Orthogonally functionalizable polyacetals: a versatile platform for the design of acid sensitive amphiphilic copolymers

To expand the range of hydrolytically degradable functional polymers, copolyacetals of various compositions were synthesized and fully characterized, and their self-assembly into nanoparticles was studied. First, functionalized copolyacetals were obtained by polyaddition of alkyne- and activated est...

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Bibliographic Details
Published inPolymer chemistry Vol. 1; no. 38; pp. 5215 - 5227
Main Authors Moreno, Adrian, Lligadas, Gerard, Ronda, Juan Carlos, Galià, Marina, Cádiz, Virginia
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 14.10.2019
Subjects
Addition polymerization
Alkynes
Butanediol
Chemical reactions
Composition
Copolymers
Diols
Dismantling
Drug delivery systems
Folic acid
Micelles
Monomers
Nanoparticles
NMR
Nuclear magnetic resonance
Organic chemistry
Polymer chemistry
Self-assembly
Transesterification
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Summary:To expand the range of hydrolytically degradable functional polymers, copolyacetals of various compositions were synthesized and fully characterized, and their self-assembly into nanoparticles was studied. First, functionalized copolyacetals were obtained by polyaddition of alkyne- and activated ester-functionalized diols with 1,4-butanediol divinyl ether (DVE). Second, the copolymers were functionalized by using two orthogonal chemical reactions, the thiol-yne click reaction and transesterification/amidation. Amphiphilic copolymers of varying compositions, i.e. different hydrophilic/hydrophobic balance, were obtained and self-assembled in water to afford well-defined nanostructures. The size of the micelles and the critical micelle concentration were correlated to the chemical nature and to the modification degree of the copolymers. The micelles displayed high drug loading capacity and encapsulation efficiency and could be disassembled in mildly acidic media showing a pH-dependent drug release behavior. Subsequent orthogonal modification to introduce folic acid moieties allowed the preparation of site-specific drug delivery systems, showing the versatility of this approach. Dually functionalized amphiphilic copolyacetals as rational approach to the development of pH-responsive site-specific drug delivery systems.
Bibliography:1
Electronic supplementary information (ESI) available: Synthesis and characterization data of diol monomers and model compounds.
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F NMR spectra of monomers, model compounds, polyacetals and copolyacetals. Additional data for polymer modification and micelles characterization. See DOI
10.1039/c9py01107b
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19
ISSN:1759-9954
1759-9962
DOI:10.1039/c9py01107b