Chemosensors for the marine toxin saxitoxin

Journal of the American Chemical Society

Volumn 124, Issue 45, 2002, Pages 13448-13453

  Gawley, Robert E ^a   Pinet, Sandra ^a   Cardona, Claudia M ^a   Datta, Probal K ^a   Ren, Tong ^a   Guida, Wayne C ^b   Nydick, Jason ^b   Leblanc, Roger M ^a  

^a Department of Biology   (United States)

^b ECKERD COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CROWN ETHERS; ETHANOL; FLUORESCENCE; TOXIC MATERIALS;

FLUORESCENCE SENSORS;

CHEMICAL SENSORS;

ALCOHOL; CROWN ETHER DERIVATIVE; PHOSPHATE; SAXITOXIN;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; CRYSTAL STRUCTURE; ELECTRON TRANSPORT; FLUORESCENCE; SENSOR; SYNTHESIS;

EID: 0037073218     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027507p     Document Type: Article

References (58)

1. (a) Fenical, W.; Baden, D.; Burg, M.; de Goyet, C. d. V.; Grimes, D. J.; Katz, M.; Marcus, N.; Pomponi, S.; Rhines, P.; Tester, P.; Vena, J. From Monsoons to Microbes: Understanding the Ocean's Role in Human Health; National Academy Press: Washington, DC, 1999.
2. (b) Botana, L. M., Ed. Seafood and Freshwater Toxins. Pharmacology, Physiology, and Detection; Marcel Dekker: New York, 2000.
3. (c) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897-1909.
4. (d) Shimizu, Y. Chem. Rev. 1993, 93, 1685-1698.
5. (a) Meyer, K. F. New Engl. J. Med. 1953, 249, 843-852.
6. (b) Ayres, P. A.; Cullum, M. Paralytic Shellfish Poisoning, Technical Report No. 4; Ministry of Agriculture, Fisheries and Food, 1978.
7. Sommer, H.; Meyer, K. F. Arch. Pathol. 1937, 560-598.
8. (a) Gessner, B. D.; Middaugh, J. P. Am. J. Epidemiol. 1995, 141, 766-770.
9. (b) Gessner, B. D.; Bell, P.; Doucette, G. J.; Moczydlowski, E.; Poli, M. A.; Dolah, F. V.; Hall, S. Toxicon 1997, 35, 711-722.
10. (c) de Carvalho, M.; Jacinto, J.; Ramos, N.; de Oliveira, V.; Melo, T. P. E.; de Sa, J. J. Neurol. 1998, 245, 551-554.
11. (a) Shimizu, Y. In Handbook of Natural Toxins; Tu, A. T., Ed.; Marcel Dekker: New York, 1988: Vol. 3, pp 63-85.
12. (b) Hall, S.; Strichartz, G.; Moczydlowski, E.; Ravindran, A.; Reichardt, P. B. In Marine Toxins; Origin, Structure, and Molecular Pharmacology; Hall, S., Strichartz, G., Eds.; American Chemical Society: Washington, DC, 1990; Vol. 418, pp 29-65.
13. (c) Kao, C. Y. In Algal Toxins in Seafood and Drinking Water; Falconer, I. R., Ed.; Academic Press: London, 1993; pp 75-104.
14. Baden, D. G.; Fleming, L. E.; Bean, J. A. In Handbook of Clinical Neurology: Intoxications of the Nervous System, Part III; de Wolff, F. A., Ed.; Elsevier: Amsterdam, 1995; Vol. 21, pp 141-175.
15. Fernandez, M.; Cembella, A. D. In Manual on Harmful Marine Microalgae, IOC Manuals and Guides, No. 33: Hallegraeff, G. M., Anderson, D. M., Cembella, A. D., Eds.; UNESCO: Paris, 1995; pp 213-228.
16. Rodrigue, D. C.; Etzel, R. A.; Hall, S.; de Porras, E.; Velasquez, O. H.; Tauxe, R. V.; Kilbourne, E. M.; Blake, P. A. Am. J. Trop. Med. Hyg. 1990, 42, 267-271.
17. (a) Sullivan, J. J.; Wekell, M. M.; Hall, S. In Hanbook of Natural Toxins; Tu, A. T., Ed.; Marcel Dekker: New York, 1988; Vol. 3, pp 87-106.
18. (b) Vanegmond, H. P.; Vandentop, H. J.; Paulsch, W. E.; Goenaga, X.; Vieytes, M. R. Food Addit. Contam. 1994, 11, 39-56.
19. (c) Quilliam, M. A. J. AOAC Int. 1997, 80, 131-136.
20. McElhiney, J.; Lawton, L. A.; Edwards, C.; Gallacher, S. Toxicon 1998, 36, 417-420.
21. (a) Cheun, B. S.; Watanabe, E. Agro-Food-Ind. Hi-Tech. 1998, 9, 36-39.
22. (b) Cheun, B. S.; Takagi, S.; Hayashi, T.; Nagashima, Y.; Watanabe, E. J. Nat. Toxins 1998, 7, 109-120.
23. (a) Vieytes, M. R.; Cabado, A. G.; Alfonso, A.; Louzao, M. C.; Botana, A. M.; Botana, L. M. Anal. Biochem. 1993, 211, 87-93.
24. (b) Dolah, F. M. V.; Finley, E. L.; Haynes, B. L.; Doucette, G. J.; Moeller, P. D.; Ramsdell, J. S. Nat. Toxins 1994, 2, 189-196.
25. (c) Dolah, F. M. V. In Workshop Conference on Seafood Intoxications: Pan American Implications of Natural Toxins in Seafood; Baden, D. G., Ed.; University of Miami: Rosenstiel School of Marine and Atmospheric Science, 1995; pp 50-56.
26. (d) Llewellyn, L. E.; Doyle, J.; Negri, A. P. Anal. Biochem. 1998, 261, 51-56.
27. (e) Doucette, G. J.; Logan, M. M.; Ramsdell, J. S.; Van Dolah, F. M. Toxicon 1997, 35, 625-636.
28. (f) Negri, A.; Llewellyn, L. Toxicon 1998, 36, 283-298.
29. Kerr, D. S.; Briggs, D. M.; Saba, H. I. Toxicon 1999, 37, 1803-1825.
30. Jellett, J. F.; Doucette, L. I.; Belland, E. R. J. Shellfish Res. 1998, 17, 1653-1655.
31. (a) Oshima, Y. In Manual on Harmful Marine Microalgae, IOC Manuals and Guides, No. 33; Hallegraeff, G. M., Anderson, D. M., Cembella, A. D., Eds.; UNESCO: Paris. 1995; pp 81-94.
32. (b) Oshima, Y.; Sugino, K.; Yasumoto, T. In Mycotoxins and Phycotoxins '88: A Collection of Invited Papers at the Seventh International IUPAC Symposium on Mycotoxins and Phycotoxins; Tokyo, Japan, 16-19 August, 1988; Elsevier: Amsterdam, 1989; pp 319-326.
33. (c) Sullivan, J. J. In Marine Toxins. Origin, Structure, and Molecular Pharmacology; Hall, S., Strichartz, G., Eds.; American Chemical Society: Washington, DC, 1990; Vol. 418, pp 66-77.
34. (d) Oshima, Y. J. AOAC Int. 1995, 78, 528-532.
35. (e) Lawrence, J. F.; Wong, B. J. Chromatogr. A 1996, 755, 227-233.
36. Mirocha, C. J.; Cheong, W.; Mirza, U.; Kim, Y. B. Rapid Commun. Mass Spectrom. 1992, 6, 128-134.
37. Gallacher, S.; Mackintosh, F.; Shanks, A. M.; O'Neill, S.; Riddoch, I.; Howard, F. G. J. Shellfish Res. 1998, 17, 1647-1651.
38. A preliminary report of some of this work has appeared: Gawley, R. E.; Zhang, Q.; Higgs, P. I.; Wang, S.; Leblanc, R. M. Tetrahedron Lett. 1999, 40, 5461-5465. Corrigendum 6135.
39. (a) Wang, S.; Zhang, Q.; Datta, P. K.; Gawley, R. E.; Leblanc, R. M. Langmuir 2000, 16, 4607-4612.
40. (b) Kele, P.; Orbulescu, J.; Calhoun, T. L.: Gawley, R. E.; Leblanc, R. M. Langmuir 2002, 18, 8523-8526.
41. (a) Bissell, R. A.; Calle, E.; de Silva, A. P.; de Silva, S. A.; Gunaratne, H. Q. N.; Habib-Jiwan, J.-L.; Peiris, S. L. A.; Rupasinghe, R. A. D. D.; Samarasinghe, T. K. S. D.; Sandanayake, K. R. A. S.; Soumillion, J.-P. J. Chem. Soc., Perkin Trans. 2 1992, 1559-1564.
42. (b) de Silva, A. P.; de Silva, S. A. J. Chem. Soc., Chem. Commun. 1986, 1709-1710.
43. de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515-1566.
44. (a) Bordner, J.; Thiessen, W. E.; Bates, H. A.; Rapoport, H. J. Am. Chem. Soc. 1975, 97, 6008-6012.
45. (b) Wong, J. L.; Oesterlin, R.; Rapoport, H. J. Am. Chem. Soc. 1971, 93, 7344-7345.
46. Kele, P.; Orbulescu, J.; Calhoun, T. L.; Gawley, R. E.; Leblanc, R. M. Tetrahedron Lett. 2002, 43, 4413-4416.
47. (a) Connors, K. A. In Binding Constants: The Measurement of Molecular Complex Stability; Wiley-Interscience: New York, 1987; pp 24-28.
48. (b) Bruneau, E.; Lavabre, D.; Levy, G.; Micheau, J. C. J. Chem. Educ. 1992, 69, 833-838.
49. (c) Beltran-Porter, A.; Beltran-Porter, D.; Cervilla, A.; Ramirez, J. A. Talanta 1983, 30, 124-126.
50. Connors, K. A. In Binding Constants: The Measurement of Molecular Complex Stability; Wiley-Interscience: New York, 1987; pp 339-343.
51. Hand, C. W.; Blewitt, H. L. In Acid-Base Chemistry; Macmillan: New York, 1986; pp 246-254.
52. (a) Bissell, R. A.; de Silva, A. P.; Gunaratne, H. Q. N.; Lynch, P. L. M.; Maguire, G. E. M.; McCoy, C. P.; Sandanayake, K. R. A. S. Top. Curr. Chem. 1993, 168, 223-264.
53. Valeur, B.; Bourson, J.; Pouget, J. In Fluorescent Chemosensors for Ion and Molecule Recognition; Czarnik, A. W., Ed.; American Chemical Society: Washington, DC, 1993: Vol. 538, pp 25-44.
54. Kyba, K. P.; Helgeson, R. C.; Madan, K.; Gokel, G. W.; Tarnowski, T. L.; Moore, S. S.; Cram, D. J. J. Am. Chem. Soc. 1977, 99, 2564-2571.
55. (a) Watson, W. H.; Galloy, J.; Grossie, D. A.; Vögtle, F.; Müller, W. M. J. Org. Chem. 1984, 49, 347-353.
56. (b) Harkema, S.; van Hummel, G. J.; Daasvatn, K.; Reinhoudt, D. N. J. Chem. Soc., Chem. Commun. 1981, 368-369.
57. (c) Uiterwijk, J. W. H. M.; Harkema, S.; Reinhoudt, D. N.; Daasvatn, K.; den Hertog, H. J., Jr.; Geevers, J. Angew. Chem., Int. Ed. Engl. 1982, 21, 450-451.
58. Kolossvary, I.; Guida, W. C. J. Comput. Chem. 1999, 20, 1671-1684.