Stimuli-Responsive Thiomorpholine Oxide-Derived Polymers with Tailored Hydrophilicity and Hemocompatible Properties
Abstract
:1. Introduction
2. Experimental Section
2.1. Materials
2.2. Instrumentation
2.3. Synthesis of 2-Bromoethyl Methacrylate
2.4. Synthesis of Ethylthiomorpholine Methacrylate (THMA)
2.5. Synthesis of Ethylthiomorpholine Oxyde Methacrylate (THOXMA)
2.6. Synthesis of Poly(ehylthiomorpholine oxide methacrylate) P(THOXMA)100 Homopolymer and Statistical Copolymers Poly(ethylthiomorpholine oxide methacrylate-stat-hydroxyethylmethacrylate) P(THOXMAn-stat-HEMAm) by RAFT
2.7. Determination of the pKa of the Monomers and Polymers
2.8. Evaluation of the LCST of P(THOXMA100) and P(THOXMAn-stat-HEMAm) Statistical Copolymers
2.9. Cytotoxicity Assays
2.10. Haemolysis Tests
2.11. Erythrocyte Aggregation
3. Results and Discussion
3.1. Synthesis of Monomers and Hydrophobic/Hydrophilic Polymers
3.2. Acido-Basic Properties of THOXMA and PTHOXMA
3.3. Determination of LCST
3.4. Biocompatibility of PTHOXMA
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Entry | Conversion of Monomers (%) a | Experimental DP b | DPTarget c | Mn (g/mol) d | Mn (g/mol) e | Dispersity (Đ) e | |
---|---|---|---|---|---|---|---|
THOXMA | HEMA | ||||||
P(THOXMA100) | 99.3 | - | 111 | 100 | 25,640 | 21,570 | 1.21 |
P(THOXMA80-stat-HEMA20) | 95.6 | 98.1 | 80 | 100 | 16,900 | 14,100 | 1.19 |
P(THOXMA50-stat-HEMA50) | 98 | 99 | 82 | 100 | 14,970 | 18,200 | 1.24 |
P(THOXMA40-stat-HEMA60) | 97 | 99.5 | 81 | 100 | 14,600 | 16,100 | 1.22 |
P(THOXMA35-stat-HEMA65) | 98.5 | 99.3 | 80 | 100 | 13,000 | 17,900 | 1.19 |
P(THOXMA30-stat-HEMA70) | 99 | 99.2 | 82 | 100 | 13,100 | 19,110 | 1.2 |
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Arsenie, L.V.; Hausig, F.; Kellner, C.; Brendel, J.C.; Lacroix-Desmazes, P.; Ladmiral, V.; Catrouillet, S. Stimuli-Responsive Thiomorpholine Oxide-Derived Polymers with Tailored Hydrophilicity and Hemocompatible Properties. Molecules 2022, 27, 4233. https://doi.org/10.3390/molecules27134233
Arsenie LV, Hausig F, Kellner C, Brendel JC, Lacroix-Desmazes P, Ladmiral V, Catrouillet S. Stimuli-Responsive Thiomorpholine Oxide-Derived Polymers with Tailored Hydrophilicity and Hemocompatible Properties. Molecules. 2022; 27(13):4233. https://doi.org/10.3390/molecules27134233
Chicago/Turabian StyleArsenie, Laura Vasilica, Franziska Hausig, Carolin Kellner, Johannes C. Brendel, Patrick Lacroix-Desmazes, Vincent Ladmiral, and Sylvain Catrouillet. 2022. "Stimuli-Responsive Thiomorpholine Oxide-Derived Polymers with Tailored Hydrophilicity and Hemocompatible Properties" Molecules 27, no. 13: 4233. https://doi.org/10.3390/molecules27134233