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Turn-On” Fluorescence Sensing of Bilirubin Using Water-Soluble Conjugated Polymer

T. Senthil Kumar, Vedant Joshi, Sachin ., Nishtha Arora, Aruna Kukreti

Abstract


Early detection of bilirubin is important to detect jaundice and hepatitis disease at the early stage. Currently, there is no fast method available to detect bilirubin level directly in the presence of crucial interference. This report presents a novel water-soluble poly(fluorenes-alt-benzothiadiazole) for turnon sensing of bilirubin in water and human blood serum. The probe is the water-soluble conjugated polymer poly(fluorenes-alt-benzothiadiazole) functionalized with a D-glucuronic acid named PF-BTGlcA. D-glucuronic acid acts as an interacting site for bilirubin, and the sensing experiment is carried out in clinically significant human blood serum. The PF-BT-GlcA polymer is synthesized via a two-step process; in the first step, Suzuki cross-coupling polymerization reaction between benzothiadiazole bisboronic ester with glucuronic acid-functionalized fluorene monomer (1) to yield PF-BT-GlcP. In the second step, PF-BT-GlcP is deprotected to give a water-soluble PF-BT-GlcA polymer. The protected and deprotected polymers are characterized with NMR and GPC techniques. The synthesized PF-BTGlcA shows excellent absorption and fluorescence properties in water. PF-BT-GlcA showed absorption maximum at 272, 312, and 423 nm and emission maximum at 548 nm, respectively. The spectral overlap between the bilirubin and PF-BT-GlcA polymer and hydrogen bonding interaction between glucuronic acid moiety and bilirubin brings them in the vicinity helps better turn-on sensing activity in water and human blood serum. The sensitivity and selectivity of bilirubin sensing using PF-BT-GlcA and the results found excellent in human blood serum. The selectivity of bilirubin sensing was verified with crucial interferences such as biliverdin, cholesterol, glucose, rhodamine, sucrose, sodium and potassium ions in human blood serum. The sensitivity of detection was found to be 180 nm.


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References


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