Synthesis and Inverse Emulsion Polymerization of Aminated Acrylamidodextran

Author:

Daubresse C1,Grandfils C1,Jéräme R1,Teyssié Ph1,Goethals P2,Schacht E2

Affiliation:

1. Centre d'Etudes et de Recherches sur les Macromolécules, University of Liège, Sart-Tilman B6, 4000 Liège, Belgium

2. Laboratory of Organic Chemistry, Rijkuniversiteit Gent, Krijgslaan 281 (S-4), B-9000 Gent, Belgium

Abstract

Abstract A chemically modified form of dextran was prepared, having a polymerizable moiety (acrylamide) and a reactive functional group (primary amine). Dextran was activated with 4-nitrophenyl-chloroformate (24 mol per polysaccharide, 9·8 mol per 100 glucose residues); 9·8% glucose residues were converted to aliphatic carbonates and 5·2% were converted to cyclic carbonates. The activated dextran was coupled with trityldiaminoethane (8 mol per 100 glucose residues), reactivated with 4-nitrophenylchloro-formate, then coupled with acryloamidodiaminohexane (6·8 mol per 100 glucose residues). The trityl group was removed by hydrolysis with trifluoroacetic acid to yield the required aminated acryloamidodextran. The modified dextran was shown to be polymerizable by inverse emulsion polymerization. Submicron particles were successfully prepared, containing functional amine groups suitable for preparing drug conjugates or for modifying the surface properties of this biomaterial.

Publisher

Oxford University Press (OUP)

Subject

Pharmaceutical Science,Pharmacology

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