Construction of artificial signal transducers on a lectin surface by post-photoaffinity-labeling modification for fluorescent saccharide biosensors

Chemistry - A European Journal

Volumn 9, Issue 15, 2003, Pages 3660-3669

  Nagase, Tsuyoshi ^a   Nakata, Eiji ^a   Shinkai, Seiji ^a   Hamachi, Itaru ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Glycochemistry; Lectins; Photoaffinity labeling; Protein engineering; Saccharide biosensors

Indexed keywords

CATALYSIS; FLUORESCENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPHOBICITY; MASS SPECTROMETRY; PROTEINS; TRANSDUCERS;

LECTIN;

BIOSENSORS;

AMINOBENZOIC ACID DERIVATIVE; CARBOHYDRATE; CARBOHYDRATE BINDING PROTEIN; CONCANAVALIN A; COUMARIN; DANSYL CHLORIDE; DIMETHYLAMINOBENZOATE; DISULFIDE; LECTIN; MANNOSIDE; REAGENT; THIOL GROUP; UNCLASSIFIED DRUG;

ANISOTROPY; ARTICLE; BINDING AFFINITY; BIOSENSOR; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; COMPLEX FORMATION; DISULFIDE BOND; FLUORESCENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPHILICITY; HYDROPHOBICITY; LIGHT IRRADIANCE; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PHOTOAFFINITY LABELING; REACTION ANALYSIS; REDUCTION; SIGNAL TRANSDUCTION; SYNTHESIS; TANDEM MASS SPECTROMETRY; TITRIMETRY; TRANSDUCER;

BINDING SITES; BIOSENSING TECHNIQUES; CANAVALIA; CONCANAVALIN A; DISULFIDES; FLUORESCENT DYES; MANNOSE; MODELS, MOLECULAR; PHOTOAFFINITY LABELS; PROTEIN BINDING; PROTEIN ENGINEERING; SIGNAL TRANSDUCTION; SPECTROMETRY, FLUORESCENCE;

EID: 0043032818     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200304925     Document Type: Article

References (69)

1. a) A. W. Czarnik, Acc. Chem. Res. 1994, 27, 302-308;
2. b) A. P. de Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher, T. E. Rice, Chem. Rev. 1997, 97, 1515-1566.
3. a) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Angew. Chem. 1996, 108, 2038-2050; Angew. Chem. Int. Ed. Engl. 1996, 35, 1910-1922;
4. a) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Angew. Chem. 1996, 108, 2038-2050; Angew. Chem. Int. Ed. Engl. 1996, 35, 1910-1922;
5. b) C. T. Chen, H. Wagner, W. C. Still, Science 1998, 279, 851-853;
6. c) A. Sugasaki, K. Sugiyasu, M. Ikeda, M. Takeuchi, S. Shinkai, J. Am. Chem. Soc. 2001, 123, 10239-10244.
7. a) H. W. Hellinga, J. S. Marvin, Trends Biotechnol. 1998, 16, 183-189;
8. b) D. A. Zachrias, G. S. Baird, R. Y. Tsien, Curr. Opin. Neurobiol. 2000, 10, 416-421;
9. c) L. Tolosa, I. Gryczynski, L. R. Eichhorn, J. D. Dattelbaum, F. N. Castellano, G. Rao, J. R. Lakowicz, Anal. Biochem. 1999, 267, 114-120;
10. d) M. Hirshberg, K. Henrick, L. L. Haire, N. Vasisht, M. Brune, J. E. T. Corrie, M. R. Webb, Biochemistry 1998, 37, 10381-10385;
11. e) J. D. Brennan, K. K. Flora, G. N. Bendiak, G. A. Baker, M. A. Kane, S. Pandey, F. V. Bright, J. Phys. Chem. B 2000, 104, 10100-10110;
12. f) G. J. Cotton, B. Ayers, R. Xu, T. W. Muir, J. Am. Chem. Soc. 1999, 121, 1100-1101;
13. g) I. Hamachi, R. Eboshi, J. Watanabe, S. Shinkai, J. Am. Chem. Soc. 2000, 122, 4530-4531;
14. h) T. Morii, K. Sugimoto, K. Makino, M. Otsuka, K. Imoto, Y. Mori, J. Am. Chem. Soc. 2002, 124, 1138-1139.
15. a) A. Miyawaki, J. Llopis, R. Heim, J. M. McCaffery, J. A. Adams, M. Ikura, R. Y. Tsien, Nature 1997, 388, 882-887;
16. b) M. Zaccolo, F. De Giorgi, C. Y. Cho, L. Feng, T. Knapp, P. A. Negulescu, S. S. Taylor, R. Y. Tsien, T. Pozzan, Nat. Cell. Biol. 2000, 2, 25-29.
17. G. K. Walkup, B. Imperiali, J. Am. Chem. Soc. 1997, 119, 3443-3450.
18. H. A. Godwin, J. M. Berg, J. Am. Chem. Soc. 1996, 118, 6514-6515.
19. a) D. E. Benson, D. W. Conrad, R. M. de Lorimier, S. A. Trammell, H. W. Hellinga, Science 2001, 293, 1641-1644;
20. b) J. S. Marvin, H. W. Hellinga, J. Am. Chem. Soc. 1998, 120, 7-11;
21. c) G. Gilardi, L. Q. Zhou, L. Hibbert, A. E. G. Cass, Anal. Chem. 1994, 66, 3840-3847.
22. a) R. B. Thompson, B. P. Maliwal, V. L. Feliccia, C. A. Fierke, K. McCall, Anal. Chem. 1998, 70, 4717-4723;
23. b) D. Elbaum, S. K. Nair, M. W. Patchan, R. B. Thompson, D. W. Christianson, J. Am. Chem. Soc. 1996, 118, 8381-8387;
24. c) R. B. Thompson, B. P. Maliwal, C. A. Fierke, Anal. Biochem. 1999, 267, 185-195.
25. a) C. R. Bertozzi, L. L. Kiessling, Science 2001, 291, 2357-2364;
26. b) P. M. Rudd, T. Elliott, P. Cresswell, I. A. Wilson, R. A. Dwek, Science 2001, 291, 2370-2376.
27. A. Riklin, E. Katz, I. Willner, A. Stocker, A. F. Buckmann, Nature 1995, 376, 672-675.
28. a) H. Lis, N. Sharon, Chem. Rev. 1998, 98, 637-674, and references therein;
29. b) H. Bittiger, H. P. Schnebli, Concanavalin A as a Tool, John Wiley and Sons, New York, 1976.
30. a) D. K. Mandal, N. Kishore, C. F. Brewer, Biochemistry 1994, 33, 1149-1156;
31. b) J. H. Naismith, R. A. Field, J. Biol. Chem. 1996, 271, 972-976;
32. c) R. Loris, D. Maes, F. Poortmans, L. Wyns, J. Bouckaert, J. Biol. Chem. 1996, 271, 30614-30618.
33. C. Emmerich, J. R. Helliwell, M. Redshaw, J. H. Naismith, S. J. Harrop, J. Raftery, A. J. Kalb, J. Yariv, Z. Dauter, K. S. Wilson, Acta Crystallogr. Sect. D 1994, 50, 749-756.
34. a) I. J. Goldstein, C. E. Hollerman, E. E. Smith, Biochemistry 1965, 4, 876-883;
35. b) Z. Derevenda, J. Yariv, J. R. Helliwell, A. J. Kalb, E. J. Dodson, M. Z. Papiz, T. Wan, J. Campbell, EMBO J. 1989, 8, 2189-2193;
36. c) J. H. Naismith, C. Emmerich, J. Habash, S. J. Harop, J. R. Helliwell, W. N. Hunter, J. Raftery, A. J. Kalb (Gilboa), J. Yariv, Acta Crystallogr. 1994, D50, 847-858;
37. d) T. K. Dam, C. F. Brewer, Chem. Rev. 2002, 102, 387-429.
38. a) I. Hamachi, T. Nagase, S. Shinkai, J. Am. Chem. Soc. 2000, 122, 12065-12066;
39. b) T. Nagase, S. Shinkai, I. Hamachi, Chem. Commun. 2001, 229-230.
40. F. P. Schwarz, K. D. Puri, R. G. Bhat, A. Surolia, J. Biol. Chem. 1993, 268, 7668-7677.
41. a) G. Dorman, G. D. Prestwich, Trends Biotechnol. 2000, 18, 64-77;
42. b) S. A. Fleming, Tetrahedron 1995, 51, 12479-12520;
43. c) J. Brunner,Annu. Rev. Biochem. 1993, 62, 483-514;
44. d) D. G. Knorre, T. S. Godovikova, FEBS Lett. 1998, 433, 9-14.
45. a) Y. Hatanaka, M. Hashimoto, Y. Kanaoka, J. Am. Chem. Soc. 1998, 120, 453-454;
46. b) K. Fang, M. Hashimoto, S. Jockusch, N. J. Turro, K. Nakanishi, J. Am. Chem. Soc. 1998,120, 8543-8544;
47. c) H. Li, Y. Liu, K. Fang, K. Nakanishi, Chem. Commun. 1999, 365-366.
48. a) M. Nassal, Liebigs Ann. Chem. 1983, 1510-1523;
49. b) Y. Hatanaka, M. Hashimoto, H. Kurihara, H. Nakayama, Y. Kanaoka, J. Org. Chem. 1994, 59, 383-387;
50. c) J. Brunner, H. Senn, F. M. Richards, J. Biol. Chem. 1980, 255, 3313-3318;
51. d) Y. Hatanaka, M. Hashimoto, H. Nakayama, Y. Kanaoka, Chem. Pharm. Bull. 1994, 42, 826-831;
52. e) M. Nassal, J. Am. Chem. Soc. 1984, 106, 7540-7545.
53. M. Beppu, T. Terao, T. Osawa, J. Biochem. 1975, 78, 1013-1019.
54. We confirmed that the sensing capability of the IAEDANS-Con A prepared from fractions making up the second peak is comparable to that of IAEDANS-Con A prepared from fractions making up the first peak.
55. a) J. L. Wang, B. A. Cunningham, G. M. Edelman, Proc. Nat. Acad. Sci. USA 1971, 68, 1130-1134;
56. b) J. L. Wang, B. A. Cunningham, M. J. Waxdal, G. M. Edelman, J. Biol. Chem. 1972, 250, 1490-1502.
57. M. S. Herrmann, L. M. Richardson, L. M. Setzler, W. D. Behnke, Biopolymers 1978, 17, 2107-2120.
58. Y. Shikata, M. Kuwada, Y. Hayashi, A. Hashimoto, A. Koide, N. Asakawa, Anal. Chim. Acta 1998, 365, 241-247.
59. a) E. N. Hudson, G. Weber, Biochemistry 1973, 12, 4154-4161;
60. b) R. P. Haugland, Handbook of Fluorescent Probes and Research Chemicals, 6th ed., Molecular Probes, Inc., Eugene, OR, 1996.
61. H. Benesi, J. H. Hildebrand, J. Am. Chem. Soc. 1949, 71, 2703-2707.
62. K. Hamasaki, H. Ikeda, A. Nakamura, A. Ueno, F. Toda, I. Suzuki, T. Osa, J. Am. Chem. Soc. 1993, 115, 5035-5040.
63. S. J. Pollack, G. R. Nakayama, P. G. Schultz, Science 1988, 242, 1038-1040.
64. P. N. Kanellopoulos, K. Pavlou, A. Perrakis, B. Agianian, C. E. Vorgias, C. Mavrommatis, M. Soufi, P. A. Tucker, S. J. Hamodrakas, J. Struct. Biol. 1996, 116, 345-355.
65. H. Lis, N. Sharon, Annu. Rev. Biochem. 1986, 55, 35-67.
66. J. L. Wang, G. M. Edelman, J. Biol. Chem. 1978, 253, 3000-3007.
67. G. L. Ellman, Arch. Biochem. Biophys. 1959, 82, 70-77.
68. 2+ ions are essential for the selective and tight binding of sugars to Con A, we added these metal cations to the solution both in the PPALM step and the fluorescence titration process. Without them, we observed a decrease of the binding affinity.
69. G. Weber, Adv. Protein Chem. 1953, 8, 415-459.