Concurrent Block Copolymer Polymersome Stabilization and Bilayer Permeabilization by Stimuli-Regulated "Traceless" Crosslinking

The fabrication of block copolymer (BCP) vesicles (polymersomes) exhibiting synchronized covalent crosslinking and bilayer permeabilization remains a considerable challenge as crosslinking typically leads to compromised membrane permeability. Herein it is demonstrated how to solve this dilemma by em...

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Published in	Angewandte Chemie International Edition Vol. 53; no. 12; pp. 3138 - 3142
Main Authors	Wang, Xiaorui, Liu, Guhuan, Hu, Jinming, Zhang, Guoying, Liu, Shiyong
Format	Journal Article
Language	English
Published	Weinheim WILEY-VCH Verlag 17.03.2014 WILEY‐VCH Verlag Wiley Subscription Services, Inc
Edition	International ed. in English
Subjects	Amines Block copolymers Copolymers Covalence Crosslinking Fabrication Membranes Molecular Structure permeability Polymers - chemistry polymersomes self-assembly Solubility Stabilization Strategy Vesicles Water - chemistry block copolymers self-assembly crosslinking polymersomes permeability
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Abstract	The fabrication of block copolymer (BCP) vesicles (polymersomes) exhibiting synchronized covalent crosslinking and bilayer permeabilization remains a considerable challenge as crosslinking typically leads to compromised membrane permeability. Herein it is demonstrated how to solve this dilemma by employing a stimuli‐triggered crosslinking strategy with amphiphilic BCPs containing photolabile carbamate‐caged primary amines. Upon self‐assembling into polymersomes, light‐triggered self‐immolative decaging reactions release primary amine moieties and extensive amidation reactions then occur due to suppressed amine pKa within hydrophobic milieu. This leads to serendipitous vesicle crosslinking and the process is associated with bilayer hydrophobicity‐to‐hydrophilicity transition and membrane permeabilization. Two processes in one: A stimuli‐triggered crosslinking strategy was developed to concurrently crosslink and permeabilize block copolymer assemblies. Upon self‐assembling into polymersomes (see picture), light‐triggered self‐immolative decaging reactions release primary amine moieties and lead to extensive amidation reactions.
AbstractList	The fabrication of block copolymer (BCP) vesicles (polymersomes) exhibiting synchronized covalent crosslinking and bilayer permeabilization remains a considerable challenge as crosslinking typically leads to compromised membrane permeability. Herein it is demonstrated how to solve this dilemma by employing a stimuli-triggered crosslinking strategy with amphiphilic BCPs containing photolabile carbamate-caged primary amines. Upon self-assembling into polymersomes, light-triggered self-immolative decaging reactions release primary amine moieties and extensive amidation reactions then occur due to suppressed amine pKa within hydrophobic milieu. This leads to serendipitous vesicle crosslinking and the process is associated with bilayer hydrophobicity-to-hydrophilicity transition and membrane permeabilization. [PUBLICATION ABSTRACT] The fabrication of block copolymer (BCP) vesicles (polymersomes) exhibiting synchronized covalent crosslinking and bilayer permeabilization remains a considerable challenge as crosslinking typically leads to compromised membrane permeability. Herein it is demonstrated how to solve this dilemma by employing a stimuli-triggered crosslinking strategy with amphiphilic BCPs containing photolabile carbamate-caged primary amines. Upon self-assembling into polymersomes, light-triggered self-immolative decaging reactions release primary amine moieties and extensive amidation reactions then occur due to suppressed amine pKa within hydrophobic milieu. This leads to serendipitous vesicle crosslinking and the process is associated with bilayer hydrophobicity-to-hydrophilicity transition and membrane permeabilization. The fabrication of block copolymer (BCP) vesicles (polymersomes) exhibiting synchronized covalent crosslinking and bilayer permeabilization remains a considerable challenge as crosslinking typically leads to compromised membrane permeability. Herein it is demonstrated how to solve this dilemma by employing a stimuli-triggered crosslinking strategy with amphiphilic BCPs containing photolabile carbamate-caged primary amines. Upon self-assembling into polymersomes, light-triggered self-immolative decaging reactions release primary amine moieties and extensive amidation reactions then occur due to suppressed amine pK sub(a) within hydrophobic milieu. This leads to serendipitous vesicle crosslinking and the process is associated with bilayer hydrophobicity-to-hydrophilicity transition and membrane permeabilization. Two processes in one: A stimuli-triggered crosslinking strategy was developed to concurrently crosslink and permeabilize block copolymer assemblies. Upon self-assembling into polymersomes (see picture), light-triggered self-immolative decaging reactions release primary amine moieties and lead to extensive amidation reactions. The fabrication of block copolymer (BCP) vesicles (polymersomes) exhibiting synchronized covalent crosslinking and bilayer permeabilization remains a considerable challenge as crosslinking typically leads to compromised membrane permeability. Herein it is demonstrated how to solve this dilemma by employing a stimuli‐triggered crosslinking strategy with amphiphilic BCPs containing photolabile carbamate‐caged primary amines. Upon self‐assembling into polymersomes, light‐triggered self‐immolative decaging reactions release primary amine moieties and extensive amidation reactions then occur due to suppressed amine p K a within hydrophobic milieu. This leads to serendipitous vesicle crosslinking and the process is associated with bilayer hydrophobicity‐to‐hydrophilicity transition and membrane permeabilization. The fabrication of block copolymer (BCP) vesicles (polymersomes) exhibiting synchronized covalent crosslinking and bilayer permeabilization remains a considerable challenge as crosslinking typically leads to compromised membrane permeability. Herein it is demonstrated how to solve this dilemma by employing a stimuli-triggered crosslinking strategy with amphiphilic BCPs containing photolabile carbamate-caged primary amines. Upon self-assembling into polymersomes, light-triggered self-immolative decaging reactions release primary amine moieties and extensive amidation reactions then occur due to suppressed amine pKa within hydrophobic milieu. This leads to serendipitous vesicle crosslinking and the process is associated with bilayer hydrophobicity-to-hydrophilicity transition and membrane permeabilization.The fabrication of block copolymer (BCP) vesicles (polymersomes) exhibiting synchronized covalent crosslinking and bilayer permeabilization remains a considerable challenge as crosslinking typically leads to compromised membrane permeability. Herein it is demonstrated how to solve this dilemma by employing a stimuli-triggered crosslinking strategy with amphiphilic BCPs containing photolabile carbamate-caged primary amines. Upon self-assembling into polymersomes, light-triggered self-immolative decaging reactions release primary amine moieties and extensive amidation reactions then occur due to suppressed amine pKa within hydrophobic milieu. This leads to serendipitous vesicle crosslinking and the process is associated with bilayer hydrophobicity-to-hydrophilicity transition and membrane permeabilization. The fabrication of block copolymer (BCP) vesicles (polymersomes) exhibiting synchronized covalent crosslinking and bilayer permeabilization remains a considerable challenge as crosslinking typically leads to compromised membrane permeability. Herein it is demonstrated how to solve this dilemma by employing a stimuli‐triggered crosslinking strategy with amphiphilic BCPs containing photolabile carbamate‐caged primary amines. Upon self‐assembling into polymersomes, light‐triggered self‐immolative decaging reactions release primary amine moieties and extensive amidation reactions then occur due to suppressed amine pKa within hydrophobic milieu. This leads to serendipitous vesicle crosslinking and the process is associated with bilayer hydrophobicity‐to‐hydrophilicity transition and membrane permeabilization. Two processes in one: A stimuli‐triggered crosslinking strategy was developed to concurrently crosslink and permeabilize block copolymer assemblies. Upon self‐assembling into polymersomes (see picture), light‐triggered self‐immolative decaging reactions release primary amine moieties and lead to extensive amidation reactions.
Author	Zhang, Guoying Liu, Guhuan Hu, Jinming Wang, Xiaorui Liu, Shiyong
Author_xml	– sequence: 1 givenname: Xiaorui surname: Wang fullname: Wang, Xiaorui organization: CAS Key Laboratory of Soft Matter Chemistry, Hefei National Laboratory for Physical, Sciences at the Microscale, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei, Anhui 230026 (China) – sequence: 2 givenname: Guhuan surname: Liu fullname: Liu, Guhuan organization: CAS Key Laboratory of Soft Matter Chemistry, Hefei National Laboratory for Physical, Sciences at the Microscale, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei, Anhui 230026 (China) – sequence: 3 givenname: Jinming surname: Hu fullname: Hu, Jinming organization: CAS Key Laboratory of Soft Matter Chemistry, Hefei National Laboratory for Physical, Sciences at the Microscale, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei, Anhui 230026 (China) – sequence: 4 givenname: Guoying surname: Zhang fullname: Zhang, Guoying organization: CAS Key Laboratory of Soft Matter Chemistry, Hefei National Laboratory for Physical, Sciences at the Microscale, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei, Anhui 230026 (China) – sequence: 5 givenname: Shiyong surname: Liu fullname: Liu, Shiyong email: sliu@ustc.edu.cn organization: CAS Key Laboratory of Soft Matter Chemistry, Hefei National Laboratory for Physical, Sciences at the Microscale, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei, Anhui 230026 (China)
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Keywords	block copolymers self-assembly crosslinking polymersomes permeability
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Notes	The financial support from National Natural Scientific Foundation of China (NNSFC) project (grant numbers 21274137, 51273190, 91027026, and 51033005) and Specialized Research Fund for the Doctoral Program of Higher Education (SRFDP, grant number 20123402130010) is gratefully acknowledged. Specialized Research Fund for the Doctoral Program of Higher Education - No. 20123402130010 ark:/67375/WNG-5Q91HJT6-Q National Natural Scientific Foundation of China (NNSFC) - No. 21274137; No. 51273190; No. 91027026; No. 51033005 ArticleID:ANIE201310589 istex:F94EC95EE5F5C56832827D73EB49FDD46729AD9C ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23
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Snippet	The fabrication of block copolymer (BCP) vesicles (polymersomes) exhibiting synchronized covalent crosslinking and bilayer permeabilization remains a...
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SubjectTerms	Amines Block copolymers Copolymers Covalence Crosslinking Fabrication Membranes Molecular Structure permeability Polymers - chemistry polymersomes self-assembly Solubility Stabilization Strategy Vesicles Water - chemistry
Title	Concurrent Block Copolymer Polymersome Stabilization and Bilayer Permeabilization by Stimuli-Regulated "Traceless" Crosslinking
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