Hydrolysis of hydrophobic poly(2-oxazoline)s and their subsequent modification via aza-Michael addition

References

• Sedlacek O, Monnery BD, Filippov SK, et al. Poly(2-oxazoline)s – are they more advantageous for biomedical applications than other polymers? Macromol Rapid Commun. 2012;33(19):1648–1662. doi: 10.1002/marc.201200453
   PubMed Web of Science ®Google Scholar
• Adams N, Schubert US. Poly(2-oxazolines) in biological and biomedical application contexts. Adv Drug Deliv Rev. 2007;59(15):1504–1520. doi: 10.1016/j.addr.2007.08.018
   PubMed Web of Science ®Google Scholar
• de la Rosa VR. Poly(2-oxazoline)s as materials for biomedical applications. J Mater Sci Mater Med. 2014;25(5):1211–1225. doi: 10.1007/s10856-013-5034-y
   PubMed Web of Science ®Google Scholar
• Schlaad H, Diehl C, Gress A, et al. Poly(2-oxazoline)s as smart bioinspired polymers. Macromol Rapid Commun. 2010;31(6):511–525. doi: 10.1002/marc.200900683
   PubMed Web of Science ®Google Scholar
• Glassner M, Vergaelen M, Hoogenboom R. Poly(2-oxazoline)s: a comprehensive overview of polymer structures and their physical properties. Polym Int. 2018;67(1):32–45. doi: 10.1002/pi.5457
   Web of Science ®Google Scholar
• Cesana S, Kurek A, Baur MA, et al. Polymer-Bound thiol groups on Poly(2-oxazoline)s. Macromol Rapid Commun. 2007;28(5):608–615. doi: 10.1002/marc.200600737
   Web of Science ®Google Scholar
• Yilmaz G, Uzunova V, Hartweg M, et al. The effect of linker length on ConA and DC-SIGN binding of S-glucosyl functionalized poly(2-oxazoline)s. Polym Chem. 2018;9(5):611–618. doi: 10.1039/C7PY01939D
   Web of Science ®Google Scholar
• Šrámková P, Zahoranová A, Kroneková Z, et al. Poly(2-oxazoline) hydrogels by photoinduced thiol-ene “click” reaction using different dithiol crosslinkers. J Polym Res. 2017;24(5):82. doi: 10.1007/s10965-017-1237-0
   Web of Science ®Google Scholar
• Dargaville TR, Forster R, Farrugia BL, et al. Poly(2-oxazoline) hydrogel monoliths via thiol-ene coupling. Macromol Rapid Commun. 2012;33(19):1695–1700. doi: 10.1002/marc.201200249
   PubMed Web of Science ®Google Scholar
• Luef KP, Petit C, Ottersböck B, et al. UV-mediated thiol-ene click reactions for the synthesis of drug-loadable and degradable gels based on copoly(2-oxazoline)s. Eur Polym J. 2017;88:701–712. doi: 10.1016/j.eurpolymj.2016.08.012
   PubMed Web of Science ®Google Scholar
• Drain BA, Becer CR. Eur. Polym J. 2019;119:344–351. doi: 10.1016/j.eurpolymj.2019.07.047
   Google Scholar
• Cook AB, Peltier R, Zhang J, et al. Hyperbranched poly(ethylenimine cooxazoline) by thiolyne chemistry for non-viral gene delivery: investigating the role of polymer architecture. Polym Chem. 2019;10(10):1202–1212. doi: 10.1039/C8PY01648H
   Web of Science ®Google Scholar
• Rudolph T, Crotty S, Von der Lühe M, et al. Synthesis and solution properties of Double hydrophilic poly(ethylene oxide)-block-poly(2-ethyl-2-oxazoline) (PEO-b-PEtOx) star block copolymers. Polymers. 2013;5(3):1081–1101. doi: 10.3390/polym5031081
   Web of Science ®Google Scholar
• Rudolph T, Crotty S, Schubert US, et al. Star-shaped poly(2-ethyl-2-oxazoline) featuring a porphyrin core: synthesis and metal complexation. e-Polymers. 2015;15(4):227–235. doi: 10.1515/epoly-2015-0041
   Web of Science ®Google Scholar
• Trachsel L, Romio M, Zenobi‐Wong M et al. Hydrogels Generated from Cyclic Poly(2-Oxazoline)s Display Unique Swelling and Mechanical Properties. Macromol Rapid Commun. 2020;42(7):2000658.
   Web of Science ®Google Scholar
• Yan W, Divandari M, Rosenboom J-G, et al. Design and characterization of ultrastable, biopassive and lubricious cyclic poly(2-alkyl-2-oxazoline) brushes. Polym Chem. 2018;9(19):2580–2589. doi: 10.1039/C7PY02137B
   Web of Science ®Google Scholar
• Jung Y, Kim J-H, Jang W-D. Linear and cyclic poly(2-isopropyl-2-oxazoline)s for fine control of thermoresponsiveness. Polym J. 2017;88:605–612. doi: 10.1016/j.eurpolymj.2016.09.003
   Web of Science ®Google Scholar
• Morgese G, Cavalli E, Rosenboom J-G, et al. Cyclic polymer grafts that lubricate and protect damaged cartilage. Chem Int Ed. 2018;57(6):1621–1626. doi: 10.1002/anie.201712534
   PubMed Web of Science ®Google Scholar
• Verbraeken B, Hoogenboom R. Cyclic polymers: from scientific curiosity to advanced materials for gene delivery and surface modification. Angewandte Chemie. 2017;56(25):7034–7036. doi: 10.1002/anie.201703418
   Google Scholar
• Drain BA, Beyer VP, Cattoz B, et al. Solvent dependency in the synthesis of multiblock and cyclic Poly(2-oxazoline)s. Macromolecules. 2021;54(12):5549–5556. doi: 10.1021/acs.macromol.1c00529
   Web of Science ®Google Scholar
• Huettner N, Goldmann AS, Hoogenboom R, et al. Macrocyclization efficiency for poly(2-oxazoline)s and poly(2-oxazine)s. Polym Chem. 2022;13(27):3975–3980. doi: 10.1039/D2PY00376G
   Web of Science ®Google Scholar
• Kim J, Waldron C, Cattoz B, et al. An ε-caprolactone-derived 2-oxazoline inimer for the synthesis of graft copolymers. Polym Chem. 2020;11(42):6847–6852. doi: 10.1039/D0PY01092H
   Web of Science ®Google Scholar
• Beyer VP, Cattoz B, Strong A, et al. Brush copolymers from 2-oxazoline and acrylic monomers via an inimer approach. Macromolecules. 2020;53(8):2950–2958. doi: 10.1021/acs.macromol.0c00243
   Web of Science ®Google Scholar
• Lambermont-Thijs HML, Bonami L, Du Prez FE, et al. Linear poly(alkyl ethylene imine) with varying side chain length: synthesis and physical properties. Polym Chem. 2010;1(5):747–754. doi: 10.1039/b9py00344d
   Web of Science ®Google Scholar
• Lambermont-Thijs HML, Van Der Woerdt FS, Baumgaertel A, et al. Linear poly(ethylene imine)s by acidic hydrolysis of Poly(2-oxazoline)s: kinetic screening, thermal properties, and temperature-induced solubility transitions. Macromolecules. 2010;43(2):927–933. doi: 10.1021/ma9020455
   Web of Science ®Google Scholar
• De La Rosa VR, Bauwens E, Monnery BD, et al. Fast and accurate partial hydrolysis of poly(2-ethyl-2-oxazoline) into tailored linear polyethylenimine copolymers. Polym Chem. 2014;5(17):4957–4964. doi: 10.1039/C4PY00355A
   Web of Science ®Google Scholar
• Akiyama Y, Harada A, Nagasaki Y, et al. Synthesis of poly(ethylene glycol)-block-poly(ethylenimine) possessing an Acetal group at the PEG end. Macromolecules. 2000;33(16):5841–5845. doi: 10.1021/ma000167c
   Web of Science ®Google Scholar
• Mees MA, Hoogenboom R. Full and partial hydrolysis of poly(2-oxazoline)s and the subsequent post-polymerization modification of the resulting polyethylenimine (co)polymers. Polym Chem. 2018;9(40):4968–4978. doi: 10.1039/C8PY00978C
   Web of Science ®Google Scholar
• Van Kuringen HPC, Lenoir J, Adriaens E, et al. Partial hydrolysis of Poly(2-ethyl-2-oxazoline) and potential implications for biomedical applications? Macromol biosci. 2012;12(8):1114–1123. doi: 10.1002/mabi.201200080
   PubMed Web of Science ®Google Scholar
• Haladjova E, Smolíček M, Ugrinova I, et al. DNA delivery systems based on copolymers of poly (2-methyl-2-oxazoline) and polyethyleneimine: effect of polyoxazoline moieties on the endo-lysosomal escape. J Appl Polym Sci. 2020;137(45):49400. doi: 10.1002/app.49400
   Web of Science ®Google Scholar
• Jeong JH, Song SH, Lim DW, et al. DNA transfection using linear poly(ethylenimine) prepared by controlled acid hydrolysis of poly(2-ethyl-2-oxazoline). J Control Release. 2001;73(2–3):391–399. doi: 10.1016/S0168-3659(01)00310-8
   PubMed Web of Science ®Google Scholar
• Haladjova E, Halacheva S, Momekova D, et al. Polyplex particles based on comb-like Polyethylenimine/Poly(2-ethyl-2-oxazoline) copolymers: relating biological performance with morphology and structure. Macromol biosci. 2018;18(4):1700349. doi: 10.1002/mabi.201700349
   Web of Science ®Google Scholar
• Bauer M, Tauhardt L, Lambermont-Thijs HML, et al. Rethinking the impact of the protonable amine density on cationic polymers for gene delivery: a comparative study of partially hydrolyzed poly(2-ethyl-2-oxazoline)s and linear poly(ethylene imine)s. Eur J Pharm Biopharm. 2018;133:112–121. doi: 10.1016/j.ejpb.2018.10.003
   PubMed Web of Science ®Google Scholar
• Cortez MA, Godbey WT, Fang Y, et al. The synthesis of Cyclic poly(ethylene imine) and exact linear analogues: an evaluation of gene delivery comparing polymer architectures. J Am Chem Soc. 2015;137(20):6541–6549. doi: 10.1021/jacs.5b00980
   PubMed Web of Science ®Google Scholar
• Halacheva S, Price GJ, Garamus VM. Effects of temperature and polymer composition upon the aqueous solution properties of comblike linear poly(ethylene imine)/Poly(2-ethyl-2-oxazoline)-based polymers. Macromolecules. 2011;44(18):7394–7404. doi: 10.1021/ma2012859
   Web of Science ®Google Scholar
• van Kuringen HPC, de la Rosa VR, Fijten MWM, et al. Enhanced selectivity for the hydrolysis of block Copoly(2-oxazoline)s in ethanol–water resulting in linear poly(ethylene imine) copolymers. Macromol Rapid Commun. 2012;33(9):827–832. doi: 10.1002/marc.201200046
   PubMed Web of Science ®Google Scholar
• Lambermont-Thijs HML, Heuts JPA, Hoeppener S, et al. Selective partial hydrolysis of amphiphilic copoly(2-oxazoline)s as basis for temperature and pH responsive micelles. Polym Chem. 2011;2(2):313–322. doi: 10.1039/C0PY00052C
   Web of Science ®Google Scholar
• Toncheva-Moncheva N, Veleva-Kostadinova E, Tsvetanov C, et al. Preparation and properties of positively charged mesoglobules based on poly(2-isopropyl-2-oxazoline) and evaluation of their potential as carriers of polynucleotides. Polymer. 2017;111:156–167. doi: 10.1016/j.polymer.2017.01.049
   Web of Science ®Google Scholar
• Mees M, Haladjova E, Momekova D, et al. Partially hydrolyzed poly (n-propyl-2-oxazoline): synthesis, aqueous solution properties, and preparation of gene delivery systems. Biomacromolecules. 2016;17(11):3580–3590. doi: 10.1021/acs.biomac.6b01088
   PubMed Web of Science ®Google Scholar
• Sedlacek O, Monnery BD, Hoogenboom R. Synthesis of defined high molar mass poly(2-methyl-2-oxazoline). Polym Chem. 2019;10(11):1286–1290. doi: 10.1039/C9PY00013E
   Web of Science ®Google Scholar
• Sedlacek O, Bera D, Hoogenboom R. Poly(2-amino-2-oxazoline)s: a new class of thermoresponsive polymers. Polym Chem. 2019;10(34):4683–4689. doi: 10.1039/C9PY00943D
   Web of Science ®Google Scholar
• Sedlacek O, Janouskova O, Verbraeken B, et al. Straightforward route to superhydrophilic Poly(2-oxazoline)s via acylation of well-defined polyethylenimine. Biomacromolecules. 2019;20(1):222–230. doi: 10.1021/acs.biomac.8b01366
   PubMed Web of Science ®Google Scholar
• Mees MA, Effenberg C, Appelhans D, et al. Sweet polymers: Poly(2-ethyl-2-oxazoline) glycopolymers by Reductive Amination. Biomacromolecules. 2016;17(12):4027–4036. doi: 10.1021/acs.biomac.6b01451
   PubMed Web of Science ®Google Scholar
• Bertrand E, Gonalves C, Billiet L, et al. Histidinylated linear PEI: a new efficient non-toxic polymer for gene transfer. Chem Commun. 2011;47(46):12547–12549. doi: 10.1039/c1cc15716g
   PubMed Web of Science ®Google Scholar
• de la Rosa VR, Bauwens E, Monnery BD, et al. Fast and accurate partial hydrolysis of poly(2-ethyl-2-oxazoline) into tailored linear polyethylenimine copolymers. Polym Chem. 2014;5(17):4957–4964. doi: 10.1039/C4PY00355A
   Web of Science ®Google Scholar
• Lowe AB, Hoyle CE, Bowman CN. Thiol-yne click chemistry: a powerful and versatile methodology for materials synthesis. J Mater Chem. 2010;20(23):4745–4750. doi: 10.1039/b917102a
   Web of Science ®Google Scholar