Well-Defined Polymer–Paclitaxel Prodrugs by a Grafting-from-Drug Approach

Angewandte Chemie - International Edition

Volumn 55, Issue 39, 2016, Pages 11791-11796

  Louage, Benoit ^a   Nuhn, Lutz ^a   Risseeuw, Martijn D P ^a   Vanparijs, Nane ^a   De Coen, Ruben ^a   Karalic, Izet ^a   Van Calenbergh, Serge ^a   De Geest, Bruno G ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

cancer; nanotechnology; paclitaxel; prodrugs; RAFT polymerization

Indexed keywords

HYDROPHILICITY; LIVING POLYMERIZATION; NANOTECHNOLOGY; TRACERS;

CANCER; CHAIN TRANSFER AGENTS; HYDROPHILIC MONOMERS; PACLITAXEL; POST-FUNCTIONALIZATION; PRODRUGS; RAFT POLYMERIZATION; REVERSIBLE ADDITION-FRAGMENTATION CHAIN TRANSFER POLYMERIZATION;

GRAFTING (CHEMICAL);

PACLITAXEL; POLYMER; PRODRUG;

ANALOGS AND DERIVATIVES; CELL SURVIVAL; CHEMICAL PHENOMENA; CHEMISTRY; DRUG EFFECT; HUMAN; NEOPLASM; POLYMERIZATION; SOLUBILITY; SYNTHESIS; TUMOR CELL LINE;

CELL LINE, TUMOR; CELL SURVIVAL; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; NEOPLASMS; PACLITAXEL; POLYMERIZATION; POLYMERS; PRODRUGS; SOLUBILITY;

EID: 84983466627     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201605892     Document Type: Article

References (33)

1. A. F. Wahl, K. L. Donaldson, C. Fairchild, F. Y. F. Lee, S. A. Foster, G. W. Demers, D. A. Galloway, Nat. Med. 1996, 2, 72–79.
2. A. Z. Wang, R. Langer, O. C. Farokhzad in Annu. Rev. Med., Vol. 63 (Eds.: C. T. Caskey, C. P. Austin, J. A. Hoxie), 2012, pp. 185–198.
3. M. Elsabahy, K. L. Wooley, Chem. Soc. Rev. 2012, 41, 2545–2561.
4. S. Kasmi, B. Louage, L. Nuhn, A. Van Driessche, J. Van Deun, I. Karalic, M. D. P. Risseeuw, S. Van Calenbergh, R. Hoogenboom, R. De Rycke et al., Biomacromolecules 2016, 17, 119–127.
5. B. Louage, Q. Zhang, N. Vanparijs, L. Voorhaar, S. Vande Casteele, Y. Shi, W. E. Hennink, J. Van Bocxlaer, R. Hoogenboom, B. G. De Geest, Biomacromolecules 2015, 16, 336–350.
6. N. Desai, Clin. Cancer Res. 2006, 12, 1317–1324.
7. T.-Y. Kim, Clin. Cancer Res. 2004, 10, 3708–3716.
8. Y. Shi, R. van der Meel, B. Theek, E. O. Blenke, E. H. E. Pieters, M. H. A. M. Fens, J. Ehling, R. M. Schiffelers, G. Storm, C. F. van Nostrum et al., ACS Nano 2015, 9, 3740–3752.
9. H. Chen, S. Kim, L. Li, S. Wang, K. Park, J.-X. Cheng, Proc. Natl. Acad. Sci. USA 2008, 105, 6596–6601.
10. N. Larson, H. Ghandehari, Chem. Mater. 2012, 24, 840–853.
11. F. Greco, M. J. Vicent, Adv. Drug Delivery Rev. 2009, 61, 1203–1213.
12. E. M. Pelegri-O'Day, E.-W. Lin, H. D. Maynard, J. Am. Chem. Soc. 2014, 136, 14323–14332.
13. N. Vanparijs, S. Maji, B. Louage, L. Voorhaar, D. Laplace, Q. Zhang, Y. Shi, W. E. Hennink, R. Hoogenboom, B. G. De Geest, Polym. Chem. 2015, 6, 5602–5614.
14. K. L. Heredia, D. Bontempo, T. Ly, J. T. Byers, S. Halstenberg, H. D. Maynard, J. Am. Chem. Soc. 2005, 127, 16955–16960.
15. B. S. Sumerlin, ACS Macro Lett. 2012, 1, 141–145.
16. P. De, M. Li, S. R. Gondi, B. S. Sumerlin, J. Am. Chem. Soc. 2008, 130, 11288–11289.
17. J. Xu, K. Jung, N. A. Corrigan, C. Boyer, Chem. Sci. 2014, 5, 3568.
18. Q. Zhang, M. Li, C. Zhu, G. Nurumbetov, Z. Li, P. Wilson, K. Kempe, D. M. Haddleton, J. Am. Chem. Soc. 2015, 137, 9344–9353.
19. N. Vanparijs, R. De Coen, D. Laplace, B. Louage, S. Maji, L. Lybaert, R. Hoogenboom, B. G. De Geest, Chem. Commun. 2015, 51, 13972–13975.
20. R. Tong, J. Cheng, Angew. Chem. Int. Ed. 2008, 47, 4830–4834;
21. Angew. Chem. 2008, 120, 4908–4912.
22. D. T. Bui, A. Maksimenko, D. Desmaële, S. Harrisson, C. Vauthier, P. Couvreur, J. Nicolas, Biomacromolecules 2013, 14, 2837–2847.
23. H. M. Deutsch, J. A. Glinski, M. Hernandez, R. D. Haugwitz, V. L. Narayanan, M. Suffness, L. H. Zalkow, J. Med. Chem. 1989, 32, 788–792.
24. D. G. I. Kingston, Chem. Commun. 2001, 867–880.
25. P. H. Kierstead, H. Okochi, V. J. Venditto, T. C. Chuong, S. Kivimae, J. M. J. Fréchet, F. C. Szoka, J. Controlled Release 2015, 213, 1–9.
26. Y. Shi, M. J. van Steenbergen, E. A. Teunissen, L. Novo, S. Gradmann, M. Baldus, C. F. van Nostrum, W. E. Hennink, Biomacromolecules 2013, 14, 1826–1837.
27. C. Boyer, V. Bulmus, T. P. Davis, V. Ladmiral, J. Q. Liu, S. Perrier, Chem. Rev. 2009, 109, 5402–5436.
28. H. Willcock, R. K. O'Reilly, Polym. Chem. 2010, 1, 149–157.
29. E. L. Racoosin, J. Cell Biol. 1993, 121, 1011–1020.
30. C. Ryppa, H. Mann-Steinberg, M. L. Biniossek, R. Satchi-Fainaro, F. Kratz, Int. J. Pharm. 2009, 368, 89–97.
31. M. M. Gottesman, T. Fojo, S. E. Bates, Nat. Rev. Cancer 2002, 2, 48–58.
32. A. Eldar-Boock, K. Miller, J. Sanchis, R. Lupu, M. J. Vicent, R. Satchi-Fainaro, Biomaterials 2011, 32, 3862–3874.
33. C. J. Ferguson, R. J. Hughes, D. Nguyen, B. T. T. Pham, R. G. Gilbert, A. K. Serelis, C. H. Such, B. S. Hawkett, Macromolecules 2005, 38, 2191–2204.