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Concepts for preparation of novel regioselective modified cellulose derivatives sulfated, aminated, carboxylated and acetylated for hemocompatible ultrathin coatings on biomaterials

2000; Wiley; Volume: 201; Issue: 15 Linguagem: Inglês

10.1002/1521-3935(20001001)201

1521-3935

Hanno Baumann, Alexander P. Richter, Dieter Klemm, Volker Faust,

Hydrogels: synthesis, properties, applications

Macromolecular Chemistry and PhysicsVolume 201, Issue 15 p. 1950-1962 Research Article Concepts for preparation of novel regioselective modified cellulose derivatives sulfated, aminated, carboxylated and acetylated for hemocompatible ultrathin coatings on biomaterials Hanno Baumann, Hanno Baumann [email protected] Search for more papers by this authorAlexander Richter, Alexander Richter Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstr. 10, D-07743 Jena, Germany; Fax: +49/3641/948202Search for more papers by this authorDieter Klemm, Dieter Klemm Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstr. 10, D-07743 Jena, Germany; Fax: +49/3641/948202Search for more papers by this authorVolker Faust, Volker Faust 1 ITMC, Macromolecular Chemistry and Textile Chemistry, Hemocompatible and Biocompatible Biomaterials, University of Technology Aachen, Worringer Weg 1, D-52074 Aachen, Germany; Fax: +49/241/8888176Search for more papers by this author Hanno Baumann, Hanno Baumann [email protected] Search for more papers by this authorAlexander Richter, Alexander Richter Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstr. 10, D-07743 Jena, Germany; Fax: +49/3641/948202Search for more papers by this authorDieter Klemm, Dieter Klemm Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstr. 10, D-07743 Jena, Germany; Fax: +49/3641/948202Search for more papers by this authorVolker Faust, Volker Faust 1 ITMC, Macromolecular Chemistry and Textile Chemistry, Hemocompatible and Biocompatible Biomaterials, University of Technology Aachen, Worringer Weg 1, D-52074 Aachen, Germany; Fax: +49/241/8888176Search for more papers by this author First published: 19 October 2000 https://doi.org/10.1002/1521-3935(20001001)201:15 3.0.CO;2-3Citations: 30AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract Some regioselective cellulose derivatives were synthesized on the basis of the just started longterm concept by variation of O—SO3, N—SO3, N—Ac, and N-carboxymethyl groups solely or in combination for the development of athrombogenic and antithrombogenic nanocoatings on cellulose membranes. Similar regioselectively arranged functional groups are known partially in type 1 glycosaminoglycane (dermatan sulfate DS, and chondroitin sulfate CS) and all the groups are present in type 2 GAG (heparin HE and heparansulfat HS). The goal of this concept was to use instead of the backbone structure β 1–> 4, β 1–>3 (DS, CS) or β 1–> 4, α 1–> 4 (HE, HS or regioselective desulfated HE), the β 1–> 4 backbone structure of cellulose or chitosan, with the same functional groups as in HE. Furthermore different regioselective sulfated cellulose derivatives, such as cellulose-3-sulfate, cellulose-2,6-disulfate, and cellulose-2,3-sulfates with varied sulfation degrees have been synthesized and immobilized ionically on cellulose membranes. They were tested concerning their reduction of platelet adhesion from citrated whole blood in a perfusion system as well for AT III affinity. The lowest platelet adhesion and AT III affinity was observed using cellulose-2,3-sulfates and cellulose-3-sulfate derivatives, whereas cellulose-6-O-sulfate derivatives show high AT III affinity and high platelet adhesion. This means that a high 6-O-sulfate content seems to promote anticoagulant properties of the derivatives with high (AT III) affinity, whereas low concentrations of 2-O- and 3-O-sulfate groups show the lowest platelet adhesion. The latter seems to be important for developing athrombogenic coatings for biomaterials. The starting material chitosan with molecular weight of 150 KD was used to synthesize additionally some of 2-deoxyaminocellulose derivatives containing N—Ac or N—SO3 or N—CH2—COOH and O—SO3 groups. These derivatives are structurally closer to HE and HS and should enable us to work out the influence of each heparin like functional group in cellulose derivative on the athrombogenic and antithrombogenic properties. We synthesized only some of the latter mentioned derivatives with a distribution of the functional groups according to a Bernoulli statistics. Totally sulfated 2-deoxyaminocellulose-3,6-disulfate derivatives will be regioselectively desulfated by reactions known from heparin chemistry. Citing Literature Volume201, Issue15October 2000Pages 1950-1962 RelatedInformation