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A Fluorescent Polymeric Heparin Sensor
Author(s) -
Sun Wei,
Bandmann Heinz,
Schrader Thomas
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200700677
Subject(s) - methacrylamide , chemistry , monomer , comonomer , copolymer , polymer chemistry , covalent bond , ethylene glycol , methacrylate , alkylation , polymer , combinatorial chemistry , acrylamide , organic chemistry , catalysis
Linear copolymers have been developed which carry binding sites tailored for sulfated sugars. All binding monomers are based on the methacrylamide skeleton and ensure statistical radical copolymerization. They are decorated with o ‐aminomethylphenylboronates for covalent ester formation and/or alkylammonium ions for noncovalent Coulomb attraction. Alcohol sidechains maintain a high water solubility; a dansyl monomer was constructed as a fluorescence label. Statistical copolymerization of comonomer mixtures with optimized ratios was started by AIBN (AIBN=2,2′‐azoisobutyronitrile) and furnished water‐soluble comonomers with an exceptionally high affinity for glucosaminoglucans. Heparin can be quantitatively detected with an unprecedented 30 n M sensitivity, and a neutral polymer without any ammonium cation is still able to bind the target with almost micromolar affinity. From this unexpected result, we propose a new binding scheme between the boronate and a sulfated ethylene glycol or aminoethanol unit. Although the mechanism of heparin binding involves covalent boronate ester formation, it can be completely reversed by protamine addition, similar to heparin's complex formation with antithrombin III.