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Issue 21, 2015
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“Reduction” responsive thymine-conjugated biodynamers: synthesis and solution properties

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Thioester chemistry was applied to construct the “reduction” responsive thymine-conjugated biodynamer by a transthioesterification reaction. The copolymers of N,N-dimethylacrylamide (DMA) and pyridyldisulfide ethylacrylamide (PDSEA) were obtained by reversible addition–fragmentation chain transfer (RAFT) radical polymerization, and used as a handle for incorporating thiol-reactive groups onto the copolymers. Thymine thioester reacted with the pendent thiol group produced in situ by the cleavage of PDS. The obtained thymine-conjugated biodynamer containing reversible thioester linkages can interact with the adenine-modified molecule mediated by hydrogen bonding, and demonstrate L-glutathione (GSH)-responsive feature by a thiol–thioester exchange reaction. The biodynamer can also interact with melamine and adenosine-5′-triphosphate (ATP), and form spherical aggregates in water. It is expected that this nucleobase-containing biodynamer has potential applications in the thiol-responsive controlled drug delivery and the construction of complex nanostructures and advanced materials as building blocks.

Graphical abstract: “Reduction” responsive thymine-conjugated biodynamers: synthesis and solution properties

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The article was received on 07 Feb 2015, accepted on 07 Apr 2015 and first published on 08 Apr 2015

Article type: Paper
DOI: 10.1039/C5PY00200A
Citation: Polym. Chem., 2015,6, 3934-3941

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    “Reduction” responsive thymine-conjugated biodynamers: synthesis and solution properties

    L. Liu, L. Wu, J. Tan, L. Wang, Q. Liu, P. Liu and L. Liu, Polym. Chem., 2015, 6, 3934
    DOI: 10.1039/C5PY00200A

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