Photoaffinity labeling on magnetic microspheres (PALMm) methodology for topographic mapping: Preparation of PALMm reagents and demonstration of biochemical relevance

Organic and Biomolecular Chemistry

Volumn 1, Issue 16, 2003, Pages 2821-2832

  Halbfinger, Efrat ^a   Gorochesky, Karine ^a   Lévesque, Sébastien A ^b   Beaudoin, Adrien R ^b   Sheihet, Larisa ^a   Margel, Shlomo ^a   Fischer, Bilha ^a  

^a BAR ILAN UNIVERSITY   (Israel)

^b UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AGENTS; CROSSLINKING; ENZYMES; MAGNETIC MATERIALS; POLYPEPTIDES; SURFACE TOPOGRAPHY;

APYRASE; BIOACTIVE LIGAND; HEXOKINASE; MAGNETIC MICROSPHERES; TOPOGRAPHIC MAPPING;

PROTEINS;

EID: 0042319308     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b303425a     Document Type: Article

References (100)

1. (a) F. Kotzyba-Hibert, I. Kapfer and M. Goeldner, Angew. Chem., Int. Ed. Engl., 1995, 34, 1296-1312
2. (b) S. A. Fleming, Tetrahedron, 1995, 51, 12479-12520
3. (c) M. S. Platz, Photochem. Photobiol., 1997, 65, 193-194
4. (d) G. Dorman and G. D. Pretwich, Trends Biotechnol., 2000, 18, 64-77
5. (e) G. A. Kurshunova, N. V. Sumbatyan, A. N. Sumbatyan, A. N. Topin and M. T. Mtchedlidze, Mol. Biol. (Engl. Transl.), 2000, 34, 823-839
6. (f) Y. Hatanaka and Y.Sadakane, Curr. Top. Med. Chem., 2002, 2, 271-288.
7. (a) J. Brunner, H. Senn and F. M. Richards, J. Biol. Chem., 1980, 255, 3313-3318
8. (b) T. Nakayama and H. G. Khorana, J. Biol. Chem., 1990, 265, 15762-15769.
9. (a) S. X. Cai, D. J. Glenn and J. F. W. Kenea, J. Org. Chem., 1992, 57, 1299-1304
10. (b) I. Kapfer, J. E. Hawkinson, J. E. Casida and M. P. Goeldner, J. Med. Chem., 1994, 37, 133-140.
11. F. Hucho and C. Weise, Angew. Chem., Int. Ed., 2001, 40, 3100-3116.
12. S. M. Parsons, FASEB J., 2000, 14, 2423-2434.
13. A. Favre, C. Saintome, J.-L. Fourrey, C. Pascale and L. J. Philippe, Photochem. Photobiol., 1998, 42, 109-124.
14. G. Dorman, Top. Curr. Chem., 2001, 211, 169-225.
15. (a) M. C. Olcott, M. L. Bradley and B. E. Haley, Biochemistry, 1994, 33, 11935-11941
16. (b) J. Kanaani, D. Maltby, P. Focia and C. C. Wang, Biochemistry, 1995, 34, 14987-14996
17. (c) D. Tull, S. Miao, S. G. Withers and R. Aebersold, Anal. Biochem., 1995, 224, 509-514
18. (d) R. A. Tschirret-Guth, K. F. Medzihiradszky and P. R. Ortiz de Montellano, J. Am. Chem. Soc., 1998, 120, 7404-7410.
19. Y. Hatanaka, M. Hashimoto and Y. Kanaoka, J. Am. Chem. Soc., 1998, 120, 453-454.
20. K. Muramoto and H. Kamiya, Dev. Comp. Immunol., 1992, 16, 1-8.
21. H.-J. Schafer, P. Scheurich, G. Rathgerber and K. Dose, Anal. Biochem., 1980, 104, 106-111.
22. (a) K. Fang, M. Hashimoto, S. Jokusch, N. J. Turro and K. Nakanishi, J. Am. Chem. Soc., 1998, 120, 8543-8544
23. L. Hong-yu, Y. Liu, K. Fang and K. Nakanishi, Chem. Commun., 1999, 365-366.
24. A. M. Mulichak, J. E. Wilson, K. Padmanabhan and R. M. Garavito, Nat. Struct. Biol., 1998, 5, 555-560.
25. C. Zeng and H. J. Fromm, J. Biol. Chem., 1995, 270, 10509-10513.
26. W. S. Bennett and T. A. Steitz, J. Mol. Biol., 1980, 140, 211-230.
27. A. E. Aleshin, C. Zeng, H. D. Bartunik, H. J. Fromm and R. B. Honzatko, J. Mol. Biol., 1998, 282, 345-357.
28. X. Liu, C. S. Kim, F. T. Kurbanov, R. B. Honzatko and H. J. Fromm, J. Biol. Chem., 1999, 274, 31155-31159.
29. (a) G. Burnstock, Pharmacol. Rev., 1972, 24, 509-81
30. (b) G. Burnstock, J. Theor. Biol., 1976, 62, 491-503.
31. I. Kugelgen and A. Wetter, Naunyn-Schmiedeberg's Arch. Pharmacol., 2000, 362, 310-323.
32. (a) B. F. King, A. Townsend-Nicholson and G. Burnstock, Trends Pharmacol. Sci., 1998, 19, 506-514
33. (b) F. D. Virgillo, P. Chiozzi, D. Ferrari, S. Falzoni, J. M. Sanz, A. Morelli, M. Torboli, G. Bolognesi and O. R. Baricordi, Blood, 2001, 97, 587-600.
34. (a) H. P. Baer and G. I. Drummond, Physiological and Regulatory Functions of Adenosine and Adenine Nucleotides, Raven Press, New York 1979
35. (b) M. Williams, Annu. Rev. Pharmacol. Toxicol., 1987, 27, 315-45.
36. E. A. Barnard, J. Simon and T. E. Webb, Mol. Neurobiol., 1997, 15, 103-129.
37. M. R. Boarder and S. M. O. Hourani, Trends Pharmacol. Sci., 19, 99-107.
38. (a) R. A. Olsson and J. D. Pearson, Physiol. Rev., 1990, 70, 761-845
39. (b) T. W. Stone and H. A. Simmonds, Purines: Basic and Clinical Aspects, Kluwer Academic Publishers, 1991, pp. 1-245.
40. (a) B. Fischer, Exp. Opin. Ther. Pat., 1999, 9, 385-399
41. (b) K. Inoue, Pharmacol. Res., 1998, 38, 323-331
42. (c) M. P. Abbrachio, Drug Dev. Res., 1996, 39, 393-406
43. (d) C. M. Chan, R. J. Unwin and G. Burnstock, Exp. Nephrol., 1998, 6, 200-207
44. (e) T. D. White, Pharmacol. Ther., 1988, 38, 129-68.
45. C. C. Caldwell, M. D. Davis and A. F. Knowles, Arch. Biochem. Biophys., 1999, 362, 46-58.
46. (a) K. Enjyoji, J. Sevingy, Y. Lin, P. S. Fenette, P. D. Christie, J. Schulteam Esch II, M. Imai, J. M. Edleberg, H. Rayburn, M. Lecht, D. L. Beller, E. Csizmadia, D. D. Wagner, S. C. Robson and R. D. Rosenburg, Nat. Med., 1999, 5, 101-1017
47. (b) C. Goepfert, C. Sundberg, J. Sévigny, K. Enjyoji, T. Hoshi, E. Csizadia and S. C. Robson, Circulation, 2001, 104, 3109-15
48. (c) N. Mizumoto, T. Kumamoto, S. C. Robson, J. Sévigny, H. Matsue, K. Enjyoji and A. Takashima, Nat. Med., 2002, 8, 358-365.
49. D. Lebel, G. G. Poirier, S. Phaneuf, P. St Jean, J. F. Laliberte and A. R. Beaudoin, J. Biol. Chem., 1980, 255, 1227-1233.
50. J.-F. Laliberté, P. St-Jean and A. R. Beaudoin, J. Biol. Chem., 1982, 257, 3869-3874.
51. Y. Côté, P. St-Jean, R. Béliveau, M. Potier and A. R. Beaudoin, Biochim. Biophys. Acta, 1991, 1078, 87-191.
52. (a) R. Lemmens, L. Vanduffel, A. Kittel, A. R. Beaudoin, O. Benzrezzak and J. Sevigny, Eur. J. Biochem., 2000, 267, 4106-4114
53. (b) E. J. Schulte Am, J. Sevigny, E. Kaczmarek, J. B. Siegel, M. Imai, K. Koziak, A. R. Beaudoin and S. C. Robson, Biochemistry, 1999, 38, 2248-2258.
54. T. M. Smith and T. L. Kirley, Biochemistry, 1999, 38, 321-328.
55. (a) S. C. Robson, S. Daoud, M. Bégin, Y. P. Côté, J. B. Siegel, F. H. Bach and A. R. Beaudoin, Blood Coagulation Fibrinolysis, 1997, 8, 21-27
56. (b) T. F. Wang, Y. Ou and G. Guidotti, J. Biol. Chem., 1998, 273, 24814-24821
57. (c) A. Grinthal and G. Guidotti, Biochemistry, 2002, 41, 1947-1956.
58. (a) G. V. R. Born, Nature, 1962, 194, 927-929
59. (b) H. Zimmermann, Nat. Med., 1999, 5, 987-988
60. (c) A. J. Marcus, M. J. Broekman, J. H. F. Drosopoulos, N. Islam, T. N. Alyonycheva, L. B. Safier, K. A. Hajjar, D. N. Posnett, M. A. Schoenborn, K. A. Schooley, R. B. Gayle and C. R. Maliszewski, J. Clin. Invest., 1997, 99, 1351-1360
61. (d) A. J. Marcus and L. B. Safier, FASEB J., 1993, 7, 516-522
62. (e) A. R. Beaudoin, J. Sévigny, F. P. Gendron, M. St-Georges, M. C. Leclerc, in Emerging Therapeutic Targets, ed A. Ward, Ashley Publications Ltd, 1998, Vol. II.
63. F. P. Gendron, E. Halbfinger, B. Fischer, M. Duval, P. D'Orleans-Juste and A. R. Beaudoin, J. Med. Chem., 2000, 43, 2239-2247.
64. E. Halbfinger, D. T. Major, M. Ritzmann, J. Ubl, G. Reiser, J. L. Boyer, K. T. Harden and B. Fischer, J. Med. Chem., 1999, 42, 5325-5337.
65. (a) J. Brunner, Ann. Rev. Biochem., 1993, 62, 483-514
66. (b) Y. Hatanaka, H. Nakayama and Y. Kanaoka, Rev. Heteroat. Chem., 1996, 14, 213-243
67. (c) Y. Hatanaka, M. Hashimoto, H. Nakayama, Y. Kanaoka, L. Sun and H. D. Showalter, Chemtracts: Org. Chem., 1994, 7, 235-237.
68. Y. Hatanaka, E. Yoshida, H. Nakayama and Y. KanaoKa, Bioorg. Chem., 1989, 17, 482-485.
69. (a) J. A. Burns, J. C. Butler, J. Moran and G. M. Whitesides, J. Org. Chem., 1991, 56, 2648-2650
70. (b) J. C. Han and G. Y. Han, Anal. Biochem., 1994, 220, 5-10.
71. (a) S. Margel, S. Gura, H. Bamnolker, B. Nitzan, T. Tennenbaum, B. Bar-Toov, M. Hinz, H. Seliger, in Scientific and Clinical Applications of Magnetic Carriers, ed. U. Hafeli, Plenum Press, New York, 1997
72. (b) H. Baumnolker, B. Nitzan, S. Gura and S. Margel, J. Mater. Sci. Lett., 1997, 16, 1412
73. (c) S. Margel, I. Burdygin, V. Reznikov, B. Nitzan, O. Melamed, M. Sadeh, S. Gura, G. Mandel, M. Zuberi, L. Boguslavsky, in Recent Research Developments in Polymer Science, ed. S. G. Patidalai, Transworld Research Network, 1997, Vol. 1, 51-78
74. (d) S. Margel, I. Burdygin, S. Gura, H. Bamnolker, B. Nitzan, M. Kedem, O. Melamed, M. Zuberi, J. Mandel, L. Boguslavsky, L. Sheihet, T. Tennenbaum and B. Bar-Toov, Nippon Oyo Jiki Gakkaishi, 1998, 22,(S1), 429.
75. J. E. Baldwin, C. D. Jesudason, M. G. Moloney, D. R. Morgan and A. J. Pratt, Tetrahedron, 1991, 47, 5603-5614.
76. L. Horner and E. H. Winkelmann, Angew. Chem., 1959, 71, 349-392.
77. (a) G. Li and R. Bittman, Tetrahedron Lett., 2000, 6737-3741
78. (b) C. W. G. Fishwick and J. M. Sanderson, Tetrahedron Lett., 1994, 4611-4614
79. (c) A. P. Marchand and K. A. Kumar, Tetrahedron, 1998, 15105-15112
80. (d) W. R. White, M. G. Platz, N. Chen and M. Jones, J. Am. Chem. Soc., 1990, 7794-7796
81. (e) J. E. Baldwin, C. D. Jesudason, M. G. Moloney, D. R. Morgan and A. J. Pratt, Tetrahedron, 1991, 5603-5614.
82. K. A. Jacobson, B. Fischer and X. Ji, Bioconjugate Chem., 1995, 6, 255-263.
83. B. Fischer, J. L. Boyer, C. H. V. Hoyle, A. V. Ziganshin, A. L. Brizzolara, G. E. Knight, J. Zimmet, G. Burnstock, T. K. Harden and K. A. Jacobson, J. Med. Chem., 1993, 36, 3937-3946.
84. M. R. Maurizi and A. Ginsburg, Biochemistry, 1986, 25, 131-140.
85. S. V. Kulikov and M. A. Samartsev, Khim. Prir. Soedin., 1987, 4, 613-614.
86. F. Wolfgang and C. Friedrich, Nucleic Acid Chem., 1964, 143, 827-836.
87. R. E. Humphrey, M. H. Ward and W. Hinze, Anal. Chem., 1970, 42, 698.
88. H. Bergmeyer, H. Grassl, H-E. Walter and H. U. Bergmeyer, eds. Methods of Enzymatic Analysis, 3rd ed., 1983, Vol. 2, p. 222.
89. (a) A. Traverso-Cori, H. Chatmovich and O. Cori, Arch. Biochem. Biophys., 1965, 109, 173-184
90. (b) personal observation.
91. A. A. Baykov, O. A. Evtushenko and S. M. Avaeva, Anal. Biochem., 1988, 171, 266-270.
92. T. P. Geladopoulos, T. G. Sotiroudis and A. E. Evangelopoulos, Anal. Biochem., 1991, 192, 112-116.
93. M. Zofall and B. Bartholomew, Nucleic Acids Res., 2000, 28, 4382-4390.
94. A. N. Mayer and F. Barany, Gene, 1995, 153, 1-8.
95. H. Bamnolker and S. J. Margel, J. Polym. Sci., Chem. Ed., 1996, 34, 1857-1871.
96. W. Stober, A. Fink and E. Bohn, J. Colloid Interface Sci., 1968, 26, 62-69.
97. P. Wikstrom, C. F. Mandenius and P. O. Larsson, J. Chromatogr., 1988, 455, 105-117.
98. J. Sevigny, F. P. Levesque, G. Grondin and A. R. Beaudoin, Biochim. Biophys. Acta, 1997, 1334, 73-88.
99. M. M. Bradford, Anal. Biochem., 1976, 72, 248-254.
100. A. M. Kettlun, L. Uribe, V. Calvo, S. Silva, J. Rivera, M. Mancilla, M. A. Valenzuela and A. Traverso-Cori, Phytochemistry, 1982, 21, 551-558.