancer Activity for Solasodine Rhamnosides

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