Next Article in Journal
Two-Stage Recognition Mechanism of the SARS-CoV-2 Receptor-Binding Domain to Angiotensin-Converting Enzyme-2 (ACE2)
Next Article in Special Issue
M6229 Protects against Extracellular-Histone-Induced Liver Injury, Kidney Dysfunction, and Mortality in a Rat Model of Acute Hyperinflammation
Previous Article in Journal
A Million-Cow Validation of a Chromosome 14 Region Interacting with All Chromosomes for Fat Percentage in U.S. Holstein Cows
Previous Article in Special Issue
Zn2+ Differentially Influences the Neutralisation of Heparins by HRG, Fibrinogen, and Fibronectin
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
IJMS
Volume 25
Issue 1
10.3390/ijms25010677
ijms-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Article

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

by
Mihály Herczeg
1,*,
Fruzsina Demeter
1,
Tibor Nagy
2,
Ágnes Rusznyák
3,4,
Jan Hodek
5,
Éva Sipos
6,
István Lekli
6,
Ferenc Fenyvesi
3,
Jan Weber
5,
Sándor Kéki
2 and
Anikó Borbás
1,7,*
1
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary
2
Department of Applied Chemistry, Faculty of Science and Technology, Institute of Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary
3
Department of Molecular and Nanopharmaceutics, Faculty of Pharmacy, University of Debrecen, Nagyerdei Körút 98, H-4032 Debrecen, Hungary
4
Institute of Healthcare Industry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary
5
Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nam. 2, CZ-16000 Prague, Czech Republic
6
Department of Pharmacodynamics, Faculty of Pharmacy, University of Debrecen, Nagyerdei Körút 98, H-4032 Debrecen, Hungary
7
HUN-REN-UD Molecular Recognition and Interaction Research Group, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary
*
Authors to whom correspondence should be addressed.
Int. J. Mol. Sci. 2024, 25(1), 677; https://doi.org/10.3390/ijms25010677
Submission received: 6 December 2023 / Revised: 30 December 2023 / Accepted: 31 December 2023 / Published: 4 January 2024
(This article belongs to the Special Issue Heparin, Heparan Sulfate and Heparanase in Health and Disease)
Browse Figures
Versions Notes

Abstract

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.
Keywords: malto-oligomers; sulfonic acid; polymerization; glycosylation; anti-inflammatory effect malto-oligomers; sulfonic acid; polymerization; glycosylation; anti-inflammatory effect
Graphical Abstract

Share and Cite

MDPI and ACS Style

Herczeg, M.; Demeter, F.; Nagy, T.; Rusznyák, Á.; Hodek, J.; Sipos, É.; Lekli, I.; Fenyvesi, F.; Weber, J.; Kéki, S.; et al. Block Synthesis and Step-Growth Polymerization of C-6-Sulfonatomethyl-Containing Sulfated Malto-Oligosaccharides and Their Biological Profiling. Int. J. Mol. Sci. 2024, 25, 677. https://doi.org/10.3390/ijms25010677

AMA Style

Herczeg M, Demeter F, Nagy T, Rusznyák Á, Hodek J, Sipos É, Lekli I, Fenyvesi F, Weber J, Kéki S, et al. Block Synthesis and Step-Growth Polymerization of C-6-Sulfonatomethyl-Containing Sulfated Malto-Oligosaccharides and Their Biological Profiling. International Journal of Molecular Sciences. 2024; 25(1):677. https://doi.org/10.3390/ijms25010677

Chicago/Turabian Style

Herczeg, Mihály, Fruzsina Demeter, Tibor Nagy, Ágnes Rusznyák, Jan Hodek, Éva Sipos, István Lekli, Ferenc Fenyvesi, Jan Weber, Sándor Kéki, and et al. 2024. "Block Synthesis and Step-Growth Polymerization of C-6-Sulfonatomethyl-Containing Sulfated Malto-Oligosaccharides and Their Biological Profiling" International Journal of Molecular Sciences 25, no. 1: 677. https://doi.org/10.3390/ijms25010677

APA Style

Herczeg, M., Demeter, F., Nagy, T., Rusznyák, Á., Hodek, J., Sipos, É., Lekli, I., Fenyvesi, F., Weber, J., Kéki, S., & Borbás, A. (2024). Block Synthesis and Step-Growth Polymerization of C-6-Sulfonatomethyl-Containing Sulfated Malto-Oligosaccharides and Their Biological Profiling. International Journal of Molecular Sciences, 25(1), 677. https://doi.org/10.3390/ijms25010677

Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.

Article Metrics

Back to TopTop