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Poly[(N-acryloyl glycinamide)-co-(N-acryloyl l-alaninamide)] and Their Ability to Form Thermo-Responsive Hydrogels for Sustained Drug Delivery

Department of Artificial Biopolymer, Institute for Biomolecules Max Mousseron, UMR CNRS 5247, Faculty of Pharmacy, University of Montpellier-CNRS-ENSCM, 15 Avenue Charles Flahault, BP 14491, 34093 Montpellier CEDEX 5, France
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Received: 1 January 2019 / Revised: 21 February 2019 / Accepted: 27 February 2019 / Published: 3 March 2019
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Abstract

In the presence of water, poly(N-acryloyl glycinamide) homopolymers form highly swollen hydrogels that undergo fast and reversible gel↔sol transitions on heating. According to the literature, the transition temperature depends on concentration and average molecular weight, and in the case of copolymers, composition and hydrophilic/hydrophobic character. In this article, we wish to introduce new copolymers made by free radical polymerization of mixtures of N-acryloyl glycinamide and of its analog optically active N-acryloyl l-alaninamide in various proportions. The N-acryloyl l-alaninamide monomer was selected in attempts to introduce hydrophobicity and chirality in addition to thermo-responsiveness of the Upper Critical Solubilization Temperature-type. The characterization of the resulting copolymers included solubility in solvents, dynamic viscosity in solution, Fourrier Transform Infrared, Nuclear Magnetic Resonance, and Circular Dichroism spectra. Gel→sol transition temperatures were determined in phosphate buffer (pH = 7.4, isotonic to 320 mOsm/dm3). The release characteristics of hydrophilic Methylene Blue and hydrophobic Risperidone entrapped in poly(N-acryloyl glycinamide) and in two copolymers containing 50 and 75% of alanine-based units, respectively, were compared. It was found that increasing the content in N-acryloyl-alaninamide-based units increased the gel→sol transition temperature, decreased the gel consistency, and increased the release rate of Risperidone, but not that of Methylene Blue, with respect to homo poly(N-acryloyl glycinamide). The increase observed in the case of Risperidone appeared to be related to the hydrophobicity generated by alanine residues. View Full-Text
Keywords: N-acryloyl glycinamide; N-acryloyl glycinamide (NAGA); N-acryloyl l-alaninamide; NAGA-co-N-acryloyl l-alaninamide chiral analog (NAlALA) copolymers; drug delivery; gel↔sol transition; Upper Critical Solution Temperature (UCST); thermo-responsive hydrogel N-acryloyl glycinamide; N-acryloyl glycinamide (NAGA); N-acryloyl l-alaninamide; NAGA-co-N-acryloyl l-alaninamide chiral analog (NAlALA) copolymers; drug delivery; gel↔sol transition; Upper Critical Solution Temperature (UCST); thermo-responsive hydrogel
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Boustta, M.; Vert, M. Poly[(N-acryloyl glycinamide)-co-(N-acryloyl l-alaninamide)] and Their Ability to Form Thermo-Responsive Hydrogels for Sustained Drug Delivery. Gels 2019, 5, 13.

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