Cyclodextrin-based polyrotaxanes

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 76, Issue 3-4, 2013, Pages 237-252

  Girek, Tomasz ^a  

^a JAN DLUGOSZ UNIVERSITY   (Poland)

Author keywords

Cyclodextrin; Polymer; Polyrotaxane; Ring; Thread

Indexed keywords

EID: 84880133633     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-012-0253-2     Document Type: Review

References (50)

1. Harada, A., Takashima, Y., Yamaguchi, H.: Cyclodextrin-based supramolecular polymers. Chem. Soc. Rev. 38(4), 875-882 (2009)
2. Frampton, M.J., Anderson, H.L.: Insulated molecular wires. Angew. Chem. Int. Ed. 46(7), 1028-1064 (2007)
3. Wenz, G., Han, B.-H., Mueller, A.: Cyclodextrin rotaxanes and polyrotaxanes. Chem. Rev. 106(3), 782-817 (2006)
4. Inoue, Y., Ye, L., Ishihara, K., Yui, N.: Preparation and surface properties of polyrotaxane-containing tri-block copolymers as a design for dynamic biomaterials. Colloids Surf. B 89, 223-227 (2012)
5. Brovelli, S., Cacialli, F.: Optical and electroluminescent properties of conjugated polyrotaxanes. Funct. Supramol. Archit. 2, 919-960 (2011)
6. Hyun, H., Yui, N.: Ligand accessibility to receptor binding sites enhanced by movable polyrotaxanes. Macromol. Biosci. 11(6), 765-771 (2011)
7. Oddy, F.E., Brovelli, S., Stone, M., Klotz, E.J.F., Cacialli, F., Anderson, H.L.: Influence of cyclodextrin size on fluorescence quenching in conjugated polyrotaxanes by methyl viologen in aqueous solution. J. Mater. Chem. 19(18), 2846-2852 (2009)
8. Wang, J., Wang, P.-J., Ye, L., Zhang, A.-Y., Feng, Z.-G.: Residing states of β-cyclodextrins in solid-state polyrotaxanes comprising pluronic F127 and PNIPAAm. Polymer 52(23), 5362-5368 (2011)
9. Hatakeyama, H., Akita, H., Harashima, H.: A multifunctional envelope type nano device (MEND) for gene delivery to tumours based on the EPR effect: a strategy for overcoming the PEG dilemma. Adv. Drug Deliv. 63(3), 152-160 (2011)
10. Zhu, L., Lu, M., Zhang, Q., Qu, D., Tian, H.: Construction of polypseudorotaxane from low-molecular weight monomers via dual noncovalent interactions. Macromolecules 44(11), 4092-4097 (2011)
11. Shi, J., Chen, Y., Wang, Q., Liu, Y.: Construction and efficient radical cation stabilization of cyclodextrin/aniline polypseudorotaxane and its conjugate with carbon nanotubes. Adv. Mater. 22(23), 2575-2578 (2010)
12. Noguerias-Nieto, L., Sobarzo-Sánchez, E., Gómez-Amoza, J.L., Otero-Espinar, J.: Competitive displacement of drugs from cyclodextrin inclusion complex by polypseudorotaxane formation with poloxamer: implications in drug solubilization and delivery. Eur. J. Pharm. Biopharm. 80, 585-595 (2012)
13. Otero-Espinar, F.J., Torres-Labandeira, J.J., Alvarez-Lorenzo, C., Blanco-Mendez, J.: Cyclodextrin in drug delivery systems. J. Drug Deliv. Sci. Technol. 20(4), 289-301 (2010)
14. Motoyama, K., Hayashida, K., Higashi, T., Arima, H.: Polypseudorotaxanes of pegylated α-cyclodextrin/polyamidoamine dendrimer conjugate with cyclodextrins as a sustained release system for DNA. Bioorg. Med. Chem. 20(4), 1425-1433 (2012)
15. Motoyama, K., Hayashida, K., Arima, H.: Potential use of polypseudorotaxanes of pegylated polyamidoamine dendrimer with cyclodextrins as novel sustained release systems for DNA. Chem. Pharm. Bull. 59(4), 476-479 (2011)
16. Girek, T., Goszczyński, T., Girek, B., Ciesielski, W., Boratyński, J., Rychter, P.: β-Cyclodextrin/protein conjugates as a innovative drug systems: synthesis and MS investigation. J. Incl. Phenom. Macrocycl. Chem. doi: 10.1007/s10847-012-0132-x
17. Girek, T.: Cyclodextrin-based rotaxanes. J. Incl. Phenom. Macrocycl. Chem. 74(1-4), 1-21 (2012)
18. Girek, T., Ciesielski, W.: Polymerization of β-cyclodextrin with maleic anhydride along with thermogravimetric study of polymers. J. Incl. Phenom. Macrocycl. Chem. 69(3-4), 445-451 (2011)
19. Ciesielski, W., Girek, T.: Study of thermal stability of β-cyclodextrin/metal complexes in the aspect of their future applications. J. Incl. Phenom. Macrocycl. Chem. 69(3-4), 461-467 (2011)
20. Kozlowski, C.A., Walkowiak, W., Girek, T.: Modified cyclodextrin polymers as selective ion carriers for Pb(II) separation across plasticized membranes. J. Membr. Sci. 310(1-2), 312-320 (2008)
21. Musiol, R., Girek, T.: Inclusion-dependent mechanism of modification of cyclodextrins with heterocycles. Cent. Eur. J. Chem. 3(4), 742-746 (2005)
22. Yang, Ch., Li, J.: Thermorespnsive behavior of cationic polyrotaxane composed of multiple pentaethylenehexamine-grafted α-cyclodextrin threated on poly(propylene oxide)-poly(ethylene oxide)-poly(propylene oxide) triblock copolymer. J. Phys. Chem. B. 113(3), 682-690 (2009)
23. Przybylski, C., Jarroux, N.: Analysis of a polydisperse polyrotaxane based on poly(ethylene oxide) and α-cyclodextrins using nanoelectrospray and LTQ-orbitrap. Anal. Chem. 83(22), 8460-8467 (2011)
24. Imran, A.-B., Seki, T., Kataoka, T., Kidowaki, M., Ito, K., Takeoka, Y.: Fabrication of mechanically improved hydrogels using a movable cross-linker based on vinyl modified polyrotaxane. Chem. Commun. 41, 5227-5229 (2008)
25. Sun, H., Han, J., Gao, C.: High yield production of high molecular weight poly(ethylene glycol)/α-cyclodextrin polyrotaxanes by aqueous one-pot approach. Polymer 53(14), 2884-2889 (2012)
26. Wu, J.Y., He, H.K., Gao, C.: β-Cyclodextrin-capped polyrotaxanes: one-pot facile synthesis via click chemistry and use as templates for platinum nanowires. Macromolecules 43(5), 2252-2260 (2010)
27. Nakazano, K., Takashima, T., Arai, T., Koyama, Y., Takata, T.: High-yield one-pot synthesis of permethylated α-cyclodextrin-based polyrotaxane in hydrocarbon solvent through an efficient heterogeneous reaction. Macromolecules 43(2), 691-696 (2010)
28. Arai, T., Hayashi, M., Takagi, N., Takata, T.: One-pot synthesis of native and permethylated α-cyclodextrin-containing polyrotaxanes in water. Macromolecules 42(6), 1881-1887 (2009)
29. Soliman, M., Allen, S., Davies, M.C., Alexander, C.: Responsive polyelectrolyte complexes for triggered release of nucleic acid therapeutics. Chem. Commun. 46, 5421-5433 (2010)
30. Davis, M.E., Zuckerman, J.E., Choi, C.H.J., Seligson, D., Tolcher, A., Alabi, C.A., Yen, Y., Heidel, J.D., Ribas, A.: Evidence of RNAi in humans from systemically administered siRNA via targeted nanoparticles. Nature 464(7291), 1067-1070 (2010)
31. Thiele, C., Auerbach, D., Jung, G., Wenz, G.: Inclusion of chemotherapeutic agents in substituted β-cyclodextrin derivatives. J. Incl. Phenom. Macrocycl. Chem. 69(3-4), 303-307 (2011)
32. Thiele, C., Auerbach, D., Jung, G., Qiong, L., Schneider, M., Wenz, G.: Nanoparticles of anionic starch and cationic cyclodextrin derivatives for the targeted delivery of drugs. Polym. Chem. 2(1), 209-215 (2010)
33. Wenz, G.: Cyclodextrin polyrotaxanes assembled from a molecular construction kit in aqueous solution. J. Polym. Sci. Part A Polym. Chem. 47(23), 6333-6341 (2009)
34. Alzabut, T., Keil, M., Ellis, J., Alexander, C., Wenz, G.: Transfection of luciferase DNA into various cells by cationic cyclodextrin polyrotaxanes derived from ionene-11. J. Mater. Chem. 22(17), 8558-8565 (2012)
35. Ooya, T., Choi, H.S., Yamashita, A., Yui, N., Sugaya, Y., Kano, A., Maruyama, A., Akita, H., Ito, R., Kogure, K., Harashima, J.: Biocleavable polyrotaxane-plasmid DNA polyplex for enhanced gene delivery. J. Am. Chem. Soc. 128(12), 3852-3853 (2006)
36. Latini, G., Parrot, L.-J., Brovelli, S., Frampton, M.J., Anderson, H.L., Cacialli, F.: Cyclodextrin-threaded conjugated polyrotaxanes for organic electronics: the influence of the counter cations. Adv. Funct. Mater. 18(16), 2419-2427 (2008)
37. Taniguchi, M., Nojima, Y., Yokota, K., Terao, J., Sato, K., Kambe, N., Kawai, T.: J. Am. Chem. Soc. 128(47), 15062-15063 (2006)
38. Brovelli, S., Guan, H., Winroth, G., Fenwick, O., Di Stasio, F., Daik, R., Feast, W.J., Meinardi, F., Cacialli, F.: White luminescence from single-layer devices of nonresonant polymer blends. Appl. Phys. Lett. 96(21), 213301 (2010)
39. Brovelli, S., Meinardi, F., Winroth, G., Fenwick, O., Sforazzini, G., Frampton, M.J., Zalewski, L., Levitt, J.A., Marinello, F., Schiavuta, P., Suhling, K., Anderson, H.L., Cacialli, F.: White electroluminescence by supramolecular control of energy transfer in blends of organic-soluble encapsulated polyfluorenes. Adv. Mater. 20(2), 272-280 (2010)
40. Sugiyasu, K., Honsho, Y., Harrison, R.M., Sato, A., Yasuda, T., Seki, S., Takeuchi, M.: A self-threading polythiophene: defect-free insulated molecular wires endowed with long effective conjugation length. J. Am. Chem. Soc. 132(42), 14754-14756 (2010)
41. Chen, Y.J., Wu, W., Pu, W.G., He, S.X.: Preparation and characterization of conjugated polypseudorotaxane poly(pyrrole/α-cyclodextrin). Int. J. Polym. Anal. Charact. 15(1), 43-53 (2010)
42. Grigiras, M., Stafie, L.: Electrically insulated molecular wires. Supramol. Chem. 22(4), 237-248 (2010)
43. Zalewski, L., Wykes, M., Brovelli, S., Bonini, M., Breiner, T., Kastler, M., Dotz, F., Beljonne, D., Anderson, H.L., Cacialli, F., Samori, P.: A conjugated thiophene-based rotaxane: synthesis, spectroscopy, and modeling. Chem. Eur. J. 16(13), 3933-3941 (2010)
44. Farcas, A., Ghosh, I., Grigoras, V.C., Stoica, I., Peptu, C., Nau, W.M.: Effect of rotaxane formation on the photophysical, morphological, and adhesion properties of poly[2,7-(9,9-dioctylfluorene)-alt-(5,5′-bithiophene)] main-chain polyrotaxanes. Macromol. Chem. Phys. 212(10), 1022-1031 (2011)
45. Farcas, A., Stoica, I., Stefanache, A., Peptu, C., Farcas, F., Marangoci, N., Sacarescu, L., Harabagiu, V., Guégan, P.: Surface properties of conjugates main-chain polyrotaxanes. Chem. Phys. Lett. 508(1-3), 111-116 (2011)
46. Michels, J.J., O'Connell, M.J., Taylor, P.N., Wilson, J.S., Cacialli, F., Anderson, H.L.: Synthesis of conjugated polyrotaxanes. Chem.A Eur. J. 9(24), 6167-6176 (2003)
47. Frampton, M.J., Sforazzini, G., Brovelli, S., Latini, G., Townsend, E., Wiliams, C.C., Charas, A., Zalewski, L., Kaka, N.S., Sirish, M., Parrott, L.J., Wilson, J.S., Cacialli, F., Anderson, H.L.: Synthesis and optoelectronc properties of nonpolar polyrotaxane insulated molecular wires with high solubility in organic solvents. Adv. Funct. Mater. 18(21), 3367-3376 (2008)
48. Miyawaki, A., Miyauchi, M., Takashima, Y., Yamaguchi, H., Harada, A.: Formation of supramolecular isomers; poly[2]rotaxane and supramolecular assembly. Chem. Commun. 4, 456-458 (2008)
49. Farcas, A., Jarroux, N., Ghosh, I., Guégan, P., Nau, W.M., Harabagiu, V.: Polyrotaxanes of pyrene-triazole conjugated azomethine and α-cyclodextrin with high fluorescence properties. Macromol. Chem. Phys. 210(17), 1440-1449 (2009)
50. Terao, J., Tsuda, S., Tanaka, Y., Okoshi, K., Fujihara, T., Tsuji, Y., Kambe, N.: Synthesis of organic-soluble conjugated polyrotaxanes by polymerization of linked rotaxanes. J. Am. Chem. Soc. 131(44), 16004-16005 (2009)