Ring Opening Metathesis Polymerization of Bicyclic α,β‐Unsaturated Anhydrides for Ready‐to‐be‐grafted Polymers Having Tailored pH‐Responsive Degradability

Polymers having α,β‐unsaturated anhydrides as repeating units were synthesized by ring opening metathesis polymerization (ROMP). The anhydride moieties were ready‐to‐be‐grafted with amines to form acid‐labile cis‐α,β‐unsaturated acid amide linkages. The pH‐responsive reversible de‐grafting can be co...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-09, Vol.57 (38), p.12468-12472
Main Authors: Kim, Heejin, Kim, Sungwhan, Kang, Sunyoung, Song, Youngjun, Shin, Suyong, Lee, Seonju, Kang, Minji, Nam, So Hee, Lee, Yan
Format: Article
Language:English
Subjects:
Alendronic acid
Amines
Anhydrides
bicyclic anhydrides
Bisphosphonates
Chemical synthesis
Cytotoxicity
Degradability
Grafting
Metathesis
pH degradability
pH effects
Polymerization
Polymers
reversible grafting and release
Ring opening polymerization
ROMP
Toxicity
α,β-unsaturated amides
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Summary:Polymers having α,β‐unsaturated anhydrides as repeating units were synthesized by ring opening metathesis polymerization (ROMP). The anhydride moieties were ready‐to‐be‐grafted with amines to form acid‐labile cis‐α,β‐unsaturated acid amide linkages. The pH‐responsive reversible de‐grafting can be controlled by changing the intramolecular accessibility between acid and amide groups. The alendronate‐grafted ROMP polymers showed distinct pH‐dependent cytotoxicity according to the anhydride structures. ROMP polymers were synthesized having α,β‐unsaturated anhydrides for high‐density grafting and pH‐responsive release of amine side chains via acid‐labile β‐carboxylic acid amide linkages. The pH‐responsive degradability of the linkages can be tuned by the modulation of the ring structure for the de‐grafting of the side chains in suitable pH conditions.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201806763