Cysteine and pH-responsive hydrogel based on a saccharide derivative with an aldehyde group

Langmuir

Volumn 26, Issue 5, 2010, Pages 3165-3168

  Chen, Qun ^a,b   Lv, Yuxia ^a,b   Zhang, Deqing ^a   Zhang, Guanxin ^a   Liu, Chenyang ^a   Zhu, Daoben ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL GROUPS; DIFFUSION PROCESS; GELATORS; GLUCOPYRANOSIDE; GUEST MOLECULES; HYDROGELATORS; INTERMOLECULAR INTERACTIONS; PH-RESPONSIVE HYDROGELS; PROOF OF PRINCIPLES; REACTIVE CHEMICALS; REACTIVE GROUP;

ALDEHYDES; MOLECULES;

HYDROGELS;

CYSTEINE; GLUCOSIDE; METHYL 4,6 O (4' ALDEHYDEPHENYLIDENE) ALPHA D GLUCOPYRANOSIDE; METHYL-4,6-O-(4'-ALDEHYDEPHENYLIDENE)-ALPHA-D-GLUCOPYRANOSIDE;

ARTICLE; CHEMISTRY; ELASTICITY; HYDROGEL; PH; SPECTROFLUOROMETRY; VISCOSITY;

CYSTEINE; ELASTICITY; GLUCOSIDES; HYDROGEL; HYDROGEN-ION CONCENTRATION; SPECTROMETRY, FLUORESCENCE; VISCOSITY;

EID: 77749340665     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la903102z     Document Type: Article

References (62)

1. Ajayaghosh, A.; Praveen, V. K.; Vijayakumar C. Chem. Soc. Rev. 2008, 37, 109-122.
2. Ajayaghosh, A.; Praveen, V. K. Acc. Chem. Res. 2007, 40, 644-656.
3. Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133-3159.
4. Abdallah, D. J.; Weiss, R.G. Adv. Mater. 2000, 12, 1237-1247.
5. George, M.; Weiss, R. G. Acc. Res. 2006, 39, 489-497.
6. Wang, S.; Shen, W.; Feng, Y. L.; Tian, H. Chem. Commun. 2006,1497-1499.
7. Zhu, L. L.; Ma, X.; Ji, F. Y.; Wang, Q. C.; Tian, H. Chem.-Eur. J. 2007, 13, 9216-9222.
8. Wang, R.; Geiger, C.; Chen, L. H.; Swanson, B.; Whitten, D. G. J. Am. Chem. Soc. 2000, 122, 2399-2400.
9. Geiger, C.; Stanescu, M.; Chen, L. H.; Whitten, D. G. Langmuir 1999, 15, 2241-2245.
10. Estroff, L. A.; Hamilton, A. D. Chem. Rev. 2004, 104, 1201-1217.
11. Sangeetha, N. M.; Maitra, U. Chem. Soc., Rev. 2005, 34, 821-836.
12. Vemula, P. K.; John, G. Acc. Chem. Res. 2008, 41, 769-782.
13. Yang, Z. M.; Xu, B. J. Mater. Chem. 2007, 17, 2385-2393.
14. Xu, B. Langmuir 2009 ,25, 8375-8377.
15. Zhao, FTMa, M. L.; Xu, B. Chem. Soc. Rev. 2009, 38, 883-891.
16. Ulijn, R. V.; Smith, A. M. Chem. Soc, Rev. 2008, 37, 664-675.
17. Zhao, X. J.; Zhang, S. G. Chem. Soc. Rev. 2006, 35, 1105-1110.
18. de Loos, M.; Feringa, B. L.; van Esch, J. H. Eur. J. Org. Chem. 2005, 17, 3615-3631.
19. Gronwald, O.; Sakurai, K.; Luboradzki, R.; Kimura, T.; Shinkai, S. Carbohydr. Res. 2001, 331, 307-318.
20. Luboradzki, R.; Gronwald, O.; Ikeda, M.; Shinkai, S.; Reinhoudt, D. N. Tetrahedron 2000, 56, 9595-9599.
21. Yoza, K.; Amanokura, N.; Ono, Y.; Akao, T.; Shinmori, H.; Takeuchi, M.; Shinkai, S.; Reinhoudt, D. N. Chem.-Eur. J. 1999, 5, 2722-2729.
22. Amanokura, N.; Yoza, K.; Shinmori, H.; Shinkai, S.; Reinhoudt, D. N. J. Chem. Soc, Perkin Trans. 2 1998, 2585-2591.
23. Yoza, K.; Ono, Y.; Yoshihara, K.; Akao, T.; Shinmori, H.; Takeuchi, M.; Shinkai, S.; Reinhoudtd, D. N. Chem. Commun. 1998, 907-908.
24. Amanokura, N.; Kanekiyo, Y.; Shinkai, S.; Reinhoudt, D. N. J. Chem. Soc., Perkin Trans. 2 1999, 1995-2000.
25. Kiyonaka, S.; Shinkai, S.; Hamachi, I. Chem.-Eur. J. 2003, 9, 976-983.
26. Gronwald, O.; Shinkai, S. Chem.-Eur. J. 2001, 7, 4328-11334
27. Friggeri, A.; Gronwald, O.; van Bommel, K. J. C.; Shinkai, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2002, 724, 10754-10758.
28. Sakurai, K.; Jeong, Y.; Koumoto, K.; Friggeri, A.; Gronwald, O.; Sakurai, S.; Okamoto, S.; Inoue, K..; Shinkai, S. Langmuir 2003, 19, 8211-8217.
29. Jung, J. H.; Shinkai, S.; Shimizu,T. Nano Lett. 2002, 2, 17-20.
30. Kobayashi, H.; Friggeri, A.; Koumoto, K.; Amaike, M.; Shinkai, S.; Reinhoudt, D. N. Org. Lett. 2002, 4, 1423-1426.
31. Cheuk, S.; Stevens, E. D.; Wang, G. J. Carbohydr. Res. 2009, 344,417-1415
32. Bao, C.; Lu, R.; Jin, M.; Xue, P.; Tan, C.; Zhao, Y. Carbohydr. Res. 2004, 339, 1311-1316.
33. Luboradzki, R.; Pakulskib, Z.; Sartowska, B. Tetrahedron 2005, 61, 10122-10128.
34. John, G.; Jung, J. H.; Masuda, M.; Shimizu, T. Langmuir 2004, 20, 2060-2065.
35. Vemula, P. K.; Cruikshank, G.; Karp, J. M.; John, G. Biomaterials 2009, 30, 383-393.
36. Sreenivasachary, N.; Lehn, J. M. Chem. Asian J. 2008, 3, 134-139.
37. Deng, W.; Yamaguchi, H.; Takashima, Y.; Harada, A. Angew. Chem., Int. Ed. 2007, 46, 5144-5147.
38. Shi, N.; Dong, H.; Yin, G.; Xu, Z.; Li, S. Adv. Funct. Mater. 2007, 17, 1837-1843.
39. Sreenivasachary, N.; Lehn, J. M. Proc. Natl. Acad. Sci U.S.A. 2005, 102, 5938-5943.
40. Yang, Z. M.; Liang, G. L.; Xu, B. Acc. Chem. Res. 2008, 41, 315-326.
41. Kobayashi, H.; Koumoto, K.; Jung, J. H.; Shinkai, S. J. Chem. Soc., Perkin Trans. 2 2002, 1930-1936.
42. Khatua, D.; Maitib, R.; Dey, J. Chem. Commun. 2006, 4903-4905.
43. Yang, Z.; Liang, G.; Ma, M.; Abbah, A.; Luc, W.; Xu, B. Chem. Commun., 2007, 843-845.
44. Panda, J.; Mishra, A.; Basu, A.; Chauhan, V. Biomacromolecules 2008, 9, 2244-2250.
45. Vemula, P.; Li, J.; George, J. J. Am. Chem. Soc. 2006, 128, 8932-8938.
46. Shome, A.; Debnath, S.; Das, P. K. Langmuir 2008, 24, 4280-4288.
47. Chen, L.; Wu, J.; Yuwen, L.; Shu, T.; Xu, M.; Zhang, M.; Yi, T. Lanemuir 2009, 25, 8434-8438.
48. Sutton, S.; Campbell, N.; Cooper, A.; Kirkland, M.; Frith, W.; Adams, D. Langmuir 2009, 25, 10285-10291.
49. Kiyonaka, S.; Sada, K.; Yoshimura, I.; Shinkai, S.; Kato, N.; Hamachi, I, Nat. Mater. 2004, 3, 58-64.
50. Yoshimura, I.; Miyahara, Y.; Kasagi, N.; Yamane, H.; Ojida, A.; Hamachi, I. J. Am. Chem. Soc. 2004, 126, 12204-12205.
51. Koshi, Y.; Nakata, E.; Yamane, H.; Hamachi, I, J. Am., Chem. Soc. 2006, 128, 10413-10422.
52. Wada, A.; Tamaru, S.; Ikeda, M.; Hamachi, I. J. Am. Chem. Soc, 2009, 131, 5321-5330.
53. Komatsu, H.; Matsumoto, S.; Tamaru, S.; Kaneko, K.; Ikeda, M.; Hamachi, I. J. Am. Chem. Soc. 2009, 131, 5580-5585.
54. Yang, Z.; Liang, G.; Wang, L.; Xu, B. J. Am. Chem. Soc. 2006, 128, 3038-3043.
55. Yang, Z. M.; Ho, P. L.; Liang, G. L.; Chow, K. H.; Wang, Q. G.; Cao, Y.; Guo, Z. H.; Xu, B. J. Am. Chem. Soc. 2007, 129, 266-267.
56. Liang, G.; Yang, Z.; Zhang, R.; Li, L.; Fan, Y.; Kuang, Y.; Gao, Y.; Wang, T.; Lu, W.; Xu, B. Langmuir 2009, 25, 8419-8422.
57. Chen, Q.; Zhang, D.; Zhang, G.; Zhu, D. Langmuir 2009, 25, 11436-11441.
58. Lin, W.; Long, L.; Yuan, L.; Cao, Z.; Chen, B.; Tan, W. Org. Lett. 2008, 10, 5577-5580.
59. Wang, W.; Rusin, O.; Xu, X.; Kim, K.; Escobedo, J.; Fakayode, S.; Fletcher, K.; Lowry, M.; Schowalter, C.; Lawrence, C.; Fronczek, F.; Warner, I.; Strongin, R. J. Am. Chem. Soc. 2005, 127, 15949-15958.
60. Rusin, O.; Luce, N.; Agbaria, R.; Escobedo, J.; Jiang, S.; Warner, I.; Dawan, F.; Lian, K.; Strongin, R. J. Am. Chem. Soc, 2004, 126, 438-439.
61. Kallen, R. J. Am. Chem. Soc. 1971, 93, 6236-6248.
62. The energy-minimized molecular conformations of compounds 1 were obtained with MM2 program incorporated in Chem 3D program. The corresponding molecular length was estimated by measuring the distance between two farthest apart atoms.