Synthesis of PEGylated lactose analogs for inhibition studies on T.cruzi trans-sialidase.

Glycoconjugate Journal
M Eugenia GiorgiRosa M de Lederkremer

Abstract

Trypanosoma cruzi, the agent of Chagas disease, expresses a unique enzyme, the trans-sialidase (TcTS) involved in the transfer of sialic acid from host glycoconjugates to mucins of the parasite. The enzyme is shed to the medium and may affect the immune system of the host. We have previously described that lactose derivatives effectively inhibited the transfer of sialic acid to N-acetyllactosamine. Lactitol also prevented the apoptosis caused by the TcTS, although it is rapidly eliminated from the circulatory system. In this paper we report covalent conjugation of polyethylene glycol (PEG) with lactose, lactobionolactone and benzyl beta-D-galactopyranosyl-(1-->6)-2-amino-2-deoxy-alpha-D-glucopyranoside (1) with the hope to improve the bioavailability, though retaining their inhibitory properties. Different conjugation methods have been used and the behavior of the PEGylated products in the TcTS reaction was studied.

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Citations

Oct 23, 2013·Future Medicinal Chemistry·Bill R Miller, Adrian E Roitberg
Jan 10, 2016·Acta Tropica·José BermudezSantiago Palma
Apr 5, 2013·Biological Reviews of the Cambridge Philosophical Society·Eyal KamhiRobert J Linhardt
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May 21, 2019·PLoS Neglected Tropical Diseases·María de Los Milagros CámaraCarlos A Buscaglia
Jul 6, 2014·Beilstein Journal of Organic Chemistry·M Eugenia GiorgiRosa M de Lederkremer
Jun 8, 2011·Carbohydrate Research·M Eugenia Giorgi, Rosa M de Lederkremer

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