Block Synthesis and Step-Growth Polymerization of C-6-Sulfonatomethyl-Containing Sulfated Malto-Oligosaccharides and Their Biological Profiling

0581694 - ÚOCHB 2025 RIV CH eng J - Journal Article
Herczeg, M. - Demeter, F. - Nagy, T. - Rusznyák, A. - Hodek, Jan - Sipos, E. - Lekli, I. - Fenyvesi, F. - Weber, Jan - Kéki, S. - Borbás, A.
Block Synthesis and Step-Growth Polymerization of C-6-Sulfonatomethyl-Containing Sulfated Malto-Oligosaccharides and Their Biological Profiling.
International Journal of Molecular Sciences. Roč. 25, č. 1 (2024), č. článku 677. ISSN 1661-6596
R&D Projects: GA MŠMT(CZ) LX22NPO5103
Institutional support: RVO:61388963
Keywords : malto-oligomers * sulfonic acid * polymerization * glycosylation * anti-inflammatory effect
OECD category: Virology
Impact factor: 5.6, year: 2022
Method of publishing: Open access
https://doi.org/10.3390/ijms25010677

Highly sulfated malto-oligomers, similar to heparin and heparan-sulfate, have good antiviral, antimetastatic, anti-inflammatory and cell growth inhibitory effects. Due to their broad biological activities and simple structure, sulfated malto-oligomer derivatives have a great therapeutic potential, therefore, the development of efficient synthesis methods for their production is of utmost importance. In this work, preparation of alpha-(1> 4)-linked oligoglucosides containing a sulfonatomethyl moiety at position C-6 of each glucose unit was studied by different approaches. Malto-oligomeric sulfonic acid derivatives up to dodecasaccharides were prepared by polymerization using different protecting groups, and the composition of the product mixtures was analyzed by MALDI-MS methods and size-exclusion chromatography. Synthesis of lower oligomers was also accomplished by stepwise and block synthetic methods, and then the oligosaccharide products were persulfated. The antiviral, anti-inflammatory and cell growth inhibitory activity of the fully sulfated malto-oligosaccharide sulfonic acids were determined by in vitro tests. Four tested di- and trisaccharide sulfonic acids effectively inhibited the activation of the TNF-alpha-mediated inflammatory pathway without showing cytotoxicity.
Permanent Link: https://hdl.handle.net/11104/0349883