Exploiting ionisable nature of PEtOx-co-PEI to prepare pH sensitive, doxorubicin-loaded micelles

References

• Bauer, M., et al., 2012. Poly(2-ethyl-2-oxazoline) as alternative for the stealth polymer poly(ethylene glycol): comparison of in vitro cytotoxicity and hemocompatibility. Macromolecular bioscience, 12 (7), 986–998.
   PubMed Web of Science ®Google Scholar
• Bauwens, E., 2013. Hydrolysis of poly-(2-ethyl-2-oxazoline). Ghent: Gent University.
   Google Scholar
• Ciapetti, G., et al., 2003. Osteoblast growth and function in porous poly epsilon -caprolactone matrices for bone repair: a preliminary study. Biomaterials, 24 (21), 3815–3824.
   PubMed Web of Science ®Google Scholar
• Ciofani, G., et al., 2008. Cytocompatibility, interactions, and uptake of polyethyleneimine-coated boron nitride nanotubes by living cells: confirmation of their potential for biomedical applications. Biotechnology and bioengineering, 101 (4), 850–858.
   PubMed Web of Science ®Google Scholar
• Cunningham, A.J., et al., 2018. Bile acid-based drug delivery systems for enhanced doxorubicin encapsulation: comparing hydrophobic and ionic interactions in drug loading and release. Molecular pharmaceutics, 15 (3), 1266–1276.
   PubMed Web of Science ®Google Scholar
• Fernandes, J.C., et al., 2013. Linear polyethylenimine produced by partial acid hydrolysis of poly(2-ethyl-2-oxazoline) for DNA and siRNA delivery in vitro. International journal of nanomedicine, 8, 4091–4102.
   PubMed Web of Science ®Google Scholar
• Gaucher, G., et al., 2005. Block copolymer micelles: preparation, characterization and application in drug delivery. Journal of controlled release, 109 (1–3), 169–188.
   PubMed Web of Science ®Google Scholar
• Godbey, W.T., et al., 1999. Improved packing of poly(ethylenimine)/DNA complexes increases transfection efficiency. Gene therapy, 6 (8), 1380–1388.
   PubMed Web of Science ®Google Scholar
• Gou, M., et al., 2011. Curcumin-loaded biodegradable polymeric micelles for colon cancer therapy in vitro and in vivo. Nanoscale, 3 (4), 1558–1567.
   PubMed Web of Science ®Google Scholar
• Gulyuz, S., et al., 2018. In-vitro cytotoxic activities of poly (2-ethyl-2-oxazoline)-based amphiphilic block copolymers prepared by CuAAC click chemistry. Express polymer letters, 12 (2), 146–158.
   Web of Science ®Google Scholar
• Hamaguchi, T., et al., 2005. NK105, a paclitaxel-incorporating micellar nanoparticle formulation, can extend in vivo antitumour activity and reduce the neurotoxicity of paclitaxel. British journal of cancer, 92 (7), 1240–1246.
   PubMed Web of Science ®Google Scholar
• Han, M., et al., 2012. Overcoming drug resistance of MCF-7/ADR cells by altering intracellular distribution of doxorubicin via MVP knockdown with a novel siRNA polyamidoamine-hyaluronic acid complex. Journal of controlled release : official journal of the controlled release society, 163 (2), 136–144.
   PubMed Web of Science ®Google Scholar
• Hoogenboom, R., 2009. Poly(2-oxazoline)s: a polymer class with numerous potential applications. Angewandte chemie (international ed. in English), 48 (43), 7978–7994.
   PubMed Web of Science ®Google Scholar
• Hsiue, G.-H., et al., 2006. Environmental-sensitive micelles based on poly(2-ethyl-2-oxazoline)-b-poly(L-lactide) diblock copolymer for application in drug delivery. International journal of pharmaceutics, 317 (1), 69–75.
   PubMed Web of Science ®Google Scholar
• Hu, F.-Q., et al., 2009. Synthesis and antitumor activity of doxorubicin conjugated stearic acid-g-chitosan oligosaccharide polymeric micelles. Biomaterials, 30 (36), 6955–6963.
   PubMed Web of Science ®Google Scholar
• Hu, Y., et al., 2015. Thermo-responsive drug release from self-assembled micelles of brush-like PLA/PEG analogues block copolymers. International journal of pharmaceutics, 491 (1–2), 152–161.
   PubMed Web of Science ®Google Scholar
• Ishida, O., et al., 1999. Size-dependent extravasation and interstitial localization of polyethyleneglycol liposomes in solid tumor-bearing mice. International journal of pharmaceutics, 190 (1), 49–56.
   PubMed Web of Science ®Google Scholar
• Ishida, T., and Kiwada, H., 2008. Accelerated blood clearance (ABC) phenomenon upon repeated injection of PEGylated liposomes. International journal of pharmaceutics, 354 (1–2), 56–62.
   PubMed Web of Science ®Google Scholar
• Kara, A., et al., 2018. Development of novel self-assembled polymeric micelles from partially hydrolysed poly(2-ethyl-2-oxazoline)-co-PEI-b-PCL block copolymer as non-viral vectors for plasmid DNA in vitro transfection. Artificial cells, nanomedicine, and biotechnology, 46 (Sup3), S264–S273.
   PubMed Web of Science ®Google Scholar
• Kataoka, K., Harada, A., and Nagasaki, Y., 2012. Block copolymer micelles for drug delivery: design, characterization and biological significance. Advanced drug delivery reviews, 64, 37–48.
   Web of Science ®Google Scholar
• Kataoka, K., et al., 2000. Doxorubicin-loaded poly (ethylene glycol)–poly (β-benzyl-l-aspartate) copolymer micelles: their pharmaceutical characteristics and biological significance. Journal of controlled release, 64 (1–3), 143–153.
   PubMed Web of Science ®Google Scholar
• Kawano, K., et al., 2006. Enhanced antitumor effect of camptothecin loaded in long-circulating polymeric micelles. Journal of controlled release, 112 (3), 329–332.
   PubMed Web of Science ®Google Scholar
• Kim, C., et al., 2000. Phase‐transition characteristics of amphiphilic poly (2‐ethyl‐2‐oxazoline)/poly (ε‐caprolactone) block copolymers in aqueous solutions. Journal of polymer science part B: polymer physics, 38 (18), 2400–2408.
   Web of Science ®Google Scholar
• Kim, D., et al., 2009a. In vivo evaluation of doxorubicin-loaded polymeric micelles targeting folate receptors and early endosomal pH in drug-resistant ovarian cancer. Molecular pharmaceutics, 6 (5), 1353–1362.
   PubMed Web of Science ®Google Scholar
• Kim, J.O., Kabanov, A.V., and Bronich, T.K., 2009b. Polymer micelles with cross-linked polyanion core for delivery of a cationic drug doxorubicin. Journal of controlled release, 138 (3), 197–204.
   PubMed Web of Science ®Google Scholar
• Klemm, A.R., Young, D., and Lloyd, J.B., 1998. Effects of polyethyleneimine on endocytosis and lysosome stability. Biochemical pharmacology, 56 (1), 41–46.
   PubMed Web of Science ®Google Scholar
• Knop, K., et al., 2010. Poly(ethylene glycol) in drug delivery: pros and cons as well as potential alternatives. Angewandte chemie (international ed. in English), 49 (36), 6288–6308.
   PubMed Web of Science ®Google Scholar
• Koide, H., et al., 2012. Size-dependent induction of accelerated blood clearance phenomenon by repeated injections of polymeric micelles. International journal of pharmaceutics, 432 (1–2), 75–79.
   PubMed Web of Science ®Google Scholar
• Kwon, G., et al., 1997. Block copolymer micelles for drug delivery: loading and release of doxorubicin. Journal of controlled release, 48 (2–3), 195–201.
   Web of Science ®Google Scholar
• Kwon, G.S. and Kataoka, K., 1995. Block copolymer micelles as long-circulating drug vehicles. Advanced drug delivery reviews, 16 (2–3), 295–309.
   Web of Science ®Google Scholar
• Lee, A.V., Oesterreich, S., and Davidson, N.E., 2015. MCF-7 cells—changing the course of breast cancer research and care for 45 years. Journal of the national cancer institute, 107 (7), djv073.
   PubMedGoogle Scholar
• Lee, E.S., Na, K., and Bae, Y.H., 2005. Doxorubicin loaded pH-sensitive polymeric micelles for reversal of resistant MCF-7 tumor. Journal of controlled release, 103 (2), 405–418.
   PubMed Web of Science ®Google Scholar
• Lee, R.-S. and Huang, Y.-T., 2010. Tuning the hydrophilic–hydrophobic balance of block-graft copolymers by click strategy: synthesis and characterization of amphiphilic PCL-b-(PαN3CL-g-PBA) copolymers. Polymer journal, 42 (4), 304–312.
   Web of Science ®Google Scholar
• Lee, S.C., et al., 1999. Synthesis and micellar characterization of amphiphilic diblock copolymers based on poly (2-ethyl-2-oxazoline) and aliphatic polyesters. Macromolecules, 32 (6), 1847–1852.
   Web of Science ®Google Scholar
• Lee, S.C., et al., 2003. Polymeric micelles of poly(2-ethyl-2-oxazoline)-block-poly(ε-caprolactone) copolymer as a carrier for paclitaxel. Journal of controlled release, 89 (3), 437–446.
   PubMed Web of Science ®Google Scholar
• Li, J., et al., 2012. Redox-sensitive micelles self-assembled from amphiphilic hyaluronic acid-deoxycholic acid conjugates for targeted intracellular delivery of paclitaxel. Biomaterials, 33 (7), 2310–2320.
   PubMed Web of Science ®Google Scholar
• Maeda, H., et al., 2000. Tumor vascular permeability and the EPR effect in macromolecular therapeutics: a review. Journal of controlled release, 65 (1–2), 271–284.
   PubMed Web of Science ®Google Scholar
• Markovsky, E., et al., 2012. Administration, distribution, metabolism and elimination of polymer therapeutics. Journal of controlled release, 161 (2), 446–460.
   PubMed Web of Science ®Google Scholar
• Matsumura, Y. and Maeda, H., 1986. A new concept for macromolecular therapeutics in cancer chemotherapy: mechanism of tumoritropic accumulation of proteins and the antitumor agent smancs. Cancer research, 46 (12 Pt 1), 6387–6392.
   PubMed Web of Science ®Google Scholar
• Moghimi, S.M., et al., 1993. An investigation of the filtration capacity and the fate of large filtered sterically-stabilized microspheres in rat spleen. Biochimica et biophysica acta (bba) – general subjects, 1157 (2), 233–240.
   PubMed Web of Science ®Google Scholar
• Mondal, D., Griffith, M., and Venkatraman, S.S., 2016. Polycaprolactone-based biomaterials for tissue engineering and drug delivery: current scenario and challenges. International journal of polymeric materials and polymeric biomaterials, 65 (5), 255–265.
   Web of Science ®Google Scholar
• Nah, J.-W., Jeong, Y.-I., and Cho, C.-S., 2000. Polymeric micelle formation of multiblock copolymer composed of poly(γ-benzyl L-glutamate) and poly(ethylene oxide). Bulletin of the Korean chemical society, 21 (4), 383–388.
   Web of Science ®Google Scholar
• Nakanishi, T., et al., 2001. Development of the polymer micelle carrier system for doxorubicin. Journal of controlled release, 74 (1–3), 295–302.
   PubMed Web of Science ®Google Scholar
• Ng, K.E., et al., 2016. pH-responsive triblock copolymeric micelles decorated with a cell-penetrating peptide provide efficient doxorubicin delivery. Nanoscale research letters, 11 (1), 539.
   PubMed Web of Science ®Google Scholar
• Nishiyama, N. and Kataoka, K., 2006. Current state, achievements, and future prospects of polymeric micelles as nanocarriers for drug and gene delivery. Pharmacology & therapeutics, 112 (3), 630–648.
   PubMed Web of Science ®Google Scholar
• Nishiyama, N., et al., 2003. Novel cisplatin-incorporated polymeric micelles can eradicate solid tumors in mice. Cancer research, 63 (24), 8977–8983.
   PubMed Web of Science ®Google Scholar
• Owen, S.C., Chan, D.P.Y., and Shoichet, M.S., 2012. Polymeric micelle stability. Nano today, 7 (1), 53–65.
   Web of Science ®Google Scholar
• Patil, R.R., Guhagarkar, S.A., and Devarajan, P.V., 2008. Engineered nanocarriers of doxorubicin: a current update. Critical reviews in therapeutic drug carrier systems, 25 (1), 1–61.
   PubMed Web of Science ®Google Scholar
• Peer, D., et al., 2007. Nanocarriers as an emerging platform for cancer therapy. Nature nanotechnology, 2 (12), 751–760.
   PubMed Web of Science ®Google Scholar
• Ponta, A. and Bae, Y., 2010. PEG-poly (amino acid) block copolymer micelles for tunable drug release. Pharmaceutical research, 27 (11), 2330–2342.
   PubMed Web of Science ®Google Scholar
• Qiu, L.Y., et al., 2013. Folate-modified poly(2-ethyl-2-oxazoline) as hydrophilic corona in polymeric micelles for enhanced intracellular doxorubicin delivery. International journal of pharmaceutics, 456 (2), 315–324.
   PubMed Web of Science ®Google Scholar
• Rösler, A., Vandermeulen, G.W.M., and Klok, H.-A., 2012. Advanced drug delivery devices via self-assembly of amphiphilic block copolymers. Advanced drug delivery reviews, 64, 270–279.
   Web of Science ®Google Scholar
• Sahay, G., Batrakova, E.V., and Kabanov, A.V., 2008. Different internalization pathways of polymeric micelles and unimers and their effects on vesicular transport. Bioconjugate chemistry, 19 (10), 2023–2029.
   PubMed Web of Science ®Google Scholar
• Sedlacek, O., et al., 2017. Poly(2-ethyl-2-oxazoline) conjugates with doxorubicin for cancer therapy: in vitro and in vivo evaluation and direct comparison to poly[N-(2-hydroxypropyl)methacrylamide] analogues. Biomaterials, 146, 1–12.
   PubMed Web of Science ®Google Scholar
• Seymour, L.W., et al., 1987. Effect of molecular weight (Mw) of N-(2-hydroxypropyl)methacrylamide copolymers on body distribution and rate of excretion after subcutaneous, intraperitoneal, and intravenous administration to rats. Journal of biomedical materials research, 21 (11), 1341–1358.
   PubMed Web of Science ®Google Scholar
• Stolnik, S., Illum, L., and Davis, S.S., 2012. Long circulating microparticulate drug carriers. Advanced drug delivery reviews, 64, 290–301.
   Web of Science ®Google Scholar
• Torchilin, V., 2011. Tumor delivery of macromolecular drugs based on the EPR effect. Advanced drug delivery reviews, 63 (3), 131–135.
   PubMed Web of Science ®Google Scholar
• Torchilin, V.P., 2014. Multifunctional, stimuli-sensitive nanoparticulate systems for drug delivery. Nature reviews. Drug discovery, 13 (11), 813–827.
   PubMed Web of Science ®Google Scholar
• Ulery, B.D., Nair, L.S., and Laurencin, C.T., 2011. Biomedical applications of biodegradable polymers. Journal of polymer science. Part B, polymer physics, 49 (12), 832–864.
   PubMed Web of Science ®Google Scholar
• Van Domeselaar, G.H., et al., 2003. Application of solid phase peptide synthesis to engineering PEO–peptide block copolymers for drug delivery. Colloids and surfaces B: biointerfaces, 30 (4), 323–334.
   Web of Science ®Google Scholar
• Wang, J., et al., 2013a. Cationic amphiphilic drugs self-assemble to the core-shell interface of PEGylated phospholipid micelles and stabilize micellar structure. Philosophical transactions. Series A, mathematical, physical, and engineering sciences, 371 (2000), 20120309.
   PubMed Web of Science ®Google Scholar
• Wang, Y., et al., 2013b. Glycopolymer micelles with reducible ionic cores for hepatocytes-targeting delivery of DOX. International journal of pharmaceutics, 441 (1–2), 170–180.
   PubMed Web of Science ®Google Scholar
• Wu, P., et al., 2017. Ultrasound-responsive polymeric micelles for sonoporation-assisted site-specific therapeutic action. ACS applied materials & interfaces, 9 (31), 25706–25716.
   PubMed Web of Science ®Google Scholar
• Yamamoto, Y., et al., 2001. Long-circulating poly (ethylene glycol)–poly (d, l-lactide) block copolymer micelles with modulated surface charge. Journal of controlled release, 77 (1–2), 27–38.
   PubMed Web of Science ®Google Scholar
• Yamaoka, T., Tabata, Y., and Ikada, Y., 1995. Fate of water-soluble polymers administered via different routes. Journal of pharmaceutical sciences, 84 (3), 349–354.
   PubMed Web of Science ®Google Scholar
• Yokoyama, M., 2014. Polymeric micelles as drug carriers: their lights and shadows. Journal of drug targeting, 22 (7), 576–583.
   PubMed Web of Science ®Google Scholar
• Yokoyama, M., et al., 1987. Preparation of adriamycin‐conjugated poly (ethylene glycol)‐poly (aspartic acid) block copolymer. A new type of polymeric anticancer agent. Die makromolekulare chemie, rapid communications, 8 (9), 431–435.
   Google Scholar
• Yokoyama, M., et al., 1999. Selective delivery of adriamycin to a solid tumor using a polymeric micelle carrier system. Journal of drug targeting, 7 (3), 171–186.
   PubMed Web of Science ®Google Scholar
• Yoo, H.S. and Park, T.G., 2001. Biodegradable polymeric micelles composed of doxorubicin conjugated PLGA–PEG block copolymer. Journal of controlled release, 70 (1–2), 63–70.
   PubMed Web of Science ®Google Scholar
• Zhang, L., et al., 2012a. Paclitaxel-loaded polymeric micelles based on poly(ɛ-caprolactone)-poly(ethylene glycol)-poly(ɛ-caprolactone) triblock copolymers: in vitro and in vivo evaluation. Nanomedicine : nanotechnology, biology, and medicine, 8 (6), 925–934.
   PubMed Web of Science ®Google Scholar
• Zhang, Z., et al., 2012b. Cellular uptake and intracellular trafficking of PEG-b-PLA polymeric micelles. Biomaterials, 33 (29), 7233–7240.
   PubMed Web of Science ®Google Scholar
• Zhao, Y., et al., 2015. pH-responsive polymeric micelles based on poly(2-ethyl-2-oxazoline)-poly(D,L-lactide) for tumor-targeting and controlled delivery of doxorubicin and P-glycoprotein inhibitor. Acta biomaterialia, 17, 182–192.
   PubMed Web of Science ®Google Scholar
• Zhou, Q., et al., 2018. Stimuli-responsive polymeric micelles for drug delivery and cancer therapy. International journal of nanomedicine, 13, 2921–2942.
   PubMed Web of Science ®Google Scholar