Synthesis and anticoagulant activity of heparin immobilized "end-on" to polystyrene microspheres coated with end-group activated polyethylene oxide

Journal of Biomedical Materials Research - Part B Applied Biomaterials

Volumn 94, Issue 1, 2010, Pages 187-195

  Fry, Allyson K ^a   Schilke, Karl F ^a   McGuire, Joseph ^a   Bird, Karyn E ^b  

^a Oregon State University   (United States)

^b OREGON STATE UNIVERSITY   (United States)

Author keywords

Anticoagulant activity; End aminated heparin; Heparin containing block copolymer; Microspheres; PEO PPO PEO triblock polymer; Zeta potential

Indexed keywords

2-IMINOTHIOLANE; ACTIVATED PARTIAL THROMBOPLASTIN TIME; ANTICOAGULANT ACTIVITIES; ANTICOAGULANT ACTIVITY; END GROUPS; END-AMINATED HEPARIN; FACTOR XA; POLYSTYRENE MICRO-SPHERE; PRIMARY AMINES; SELECTIVE MODIFICATION; STERIC CONSTRAINT; SURFACE LOADING; THIOL GROUPS; TRIBLOCK COPOLYMERS; TRIBLOCK POLYMERS; UNFRACTIONATED HEPARINS;

AMINATION; BLOCK COPOLYMERS; COPOLYMERIZATION; ETHYLENE; MICROSPHERES; POLYETHYLENE GLYCOLS; POLYETHYLENE OXIDES; POLYETHYLENES; POLYSTYRENES; PROPYLENE; SYNTHESIS (CHEMICAL); ZETA POTENTIAL;

POLYSACCHARIDES;

2 IMINOTHIOLANE; AMINE; ANTITHROMBIN; BLOOD CLOTTING FACTOR 10A; COPOLYMER; HEPARIN; MACROGOL; MICROSPHERE; POLOXAMER; POLYSTYRENE; PROPYLENE OXIDE;

ANTICOAGULATION; ARTICLE; COMPLEX FORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; PARTIAL THROMBOPLASTIN TIME; STATISTICAL SIGNIFICANCE; SURFACE PROPERTY; ZETA POTENTIAL;

ADSORPTION; AMINES; ANTICOAGULANTS; BIOCOMPATIBLE MATERIALS; BLOOD COAGULATION; FACTOR XA; HEPARIN; HUMANS; MATERIALS TESTING; MICROSPHERES; MOLECULAR STRUCTURE; PARTIAL THROMBOPLASTIN TIME; POLYETHYLENE GLYCOLS; POLYSTYRENES; PROPYLENE GLYCOLS; SULFHYDRYL COMPOUNDS;

EID: 77954110124     PISSN: 15524973     EISSN: 15524981     Source Type: Journal    
DOI: 10.1002/jbm.b.31640     Document Type: Article

References (39)

1. Mao C, Qiu Y, Sang J, Mei H, Zhu A, Shen J, Lin S. Various approaches to modify biomaterial surfaces for improving hemocompatibility. Adv Coll Inter Sci 2004;110:5-17.
2. Ratner B. The catastrophe revisited: Blood compatibility in the 21st century. Biomaterials 2007;28:5144-5147. (Pubitemid 47488493)
3. Mahoney D, Whittle J, Milner C, Clark S, Mulloy B, Buttle D, Jones G, Day A, Short R. A method for the non-covalent immobilization of heparin to surfaces. Anal Biochem 2004;330:123-129. (Pubitemid 38746983)
4. Chung Y-I, Tae G, Yuk S. A facile method to prepare heparin- functionalized nanoparticles for controlled release of growth factors. Biomaterials 2006;27:2621-2626. (Pubitemid 43113286)
5. Nguyen Q, Ping Z, Nguyen T, Rigal P. Simple method for immobilization of bio-macromolecules onto membranes of different types. J Membr Sci 2003;213:85-95. (Pubitemid 36169978)
6. Byun Y, Jacobs H, Kim SW. Binding of antithrombin III to thrombin to immobilized heparin under flow conditions. Biotechnol Progr 1996;12:217-225. (Pubitemid 126545766)
7. Nadkarni V, Linhardt R. Directional immobilization of heparin onto the nonporous surface of polystyrene microplates. Biotechniques 1997;23:382-385. (Pubitemid 27398180)
8. Marconi W, Benvenuti F, Piozzi A. covalent bonding of heparin to a vinyl copolymer for biomedical application. Biomaterials 1997;18:885-890. (Pubitemid 27239152)
9. Che A-F, Nie F-Q, Huang X-D, Xu Z-K, Yao K. Acrylonitrile-based copolymer membranes containing reactive groups: Surface modification by the immobilization of biomacromolecules. Polymer 2005;46:11060-11065. (Pubitemid 41530698)
10. Lin D-J, Lin D-T, Young T-H, Huang F-M, Chen C-C, Cheng L-P. Immobilization of heparin on PVDF membranes with microporous structures. J Memb Sci 2004;245:137-146. (Pubitemid 39434362)
11. Wissink M, Beernink R, Pieper J, Poot A, Engbers G, Beugeling T, Aken W van, Feijen J. Immobilization of heparin to EDC/NHS-crosslinked collagen. Characterization and in vitro evaluation. Biomaterials 2001;22:151-163.
12. Wang A, Cao T, Tang H, Liang X, Salley S, Ng K. In vitro haemocompatibility and stability of two types of heparin-immobilized silicon surfaces. Colloids Surf B Biointerf 2005;43:245-255.
13. Comper W. Heparin (and Related Polysaccharides), Structural and Functional Properties. New York: Gordon and Breach Science Publishers; 1981.
14. Joshi P. Ph.D. Dissertation, Oregon State University, Corvallis, 2007. 158 p.
15. Petitou M, Casu B, Lindahl U. 1976-1983, a critical period in the history of heparin: The discovery of the antithrombin binding site. Biochimie 2003;85:83-89.
16. Nardella C, Steinkuhler C. Radiolabeled heparan sulfate immobilized on microplate as substrate for the detection of heparanase activity. Anal Biochem 2004;332:368-375.
17. Tseng P-Y, Rele S, Sun X-L, Chaikof E. Fabrication and characterization of heparin functionalized membrane-mimetic assemblies. Biomaterials 2006;27:2627-2636.
18. Larm O, Larsson R, Olsson P. A new non-thrombogenic surface prepared by selective covalent binding of heparin via a modified reducing terminal residue. Biomater Med Devices Artif Organs 1983;11:161-173.
19. Bjorklund M, Hearn M. Characterisation of silica-based heparin affinity sorbents from equilibrium binding studies on plasma fractions containing thrombin. J Chromotogr A 1997;762:113-133. (Pubitemid 27122824)
20. Denizli A. Heparin-immobilized poly(2-hydroxyethylmethacrylate)-based microspheres. J Appl Polym Sci 1999;74:655-662.
21. Ampofo S, Wang H, Linhardt R. Disaccharide composition analysis of heparin and heparin sulfate using capillary zone electrophoresis Anal Biochem 1991;199:249-255.
22. Nadkarni V, Pervin A, Linhardt R. Directional immobilization of heparin onto beaded supports. Anal Biochem 1994;222:59-67. (Pubitemid 24319526)
23. Osmond R, Kett W, Skett S, Coombe D. Protein-heparin interactions measured by BIAcore 2000 are affected by the method of heparin immobilization. Anal Biochem 2002;310:199-207.
24. Li J-T, Carlsson J, Lin J-N, Caldwell KD. Chemical modification of surface active poly(ethylene oxide)-poly(propylene oxide) triblock copolymers. Bioconjugate Chem 1996;7:592-599. (Pubitemid 26369624)
25. Neff J, Caldwell K, Tresco P. A novel method for surface modification to promote cell attachment to hydrophobic substrates. J Biomed Mater Res 1997;40:511-519. (Pubitemid 28225835)
26. Neff J, Tresco P, Caldwell K. Surface modification for controlled studies of cell-ligand interactions. Biomaterials 1999;20:2377-2393.
27. Andersson J, Bexborn F, Klinth J, Nilsson B, Ekdahl K. Surface-attached PEO in the form of activated pluronic with immobilized factor H reduces both coagulation and complement activation in a whole-blood model. J Biomed Mater Res 2006;76:25-34.
28. Parsons T, Maita Y, Lalli CM. A manual of chemical and biological methods for seawater analysis. New York: Pergamon Press; 1984. pp 40-55.
29. Traut R, Bollen A, Sun T-T, Hershey J, Sundberg J, Pierce L. Methyl 4-mercaptobutyrimidate as a cleavable cross-linking reagent and its application to the Escherichia coli 30S ribosome. Biochemistry 1973;12:3266-3273.
30. Singh R, Kats L, Blaetller WA, Lambert JM. Formation of N-substituted 2-iminothiolanes when amino groups in proteins and peptides are modified by 2-iminothiolane. Anal Biochem 1996;236:114-125.
31. Bernkop-Schnurch A, Hornof M, Zoidl T. Thiolated polymers-thiomers: Synthesis and in vitro evaluation of chitosan-2-Iminothiolane conjugates. Int J Pharm 2003;260:229-237. (Pubitemid 36773920)
32. Alagon A, King T. Activation of polysaccharides with 2-iminothiolane and its uses. Biochemistry 1980;19:4341-4345.
33. Tarentino A, Phelan A, Plummer T. 2-Iminothiolane: Areagent for the introduction of sulphydryl groups into oligosaccharides derived from asparagine-linked glycans. Glycobiology 1993;3:279-285. (Pubitemid 23232162)
34. Ellman G. Tissue sulfhydryl groups. Arch Biochem Biophys 1959;82:70-77.
35. Riddles PW, Blakeley RL, Zerner B. Ellman's reagent: 5,5′- dithiobis(2-nitrobenzoic acid)-a reexamination. Anal Biochem 1979;94:75-81.
36. Rosner B. Fundamentals of Biostatistics. Pacifi Grove, CA: Duxbury; 2000.
37. Toida T, Yoshida H, Toyoda H, Koshiishi I, Imanari T, Hileman R, Fromm J, Linhardt R. Structural differences and the presence of unsubstituted amino groups in heparan sulphates from different tissues and species. Biochem J 1997;322:499-506.
38. Pavlov G, Finet S, Tatarenko K, Korneeva E, Ebel C. Conformation of heparin studied with macromolecular hydrodynamic methods and X-ray scattering. Eur Biophys J 2003;32:437-449.
39. Hirsh J, Warkentin T, Raschke R, Granger C, Ohman E, Dalen J. Heparin and low-molecular-weight heparin: Mechanisms of action, pharmacokinetics, dosing considerations, monitoring, efficacy, and safety. Chest 1998;114:489-510.