Covalent protein-oligonucleotide conjugates by copper-free click reaction

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 14, 2012, Pages 4532-4539

  Khatwani, Santoshkumar L ^a   Kang, Jun Sung ^a   Mullen, Daniel G ^a   Hast, Michael A ^b   Beese, Lorena S ^b   Distefano, Mark D ^a   Taton, T Andrew ^a  

^a University of Minnesota   (United States)

^b DUKE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Bioconjugation; Click chemistry; Protein immobilization; Protein prenylation; Protein oligodeoxynucleotide conjugates

Indexed keywords

ALKYNE; AZIDE; AZIDOPHRENYL DIPHOSPHATE; COPPER; DIBENZOCYCLOOCTYNE; OLIGONUCLEOTIDE; PROTEIN; PROTEIN OLIGONUCLEOTIDE CONJUGATE; UNCLASSIFIED DRUG;

ARTICLE; BIOCATALYSIS; CARBOXY TERMINAL SEQUENCE; CHEMICAL STRUCTURE; CONJUGATION; CONTROLLED STUDY; COVALENT BOND; CYCLOADDITION; FREE CLICK REACTION; GEL ELECTROPHORESIS; GEL PERMEATION CHROMATOGRAPHY; NONHUMAN; PROTEIN PRENYLATION; SYNTHESIS;

ALKYNES; AZIDES; CLICK CHEMISTRY; COPPER; GREEN FLUORESCENT PROTEINS; LUMINESCENT PROTEINS; OLIGONUCLEOTIDES; PROTEINS;

EID: 84863227787     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.05.017     Document Type: Article

References (67)

1. C.M. Niemeyer Angew. Chem., Int. Ed. 49 2010 1200
2. C.M. Niemeyer Trends Biotechnol. 20 2002 395
3. R.C. Bailey, G.A. Kwong, C.G. Radu, O.N. Witte, and J.R. Heath J. Am. Chem. Soc. 2007 1959 129
4. C.M. Niemeyer, L. Boldt, B. Ceyhan, and D. Blohm Anal. Biochem. 268 1999 54
5. C.M. Niemeyer, T. Sano, C.L. Smith, and C.R. Cantor Nucleic Acids Res. 22 1994 5530
6. T. Sano, C. Smith, and C. Cantor Science 258 1992 120
7. L. Zhang, S. Kasif, and R.C. Cantor Proc. Natl. Acad. Sci. U.S.A. 104 2007 3061
8. S.B. Rajur, C.M. Roth, J.R. Morgan, and M.L. Yarmush Bioconjugate Chem. 8 1997 935
9. F. Diezmann, and O. Seitz Chem. Soc. Rev. 40 2011 5789
10. B.P. Duckworth, Z. Zhang, A. Hosokawa, and M.D. Distefano ChemBioChem 8 2007 98
11. S.H. Park, P. Yin, Y. Liu, J.H. Reif, T.H. LaBean, and H. Yan Nano Lett. 5 2005 729
12. H. Yan, S.H. Park, G. Finkelstein, J.H. Reif, and T.H. LaBean Science 2003 1882 301
13. R. Chhabra, J. Sharma, Y. Ke, Y. Liu, S. Rinker, S. Lindsay, and H. Yan J. Am. Chem. Soc. 129 2007 10304
14. R.P. Goodman, C.M. Erben, J. Malo, W.M. Ho, M.L. McKee, A.N. Kapanidis, and A.J. Turberfield ChemBioChem 10 2009 1551
15. E. Jablonski, E.W. Moomaw, R.H. Tullis, and J.L. Ruth Nucleic Acids Res. 14 1986 6115
16. D. Corey, and P. Schultz Science 238 1987 1401
17. W. Ou, T. Uno, H. Chiu, J. Grünewald, S.E. Cellitti, T. Crossgrove, X. Hao, Q. Fan, L.L. Quinn, P. Patterson, L. Okach, D.H. Jones, S.A. Lesley, A. Brock, and B.H. Geierstanger Proc. Natl. Acad. Sci. U.S.A. 108 2011 10437
18. M. Lovrinovic, R. Seidel, R. Wacker, H. Schroeder, O. Seitz, M. Engelhard, R.S. Goody, and C.M. Niemeyer Chem. Commun. 2003 822
19. S. Takeda, S. Tsukiji, and T. Nagamune Bioorg. Med. Chem. Lett. 14 2004 2407
20. M.A. Jongsma, and R.H. Litjens Proteomics 6 2006 2650
21. J. Tominaga, Y. Kemori, Y. Tanaka, T. Maruyama, N. Kamiya, and M. Goto Chem. Commun. 2007 401
22. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 2596
23. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 2001 2004 40
24. J.M. Baskin, and C.R. Bertozzi QSAR Comb. Sci. 26 2007 1211
25. M.D. Best Biochemistry 48 2009 6571
26. B.P. Duckworth, J. Xu, T.A. Taton, A. Guo, and M.D. Distefano Bioconjugate Chem. 17 2006 967
27. J.R. Requena, C. Chao, R.L. Levine, and E.R. Stadtman Proc. Natl. Acad. Sci. U.S.A. 98 2001 69
28. C.J. Burrows, and J.G. Muller Chem. Rev. 98 1998 1109
29. D.S. Sigman, A. Mazumder, and D.M. Perrin Chem. Rev. 93 1993 2295
30. C.R. Becer, R. Hoogenboom, and U.S. Schubert Angew. Chem., Int. Ed. 48 2009 4900
31. P. Kele, G. Mezö, D. Achatz, and O.S. Wolfbeis Angew. Chem., Int. Ed. 48 2009 344
32. K.E. Beatty, J.D. Fisk, B.P. Smart, Y.Y. Lu, J. Szychowski, M.J. Hangauer, J.M. Baskin, C.R. Bertozzi, and D.A. Tirrell ChemBioChem 11 2010 2092
33. J.C. Jewett, and C.R. Bertozzi Chem. Soc. Rev. 39 2010 1272
34. J.M. Baskin, J.A. Prescher, S.T. Laughlin, N.J. Agard, P.V. Chang, I.A. Miller, A. Lo, J.A. Codelli, and C.R. Bertozzi Proc. Natl. Acad. Sci. U.S.A. 104 2007 16793
35. J. Dommerholt, S. Schmidt, R. Temming, L.J.A. Hendriks, F.P.J.T. Rutjes, J.C.M. van Hest, D.J. Lefeber, P. Friedl, and F.L. van Delft Angew. Chem., Int. Ed. 49 2010 9422
36. P.V. Chang, J.A. Prescher, E.M. Sletten, J.M. Baskin, I.A. Miller, N.J. Agard, A. Lo, and C.R. Bertozzi Proc. Natl. Acad. Sci. U.S.A. 2010 1821 107
37. A.B. Neef, and C. Schultz Angew. Chem., Int. Ed. 48 2009 1498
38. S.T. Laughlin, J.M. Baskin, S.L. Amacher, and C.R. Bertozzi Science 320 2008 664
39. D.C. Dieterich, J.J.L. Hodas, G. Gouzer, I.Y. Shadrin, J.T. Ngo, A. Triller, D.A. Tirrell, and E.M. Schuman Nat. Neurosci. 13 2010 897
40. C.A. DeForest, E.A. Sims, and K.S. Anseth Chem. Mater. 22 2010 4783
41. C. Ornelas, J. Broichhagen, and M. Weck J. Am. Chem. Soc. 132 2010 3923
42. A. Bernardin, A.I. Cazet, L. Guyon, P. Delannoy, F. Vinet, D. Bonnaffé, and I. Texier Bioconjugate Chem. 21 2010 583
43. L.A. Canalle, S.S. van Berkel, L.T. de Haan, and J.C.M. van Hest Adv. Funct. Mater. 19 2009 3464
44. A. Kuzmin, A. Poloukhtine, M.A. Wolfert, and V.V. Popik Bioconjugate Chem. 21 2010 2076
45. N.J. Agard, J.A. Prescher, and C.R. Bertozzi J. Am. Chem. Soc. 126 2004 15046
46. J.A. Codelli, J.M. Baskin, N.J. Agard, and C.R. Bertozzi J. Am. Chem. Soc. 130 2008 11486
47. J.C. Jewett, E.M. Sletten, and C.R. Bertozzi J. Am. Chem. Soc. 132 2010 3688
48. X. Ning, J. Guo, M.A. Wolfert, and G.-J. Boons Angew. Chem., Int. Ed. 47 2008 2253
49. P. van Delft, N.J. Meeuwenoord, S. Hoogendoorn, J. Dinkelaar, H.S. Overkleeft, G.A. van der Marel, and D.V. Filippov Org. Lett. 12 2010 5486
50. I.S. Marks, J.S. Kang, B.T. Jones, K.J. Landmark, A.J. Cleland, and T.A. Taton Bioconjugate Chem. 22 2011 1259
51. J. Xu, A.J. DeGraw, B.P. Duckworth, S. Lenevich, C.-M. Tann, E.C. Jenson, S.J. Gruber, G. Barany, and M.D. Distefano Chem. Biol. Drug Des. 68 2006 85
52. A.V. Tataurov, Y. You, and R. Owczarzy Biophys. Chem. 133 2008 66
53. J.A. Chung, J.W. Wollack, M.L. Hovlid, A. Okesli, Y. Chen, J.D. Mueller, M.D. Distefano, and T.A. Taton Anal. Biochem. 386 2009 1
54. R. Heim, A.B. Cubitt, and R.Y. Tsien Nature 373 1995 663
55. N.C. Shaner, R.E. Campbell, P.A. Steinbach, B.N.G. Giepmans, A.E. Palmer, and R.Y. Tsien Nat. Biotech. 22 2004 1567
56. M. Rashidian, J.M. Song, R.E. Pricer, and M.D.J. Distefano Am. Chem. Soc. 134 2012 8455
57. H.-W. Liu, G. Cosa, C.F. Landes, Y. Zeng, B.J. Kovaleski, D.G. Mullen, G. Barany, K. Musier-Forsyth, and P.F. Barbara Biophys. J. 89 2005 3470
58. D.S. King, C.G. Fields, and G.B. Fields Int. J. Pept. Protein Res. 36 1990 255
59. M. Zhong, J. Fang, and Y. Wei Bioconjugate Chem. 21 2010 1177
60. M. Lovrinovic, and C.M. Niemeyer Biochem. Biophys. Res. Commun. 335 2005 943
61. L.M. Hellman, and M.G. Fried Nat. Protocols 2007 1849 2
62. P.M. Schaeffer, and N.E. Dixon Aust. J. Chem. 62 2009 1328
63. D.B. Dahdah, I. Morin, M.J.J. Moreau, N.E. Dixon, and P.M. Schaeffer Chem. Commun. 2009 3050
64. U. Feldkamp, and C.M. Niemeyer Angew. Chem., Int. Ed. 2006 1856 45
65. S. Sawoo, P. Dutta, A. Chakraborty, R. Mukhopadhyay, O. Bouloussa, and A. Sarkar Chem. Commun. 2008 5957
66. J.L. Zimmermann, T. Nicolaus, G. Neuert, and K. Blank Nat. Protocols 5 2010 975
67. C. Boozer, J. Ladd, S. Chen, and S. Jiang Anal. Chem. 78 2006 1515