2,7-Bis(1H-pyrrol-2-yl)ethynyl-1,8-naphthyridine: An Ultrasensitive Fluorescent Probe for Glucopyranoside

Organic Letters

Volumn 4, Issue 18, 2002, Pages 3107-3110

  Liao, Jen Hai ^a   Chen, Chao Tsen ^a   Chou, He Chun ^a   Cheng, Chung Chih ^a,c   Chou, Pi Tai ^a   Fang, Jim Min ^a   Slanina, Zdenek ^b   Chow, Tashin J ^b  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b INSTITUTE OF CHEMISTRY   (Taiwan)

^c FU JEN CATHOLIC UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

2,7 BIS(1H PYRROL 2 YL)ETHYNYL 1,8 NAPHTHYRIDINE; 2,7-BIS(1H-PYRROL-2-YL)ETHYNYL-1,8-NAPHTHYRIDINE; DIAGNOSTIC AGENT; FLUORESCENT DYE; GLUCOSIDE; NAPHTHYRIDINE DERIVATIVE; OCTYL BETA GLUCOSIDE; OCTYL-BETA-D-GLUCOSIDE; PYRROLE DERIVATIVE;

ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; SENSITIVITY AND SPECIFICITY; SPECTROSCOPY; SYNTHESIS;

BINDING SITES; FLUORESCENT DYES; GLUCOSIDES; HYDROGEN BONDING; MOLECULAR STRUCTURE; NAPHTHYRIDINES; PYRROLES; SENSITIVITY AND SPECIFICITY; SPECTRUM ANALYSIS;

EID: 0037026465     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0264096     Document Type: Article

References (42)

1. For general reviews, see: (a) Aoyama, Y. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Elsevier: Oxford, 1996; Vol. 2, Chapter 9, pp 279-307. (b) Davis, A. P.; Wareham, R. S. Angew. Chem., Int. Ed. 1999, 38, 2978.
2. For general reviews, see: (a) Aoyama, Y. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Elsevier: Oxford, 1996; Vol. 2, Chapter 9, pp 279-307. (b) Davis, A. P.; Wareham, R. S. Angew. Chem., Int. Ed. 1999, 38, 2978.
3. (a) Kobayashi, K.; Asakawa, Y.; Kato, Y.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 1030.
4. (b) Bhattarai, K. M.; Bonar-Law, R. P.; Davis, A. P.; Murray, B. A. Chem. Commun. 1992, 752.
5. (c) Liu, R.; Still, W. C. Tetrahedron Lett. 1993, 34, 2573.
6. (d) Huang, C.-Y.; Cabell, L. A.; Anslyn, E. V. J. Am. Chem. Soc. 1994, 116, 2778.
7. (e) Das, G.; Hamilton, A. D. J. Am. Chem. Soc. 1994, 116, 11139.
8. (f) Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596.
9. (g) Jiménez-Barbero, J.; Junquera, E.; Martín-Pastor, M.; Sharma, S.; Vicent, C.; Penadés, S. J. Am. Chem. Soc. 1995, 117, 11198.
10. (h) Mizutani, T.; Kurahashi, K.; Murakami, T.; Matsumi, N.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 8991.
11. (i) Davis, A. P.; Wareham, R. S. Angew. Chem., Int. Ed. 1998, 37, 2270.
12. (j) Inouye, M.; Takahashi, K.; Nakazumi, H. J. Am. Chem. Soc. 1999, 121, 341.
13. (k) Mazik, M.; Sicking, W. Chem. Eur. J. 2001, 7, 664.
14. (l) Král, V.; Rusin, O.; Schmidtchen, F. P. Org. Lett. 2001, 3, 873.
15. (m) Bitta, J.; Kubik, S. Org. Lett. 2001, 3, 2637.
16. (n) Benito, J. M.; Gómez-García, M.; Blanco, J. L. J.; Mellet, C. O.; Fernández, J. M. G. J. Org. Chem. 2001, 66, 1366.
17. (a) James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1910.
18. (b) Eggert, H.; Frederiksen, J., Morin, C.; Norrild, J. C. J. Org. Chem. 1999, 64, 3846.
19. (c) Kukrer, B.; Akkaya, E. U. Tetrahedron Lett. 1999, 40, 9125.
20. (d) DiCesare, N.; Lakowicz, J. R. Chem. Commun. 2001, 2022.
21. (e) DiCesare, N.; Lakowicz, J. R. J. Phys. Chem. 2001, 105, 6834.
22. (f) Yang, W.; He, H.; Drueckhammer, D. G. Angew. Chem., Int. Ed. 2001, 40, 1714.
23. (a) Kikuchi, Y.; Kobayashi, K.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 1351.
24. (b) Inouye, M.; Miyake, T.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1995, 117, 12416.
25. (c) Mizutani, T.; Kurahashi, T.; Murakami, T.; Matsumi, N.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 8991.
26. (d) Tamaru, S.-i.; Yamamoto, M.; Shinkai, S.; Khasanov, A. B.; Bell, T. W. Chem. Eur. J. 2001, 7, 5270.
27. (e) Tamaru, S.-i.; Shinkai, S.; Khasanov, A. B.; Bell, T. W. Proc. Natl. Acad. Sci. 2002, 99, 4972.
28. (a) Newkome, G. R.; Garbis, S. J.; Majestic, V. K.; Fronczek, F. R.; Chiari, G. J. Org. Chem. 1981, 46, 833.
29. (b) Ziessel, R.; Suffert, J.; Youinou, M.-T. J. Org. Chem. 1996, 61, 6535.
30. The carbohydrate recognition properties of some naphthyridine derivatives have been demonstrated in refs 2k, 4d, and 4e. Compounds containing pyrrole moieties have been used to bind fluoride ion. See a recent example: (c) Mizuno, T.; Wei, W.-H.; Eller, L. R.; Sessler, J. L. J. Am. Chem. Soc. 2002, 124, 1134.
31. (a) McFarland, S. A.; Finney, N. S. J. Am. Chem. Soc. 2001, 123, 1260.
32. (b) Mello, J. V.; Finney, N. S. Angew. Chem., Int. Ed. 2001, 40, 1536.
33. (c) Choi, K.; Hamilton, A. D. Angew. Chem., Int. Ed. 2001, 40, 3912.
34. (d) McFarland, S. A.; Finney, N. S. J. Am. Chem. Soc. 2002, 124, 1178.
35. (a) Sandanayaka, K. R. A. S.; Nakashima, K.; Shinkai, S. Chem. Commun. 1994, 1621.
36. (b) Takeuchi, M.; Yoda, S.; Imada, T.; Shinkai, S. Tetrahedron 1997, 53, 8335.
37. 0, A, and F denote, respectively, the absorbance and fluorescent intensity of free BPN and in solution after adding monosaccharides at a selective wavelength.
38. Connors, K. A. Binding Constants; Wiley: New York, 1987.
39. (a) Bell, T. W.; Beckles, D. L.; Cragg, P. J.; Liu, J.; Maioriello, J.; Papoulis, A. T.; Santora, V. J. In Fluorescent Chemosensors for Ion and Molecular Recognition; Czarnik, A. W., Ed.; American Chemical Society: Washington, DC, 1993; Chapter 7, pp 85-103.
40. (b) Bell, Z. T.; Hou, W.; Luo, Y.; Drew, M. G. B.; Chapoteau, E.; Czech, B. P.; Kumar, A. Science 1995, 269, 671.
41. (c) Lüning, U.; Kühl, C. Tetrahedron Lett. 1998, 39, 5735.
42. (d) Corbin, P. S.; Zimmerman, S. C. J. Am. Chem. Soc. 2000, 122, 3779.