Issue 48, 2020

Chemical synthesis and immunological evaluation of entirely carbohydrate conjugate Globo H-PS A1

Abstract

An anticancer, entirely carbohydrate conjugate, Globo H-polysaccharide A1 (Globo H-PS A1), was chemically prepared and immunologically evaluated in C57BL/6 mice. Tumor associated carbohydrate antigen Globo H hexasaccharide was synthesized in an overall 7.8% yield employing a convergent [3 + 3] strategy that revealed an anomeric aminooxy group used for conjugation to oxidized PS A1 via an oxime linkage. Globo H-PS A1, formulated with adjuvants monophosphoryl lipid A and TiterMax® Gold. After immunization an antigen specific immune response was observed in ELISA with anti-Globo H IgG/IgM antibodies. Specificity of the corresponding antibodies was determined by FACS showing cell surface binding to Globo H-positive cancer cell lines MCF-7 and OVCAR-5. The anti-Globo H antibodies also exhibited complement-dependent cellular cytotoxicity against MCF-7 and OVCAR-5 cells.

Graphical abstract: Chemical synthesis and immunological evaluation of entirely carbohydrate conjugate Globo H-PS A1

Supplementary files

Article information

Article type
Edge Article
Submitted
20 Aug 2020
Accepted
15 Oct 2020
First published
19 Oct 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2020,11, 13052-13059

Chemical synthesis and immunological evaluation of entirely carbohydrate conjugate Globo H-PS A1

S. Ghosh, K. R. Trabbic, M. Shi, S. Nishat, P. Eradi, K. A. Kleski and P. R. Andreana, Chem. Sci., 2020, 11, 13052 DOI: 10.1039/D0SC04595K

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