The Role of Regioselectively Sulfated and Acetylated Polysaccharide Coatings of Biomaterials for Reducing Platelet and Plasma Protein Adhesion

Hanno Baumann

doi:10.1055/s-2001-17955

Seminars in Thrombosis and Hemostasis, Table of Contents

Semin Thromb Hemost 2001; 27(5): 445-464
DOI: 10.1055/s-2001-17955

The Role of Regioselectively Sulfated and Acetylated Polysaccharide Coatings of Biomaterials for Reducing Platelet and Plasma Protein Adhesion

Hanno Baumann

ITMC, Macromolecular Chemistry and Textile Chemistry, Hemocompatible and Biocompatible Biomaterials, Technology University of Aachen, Aachen, Germany

Abstract

ABSTRACT

A brief survey is given about the role of natural polysaccharides such as heparin (HE), heparan sulfate (HS), chondroitin sulfate (CS), and dermatan sulfate (DS) in reducing blood coagulation and their potential use as athrombogenic coatings in the development of tailor-made athrombogenic biomaterials. Furthermore, known literature and new results about platelet adhesion on regioselectively modified polysaccharides such as HE, chitosan with HE-like functional groups, and sulfated cellulose are presented in two different perfusion systems at different shear rates. Regioselectively modified polysaccharides were tested as coatings of two polymers. The strongest influence on platelet adhesion was observed when the three regioselectively modified polysaccharides contained 6-O-sulfo- groups. No or little influence was seen with 3-O-sulfo- groups. A variable effect on platelet adhesion was found in position 2. N-sulfo- groups in HE induced a medium platelet adhesion, and O-sulfo- groups of iduronic acid moiety in HE induced none. Cellulose containing 2-O-sulfo- groups induced little platelet adhesion, and 2-N- sulfo- groups in chitosan induced a variable platelet adhesion response, depending on the N-SO₃/NAc ratio. Preliminary plasma protein adhesion measurements on immobilized HE derivatives with four different fluorescence-labeled plasma proteins showed a regioselective influence with serum albumin and fibrinogen. 6-O-desulfated HE gave the strongest reduction in protein adsorption followed by N-desulfation and 2-O-desulfation; the lowest reduction was observed with 3-O-desulfation. Tailor-made athrombogenic coatings of HE should not carry high amounts of 6-O-sulfo- groups or of N-sulfo- groups. Regioselectively modified cellulose and chitosan may become suitable for tailor-made athrombogenic biomaterials when regioselective reactions are further optimized.

KEYWORD

Heparin - heparan sulfate - chondroitin sulfate - regioselectively modified heparin - regioselectively sulfated cellulose - regioselectively modified chitosan with heparin-like functional groups - platelet adhesion - plasma protein adhesion - fluorescence labeling - biomaterials

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References

REFERENCES

1 Palmer R MJ, Ashton D S, Moncada S. Vascular endothelial cells synthesize nitric oxide from L-arginine. Nature . 1988; 33 664-666
2 Weiss H J, Turitto V T. Prostacyclin (prostaglandin I₂, PGI₂) inhibits platelet adhesion and thrombus formation on subendothelium. Blood . 1979; 53 244-250
3 Moncada S, Gryglewski R, Bunting S, Vane J R. An enzyme isolated from arteries transforms prostaglandin endoperoxides to an unstable substance that inhibits platelet aggregation. Nature . 1976; 263 663-665
4 Marcus A J, Broekman M J, Weksler B B. Arachidonic acid metabolism in endothelial cells and platelets. Ann NY Acad Sci . 1982; 401 195
5 Diamond S L, Eskin S G, McIntire L V. Fluid flow stimulates tissue plasminogen activator secretion by human endothelial cells. Science . 1989; 243 1483-1485
6 Rangi G J, Mumby S M, Abbott-Brown D, Bornstein P. Thrombospondin: synthesis and secretion by cells in culture. J Cell Biol . 1982; 195 351
7 Bourin M C, Lindahl U. Functional role of the polysaccharide component of rabbit thrombomodulin proteoglycan. Biochem J . 1990; 270 419-425
8 Bourin M C, Lindahl U. Glycosaminoglycans and the regulation of blood coagulation. Biochem J . 1993; 289 313-330
9 Esmon N L, Owen W G, Esmon C T. Isolation of a membrane-bound cofactor for thrombin-catalyzed activation of protein C. J Biol Chem . 1982; 257 859-864
10 Baumann H, Kokott A. Surface modification of the polymers present in a polysulfone hollow fiber immodialyser by covalent binding of heparin of endothelial cell surface heparan sulfate: flow characteristic and platelet adhesion. J Biomater Sci Polym Ed . 2000; 11 245-272
11 Baumann H, Müller U, Keller R. Which glycosaminoglycans are suitable for antithrombogenic or athrombogenic coatings of biomaterials?. <~>Part I: Basic concepts of immobilized GAGs on partially cationized cellulose membrane. Semin Thromb Hemost . 1997; 23 203-213
12 Baumann H, Keller R. Which glycosaminoglycans are suitable for antithrombogenic or athrombogenic coatings of biomaterials?. <~>Part II: Covalently immobilized endothelial cell surface heparan sulfate (ESHS) and heparin (HE) on synthetic polymers and results of animal experiments. Semin Thromb Hemost . 1997; 23 215-223
13 Baumann H, Keller R, Baumann U. Development of microvascular artificial platelet inert blood vessels, basic principle and animal experiments. In: Ottenbrite R, Chiellini E, Cohn D, Migliaresi C, Sunamoto J, eds. Frontiers in Biomedical Polymer Applications, Vol 2 Lancaster: Technomic 1999: 159-174
14 Baumann H, Faust V, Kokott A. Entwicklung einer multifunktionellen hämokompatiblen Beschichtung für Katheter zur Infusionstherapie und parenteralen Ernährung. In: Blank H, Stallfort H, eds. Symposium 4: Werkstoffe für die Medizintechnik, Vol. 4. Wiley VCH 1998: 195-200
15 Marcum J D, Rosenberg D. The biochemistry, cell biology, and pathophysiology of anticoagulantly active heparin-like molecules of the vessel wall. In: Lane DA, Lindahl U, eds. Heparin: Chemical and Biological Properties, Clinical Applications London: Edward Arnold 1989: 275-291
16 Tollefsen D M, Majerus D W, Blank M K. Heparin cofactor II purification and properties of a heparin-dependent inhibitor of thrombin in human plasma. J Biol Chem . 1982; 257 2162-2169
17 Jin L, Abrahams J P, Skinner R. The anticoagulant activation of antithrombin by heparin. Proc Natl Acad Sci USA . 1997; 94 14683-14688
18 Tollefsen D M. The interaction of glycosaminoglycans with heparin cofactor II: structure and activity of a high-affinity dermatan sulfate hexasaccharide. In: Lane DA, Björk, J, Lindahl U, eds. Heparin and Related Polysaccharides. Advances in Experimental Medicine and Biology, Vol. 313, New York: Plenum Press 1992: 167-176
19 Maimone M M, Tollefsen D M. Structure of a dermatan sulfate hexasaccharide that binds to heparin cofactor II with high affinity. J Biol Chem . 1990; 265 18263-18271
20 Gallagher J T, Lyon M. Molecular organisation and functions of heparan sulfate. In: Lane DA, Lindahl U, eds. Heparin: Chemical and Biological Properties, Clinical Applications London: Edward Arnold 1989: 135-158
21 Otto V, Wolff C, Baumann H, Keller R. Entwicklung von hämokompatiblen Oberflächen durch Modifizierung von Werkstoffen mit Endothelzelloberflächen-Heparansulfat (ES-HS). In: Breme J, ed. Werkstoffwoche 96, Symposium 4: Werkstoffe für die Medizintechnik, Frankfurt: DGM Informationsgesellschaft mbH; 1996: 161-169
22 Baumann H, Linssen M. Influence of plasma protein and platelet adhesion on coated biomaterials with major sequences of twenty regioselective modified N- or O-desulfated heparin/heparan derivatives. In: Chiellini E, Sumamoto J, Migliaresi C, Ottenbrite RM, Cohn D, eds. Frontiers in Biomedical Polymer Application, Biomedical Polymers and Polymer Therapeutics, Vol. 3, New York: Kluwer/Plenum; 2001: 177-193
23 Huppertz B, Baumann H, Keller R. The influence of semisynthetic heparinlike molecules with regioselective varied sulfate groups covalently immobilized on polymer surface on thrombocyte adhesion. In: Ottenbrite RM, Chiellini E, Cohn D, Migliaresi C, Sunamoto J, eds. Frontiers in Biomedical Polymer Applications, Vol 2. Lancaster: Technomic 1999: 115-129
24 Baumann H, Scheen H, Huppertz B, Keller R. Novel regio- and stereoselective O-6-desulfation of the glucosamine moiety of heparin with N-methylpyrrolidinone-water or N,N-dimethylformamide-water mixtures. Carbohydr Res . 1998; 308 381-388
25 Baumann H, Richter A, Klemm D, Faust V. Concepts for preparation of novel regioselective modified cellulose derivatives sulfated, aminated for hemocompatible ultrathin coatings on biomaterials. Macromol Chem Phys . 2000; 201 1950-1962
26 Baumann H, Faust V. Concepts for improved regioselectivity of O-sulfo, N-sulfo, N-acetyl and N-carboxymethylgroups in chitosan derivatives. Carbohydr Res . 2001; 331 43-57
27 Lindahl U. Biosynthesis of heparin and related polysaccharides. In: Lane DA, Lindahl U, eds. Heparin: Chemical and Biological Properties, Clinical Applications London: Edward Arnold, 1989: 159-189
28 Salzman E W, Merrill E W, Kent K C. Interaction of blood with artificial surfaces. In: Colman RW, Hirsch J, Marder VJ, Salzman EW, eds. Hemostasis and Thrombosis: Basic Principles and Clinical Practice, 3rd ed Philadelphia: Lippincott 1994: 1469-1485
29 Colman R W, Marder V J, Salzman E W, Hirsch J. Plasma coagulation factors. In: Colman RW, Hirsch J, Marder VJ, Salzman EW, eds. Hemostasis and Thrombosis: Basic Principles and Clinical Practice, 3rd ed Philadelphia: Lippincott 1994: 3-18
30 Casu B, Johnson E A, Forster M J. Correlation between structure, fat-clearing and anticoagulant properties of heparin and heparan sulphates. Arzneimittelforschung/Drug Res . 1983; 33 136-142
31 Takano R, Ye Z, Van Ta T. Specific 6-O-desulfation of heparin. Carbohydr Lett . 1998; 3 71-77
32 Engvall E, Ruoslathi E. Binding of soluble form of fibroblast surface protein, fibronectin to collagen. Int J Cancer . 1977; 20 1-5
33 Maeda H, Ishida N, Kawauchi H, Tuzimura K. Reaction of fluorescein-isothiocyanate with proteins and amino acids. J Biol Biochem . 1969; 65 777-783
34 Faraday N, Soldsomidt-Clermont P, Diso V, Bray P F. Quantitation of soluble fibrinogen binding to platelets by fluorescence-activated flow cytometry. J Lab Clin Med . 1994; 123 728-740
35 Miekka S I, Ingham K C. Influence of hetero-association on the precipitation of proteins by poly(ethylene) glycol. Arch Biochem Biophys . 1980; 203 630-641
36 Baumann H, Keller R, Ruzicka E. Partially cationized cellulose for non-thrombogenic membrane in the presence of heparin and endothelial-cell-surface-heparan sulfate (ES-HS). J Membr Sci . 1991; 61 253-268
37 Sakariassen K S, Aarts P M M A, de Groot G P, Houdijk W PM, Sixma J J. A perfusion chamber developed to investigate platelet interaction in flowing blood with human vessel wall cells, their extracellular matrix and purified components. J Lab Clin Med . 1983; 102 522-535
38 Jaseja M, Rey R N, Perlin A S. Novel regio- and stereoselective modifications of heparin in alkaline solution; nuclear magnetic resonance spectroscopy evidence. Can J Chem . 1989; 67 1449-1456
39 Uchiyama H, Nagasawa K. Changes in the structure and biological property of N-O sulfotetransferred, N-resulfated heparin. J Biol Chem . 1991; 266 6756-6760
40 Inoue Y, Nagasawa K. Selective N-desulfation of heparin with dimethylsulfoxide containing water or methanol. Carbohydr Res . 1976; 46 87-95
41 Ogamo A, Metori A, Uchiyama H, Nagasawa K. Reactivity toward chemical sulfation of hydroxylgroups of heparin. Carbohydr Res . 1989; 193 165-172
42 Walsh P N, Griffin J H. Contributions of human platelets to the proteolytic activation of blood coagulation factors XII and XI. Blood . 1981; 57 106-118
43 Schmaier A H, Smith P M, Purdon A D, White J G, Colman R W. High molecular weight kininogen: Localization in the unstimulated and activated platelet and activation by a platelet calpain(s). Blood . 1986; 67 119-130
44 Scully M F, Weerasinghe K, Kakkar V V. Inhibition of contact activation by platelet factor 4. Thromb Res . 1980; 20 461-466
45 Baier R E, Depalma V A, Goupil D W, Cohen E. Human platelet spreading on substrata of known surface chemistry. J Biomed Mater Res . 1985; 19 1157-1167
46 Zucker M B, Vroman L. Platelet adhesion induced by fibrinogen adsorbed onto glass. Proc Soc Exp Biol Med . 1969; 131 318-320
47 Packham M A, Evans G, Glynn M F. Effect of plasma proteins on interaction of platelets with glass surfaces. J Lab Clin Med . 1969; 73 686-697
48 Hynes R O. Integrins: A family of cell surface receptors. Cell . 1987; 48 549-554
49 Charo I F, Kieffer N, Phillips D R. Platelet membrane glycoproteins. In: Colman RW, Hirsh J, Marder VJ, Salzman EW, eds. Hemostasis and Thrombosis: Basic Principles and Clinical Practice, 3rd ed Philadelphia: Lippincott 1994: 489-507
50 Doolittle R F, Watt K WK, Cottrell B A. The amino acid sequence of the α-chain of human fibrinogen. Nature . 1979; 280 464-468
51 Kloczewiak M, Timmons S, Lukas T J, Hawiger J. Platelet receptor recognition site on human fibrinogen. Synthesis and structure-function relationship of peptides corresponding to the carboxyterminal segment of the γ chain. Biochemistry . 1984; 23 1767-1774
52 Baumgartner H R. The role of blood flow in platelet adhesion, fibrin deposition, and formation of mural thrombi. Microvasc Res . 1973; 5 167-179
53 Turitto V T, Baumgartner H R. Initial deposition of platelets and fibrin on vascular surface in flowing blood. In: Colmann WR, Hirsh J, Marder VJ, Salzman EW, eds. Hemostasis and Thrombosis, Basic Principles and Clinical Practice, 3rd ed Philadelphia: Lippincott 1994: 805-822
54 Scully M F, Ellis V, Seno N, Kakkar V V. The anticoagulant properties of mast cell product, chondroitin sulphate E. Biochem Biophys Res Commun. 198; 6137 15-22
55 Salzman E W, Merrill E W, Binder A. Protein-platelet interaction on heparinized surfaces. J Biomed Mater Res . 1969; 3 69-81
56 Brash L J, Wojcieckowski P. Interfacial Phenomena and Bioproducts. New York: Marcel Dekker; 1996
57 Baumann H, Jerg R, Keller R, Baumann U. Domain structure of endothelial cell surface heparan sulfate (ESHS). Int J Exp Pathol . 1993; 75 A73
58 Hojima V, Cochrane C, Wiggins R C. In vitro activation of the contact (Hageman factor) system of plasma by heparin and chondroitin sulfate E. Blood . 1984; 63 1453-1459
59 Vroman L, Adams A L. Identification of rapid changes of plasma-solid interfaces. J Biomed Mater Res . 1969; 3 43-67
60 Vroman L, Adams A L, Fischer G L, Munoz P L. Interaction of high molecular weight kininogen, factor XII and fibrinogen in plasma interfaces. Blood . 1980; 55 156-159
61 Brash J L, Scott C F, ten Hove P. Mechanism of transient adsorption of fibrinogen from plasma to solid surfaces. Role of the contact and fibrinolytic system. Blood . 1988; 71 932-939