Diazirine based photoaffinity labeling

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 2, 2012, Pages 554-570

  Dubinsky, Luba ^a   Krom, Bastiaan P ^b   Meijler, Michael M ^a  

^a BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

^b UNIVERSITY MEDICAL CENTER GRONINGEN   (Netherlands)

Author keywords

Chemical proteomics; Diazirine; Photoaffinity labeling; Photochemistry; Protein profiling

Indexed keywords

4 AMINOBUTYRIC ACID RECEPTOR BLOCKING AGENT; AMINO ACID DERIVATIVE; ANESTHETIC AGENT; ANTIBIOTIC AGENT; ANTINEOPLASTIC AGENT; ARYLAZIDE DERIVATIVE; BAFILOMYCIN A1; BENZOPHENONE DERIVATIVE; BRASSINOSTEROID; CERAMIDE DIAZIRINE DERIVATIVE; DANTROLENE; DIAZIRINE DERIVATIVE; DIAZIRINNYL AMINOACID; ETOMIDATE; FUBENDIAMIDE DIAZIRINE DERIVATIVE; HARKOSERIDE; ISOLESPEDEZATE POTASSIUM; ISPINESIB; JASMONIC ACID; LIPOXYGENASE INHIBITOR; MATRIX METALLOPROTEINASE INHIBITOR; PAEONIFLORIN; PHYTOHORMONE; PROPOFOL; PROTEASOME INHIBITOR; PROTEIN KINASE INHIBITOR; SIALIC ACID DERIVATIVE; TANSHINONE; TRIFLUOROMETHYLDIAZIRINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

AMINO ACID COMPOSITION; BIOLOGICAL ACTIVITY; CALCIUM SIGNALING; CALCIUM TRANSPORT; DRUG BINDING SITE; DRUG DESIGN; DRUG LABELING; DRUG MECHANISM; DRUG OXIDATION; DRUG PROTEIN BINDING; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; HUMAN; IRRADIATION; LIGAND BINDING; MALIGNANT HYPERTHERMIA; NEUROCHEMISTRY; NONHUMAN; PHOTOAFFINITY LABELING; PHOTOCHEMISTRY; PROTEIN ANALYSIS; PROTEIN ISOLATION; PROTEIN LIPID INTERACTION; PROTEIN PROTEIN INTERACTION; PROTEOMICS; RECEPTOR AFFINITY; REVIEW; THERMOSTABILITY;

EID: 84855816511     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.06.066     Document Type: Article

References (125)

1. A. Singh, E.R. Thornton, and F.H. Westheimer J. Biol. Chem. 237 1962 3006
2. A. Sinz ChemMedChem 2 2007 425
3. G.D. Prestwich, G. Dorman, J.T. Elliott, D.M. Marecak, and A. Chaudhary Photochem. Photobiol. 65 1997 222
4. M.S. Platz Acc. Chem. Res. 28 1995 487
5. W.L. Karney, and W.T. Borden J. Am. Chem. Soc. 119 1997 3347
6. H. Nakayama, Y. Hatanaka, M. Taki, E. Yoshida, and Y. Kanaoka Ann. N.Y. Acad. Sci. 707 1993 349
7. Y. Hatanaka, and Y. Sadakane Curr. Top. Med. Chem. 2 2002 271
8. Gilchrist, T. L.; Rees, C. W. Carbenes, Nitrenes and Arynes; The Pitman Press: Bath, 1969.
9. P.H. Mueller, N.G. Rondan, K.N. Houk, J.F. Harrison, D. Hooper, B.H. Willen, and J.F. Liebman J. Am. Chem. Soc. 103 1981 5049
10. J.M. Perez J. Chem. Soc., Faraday Trans. I 78 1982 3509
11. H.D. Roth J. Am. Chem. Soc. 93 1971 4935
12. Y. Zhang, G. Burdzinski, J. Kubicki, and M.S. Platz J. Am. Chem. Soc. 130 2008 16134
13. R.A. Moss, Z. Lu, and R.R. Sauers Tetrahedron Lett. 51 2010 5940
14. B. Noller, L. Poisson, R. Maksimenka, O. Gobert, I. Fischer, and J.M. Mestdagh J. Phys. Chem. A 113 2009 3041
15. B. Noller, P. Hemberger, I. Fischer, C. Alcaraz, G.A. Garcia, and H. Soldi-Lose Phys. Chem. Chem. Phys. 11 2009 5384
16. R.A.G. Smith, and J.R. Knowles J. Am. Chem. Soc. 95 1973 5072
17. J. Brunner, H. Senn, and F.M. Richards J. Biol. Chem. 255 1980 3313
18. J. Wang, J. Kubicki, H. Peng, and M.S. Platz J. Am. Chem. Soc. 130 2008 6604
19. A. Blencowe, and W. Hayes Soft Matter 1 2005 178
20. N. Burkard, T. Bender, J. Westmeier, C. Nardmann, M. Huss, H. Wieczorek, S. Grond, and P. von Zezschwitz Eur. J. Org. Chem. 11 2010 2176
21. Z. Song, and Q. Zhang Org. Lett. 11 2009 4882
22. G. Keglevich, I. Csontos, N. Szilagyi, and I. Greiner Chem. Eng. Technol. 31 2008 421
23. S.S. Carrera, J.L. Kerdelhué, K.J. Langenwalter, N. Brown, and R. Warmuth Eur. J. Org. Chem. 2005 2005 2239
24. N.S. Kumar, and R.N. Young Bioorg. Med. Chem. 17 2009 5388
25. M. Gu, J. Yan, Z. Bai, Y.T. Chen, W. Lu, J. Tang, L. Duan, D. Xie, and F.J. Nan Bioorg. Med. Chem. 18 2010 3012
26. K.M. Broadus, and S.R. Kass J. Org. Chem. 65 2000 6566
27. L. Dubinsky, L.M. Jarosz, N. Amara, P. Krief, V.V. Kravchenko, B.P. Krom, and M.M. Meijler Chem. Commun. (Camb) 2009 7378
28. G. Wagner, W. Knoll, M.M. Bobek, L. Brecker, H.W.G. van Herwijnen, and U.H. Brinker Org. Lett. 12 2010 332
29. M. Al-Omari, K. Banert, and M. Hagedorn Angew. Chem., Int. Ed. 45 2006 309
30. M.D. Vedenyapina, V.V. Kuznetsov, E.A. Nizhnikovskii, E.D. Strel'tsova, N.N. Makhova, M.I. Struchkova, and A.A. Vedenyapin Russ. Chem. Bull. 55 2006 2013
31. B.F. Cravatt, and E.J. Sorensen Curr. Opin. Chem. Biol. 4 2000 663
32. Y. Liu, M.P. Patricelli, and B.F. Cravatt Proc. Natl. Acad. Sci. U.S.A. 96 1999 14694
33. D. Kidd, Y. Liu, and B.F. Cravatt Biochemistry 40 2001 4005
34. M.P. Patricelli, D.K. Giang, L.M. Stamp, and J.J. Burbaum Proteomics 1 2001 1067
35. D. Greenbaum, K.F. Medzihradszky, A. Burlingame, and M. Bogyo Chem. Biol. 7 2000 569
36. D. Kato, K.M. Boatright, A.B. Berger, T. Nazif, G. Blum, C. Ryan, K.A.H. Chehade, G.S. Salvesen, and M. Bogyo Nat. Chem. Biol. 1 2005 33
37. Y.M. Li, M. Xu, M.T. Lai, Q. Huang, J.L. Castro, J. DiMuzio-Mower, T. Harrison, C. Lellis, A. Nadin, J.G. Neduvelil, R.B. Register, M.K. Sardana, M.S. Shearman, A.L. Smith, X.P. Shi, K.C. Yin, J.A. Shafer, and S.J. Gardell Nature 405 2000 689
38. A. Saghatelian, N. Jessani, A. Joseph, M. Humphrey, and B.F. Cravatt Proc. Natl. Acad. Sci. U.S.A. 101 2004 10000
39. M.P. Patricelli, A.K. Szardenings, M. Liyanage, T.K. Nomanbhoy, M. Wu, H. Weissig, A. Aban, D. Chun, S. Tanner, and J.W. Kozarich Biochemistry 46 2007 350
40. D.J. Vocadlo, H.C. Hang, E.J. Kim, J.A. Hanover, and C.R. Bertozzi Proc. Natl. Acad. Sci. U.S.A. 100 2003 9116
41. C.M. Salisbury, and B.F. Cravatt Proc. Natl. Acad. Sci. U.S.A. 104 2007 1171
42. G.C. Adam, E.J. Sorensen, and B.F. Cravatt Nat. Biotechnol. 20 2002 805
43. T. Kinoshita, A. Cano-Delgado, H. Seto, S. Hiranuma, S. Fujioka, S. Yoshida, and J. Chory Nature 433 2005 167
44. J. Yan, C. Zhang, M. Gu, Z. Bai, W. Zhang, T. Qi, Z. Cheng, W. Peng, H. Luo, F. Nan, Z. Wang, and D. Xie Plant Cell 21 2009 2220
45. Y. Nakamura, R. Miyatake, and M. Ueda Angew. Chem. 47 2008 7289
46. Y. Nakamura, S. Inomata, M. Ebine, Y. Manabe, I. Iwakura, and M. Ueda Org. Biomol. Chem. 9 2011 83
47. T. Fujii, Y. Manabe, T. Sugimoto, and M. Ueda Tetrahedron 61 2005 7874
48. Y. Manabe, M. Mukai, S. Ito, N. Kato, and M. Ueda Chem. Commun. 46 2010 469
49. Y. Wang, K.D. Park, C. Salome, S.M. Wilson, J.P. Stables, R. Liu, R. Khanna, and H. Kohn ACS Chem. Neurosci. 2 2011 90
50. L. Balas, T. Durand, S. Saha, I. Johnson, and S. Mukhopadhyay J. Med. Chem. 52 2009 1005
51. D. Riber, M. Venkataramana, S. Sanyal, and T. Duvold J. Med. Chem. 49 2006 1503
52. T. Hosoya, T. Hiramatsu, T. Ikemoto, H. Aoyama, T. Ohmae, M. Endo, and M. Suzuki Bioorg. Med. Chem. Lett. 15 2005 1289
53. K. Kato, S. Kiyonaka, Y. Sawaguchi, M. Tohnishi, T. Masaki, N. Yasokawa, Y. Mizuno, E. Mori, K. Inoue, I. Hamachi, H. Takeshima, and Y. Mori Biochemistry 48 2009 10342
54. J.S. Lee, S.Y. Han, M.S. Kim, C.M. Yu, M.H. Kim, S.H. Kim, Y.K. Min, and B.T. Kim Bioorg. Med. Chem. Lett. 16 2006 4733
55. W.W. Qiu, J. Xu, D.Z. Liu, J.Y. Li, Y. Ye, X.Z. Zhu, J. Li, and F.J. Nan Bioorg. Med. Chem. Lett. 16 2006 3306
56. L. Luo, C.A. Parrish, N. Nevins, D.E. McNulty, A.M. Chaudhari, J.D. Carson, V. Sudakin, A.N. Shaw, R. Lehr, H. Zhao, S. Sweitzer, L. Lad, K.W. Wood, R. Sakowicz, R.S. Annan, P.S. Huang, J.R. Jackson, D. Dhanak, R.A. Copeland, and K.R. Auger Nat. Chem. Biol. 3 2007 722
57. R.G. Eckenhoff Mol. Interv. 1 2001 258
58. R.G. Eckenhoff, J. Xi, M. Shimaoka, A. Bhattacharji, M. Covarrubias, and W.P. Dailey ACS Chem. Neurosci. 1 2010 139
59. M.A. Hall, J. Xi, C. Lor, S. Dai, R. Pearce, W.P. Dailey, and R.G. Eckenhoff J. Med. Chem. 53 2010 5667
60. M. Bali, and M.H. Akabas Mol. Pharmacol. 65 2004 68
61. S.S. Husain, S. Nirthanan, D. Ruesch, K. Solt, Q. Cheng, G.D. Li, E. Arevalo, R.W. Olsen, D.E. Raines, S.A. Forman, J.B. Cohen, and K.W. Miller J. Med. Chem. 49 2006 4818
62. W.L. Karney, and W.T. Borden J. Am. Chem. Soc. 119 1997 1378
63. M. Liao, J.M. Sonner, S.S. Husain, K.W. Miller, R. Jurd, U. Rudolph, and E.I. Eger II Anesth. Analg. 101 2005 131
64. S.S. Husain, D. Stewart, R. Desai, A.K. Hamouda, S.G.D. Li, E. Kelly, Z. Dostalova, X. Zhou, J.F. Cotten, D.E. Raines, R.W. Olsen, J.B. Cohen, S.A. Forman, and K.W. Miller J. Med. Chem. 53 2010 6432
65. X. Li, J.H. Cao, Y. Li, P. Rondard, Y. Zhang, P. Yi, J.F. Liu, and F.J. Nan J. Med. Chem. 51 2008 3057
66. J.P. Changeux, and S.J. Edelstein Nicotinic Acetylcholine Receptors: From Molecular Biology to Cognition 2005 Odile Jacob Publishing New York
67. R.J.C. Hilf, and R. Dutzler Nature 457 2009 115
68. J.M.E. Cederholm, P.R. Schofield, and T.M. Lewis Eur. Biophys. J. 39 2009 37
69. J. Brunner, and G. Semenza Biochemistry 20 1981 7174
70. G.H. Addona, M.A. Kloczewiak, and K.W. Miller Anal. Biochem. 267 1999 135
71. E. Arevalo, D.C. Chiara, S.A. Forman, J.B. Cohen, and K.W. Miller J. Biol. Chem. 280 2005 13631
72. I.H. Yamodo, D.C. Chiara, J.B. Cohen, and K.W. Miller Biochemistry 49 2010 156
73. N.S. Kumar, M.P. Braun, A.G. Chaudhary, and R.N. Young J. Labelled Compd. Radiopharm. 54 2011 43
74. M. Sanghvi, A.K. Hamouda, M.I. Davis, R.A. Morton, S. Srivastava, A. Pandhare, P.K. Duddempudi, T.K. Machu, D.M. Lovinger, J.B. Cohen, and M.P. Blanton Biochemistry 48 2009 9278
75. A.V. Maricq, A.S. Peterson, A.J. Brake, R.M. Myers, and D. Julius Science 254 1991 432
76. D.C. Reeves, and S.C.R. Lummis Mol. Membr. Biol. 19 2002 11
77. T. Yamamoto, H. Hasegawa, T. Hakogi, and S. Katsumura Org. Lett. 8 2006 5569
78. M. Hashimoto, and Y. Hatanaka Bioorg. Med. Chem. Lett. 18 2008 650
79. M. Suchanek, A. Radzikowska, and C. Thiele Nat. Methods 2 2005 261
80. T. Durek, J. Zhang, C. He, and S.B.H. Kent Org. Lett. 9 2007 5497
81. M. Vila-Perello, M.R. Pratt, F. Tulin, and T.W. Muir J. Am. Chem. Soc. 129 2007 8068
82. A.L. MacKinnon, J.L. Garrison, R.S. Hegde, and J. Taunton J. Am. Chem. Soc. 129 2007 14560
83. C.Y. Jiao, I.D. Alves, V. Point, S. Lavielle, S. Sagan, and G. Chassaing Bioconjugate Chem. 21 2010 352
84. C. Chou, R. Uprety, L. Davis, J.W. Chin, and A. Deiters Chem. Sci. 2 2011 480
85. H. Nakashima, M. Hashimoto, Y. Sadakane, T. Tomohiro, and Y. Hatanaka J. Am. Chem. Soc. 128 2006 15092
86. D. Fillion, M. Deraet, B.J. Holleran, and E. Escher J. Med. Chem. 49 2006 2200
87. E.M. Tippmann, W. Liu, D. Summerer, A.V. Mack, and P.G. Schultz ChemBioChem 8 2007 2210
88. K. Masuda, A. Koizumi, T. Misaka, Y. Hatanaka, K. Abe, T. Tanaka, M. Ishiguro, and M. Hashimoto Bioorg. Med. Chem. Lett. 20 2010 1081
89. N. Srinivas, P. Jetter, B.J. Ueberbacher, M. Werneburg, K. Zerbe, J. Steinmann, B. Van der Meijden, F. Bernardini, A. Lederer, R.L.A. Dias, P.E. Misson, H. Henze, J. Zumbrunn, F.O. Gombert, D. Obrecht, P. Hunziker, S. Schauer, U. Ziegler, A. Kach, L. Eberl, K. Riedel, S.J. DeMarco, and J.A. Robinson Science 327 2010 1010
90. B. Oberfeld, J. Brunner, and P. Dimroth Biochemistry 45 2006 1841
91. T. Bender, M. Huss, H. Wieczorek, S. Grond, and P. von Zezschwitz Eur. J. Org. Chem. 2007 3870
92. S.M. Hancock, R. Uprety, A. Deiters, and J.W. Chin J. Am. Chem. Soc. 132 2010 14819
93. G.-L. Chee, J.C. Yalowich, A. Bodner, X. Wu, and B.B. Hasinoff Bioorg. Med. Chem. 18 2010 830
94. N. Kakutani, M. Murai, N. Sakiyama, and H. Miyoshi Biochemistry 49 2010 4794
95. M. Murai, A. Ishihara, T. Nishioka, T. Yagi, and H. Miyoshi Biochemistry 46 2007 6409
96. M.W.H. Pinkse, D.T.S. Rijkers, W.R. Dostmann, and A.J.R. Heck J. Biol. Chem. 284 2009 16354
97. M. Kaneda, S. Masuda, T. Tomohiro, and Y. Hatanaka ChemBioChem 8 2007 595
98. L.R. Odell, N. Chau, A. Mariana, M.E. Graham, P.J. Robinson, and A. McCluskey ChemMedChem 4 2009 1182
99. W.J. Mortier, J. Sauer, J.A. Lercher, and H. Noller J. Phys. Chem. 88 1984 905
100. S. Chattopadhaya, E.W.S. Chan, and S.Q. Yao Tetrahedron Lett. 46 2005 4053
101. H. Fuwa, Y. Takahashi, Y. Konno, N. Watanabe, H. Miyashita, M. Sasaki, H. Natsugari, T. Kan, T. Fukuyama, T. Tomita, and T. Iwatsubo ACS Chem. Biol. 2 2007 408
102. Y. Morohashi, T. Kan, Y. Tominari, H. Fuwa, Y. Okamura, N. Watanabe, C. Sato, H. Natsugari, T. Fukuyama, T. Iwatsubo, and T. Tomita J. Biol. Chem. 281 2006 14670
103. T. Kan, Y. Kita, Y. Morohashi, Y. Tominari, S. Hosoda, T. Tomita, H. Natsugari, T. Iwatsubo, and T. Fukuyama Org. Lett. 9 2007 2055
104. S. Baumann, N. Hottecke, R. Schubenel, K. Baumann, and B. Schmidt Bioorg. Med. Chem. Lett. 19 2009 6986
105. R. Kannappan, M. Ando, K. Furuhata, and Y. Uda Biol. Pharm. Bull. 31 2008 352
106. Y. Tanaka, and J.J. Kohler J. Am. Chem. Soc. 130 2008 3278
107. M.R. Bond, H. Zhang, P.D. Vu, and J.J. Kohler Nat. Protoc. 4 2009 1044
108. M. Wiegand, and T.K. Lindhorst Eur. J. Org. Chem. 2006 4841
109. W.-W. Qiu, J. Xu, J.-Y. Li, J. Li, and F.-J. Nan ChemBioChem 8 2007 1351
110. E.W.S. Chan, S. Chattopadhaya, R.C. Panicker, X. Huang, and S.Q. Yao J. Am. Chem. Soc. 126 2004 14435
111. S.A. Sieber, S. Niessen, H.S. Hoover, and B.F. Cravatt Nat. Chem. Biol. 2 2006 274
112. M.A. Leeuwenburgh, P.P. Geurink, T. Klein, H.F. Kauffman, G.A. van der Marel, R. Bischoff, and H.S. Overkleeft Org. Lett. 8 2006 1705
113. W. Qiu, J. Xu, X. Li, L. Zhong, J. Li, J. Li, and F. Nan Chin. J. Chem. 27 2009 825
114. H. Ovaa, P.F. van Swieten, B.M. Kessler, M.A. Leeuwenburgh, E. Fiebiger, A.M.C.H. van den Nieuwendijk, P.J. Galardy, G.A. van der Marel, H.L. Ploegh, and H.S. Overkleeft Angew. Chem. Int. Ed. Engl. 42 2003 3626
115. B.M. Kessler, D. Tortorella, M. Altun, A.F. Kisselev, E. Fiebiger, B.G. Hekking, H.L. Ploegh, and H.S. Overkleeft Chem. Biol. 8 2001 913
116. P.P. Geurink, B.I. Florea, G.A. Van der Marel, B.M. Kessler, and H.S. Overkleeft Chem. Commun. 46 2010 9052
117. M. Liebmann, F. Di Pasquale, and A. Marx ChemBioChem 7 2006 1965
118. M. Winnacker, S. Breeger, R. Strasser, and T. Carell ChemBioChem 10 2009 109
119. U.K. Shigdel, J. Zhang, and C. He Angew. Chem., Int. Ed. 47 2008 90
120. Z. Qiu, L. Lu, X. Jian, and C. He J. Am. Chem. Soc. 130 2008 14398
121. S. Kuboe, M. Yoda, A. Ogata, Y. Kitade, Y. Tomari, and Y. Ueno Chem. Commun. 46 2010 7367
122. N.B. Bongo, T. Tomohiro, and Y. Hatanaka Bioorg. Med. Chem. Lett. 19 2009 80
123. Y. Kotake, K. Sagane, T. Owa, Y. Mimori-Kiyosue, H. Shimizu, M. Uesugi, Y. Ishihama, M. Iwata, and Y. Mizui Nat. Chem. Biol. 3 2007 570
124. T. Kuroda, K. Suenaga, A. Sakakura, T. Handa, K. Okamoto, and H. Kigoshi Bioconjugate Chem. 17 2006 524
125. N. Maezawa, H. Tsuchikawa, S. Katsumura, T. Kubo, and S. Imaoka Bioorg. Med. Chem. Lett. 17 2007 5121