A fluorescent polymeric heparin sensor.

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Sun W, Bandmann H, Schrader T

A fluorescent polymeric heparin sensor.

Chemistry. 2007;13(27):7701-7.

PubMed ID

17600786 [ View in PubMed

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Abstract

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 nM 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.

DrugBank Data that Cites this Article

Drug Targets

Drug	Target	Kind	Organism	Pharmacological Action	Actions
Heparin	Antithrombin-III	Protein	Humans	Yes	Potentiator	Details