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 α-(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-α-mediated inflammatory pathway without showing cytotoxicity.

Department of Applied Chemistry Faculty of Science and Technology Institute of Chemistry University of Debrecen Egyetem tér 1 H 4032 Debrecen Hungary

Department of Molecular and Nanopharmaceutics Faculty of Pharmacy University of Debrecen Nagyerdei Körút 98 H 4032 Debrecen Hungary

Department of Pharmaceutical Chemistry Faculty of Pharmacy University of Debrecen Egyetem tér 1 H 4032 Debrecen Hungary

Department of Pharmacodynamics Faculty of Pharmacy University of Debrecen Nagyerdei Körút 98 H 4032 Debrecen Hungary

HUN REN UD Molecular Recognition and Interaction Research Group University of Debrecen Egyetem tér 1 H 4032 Debrecen Hungary

Institute of Healthcare Industry University of Debrecen Egyetem tér 1 H 4032 Debrecen Hungary

Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences Flemingovo nam 2 CZ 16000 Prague Czech Republic

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