A Reduction Sensitive Cascade Biodegradable Linear Polymer

作者：Dewit Matthew A; Beaton Annelise; Gillies Elizabeth R^*

来源：Journal of Polymer Science Part A: Polymer Chemistry , 2010, 48(18): 3977-3985.

DOI：10.1002/pola.24180

• biodegradable, biological applications of polymers, redox-sensitive polymers
• self-immolative polymers, stimuli-sensitive polymers

Cascade degradable linear polymers offer the potential for a high degree of control over the degradation process They comprise a backbone that is stable in the presence of an end cap, but upon removal of the end cap a cascade of intramolecular reactions is initiated that leads of depolymerization of the polymer backbone Reported here is a new polymer backbone based on N,N'-dimethylethylenediamine and 2-mercaptoethanol linked by carbamates and thiocarbamates. A disulfide end cap was incorporated such that its cleavage under reducing conditions revealed the thiol of 2-mercaptoethanol, leading to alternating cyclizations of the 2-mercaptoethanol and N,N'-dimethylethylenediamine moieties to provide 1,3-oxathiolan-2-one and N,N'-dimethylimidazolidinone, respectively. The degradation was monitored by (1)H NMR and GPC The expected products were observed, along with a portion of nondegradable polymer that was likely cyclic species. Overall, the results demonstrate the promise of this new class of polymers

• 出版日期2010-9-15