"Reduction" responsive thymine-conjugated biodynamers: synthesis and solution properties

作者：Liu, Lingzhi; Wu, Libin; Tan, Junyan; Wang, Lin; Liu, Qing; Liu, Pingwei; Liu, Li

来源：Polymer Chemistry, 2015, 6(21): 3934-3941.

DOI：10.1039/c5py00200a

• THIOL-THIOESTER EXCHANGE
• NATIVE CHEMICAL LIGATION
• STAR-LIKE NANOGELS
• RADICAL POLYMERIZATION
• MOLECULAR RECOGNITION
• GOLD NANOPARTICLES
• DYNAMIC POLYMERS
• NUCLEIC-ACIDS
• NUCLEOBASE
• RAFT

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.

• 出版日期2015
• 单位南开大学