Gd(III)-PyMTA label is suitable for in-cell EPR

Journal of the American Chemical Society

Volumn 136, Issue 43, 2014, Pages 15366-15378

  Qi, Mian ^a   Groß, Andreas ^b   Jeschke, Gunnar ^c   Godt, Adelheid ^a   Drescher, Malte ^b  

^a BIELEFELD UNIVERSITY   (Germany)

^b UNIVERSITY OF KONSTANZ   (Germany)

^c ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CELL MEMBRANES; CYTOLOGY; ELECTRON RESONANCE; ENZYME ACTIVITY; PARAMAGNETIC RESONANCE; PEPTIDES; SPIN DYNAMICS;

CONFORMATIONAL FLEXIBILITY; DOUBLE ELECTRON-ELECTRON RESONANCE; ELECTRON PARAMAGNETIC RESONANCE SPECTROSCOPY; INTRACELLULAR PEPTIDES; NITROXIDE SPIN LABELS; SITE-DIRECTED SPIN LABELING; STRUCTURE AND DYNAMICS; XENOPUS LAEVIS OOCYTES;

ELECTRON SPIN RESONANCE SPECTROSCOPY;

CELL EXTRACT; CYSTEINE; GADOLINIUM; AMINO ACID; ORGANOMETALLIC COMPOUND; PEPTIDE; SPIN LABELING;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; ELECTRON SPIN RESONANCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; LIPOPHILICITY; MICHAEL ADDITION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; OOCYTE; PH; PROTEIN CONFORMATION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SIGNAL NOISE RATIO; SPIN LABELING; STRUCTURE ANALYSIS; SUZUKI REACTION; SYNTHESIS; XENOPUS LAEVIS; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; CYTOLOGY; PROCEDURES; PROTEIN SECONDARY STRUCTURE;

AMINO ACIDS; ANIMALS; ELECTRON SPIN RESONANCE SPECTROSCOPY; GADOLINIUM; MODELS, MOLECULAR; OOCYTES; ORGANOMETALLIC COMPOUNDS; PEPTIDES; PROTEIN STRUCTURE, SECONDARY; SPIN LABELS; XENOPUS LAEVIS;

EID: 84908632241     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja508274d     Document Type: Article

References (96)

1. Serber, Z.; Corsini, L.; Durst, F.; Dötsch, V. In Methods in Enzymology; Thomas, L. J., Ed.; Academic Press: Burlington, 2005; Vol. 394, p 17.
2. Hubbard, J. A.; MacLachlan, L. K.; King, G. W.; Jones, J. J.; Fosberry, A. P. Mol. Microbiol. 2003, 49, 1191
3. Dedmon, M. M.; Patel, C. N.; Young, G. B.; Pielak, G. J. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 12681
4. Wieruszeski, J. M.; Bohin, A.; Bohin, J. P.; Lippens, G. J. Magn. Reson. 2001, 151, 118
5. Serber, Z.; Keatinge-Clay, A. T.; Ledwidge, R.; Kelly, A. E.; Miller, S. M.; Dötsch, V. J. Am. Chem. Soc. 2001, 123, 2446
6. Serber, Z.; Ledwidge, R.; Miller, S. M.; Dötsch, V. J. Am. Chem. Soc. 2001, 123, 8895
7. Sakai, T.; Tochio, H.; Tenno, T.; Ito, Y.; Kokubo, T.; Hiroaki, H.; Shirakawa, M. J. Biomol. NMR 2006, 36, 179
8. Selenko, P.; Serber, Z.; Gadea, B.; Ruderman, J.; Wagner, G. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 11904
9. Serber, Z.; Selenko, P.; Hansel, R.; Reckel, S.; Lohr, F.; Ferrell, J. E.; Wagner, G.; Dotsch, V. Nat. Protoc. 2007, 1, 2701
10. Miyawaki, A.; Llopis, J.; Heim, R.; McCaffery, J. M.; Adams, J. A.; Ikura, M.; Tsien, R. Y. Nature 1997, 388, 882
11. Hänsel, R.; Luh, L. M.; Corbeski, I.; Trantirek, L.; Dötsch, V. Angew. Chem., Int. Ed. 2014, 53, 2
12. Schiemann, O.; Piton, N.; Plackmeyer, J.; Bode, B. E.; Prisner, T. F.; Engels, J. W. Nat. Protoc. 2007, 2, 904
13. Hubbell, W. L.; Cafiso, D. S.; Altenbach, C. Nat. Struct. Mol. Biol. 2000, 7, 735
14. Altenbach, C.; Marti, T.; Khorana, H.; Hubbell, W. Science 1990, 248, 1088
15. Jeschke, G.; Pannier, M.; Godt, A.; Spiess, H. W. Chem. Phys. Lett. 2000, 331, 243
16. Jeschke, G. Annu. Rev. Phys. Chem. 2012, 63, 419
17. Milov, A. D.; Salikhov, K. M.; Shchirov, M. D. Fizika Tverdogo Tela 1981, 23, 975
18. Yu, D. T.; Milov, A. D.; Maryasov, A. G. Russ. Chem. Rev. 2008, 77, 487
19. Martin, R. E.; Pannier, M.; Diederich, F.; Gramlich, V.; Hubrich, M.; Spiess, H. W. Angew. Chem., Int. Ed. 1998, 37, 2833
20. Jeschke, G.; Sajid, M.; Schulte, M.; Ramezanian, N.; Volkov, A.; Zimmermann, H.; Godt, A. J. Am. Chem. Soc. 2010, 132, 10107
21. Hubbell, W. L.; Altenbach, C. Curr. Opin. Struct. Biol. 1994, 4, 566
22. Constantine, K. L. Biophys. J. 2001, 81, 1275
23. Jeschke, G.; Polyhach, Y. Phys. Chem. Chem. Phys. 2007, 9, 1895
24. Steinhoff, H.-J.; Suess, B. Methods 2003, 29, 188
25. Rabenstein, M. D.; Shin, Y. K. Proc. Natl. Acad. Sci. U. S. A. 1995, 92, 8239
26. Jeschke, G.; Bender, A.; Paulsen, H.; Zimmermann, H.; Godt, A. J. Magn. Reson. 2004, 169, 1
27. Borbat, P. P.; Davis, J. H.; Butcher, S. E.; Freed, J. H. J. Am. Chem. Soc. 2011, 126, 7746
28. Eaton, S.; Eaton, G. In Distance Measurements in Biological Systems by EPR; Berliner, L. J.; Eaton, G. R.; Eaton, S. S., Eds.; Springer: New York, NY, 2002; Vol. 19, p 1.
29. Drescher, M. In EPR Spectroscopy; Drescher, M.; Jeschke, G., Eds.; Springer: Berlin, Heidelberg, 2012; Vol. 321, p 91.
30. Ward, R.; Bowman, A.; Sozudogru, E.; El-Mkami, H.; Owen-Hughes, T.; Norman, D. G. J. Magn. Reson. 2010, 207, 164
31. Jeschke, G. ChemPhysChem 2002, 3, 927
32. Banham, J. E.; Timmel, C. R.; Abbott, R. J. M.; Lea, S. M.; Jeschke, G. Angew. Chem., Int. Ed. 2006, 45, 1058
33. Godt, A.; Schulte, M.; Zimmermann, H.; Jeschke, G. Angew. Chem., Int. Ed. 2006, 45, 7560
34. Jeschke, G.; Spiess, H. W. In Novel NMR and EPR Techniques; Dolinsek, J.; Vilfan, M.; Zumer, S.; Beig, R.; Beiglböck, W.; Domcke, W.; Englert, G.; Frisch, U.; Hänggi, P.; Hasinger, G.; Hepp, K.; Hillebrandt, W.; Imboden, D.; Jaffe, R. L.; Lipowsky, R.; Löhneysen, H. v.; Ojima, I.; Sornette, D.; Theisen, S.; Weise, W.; Wess, J.; Zittartz, J., Eds.; Springer: Berlin, 2006; Vol. 684, p 21.
35. Azarkh, M.; Okle, O.; Singh, V.; Seemann, I. T.; Hartig, J. S.; Dietrich, D. R.; Drescher, M. ChemBioChem 2011, 12, 1992
36. Azarkh, M.; Singh, V.; Okle, O.; Seemann, I. T.; Dietrich, D. R.; Hartig, J. S.; Drescher, M. Nat. Protoc. 2013, 8, 131
37. Krstic, I.; Hänsel, R.; Romainczyk, O.; Engels, J. W.; Dötsch, V.; Prisner, T. F. Angew. Chem., Int. Ed. 2011, 50, 5070
38. Singh, V.; Azarkh, M.; Exner, T. E.; Hartig, J. S.; Drescher, M. Angew. Chem., Int. Ed. 2009, 48, 9728
39. Igarashi, R.; Sakai, T.; Hara, H.; Tenno, T.; Tanaka, T.; Tochio, H.; Shirakawa, M. J. Am. Chem. Soc. 2010, 132, 8228
40. Azarkh, M.; Okle, O.; Eyring, P.; Dietrich, D. R.; Drescher, M. J. Magn. Reson. 2011, 212, 450
41. Xue, Y.; Liu, J.-q.; Zheng, K.-w.; Kan, Z.-y.; Hao, Y.-h.; Tan, Z. Angew. Chem., Int. Ed. 2011, 50, 8046
42. Xu, L.; Feng, S.; Zhou, X. Chem. Commun. 2011, 47, 3517
43. Carr, D. H.; Brown, J.; Bydder, G. M.; Steiner, R. E.; Weinmann, H. J.; Speck, U.; Hall, A. S.; Young, I. R. Am. J. Roentgenol. 1984, 143, 215
44. Bottrill, M.; Kwok, L.; Long, N. J. Chem. Soc. Rev. 2006, 35, 557
45. Lee, J.; Zylka, M. J.; Anderson, D. J.; Burdette, J. E.; Woodruff, T. K.; Meade, T. J. J. Am. Chem. Soc. 2005, 127, 13164
46. Jacques, V.; Desreux, J. In Contrast Agents I; Krause, W., Ed.; Springer: Berlin Heidelberg, 2002; Vol. 221, p 123.
47. Lueders, P.; Jeschke, G.; Yulikov, M. J. Phys. Chem. Lett. 2011, 2, 604
48. Goldfarb, D. Phys. Chem. Chem. Phys. 2014, 16, 9685
49. Song, Y.; Meade, T. J.; Astashkin, A. V.; Klein, E. L.; Enemark, J. H.; Raitsimring, A. J. Magn. Reson. 2011, 210, 59
50. Raitsimring, A. M.; Gunanathan, C.; Potapov, A.; Efremenko, I.; Martin, J. M. L.; Milstein, D.; Goldfarb, D. J. Am. Chem. Soc. 2007, 129, 14138
51. Potapov, A.; Song, Y.; Meade, T. J.; Goldfarb, D.; Astashkin, A. V.; Raitsimring, A. J. Magn. Reson. 2010, 205, 38
52. Gordon-Grossman, M.; Kaminker, I.; Gofman, Y.; Shai, Y.; Goldfarb, D. Phys. Chem. Chem. Phys. 2011, 13, 10771
53. Potapov, A.; Yagi, H.; Huber, T.; Jergic, S.; Dixon, N. E.; Otting, G.; Goldfarb, D. J. Am. Chem. Soc. 2010, 132, 9040
54. Martorana, A.; Bellapadrona, G.; Feintuch, A.; Di Gregorio, E.; Aime, S.; Goldfarb, D. J. Am. Chem. Soc. 2014, 136, 13458
55. Weinmann, H. J.; Brasch, R. C.; Press, W. R.; Wesbey, G. E. Am. J. Roentgenol. 1984, 142, 619
56. Bousquet, J. C.; Saini, S.; Stark, D. D.; Hahn, P. F.; Nigam, M.; Wittenberg, J.; Ferrucci, J. T. Radiology 1988, 166, 693
57. Cacheris, W. P.; Quay, S. C.; Rocklage, S. M. M. R. I. 1990, 8, 467
58. Chellquist, E. M.; Searle, R. J. Pharm. Biomed. Anal. 1993, 11, 985
59. Schuler, B.; Lipman, E. A.; Steinbach, P. J.; Kumke, M.; Eaton, W. A. Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 2754
60. Ungar-Waron, H.; Gurari, D.; Hurwitz, E.; Sela, M. Eur. J. Immunol. 1973, 3, 201
61. Polyhach, Y.; Bordignon, E.; Jeschke, G. Phys. Chem. Chem. Phys. 2011, 13, 2356
62. Kosen, P. A. Methods Enzymol. 1989, 177, 86
63. Griffith, O. H.; McConnell, H. M. Proc. Natl. Acad. Sci. U. S. A. 1966, 55, 8
64. Yang, Y.; Li, Q.-F.; Cao, C.; Huang, F.; Su, X.-C. Chem.-Eur. J. 2013, 19, 1097
65. Pellegatti, L.; Zhang, J.; Drahos, B.; Villette, S.; Suzenet, F.; Guillaumet, G.; Petoud, S.; Toth, E. Chem. Commun. 2008, 6591
66. Molander, G. A.; Brown, A. R. J. Org. Chem. 2006, 71, 9681
67. Braun, S.; Kalinowski, H.-O.; Berger, S. 150 and more basic NMR experiments: A practical course; VCH: Weinheim: New York, NY, 1998.
68. Burns, J. A.; Butler, J. C.; Moran, J.; Whitesides, G. M. J. Org. Chem. 1991, 56, 2648
69. Getz, E. B.; Xiao, M.; Chakrabarty, T.; Cooke, R.; Selvin, P. R. Anal. Biochem. 1999, 273, 73
70. Igarashi, R.; Sakai, T.; Hara, H.; Tenno, T.; Tanaka, T.; Tochio, H.; Shirakawa, M. J. Am. Chem. Soc. 2010, 132, 8228
71. Lopiano, L.; Chiesa, M.; Digilio, G.; Giraudo, S.; Bergamasco, B.; Torre, E.; Fasano, M. Biochim. Biophys. Acta 2000, 1500, 306
72. Jeschke, G.; Chechik, V.; Ionita, P.; Godt, A.; Zimmermann, H.; Banham, J.; Timmel, C. R.; Hilger, D.; Jung, H. Appl. Magn. Reson. 2006, 30, 473
73. Rappe, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A.; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024
74. Rucker, A. L.; Pager, C. T.; Campbell, M. N.; Qualls, J. E.; Creamer, T. P. Proteins: Struct., Funct., Bioinf. 2003, 53, 68
75. Knof, S.; Engel, J. Isr. J. Chem. 1974, 12, 165
76. Krimm, S.; Tiffany, M. L. Isr. J. Chem. 1974, 12, 189
77. Kuemin, M.; Engel, J.; Wennemers, H. J. Pept. Sci. 2010, 16, 596
78. Geisler, I.; Chmielewski, J. Bioorg. Med. Chem. Lett. 2007, 17, 2765
79. Fillon, Y. A.; Anderson, J. P.; Chmielewski, J. J. Am. Chem. Soc. 2005, 127, 11798
80. Gillespie, P. J.; Gambus, A.; Blow, J. J. Methods 2012, 57, 203
81. Kuemin, M.; Schweizer, S.; Ochsenfeld, C.; Wennemers, H. J. Am. Chem. Soc. 2009, 131, 15474
82. Horng, J.-C.; Raines, R. T. Protein Sci. 2006, 15, 74
83. Kakinoki, S.; Hirano, Y.; Oka, M. Polym. Bull. 2005, 53, 109
84. Fischer, G.; Schmid, F. X. Biochemistry 1990, 29, 2205
85. Lu, K. P.; Finn, G.; Lee, T. H.; Nicholson, L. K. Nat. Chem. Biol. 2007, 3, 619
86. Kramer, M. L.; Fischer, G. Biopolymers 1997, 42, 49
87. Lu, K. P.; Zhou, X. Z. Nat. Rev. Mol. Cell Biol. 2007, 8, 904
88. Fanghänel, J. Front. Biosci. 2004, 9, 3453
89. Dastvan, R.; Bode, B. E.; Karuppiah, M. P. R.; Marko, A.; Lyubenova, S.; Schwalbe, H.; Prisner, T. F. J. Phys. Chem. B 2010, 114, 13507
90. Kukula, H.; Veit, S.; Godt, A. Eur. J. Org. Chem. 1999, 1999, 277
91. Speight, J. G.; Lange, N. A. Lange's handbook of chemistry (70th anniversary ed.); McGraw-Hill: New York, Toronto, 2005; Vol. 16.
92. Murray, A. W. In Methods in Cell Biology; Peng, B. K. K. a. H. B., Ed.; Academic Press: San Diego, CA, 1991; Vol. 36, p 581.
93. Desai, A.; Murray, A.; Mitchison, T. J.; Walczak, C. E. In Methods in Cell Biology; Rieder, C. L., Ed.; Academic Press: Albany, NY, 1998; Vol. 61, p 385.
94. Neese, F. Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2012, 2, 73
95. Martin, M. G.; Thompson, A. P.; Nenoff, T. M. J. Chem. Phys. 2001, 114, 7174
96. Pettersen, E. F.; Goddard, T. D.; Huang, C. C.; Couch, G. S.; Greenblatt, D. M.; Meng, E. C.; Ferrin, T. E. J. Comput. Chem. 2004, 25, 1605