Synthesis of tumor-associated MUC1-glycopeptides and their multivalent presentation by functionalized gold colloids

Isabella Tavernaro; Sebastian Hartmann; Laura Sommer; Heike Hausmann; Christian Rohner; Martin Ruehl; Anja Hoffmann-Roeder; Sabine Schlecht

doi:10.1039/C4OB01339E

Synthesis of tumor-associated MUC1-glycopeptides and their multivalent presentation by functionalized gold colloids†

Isabella Tavernaro,‡^a Sebastian Hartmann,‡^b Laura Sommer,^c Heike Hausmann,^d Christian Rohner,^a Martin Ruehl,^c Anja Hoffmann-Roeder^e and Sabine Schlecht*^a

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* Corresponding authors

^a Institute of Inorganic and Analytical Chemistry, Justus-Liebig-University Giessen, Heinrich-Buff-Ring 58, 35392 Giessen, Germany
E-mail: Sabine.Schlecht@anorg.chemie.uni-giessen.de

^b Institute of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55128 Mainz, Germany

^c Institute of Food Chemistry and Food Biotechnology, Justus-Liebig-University Giessen, Heinrich-Buff-Ring 58, 35392 Giessen, Germany

^d Institute of Organic Chemistry, Justus-Liebig-University Giessen, Heinrich-Buff-Ring 58, 35392 Giessen, Germany

^e Institute of Organic Chemistry, Ludwig-Maximilian-University Munich, Butenandtstr. 5-13, Haus F, 81377 Munich, Germany

Abstract

The mucin MUC1 is a glycoprotein involved in fundamental biological processes, which can be found over-expressed and with a distinctly altered glycan pattern on epithelial tumor cells; thus it is a promising target structure in the quest for effective carbohydrate-based cancer vaccines and immunotherapeutics. Natural glycopeptide antigens indicate only a low immunogenicity and a T-cell independent immune response; however, this major drawback can be overcome by coupling of glycopeptide antigens multivalently to immunostimulating carrier platforms. In particular, gold nanoparticles are well suited as templates for the multivalent presentation of glycopeptide antigens, due to their remarkably high surface-to-volume ratio in combination with their high biostability. In this work the synthesis of novel MUC1-glycopeptide antigens and their coupling to gold nanoparticles of different sizes are presented. In addition, the development of a new dot-blot immunoassay to test the potential antigen–antibody binding is introduced.

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DOI: https://doi.org/10.1039/C4OB01339E
Article type: Paper
Submitted: 27 Jun 2014
Accepted: 29 Jul 2014
First published: 29 Jul 2014

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Org. Biomol. Chem., 2015,13, 81-97

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Synthesis of tumor-associated MUC1-glycopeptides and their multivalent presentation by functionalized gold colloids

I. Tavernaro, S. Hartmann, L. Sommer, H. Hausmann, C. Rohner, M. Ruehl, A. Hoffmann-Roeder and S. Schlecht, Org. Biomol. Chem., 2015, 13, 81 DOI: 10.1039/C4OB01339E

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Organic & Biomolecular Chemistry

Synthesis of tumor-associated MUC1-glycopeptides and their multivalent presentation by functionalized gold colloids†

Abstract

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Synthesis of tumor-associated MUC1-glycopeptides and their multivalent presentation by functionalized gold colloids

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