Thermoresponsiveness of copolymers bearing cholic acid pendants induced by complexation with β-cyclodextrin

Langmuir

Volumn 30, Issue 39, 2014, Pages 11770-11775

  Jia, Yong Guang ^a   Zhu, X X ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BETA-CYCLODEXTRIN; CHOLIC ACIDS; THERMO RESPONSIVENESS;

EID: 84907903272     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la5030873     Document Type: Article

References (42)

1. Gil, E. S.; Hudson, S. M. Stimuli-reponsive polymers and their bioconjugates Prog. Polym. Sci. 2004, 29, 1173-1222
2. Aoshima, S.; Kanaoka, S. Synthesis of stimuli-responsive polymers by living polymerization: Poly(N -isopropylacrylamide) and poly(vinyl ether)s Adv. Polym. Sci. 2007, 210, 169-208
3. Ganta, S.; Devalapally, H.; Shahiwala, A.; Amiji, M. A review of stimuli-responsive nanocarriers for drug and gene delivery J. Controlled Release 2008, 126, 187-204
4. Alarcon, C.; de las, H.; Pennadam, S.; Alexander, C. Stimuli responsive polymers for biomedical applications Chem. Soc. Rev. 2005, 34, 276-285
5. Schmaljohann, D. Thermo- and pH-responsive polymers in drug delivery Adv. Drug Delivery Rev. 2006, 58, 1655-1670
6. Weber, C.; Hoogenboom, R.; Schubert, U. S. Temperature responsive bio-compatible polymers based on poly(ethylene oxide) and poly(2-oxazoline)s Prog. Polym. Sci. 2012, 37, 686-714
7. Aluri, S.; Pastuszka, M. K.; Moses, A. S.; MacKay, J. A. Elastin-like peptide amphiphiles form nanofibers with tunable length Biomacromolecules 2012, 13, 2645-2654
8. Schmidt, B. V. K. J.; Hetzer, M.; Ritter, H.; Barner-Kowollik, C. Modulation of the thermoresponsive behavior of poly(N, N -diethylacrylamide) via cyclodextrin host/guest interactions Macromol. Rapid Commun. 2013, 34, 1306-1311
9. Nakai, K.; Tazuma, S.; Nishioka, T.; Chayama, K. B. Inhibition of cholesterol crystallization under bilirubin deconjugation: Partial characterization of mechanisms whereby infected bile accelerates pigment stone formation Biophys. Acta 2003, 1632, 48-54
10. Mukhopadhyay, S.; Maitra, U. Chemistry and biology of bile acids Curr. Sci. 2004, 87, 1666-1684
11. Hofmann, A.; Hagey, L. Bile acids: Chemistry, pathochemistry, biology, pathobiology, and therapeutics Cell. Mol. Life Sci. 2008, 65, 2461-2483
12. Zhang, Y. H.; Zhu, X. X. Polymers made from cholic acid derivatives: Selected properties Macromol. Chem. Phys. 1996, 197, 3473-3482
13. Hao, J.; Li, H.; Zhu, X. X. Synthesis of a comb-shaped cholic acid-containing polymer by atom transfer radical polymerization Biomacromolecules 2006, 7, 995-998
14. Li, C.; Lavigueur, C.; Zhu, X. X. Aggregation and thermoresponsive properties of new star block copolymers with a cholic acid core Langmuir 2011, 27, 11174-11179
15. Liu, H.; Avoce, D.; Song, Z.; Zhu, X. X. N -Isopropylacrylamide copolymers with acrylamide and methacrylamide derivatives of cholic acid: Synthesis and characterization Macromol. Rapid Commun. 2001, 22, 675-680
16. Avoce, D.; Liu, H. Y.; Zhu, X. X. N -Alkylacrylamide copolymers with derivatives of cholic acid: Synthesis and thermosensitivity Polymer 2003, 44, 1081-1087
17. Chen, Y.; Li, F.; Liu, B.-W.; Jiang, B.-P.; Zhang, H.-Y.; Wang, L.-H.; Liu, Y. Solid-state supramolecular substituents toward steroids J. Phys. Chem. B 2010, 114, 16147-16155
18. Cabrer, P. R.; Alvarez-Parrilla, E.; Meijide, F.; Seijas, J. A.; Nunez, E. R.; Tato, J. V. Complexation of sodium cholate and sodium deoxycholate by β-cyclodextrin and derivatives Langmuir 1999, 15, 5489-5495
19. Cabrer, P. R.; Alvarez-Parrilla, E.; Al-Soufi, W.; Meijide, F.; Nunez, E. R.; Tato, J. V. Complexation of bile salts by natural cyclodextrins Supramol. Chem. 2003, 15, 33-43
20. Liu, Y.; Zhao, Y.-L.; Zhang, H.-Y. Recognition-induced supramolecular porous nanosphere formation from cyclodextrin conjugated by cholic acid Langmuir 2006, 22, 3434-3438
21. Tan, Z. J.; Zhu, X. X.; Brown, G. R. Formation of inclusion complexes of cyclodextrins with bile salt anions as determined by NMR titration studies Langmuir 1994, 10, 1034-1039
22. Yim, C. T.; Zhu, X. X.; Brown, G. R. Kinetics of inclusion reactions of β-cyclodextrin with several dihydroxycholate ions studied by NMR spectroscopy J. Phys. Chem. B 1999, 103, 597-602
23. Ritter, H.; Sadowski, O.; Tepper, E. Influence of cyclodextrin molecules on the synthesis and the thermoresponsive solution behavior of N -isopropylacrylamide copolymers with adamantyl groups in the side-chains Angew. Chem.; Int. Ed. 2003, 42, 3171-3173
24. Kretschmann, O.; Choi, S. W.; Miyauchi, M.; Tomatsu, I.; Harada, A.; Ritter, H. Switchable hydrogels obtained by supramolecular cross-linking of adamantyl-containing LCST copolymers with cyclodextrin dimers Angew. Chem.; Int. Ed. 2006, 45, 4361-4365
25. Zuo, F.; Luo, C.; Ding, X.; Zheng, Z.; Cheng, X.; Peng, Y. Redox-responsive inclusion complexation between β-cyclodextrin and ferrocene-functionalized poly(N -isopropylacrylamide) and its effect on the solution properties of this polymer Supramol. Chem. 2008, 20, 559-564
26. Luo, C.; Zuo, F.; Ding, X.; Zheng, Z.; Cheng, X.; Peng, Y. Light-triggered reversible solubility of α-cyclodextrin and azobenzene moiety complexes in PDMAA- co -PAPA via molecular recognition J. Appl. Polym. Sci. 2008, 107, 2118-2125
27. Koopmans, C.; Ritter, H. Color change of N -isopropylacrylamide copolymer bearing reichardts dye as optical sensor for lower critical solution temperature and for host-guest interaction with β-cyclodextrin J. Am. Chem. Soc. 2007, 129, 3502-3503
28. Zhao, Y.; Guo, K.; Wang, C.; Wang, L. Effect of inclusion complexation with cyclodextrin on the cloud point of poly(2-(dimethylamino)ethyl methacrylate) solution Langmuir 2010, 26, 8966-8970
29. Gingter, S.; Bezdushna, E.; Ritter, H. Chiral recognition of poly(N -isopropylacrylamide- co -(d or l)- N -tryptophan-acrylamide) with methylated β-cyclodextrin Macromolecules 2010, 43, 3128-3131
30. Liu, J.; Chen, G.; Guo, M.; Jiang, M. Dual stimuli-responsive supramolecular hydrogel based on hybrid inclusion complex (HIC) Macromolecules 2010, 43, 8086-8093
31. Duan, Q.; Miura, Y.; Narumi, A.; Shen, X.; Sato, S.-I.; Satoh, T.; Kakuchi, T. Synthesis and thermoresponsive property of end-functionalized poly(N -isopropylacrylamide) with pyrenyl group J. Polym. Sci., Polym. Chem. 2006, 44, 1117-1124
32. Schmidt, B.; Rudolph, T.; Hetzer, M.; Ritter, H.; Schacher, F. H.; Barner-Kowollik, C. Supramolecular three-armed star polymers via cyclodextrin host-guest self-assembly Polym. Chem. 2012, 3, 3139-3145
33. Luo, C.; Zuo, F.; Zheng, Z.; Ding, X.; Peng, Y. Temperature/light dual responsive inclusion complexes of α-cyclodextrins and azobenzene containing polymers J. Macromol. Sci. A 2008, 45, 364-371
34. Liu, H. Y.; Zhu, X. X. Lower critical solution temperatures of N -substituted acrylamide copolymers in aqueous solutions Polymer 1999, 40, 6985-6990
35. Cao, Y.; Zhu, X. X.; Luo, J.; Liu, H. Effects of substitution groups on the RAFT polymerization of N -alkylacrylamides in the preparation of thermosensitive block copolymers Macromolecules 2007, 40, 6481-6488
36. Cheng, H.; Shen, L.; Wu, C. LLS and FTIR studies on the hysteresis in association and dissociation of poly(N- isopropylacrylamide) chains in water Macromolecules 2006, 39, 2325-2329
37. Wintgens, V.; Charles, M.; Allouache, F.; Amiel, C. Triggering the thermosensitive properties of hydrophobically modified poly(N -isopropylacrylamide) by complexation with cyclodextrin polymers Macromol. Chem. Phys. 2005, 206, 1853-1861
38. Amiel, C.; Sebille, B. Association between amphiphilic poly(ethylene oxide) and cyclodextrin polymers: Aggregation and phase separation Adv. Colloid Interface Sci. 1999, 79, 105-122
39. Casas-Solvas, J. M.; Quesada-Soriano, I.; Carreno-Gazquez, D.; Gimenez-Martinez, J. J.; Garcia-Fuentes, L.; Vargas-Berenguel, A. β-Cyclodextrin dimers linked through their secondary faces with rigid spacer arms as hosts for bile salts Langmuir 2011, 27, 9729-9737
40. Han, S. J.; Yoo, M. K.; Sung, Y. K.; Lee, Y. M.; Cho, C. S. Cloud point of poly(N -isopropylacrylamide) synthesized in the presence of cyclodextrin Macromol. Rapid Commun. 1998, 19, 403-407
41. Zhang, B.; Breslow, R. Enthalpic domination of the chelate effect in cyclodextrin dimers J. Am. Chem. Soc. 1993, 115, 9353-9354
42. Hao, J.-Q.; Li, H.; Woo, H.-G. Synthesis and characterization of cholic acid-containing biodegradable hydrogels by photoinduced copolymerization J. Appl. Polym. Sci. 2009, 112, 2976-2980