Bio-Inspired Amphiphilic Block-Copolymers Based on Synthetic Glycopolymer and Poly(Amino Acid) as Potential Drug Delivery Systems
by
Mariia Levit 1, Natalia Zashikhina 1, Alena Vdovchenko 2, Anatoliy Dobrodumov 1
, Natalya Zakharova 1, Anna Kashina 1, Eckart Rühl 3, Antonina Lavrentieva 4, Thomas Scheper 4, Tatiana Tennikova 2 and Evgenia Korzhikova-Vlakh 1,2,*
Mariia Levit 1, Natalia Zashikhina 1, Alena Vdovchenko 2, Anatoliy Dobrodumov 1, Natalya Zakharova 1, Anna Kashina 1, Eckart Rühl 3, Antonina Lavrentieva 4, Thomas Scheper 4, Tatiana Tennikova 2 and Evgenia Korzhikova-Vlakh 1,2,*
1
Institute of Macromolecular Compounds, Russian Academy of Sciences, Bolshoy pr. 31, 199004 St. Petersburg, Russia
2
Institute of Chemistry, Saint-Petersburg State University, Universitetsky pr. 26, 198504 St. Petersburg, Russia
3
Physical Chemistry, Institute of Chemistry and Biochemistry, Freie Universität Berlin, 14195 Berlin, Germany
4
Institute of Technical Chemistry, Gottfried-Wilhelm-Leibniz University of Hannover, 30167 Hannover, Germany
*
Author to whom correspondence should be addressed.
Polymers 2020, 12(1), 183; https://doi.org/10.3390/polym12010183
Received: 4 December 2019 / Revised: 3 January 2020 / Accepted: 5 January 2020 / Published: 10 January 2020
(This article belongs to the Special Issue Bioinspired and Biomimetic Polymers)
In this work, a method to prepare hybrid amphiphilic block copolymers consisting of biocompatible synthetic glycopolymer with non-degradable backbone and biodegradable poly(amino acid) (PAA) was developed. The glycopolymer, poly(2-deoxy-2-methacrylamido-D-glucose) (PMAG), was synthesized via reversible addition-fragmentation chain transfer (RAFT) polymerization. Two methods for modifying the terminal dithiobenzoate-group of PMAG was investigated to obtain the macroinitiator bearing a primary aliphatic amino group, which is required for ring-opening polymerization of N-carboxyanhydrides of hydrophobic α-amino acids. The synthesized amphiphilic block copolymers were carefully analyzed using a set of different physico-chemical methods to establish their composition and molecular weight. The developed amphiphilic copolymers tended to self-assemble in nanoparticles of different morphology that depended on the nature of the hydrophobic amino acid present in the copolymer. The hydrodynamic diameter, morphology, and cytotoxicity of polymer particles based on PMAG-b-PAA were evaluated using dynamic light scattering (DLS) and transmission electron microscopy (TEM), as well as CellTiter-Blue (CTB) assay, respectively. The redox-responsive properties of nanoparticles were evaluated in the presence of glutathione taken at different concentrations. Moreover, the encapsulation of paclitaxel into PMAG-b-PAA particles and their cytotoxicity on human lung carcinoma cells (A549) and human breast adenocarcinoma cells (MCF-7) were studied.
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Keywords:
synthetic glycopolymers; poly(amino acids); amphiphilic block copolymers; modification of terminal groups; nanoparticles; redox-responsive systems; paclitaxel; drug delivery systems
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MDPI and ACS Style
Levit, M.; Zashikhina, N.; Vdovchenko, A.; Dobrodumov, A.; Zakharova, N.; Kashina, A.; Rühl, E.; Lavrentieva, A.; Scheper, T.; Tennikova, T.; Korzhikova-Vlakh, E. Bio-Inspired Amphiphilic Block-Copolymers Based on Synthetic Glycopolymer and Poly(Amino Acid) as Potential Drug Delivery Systems. Polymers 2020, 12, 183.
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