Fluorescent β-cyclodextrins modified by isomeric aminobenzamides: Synthesis, conformational analysis, and fluorescent behaviors

Journal of Organic Chemistry

Volumn 76, Issue 12, 2011, Pages 4874-4883

  Wang, Lei ^a   Zhong, Cheng ^a   Xue, Peng ^a   Fu, Enqin ^a  

^a WUHAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE CARBOXYLATES; CDS; CIRCULAR DICHROMISM; CONFORMATIONAL ANALYSIS; DEOXYCHOLATE; FLUORESCENCE BEHAVIORS; FLUORESCENCE CHARACTERISTICS; FLUORESCENCE INTENSITIES; FLUORESCENCE QUENCHING; FLUORESCENT RESPONSE; GUEST MOLECULES; ORTHO ISOMERS;

CARBOXYLATION; CONFORMATIONS; CYCLODEXTRINS; FLUORESCENCE SPECTROSCOPY; INVESTMENTS; ISOMERS; SODIUM;

FLUORESCENCE;

AMINOBENZAMIDE; BENZAMIDE DERIVATIVE; BETA CYCLODEXTRIN; UNCLASSIFIED DRUG;

ARTICLE; CIRCULAR DICHROISM; FLUORESCENCE; ISOMERISM; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 79958841986     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2007829     Document Type: Article

References (56)

1. Trapp, O. Angew. Chem., Int. Ed. 2008, 47, 8158
2. Feng, X.; Liu, L.; Wang, S.; Zhu, D. B. Chem. Soc. Rev. 2010, 39, 2411
3. Terai, T.; Nagano, T. Curr. Opin. Chem. Biol. 2008, 12, 515
4. Tang, B.; Cao, L.; Xu, K.; Zhuo, L.; Ge, J.; Li, Q.; Yu, L. Chem.-Eur. J. 2008, 14, 3637
5. Martínez-Tomé, M. J.; Esquembre, R.; Mallavia, R.; Mateo, C. R. J. Pharm. Biomed. Anal. 2010, 51, 484
6. Han, C.; Li, H. Anal. Bioanal. Chem. 2010, 397, 1437
7. Chen, Y.; Liu, Y. Chem. Soc. Rev. 2010, 39, 495
8. Ueno, A. Supramol. Sci. 1996, 3, 31
9. Ogoshi, T.; Harada, A. Sensors 2008, 8, 4961
10. Cucinotta, V.; Contino, A.; Giuffrida, A.; Maccarrone, G.; Messina, M. J. Chromatogr. A 2010, 1217, 953
11. Manakker, F.; Vermonden, T.; Nostrum, C. F.; Hennink, W. E. Biomacromolecules 2009, 10, 3157
12. Juvancz, Z.; Kendrovics, R. B.; Iványi, R.; Szente, L. Electrophoresis 2008, 29, 1701
13. Patra, D. Biosens. Bioelectron. 2010, 25, 1149
14. Suzuki, I.; Ui, M.; Yamauchi, A. J. Am. Chem. Soc. 2006, 128, 4498
15. Xu, M.; Wu, S.; Zeng, F.; Yu, C. Langmuir 2010, 26, 4529
16. Ludden, M. J. W.; Li, X.; Greve, J.; Amerongen, A.; Escalante, M.; Subramaniam, V.; Reinhoudt, D. N.; Huskens, J. J. Am. Chem. Soc. 2008, 130, 6964
17. Ueno, A.; Ikeda, A.; Ikeda, H.; Ikeda, T.; Toda, F. J. Org. Chem. 1999, 64, 382
18. Ikeda, H.; Li, Q.; Ueno, A. Bioorg. Med. Chem. Lett. 2006, 16, 5420
19. Ikunaga, T.; Ikeda, H.; Ueno, A. Chem.-Eur. J. 1999, 5, 2698
20. Ikeda, H.; Nakamura, M.; Ise, N.; Oguma, N.; Nakamura, A.; Ikeda, T.; Toda, F.; Ueno, A. J. Am. Chem. Soc. 1996, 118, 10980
21. Murayama, T.; Tanabe, T.; Ikeda, H.; Ueno, A. Bioorg. Med. Chem. 2006, 14, 3691
22. Ikeda, H.; Murayama, T.; Ueno, A. Org. Biomol. Chem. 2005, 3, 4262
23. Ikeda, H.; Ueno, A. Chem. Commun. 2009, 4281
24. Zhong, C.; Mu, T.; Wang, L.; Fu, E.; Qin, J. Chem. Commun. 2009, 4091
25. Campos, I. B.; Brochsztain, S. J. Inclusion Phenom. Macrocycl. Chem. 2002, 44, 207
26. Wang, H.; Cao, R.; Ke, C. F.; Liu, Y.; Wada, T.; Inoue, Y. J. Org. Chem. 2005, 70, 8703
27. Nakashima, H.; Yoshida, N. Org. Lett. 2006, 8, 4997
28. Introduction to Fluorescence Sensing; Demchenko, A. P., Ed.; Springer Science: New York, 2009.
29. Molecular Fluorescence: Principles and Applications; Valeur, B., Ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2001.
30. Saroja, G.; Soujanya, T.; Ramachandram, B.; Samanta, A. J. Fluoresc. 1998, 8, 405
31. Sahu, K.; Mondal, S. K.; Ghosh, S.; Bhattacharyya, K. Bull. Chem. Soc. Jpn. 2007, 80, 1033
32. Harata, K.; Uedaira, H. Bull. Chem. Soc. Jpn. 1975, 48, 375
33. Kodaka, M. J. Phys. Chem. 1991, 95, 2110
34. Kodaka, M. J. Am. Chem. Soc. 1993, 115, 3702
35. Shimizu, H.; Kaito, A.; Hatano, M. Bull. Chem. Soc. Jpn. 1979, 52, 2678
36. Shimizu, H.; Kaito, A.; Hatano, M. Bull. Chem. Soc. Jpn. 1981, 54, 513
37. Zhao, Y. L.; Hu, L.; Gruner, G.; Stoddart, F. S. J. J. Am. Chem. Soc. 2008, 130, 16996
38. Fathalla, M.; Neuberger, A.; Li, S. C.; Schmehl, R.; Diebold, U.; Jayawickramarajah, J. J. Am. Chem. Soc. 2010, 132, 9966
39. Voskuhl, J.; Stuart, M. C.; Ravoo, B. J. Chem.-Eur. J. 2010, 16, 2790
40. Wang, H.; Wang, S.; Su, H.; Chen, K. J.; Armijo, A. L.; Lin, W. Y.; Wang, Y.; Sun, J.; Kamei, K.; Czernin, J.; Radu, C. G.; Tseng, H. R. Angew. Chem., Int. Ed. 2009, 48, 4344
41. Ollila, F.; Pentikäinen, O. T.; Forss, S.; Johnson, M. S.; Slotte, J. P. Langmuir 2001, 17, 7107
42. Liu, Y.; Yang, Y. W.; Cao, R.; Song, S. H.; Zhang, H. Y.; Wang, L. H. J. Phys. Chem. B 2003, 107, 14130
43. Liu, Y.; Shi, J.; Guo, D. S. J. Org. Chem. 2007, 72, 8227
44. Liu, Y.; Song, Y.; Chen, Y.; Li, X. Q.; Ding, F.; Zhong, R. Q. Chem.-Eur. J. 2004, 10, 3685
45. Principles and Methods in Supramolecular Chemistry; Schneider, H. J.; Yatsimirsky, A., Eds.; John Wiley & Sons: Chichester, 2000.
46. Mataga, N. Bull. Chem. Soc. Jpn. 1963, 36, 654
47. Stalin, T.; Rajendiran, N. J. Photochem. Photobiol., A 2006, 182, 137
48. Principles of Fluorescence Spectroscopy; Lakowicz, J. R., Ed.; Springer Science: Baltimore, 2006.
49. Harries, D.; Rau, D. C.; Adrian Parsegian, V. J. Am. Chem. Soc. 2005, 127, 2184
50. Goto, H.; Furusho, Y.; Yashima, E. J. Am. Chem. Soc. 2007, 129, 109
51. Rudiger, V.; Eliseev, A.; Simova, S.; Schneider, H. J.; Blandamer, M. J.; Cullis, P. M.; Meyer, A. J. J. Ghem. Soc., Perkin Trans. 2 1996, 2119
52. May, B. L.; Clements, P.; Tsanaktsidis, J.; Easton, C. J.; Lincoln, S. F. J. Chem. Soc., Perkin Trans. 1 2000, 463
53. Engeldinger, E.; Armspach, D.; Matt, D. Chem. Rev. 2003, 103, 4147
54. Szejtli, J. Chem. Rev. 1998, 98, 1743
55. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford, CT, 2009.
56. Brady, B.; Lynam, N.; O'Sullivan, T.; Ahern, C.; Darcy, R. Org. Synth. 2000, 77, 220