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Degradable Spirocyclic Polyacetal-Based Core-Amphiphilic Assemblies for Encapsulation and Release of Hydrophobic Cargo

Polymeric nanomaterials that degrade in acidic environments have gained considerable attention in nanomedicine for intracellular drug delivery and cancer therapy. Among various acid-degradable linkages, spirocyclic acetals have rarely been used to fabricate such vehicles. In addition to acid sensiti...

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Autores principales: Andrade-Gagnon, Brandon, Bélanger-Bouliga, Marilyne, Trang Nguyen, Phuong, Nguyen, Thi Hong Diep, Bourgault, Steve, Nazemi, Ali
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7826923/
https://www.ncbi.nlm.nih.gov/pubmed/33435172
http://dx.doi.org/10.3390/nano11010161
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author Andrade-Gagnon, Brandon
Bélanger-Bouliga, Marilyne
Trang Nguyen, Phuong
Nguyen, Thi Hong Diep
Bourgault, Steve
Nazemi, Ali
author_facet Andrade-Gagnon, Brandon
Bélanger-Bouliga, Marilyne
Trang Nguyen, Phuong
Nguyen, Thi Hong Diep
Bourgault, Steve
Nazemi, Ali
author_sort Andrade-Gagnon, Brandon
collection PubMed
description Polymeric nanomaterials that degrade in acidic environments have gained considerable attention in nanomedicine for intracellular drug delivery and cancer therapy. Among various acid-degradable linkages, spirocyclic acetals have rarely been used to fabricate such vehicles. In addition to acid sensitivity, they benefit from conformational rigidity that is otherwise not attainable by their non-spirocyclic analogs. Herein, amphiphilic spirocyclic polyacetals are synthesized by Cu-catalyzed alkyne–azide “click” polymerization. Unlike conventional block copolymers, which often form core–shell structures, these polymers self-assemble to form core amphiphilic assemblies capable of encapsulating Nile red as a hydrophobic model drug. In vitro experiments show that while release from these materials can occur at neutral pH with preservation of their integrity, acidic pH accelerates efficient cargo release and leads to the complete degradation of assemblies. Moreover, cellular assays reveal that these materials are fully cytocompatible, interact with the plasma membrane, and can be internalized by cells, rendering them as potential candidates for cancer therapy and/or drug delivery.
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spelling pubmed-78269232021-01-25 Degradable Spirocyclic Polyacetal-Based Core-Amphiphilic Assemblies for Encapsulation and Release of Hydrophobic Cargo Andrade-Gagnon, Brandon Bélanger-Bouliga, Marilyne Trang Nguyen, Phuong Nguyen, Thi Hong Diep Bourgault, Steve Nazemi, Ali Nanomaterials (Basel) Article Polymeric nanomaterials that degrade in acidic environments have gained considerable attention in nanomedicine for intracellular drug delivery and cancer therapy. Among various acid-degradable linkages, spirocyclic acetals have rarely been used to fabricate such vehicles. In addition to acid sensitivity, they benefit from conformational rigidity that is otherwise not attainable by their non-spirocyclic analogs. Herein, amphiphilic spirocyclic polyacetals are synthesized by Cu-catalyzed alkyne–azide “click” polymerization. Unlike conventional block copolymers, which often form core–shell structures, these polymers self-assemble to form core amphiphilic assemblies capable of encapsulating Nile red as a hydrophobic model drug. In vitro experiments show that while release from these materials can occur at neutral pH with preservation of their integrity, acidic pH accelerates efficient cargo release and leads to the complete degradation of assemblies. Moreover, cellular assays reveal that these materials are fully cytocompatible, interact with the plasma membrane, and can be internalized by cells, rendering them as potential candidates for cancer therapy and/or drug delivery. MDPI 2021-01-10 /pmc/articles/PMC7826923/ /pubmed/33435172 http://dx.doi.org/10.3390/nano11010161 Text en © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Andrade-Gagnon, Brandon
Bélanger-Bouliga, Marilyne
Trang Nguyen, Phuong
Nguyen, Thi Hong Diep
Bourgault, Steve
Nazemi, Ali
Degradable Spirocyclic Polyacetal-Based Core-Amphiphilic Assemblies for Encapsulation and Release of Hydrophobic Cargo
title Degradable Spirocyclic Polyacetal-Based Core-Amphiphilic Assemblies for Encapsulation and Release of Hydrophobic Cargo
title_full Degradable Spirocyclic Polyacetal-Based Core-Amphiphilic Assemblies for Encapsulation and Release of Hydrophobic Cargo
title_fullStr Degradable Spirocyclic Polyacetal-Based Core-Amphiphilic Assemblies for Encapsulation and Release of Hydrophobic Cargo
title_full_unstemmed Degradable Spirocyclic Polyacetal-Based Core-Amphiphilic Assemblies for Encapsulation and Release of Hydrophobic Cargo
title_short Degradable Spirocyclic Polyacetal-Based Core-Amphiphilic Assemblies for Encapsulation and Release of Hydrophobic Cargo
title_sort degradable spirocyclic polyacetal-based core-amphiphilic assemblies for encapsulation and release of hydrophobic cargo
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7826923/
https://www.ncbi.nlm.nih.gov/pubmed/33435172
http://dx.doi.org/10.3390/nano11010161
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