Dendritic Polyglycerol Sulfates as New Heparin Analogues and Potent Inhibitors of the Complement System

Bioconjugate Chemistry

Volumn 15, Issue 1, 2004, Pages 162-167

  Türk, Holger ^a,c   Haag, Rainer ^a,c   Alban, Susanne ^b  

^a UNIVERSITY OF FREIBURG   (Germany)

^b UNIVERSITY OF KIEL   (Germany)

^c TU DORTMUND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLATION; CHEMICAL ACTIVATION; DENDRIMERS; MOLECULAR WEIGHT; SULFUR COMPOUNDS;

ACTIVATED PARTIAL THROMBOPLASTIN TIME; ANTITHROMBOTIC; COMPLEMENT ACTIVATIONS; COMPLEMENT SYSTEMS; DENDRITIC POLYGLYCEROLS; MIMETICS; POLYGLYCEROLS; POLYMER BASED; POTENT INHIBITOR; THROMBIN TIME;

POLYSACCHARIDES;

ANTICOAGULANT AGENT; CARBOXYLIC ACID DERIVATIVE; COMPLEMENT INHIBITOR; DENDRIMER; GLYCEROL DERIVATIVE; HEPARIN; HEPARIN DERIVATIVE; POLYGLYCEROL CARBOXYLIC ACID DERIVATIVE; POLYGLYCEROL SULFATE; POLYMER; SULFATE; UNCLASSIFIED DRUG;

ADULT; ANTICOAGULATION; ARTICLE; CHEMICAL STRUCTURE; COMPLEMENT ALTERNATIVE PATHWAY; COMPLEMENT CLASSICAL PATHWAY; COMPLEMENT INHIBITION; HUMAN; INFLAMMATION; MOLECULAR WEIGHT; NORMAL HUMAN; PARTIAL THROMBOPLASTIN TIME; POLYMERIZATION; THROMBIN TIME;

EID: 0842306880     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc034044j     Document Type: Article

References (37)

1. Hirsh, J., Warkentin, T. E., Shaughnessy, S. G., Anand, S. S., Halperin, J. L., Raschke, R., Granger, C., Ohman, E. M., and Dalen, J. E. (2001) Heparin and Low-Molecular-Weight Heparin: Mechanisms of Action, Pharmacokinetics, Dosing, Monitoring, Efficacy, and Safety. Chest 119, 64S-94S.
2. Demir, M., Iqbal, O., Dietrich, C. P., Hoppensteadt, D., Ahmad, S., Daud, A. N., and Fareed, J. (2001) Anticoagulant and antiprotease effects of a novel heparinlike compound from shrimp (Penaeus brasiliensis) and its neutralization by heparinase I. Clin. Appl. Thromb. Hemostasis 7, 44-52.
3. Linhardt, R. J., Loganathan, D., Al-Hakim, A., Wang, H.-M., Walenga, J. M., Hoppensteadt, D., and Fareedt, J. (1990) Oligosaccharide Mapping of Low Molecular Weight Heparins: Structure and Activity Differences. J. Med. Chem. 33, 1639-1645.
4. Capila, I., and Linhardt, R. J. (2002) Heparin-Protein-Wechselwirkungen. Angew. Chem. 114, 426-450.
5. Petitou, M., Duchaussoy, P., Herbert, J.-M., Duc, G., El Hajji, M., Branellec, J.-F., Donat, F., Necciari, J., Cariou, R., Bouthier, J., and Garrigou, E. (2002) The Synthetic Pentasaccharide Fondaparinux: First in the Class of Antithrombotic Agents that Selectively Inhibit Coagulation Factor Xa. Semin. Thromb. Hemostasis 28, 393-402.
6. Hopfner, R. (2002) Ximelagatran. Curr. Opin. Investig. Drugs 3, 246-251.
7. Weiler, J. M., Edens, R. E., Linhardt, R. J., and Kapelanski, D. P. (1992) Heparin and modified heparin inhibit complement activation in vivo. J. Immunol. 148, 3210-3215.
8. Winkelhake, J. L. (1991) Will complex carbohydrate ligands of vascular selectins be the next generation of non-steroidal anti-inflammatory drugs? Glycoconjugate J. 8, 381-386.
9. Arfors, K.-E., and Ley, K. (1993) Sulfated polysaccharides in inflammation. J. Lab. Clin. Med. 121, 201-202.
10. Linhardt, R. J., and Toida, T. (1997) Heparin oligosaccharides: New analogues development and applications. Carbohydrates in Drug Design (Witczak, Z. J., and Nieforth, K. A., Eds.) pp 277-341, Marcel Dekker, New York.
11. Zacharski, L. R., and Ornstein, D. L. (1998) Heparin and cancer. Thromb. Haemostasis 80, 10-23.
12. Engelberg, H. (1991) Heparin, nonheparin glycosaminoglycans, and heparinoids: an overview of their application in atheroscerosis. Semin. Thromb. Hemostasis 17, 5-8.
13. Garg, H. G., Thompson, B. T., and Hales, C. A. (2000) Structural determinants of antiproliferative activity of heparin on pulmonary artery smooth muscle cells. Am. J. Physiol. Lung Cell. Mol. Physiol. 279, L779-L789.
14. Ley, K., Cerrito, M., and Arfors, K.-E. (1991) Sulfated polysaccharides inhibit leukocyte rolling in venules by protamin and sulfated polysaccharides. Am. J. Physiol. Heart Circ. Physiol. 260, H1667-H1673.
15. DeClercq, E. (1993) Anti-HIV activity of sulfated polysaccharides. Carbohydrates and Carbohydrate Polymers, Analysis, Biotechnology, Modification, Antiviral, Biomedical and other Application (Yalpani, M., Ed.) pp 87-100, ATL Press, Shrewsbury.
16. Hsu, L. C. (2001) Heparin-coated cardiopulmonary bypass circuits: current status. Perfusion 16, 417-428.
17. Alban, S., and Franz, G. (2001) Partial synthetic glucan sulfates as potential new antithrombotics. Biomacromolecules 2, 354-361.
18. Gunay, N. S., and Linhardt, R. J. (1999) Heparinoids: Structure, Biological Activities and Therapeutic Applications. Planta Med. 65, 301-306.
19. Alban, S. (1997) Carbohydrates with anticoagulant and antithrombotic properties. Carbohydrates in Drug Design (Witczak, Z. J., and Nieforth, K. A., Eds.) pp 209-276, Marcel Dekker, New York.
20. Sunder, A., Mülhaupt, R., Haag, R., and Frey, H. (2000) Hyperbranched Polyether Polyols: A Modular Approach to Complex Polymer Architectures. Adv. Mater. 12, 235-239.
21. Frey, H., and Haag, R. (2002) Dendritic polyglycerol: a new versatile biocompatible material. Rev. Mol. Biotech. 90, 257-267.
22. Sunder, A., Hanselmann, R., Frey, H., and Mülhaupt, R. (1999) Controlled Synthesis of Hyperbranched Polyglycerols by Ring-Opening Multibranching Polymerization. Macromolecules 32, 4240-4246.
23. Casu, B., and Gennaro, U. (1975) A conductometric method for the determination of sulphate and carboxyl groups in heparin and other mucopolysaccharides. Carbohydr. Res. 39, 168-176.
24. Alban, S., Kraus, J., and Franz, G. (1992) Synthesis of Laminarin Sulfates with Anticoagulant Activity. Arzneim.-Forsch./Drug Res. 42, 1005-1008.
25. Witt, I., Beeser, H., and Müller-Berghaus, G. (1995) Minimalanforderungen zur Gewinnung von Citratplasma für hämostaseologische Analysen. Laboratory Medicine 19, 143-145.
26. Alban, S., Classen, B., and Blaschek, W. (2002) Differentiation between the complement modulating effects of an arabinogalactan-protein from Echinacea purpurea and of heparin. Planta Med. 68, 1118-1124.
27. Haag, R., Sunder, A., and Stumbé, J.-F. (2000) An Approach to Glycerol Dendrimers and Pseudo-Dendritic Polyglycerols. J. Am. Chem. Soc. 122, 2954-2955.
28. Wilson, R., Van Schie, B. J., and Howes, D. (1998) Overview of the Preparation, Use and Biological Studies on Polyglycerol Polyricinoleate (PGPR). Food Chem. Toxicol. 36, 711-718.
29. Howes, D., Wilson, R., and James, C. T. (1998) The Fate of Ingested Glyceran Esters of Condensed Castor Oil Fatty Acids [Polyglycerol Polyricinoleate (PGPR)] in Rat. Food Chem. Toxicol. 36, 719-738.
30. Gait, M. J., Jones, A. S., and Walker, R. T. (1974) Synthetic Analogues of Polynucleotides. Part XII. Synthesis of Thymidine Derivatives containing an Oxyacetamido- or an Oxyformamido-linkage instead of a Phosphodiester Group. J. Chem. Soc., Perkin Trans. 1 1684-1686.
31. Oshima, G. (1989) The molecular-mass dependence of dextran sulfate enhancement of inactivation of thrombin and fibrinogen and on factor Xa neutralization by antithrombin III. Biol. Chem. 370, 715-721.
32. Alban, S., and Franz, G. (1994) Anticoagulant activity of Β-1,3-glucan sulfates in dependence on their molecular weight. Pure Appl. Chem. 66, 2403-2406.
33. Mauray, S., De Raucourt, E., Chaubet, F., Maiga-Revel, O., Sternberg, C., and Fischer, A. M. (1998) Comparative anticoagulant activity and influence on thrombin generation of dextran derivatives and of a fucoidan fraction. J. Biomater. Sci. Polym. Ed. 9, 373-387.
34. Chevolot, L., Foucault, A., Chaubet, F., Kervarec, N., Sinquin, C., Fisher, A. M., and Boisson-Vidal, C. (1999) Further data on the structure of brown seaweed fucans: relationships with anticoagulant activity. Carbohydr. Res. 319, 154-165.
35. Yvin, J.-C., Alban, S., and Franz, G. (2002) Antiinflammatory and healing medicine based on laminarin sulphate. PCT Int. Appl. Patent WO 2002036132.
36. Levi, M., ten Cate, H., and van der Poll, T. (2002) Endothelium: interface between coagulation and inflammation. Crit. Care Med. 30, S220-S224.
37. Black, P. H., and Garbutt, L. D. (2002) Stress, inflammation and cardiovascular disease. J. Psychosom. Res. 52, 1-23.