Synthesis and Cell Growth Inhibitory Activity of Six Heparin-Analogue Trisaccharides

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Synthesis and Cell Growth Inhibitory Activity of Six Heparin-Analogue Trisaccharides

Mihály Herczeg 1 , Erika Herczeg-Lisztes 2 , István Balázs Tóth 2 , Erika Mező 3 , Anikó Borbás 3

1 Research Group for Oligosaccharide Chemistry of Hungarian Academy of Sciences, Debrecen, Hungary, 2 Department of Physiology, University of Debrecen, Debrecen, Hungary, 3 Department of Pharmaceutical Chemistry, University of Debrecen, Debrecen, Hungary

Heparin has been employed in the medical practice since the late 1930’s as a blood-anticoagulant. Besides the anticoagulant effect, heparin and its analogues have many other biological effects such as growth factor inhibition, anti-inflammatory and cell growth inhibitory activity.[1]

Our research group has been examining the development of new synthetic anticoagulant pentasaccharides for several years. We have focussed on the synthesis of isosteric sulfonic acid analogues of the synthetic anticoagulant pentasaccharides fondaparinux (1) and idraparinux (2). Many heparin-analogue oligosaccharides (di-, tri- and pentasaccharides) have been synthesized within this research for biological and structural analyses.[2-4]

Although smaller oligosaccharides do not have anticoagulant activity, but may have other beneficial biological effects similar to heparin. Here, we present the synthesis of six heparin-analogue trisaccharides (3-8) and the study of their cell growth inhibitory effects.

Structure of fondaparinux (1), idraparinux (2) and the synthesized idraparinux analogue trisaccharides (3-8)

The authors gratefully acknowledge financial support for this research from the Premium Postdoctoral Program of HAS (PPD 461038) and from the EU and co-financed by the European Regional Development Fund under the project GINOP-2.3.2-15-2016-00008.

Garg, H. G. et al., Chemistry and Biology of Heparin and Heparan Sulfate, Elsevier, 2005, ISBN-10: 0-08-044859-3.

Herczeg, M. et al., Org. Lett., 2009, 11, 2619-2622.

Herczeg, M. et al., Chem. Eur. J., 2012, 18, (34), 10643-10652.

Herczeg, M. et al., Tetrahedron, 2014, 70, (18), 2919–2927.

Lázár, L. et al., Tetrahedron, 2012, 68, 7386-7399.

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