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Issue 3, 2016
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Double conjugation strategy to incorporate lipid adjuvants into multiantigenic vaccines

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Abstract

Conjugation of multiple peptides by their N-termini is a promising technique to produce branched multiantigenic vaccines. We established a double conjugation strategy that combines a mercapto-acryloyl Michael addition and a copper-catalysed alkyne-azide 1,3-dipolar cycloaddition (CuAAC) reaction to synthesise self-adjuvanting branched multiantigenic vaccine candidates. These vaccine candidates aim to treat cervical cancer and include two HPV-16 derived epitopes and a novel self-adjuvanting moiety. This is the first report of mercapto-acryloyl conjugation applied to the hetero conjugation of two unprotected peptides by their N-termini followed by a CuAAC reaction to conjugate a novel synthetic lipoalkyne self-adjuvanting moiety. In vivo experiments showed that the most promising vaccine candidate completely eradicated tumours in 46% of the mice (6 out of 13 mice).

Graphical abstract: Double conjugation strategy to incorporate lipid adjuvants into multiantigenic vaccines

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Supplementary files

Article information


Submitted
12 Oct 2015
Accepted
28 Dec 2015
First published
04 Jan 2016

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2016,7, 2308-2321
Article type
Edge Article
Author version available

Double conjugation strategy to incorporate lipid adjuvants into multiantigenic vaccines

W. M. Hussein, T. Liu, P. Maruthayanar, S. Mukaida, P. M. Moyle, J. W. Wells, I. Toth and M. Skwarczynski, Chem. Sci., 2016, 7, 2308
DOI: 10.1039/C5SC03859F

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