Functional tuning of nucleic acids by chemical modifications: Tailored oligonucleotides as drugs, devices, and diagnostics

Chemical Record

Volumn 3, Issue 1, 2003, Pages 51-60

  Verma, Sandeep ^a,c   Jäger, Stefan ^a   Thum, Oliver ^a,b   Famulok, Michael ^a  

^a UNIVERSITY OF BONN   (Germany)

^b NOXXON PHARMA AG   (Germany)

^c INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

DNA; Functionalized DNA; Modified nucleotides; Oligonucleotides

Indexed keywords

CARBOHYDRATE; DIAGNOSTIC AGENT; FUNCTIONAL GROUP; NUCLEIC ACID; NUCLEIC ACID BASE; OLIGONUCLEOTIDE; ORGANOPHOSPHATE; RNA; NUCLEOSIDE;

ARTICLE; BIOMOLECULAR ELECTRONICS; BIOSENSOR; CATALYSIS; CHEMICAL MODIFICATION; DNA MICROARRAY; DNA MODIFICATION; ELECTRIC CONDUCTIVITY; ENZYME MODIFICATION; POLYMERIZATION; CHEMISTRY; DRUG DESIGN; GENETIC PROCEDURES; METHODOLOGY; MOLECULAR COMPUTER; REVIEW; SYNTHESIS;

BIOSENSING TECHNIQUES; COMPUTERS, MOLECULAR; DRUG DESIGN; NUCLEIC ACIDS; NUCLEOSIDES; OLIGONUCLEOTIDES;

EID: 0038499722     PISSN: 15278999     EISSN: None     Source Type: Journal    
DOI: 10.1002/tcr.10047     Document Type: Article

References (109)

1. Cech, T.R. Angew Chem 1990, 102, 745; Agnew Chem Int Ed 1990, 29, 759.
2. Cech, T.R. Angew Chem 1990, 102, 745; Agnew Chem Int Ed 1990, 29, 759.
3. Altman, S. Angew Chem 1990, 102, 735; Agnew Chem Int Ed 1990, 29, 749.
4. Altman, S. Angew Chem 1990, 102, 735; Agnew Chem Int Ed 1990, 29, 749.
5. Doherty, E.A.; Doudna, J.A. Annu Rev Biophys Biomol Struct 2001, 30, 457.
6. Famulok, M.; Jenne, A. In: Topics in Current Chemistry, Springer-Verlag: Berlin, 1999, Vol. 202, p 101.
7. Famulok, M.; Mayer, G. Curr Top Microbiol Immun 1999, 243, 123.
8. Famulok, M.; Mayer, G.; Blind, M. Acc Chem Res 2000, 33, 591.
9. Famulok, M.; Blind, M.; Mayer, G. Chem Biol 2001, 8, 931.
10. Sági, J.; Szemzo, A.; Ebinger, K.; Szabolcs, A.; Sági, G.; Ruff, E.; Ötvös, L. Tetrahedron Lett 1993, 34, 2191.
11. Tierney, M.T.; Grinstaff, M.W. Org Lett 2000, 2, 3413.
12. Seela, F.; Zulauf, M. Helv Chim Acta 1999, 82, 1878.
13. Ramzaeva, N.; Mittelbach, C.; Seela, F. Helv Chim Acta 1997, 80, 1809.
14. Verma, S.; Eckstein, F. Annu Rev Biochem 1998, 67, 99.
15. Dey, S.; Sheppard, T.L. Org Lett 2001, 3, 3983.
16. Chambert, S.; Decout, J.L. Org Prep Proc Int 2002, 34, 27.
17. Micklefield, J. Curr Med Chem 2001, 8, 1157.
18. Andreola, M.L.; Calmels, C.; Michel, J.; Toulme, J.J.; Litvak, S. Eur J Biochem 2000, 267, 5032.
19. King, D.J.; Ventura, D.A.; Brasier, A.R.; Gorenstein, D.G. Biochemistry 1998, 37, 16489.
20. Jhaveri, S.; Olwin, B.; Ellington, A.D. Bioorg Med Chem Lett 1998, 8, 2285.
21. Milligan, J.F.; Uhlenbeck, O.C. Biochem 1989, 28, 2849.
22. Gryaznov, S.M.; Banait, N.S. Exp Opin Ther Pat 2002, 12, 543.
23. Egli, M.; Gryaznov, S.M. Cell Mol Life Sci 2000, 57, 1440.
24. Darfeuille, F.; Cazenave, C.; Gryaznov, S.; Duconge, F.; Primo, Di C.; Toulme, J.J. Nucleosides Nucleotides 2001, 20, 441.
25. Aurup, H.; Williams, D.M.; Eckstein, F. Biochemistry 1992, 31, 9636.
26. Ono, T.; Scalf, M.; Smith, L.M. Nucleic Acids Res 1997, 25, 4581.
27. Pagratis, N.C.; Bell, C.; Chang, Y.F.; Jennings, S.; Fitzwater, T.; Jellinek, D.; Dang, C. Nature Biotech 1997, 15, 68.
28. Lin, Y.; Qui, Q.; Gill, S.C.; Jayasena, S. Nucleic Acids Res 1994, 22, 5229.
29. Lin, Y.; Nieuwlandt, D.; Magallanez, A.; Feistner, B.; Jayasena, S.D. Nucleic Acids Res 1996, 24, 3407.
30. Kubik, M.F.; Bell, C.; Fitzwater, T.; Watson, S.R.; Tasset, D.M. J Immunol 1997, 159, 259.
31. Hicke, B.J.; Marion, C.; Chang, Y.-F.; Gould, T.; Lynott, C.K.; Parma, D.; Schmidt, P.G.; Warren, S. J Biol Chem 2001, 276, 48644.
32. Summerer, D.; Marx, A. Angew Chem 2001, 113, 3806; Angew Chem Int Edit 2001, 40, 3693.
33. Summerer, D.; Marx, A. Angew Chem 2001, 113, 3806; Angew Chem Int Edit 2001, 40, 3693.
34. Summerer, D.; Marx, A. J Am Chem Soc 2002, 124, 910.
35. Boiziau, C.; Toulme, J.J. Antisense Nucl Acid Drug Dev 2001, 11, 379.
36. Narlikar, G.J.; Herschlag, D. Annu Rev Biochem 1997, 66, 19.
37. Usman, N.; Blatt, L.R.M. J Clin Invest 2000, 106, 1197.
38. Lorsch, J.R.; Szostak, J.W. Nature 1994, 371, 31.
39. Zhang, B.L.; Cech, T.R. Nature 1997, 390, 96.
40. McGinness, K.E.; Joyce, G.F. Chem Biol 2002, 9, 297.
41. Saito, H.; Kourouklis, D.; Suga, H. EMBO J 2001, 20, 1797.
42. Lee, N.; Bessho, Y.; Wei, K.; Szostak, J.W.; Suga, H. Nat Struct Biol 2000, 7, 28.
43. Jenne, A.; Famulok, M. Chem Biol 1998, 5, 23.
44. Seelig, B.; Jäschke, A. Chem Biol 1999, 6, 167.
45. Sengle, G.; Eisenführ, A.; Arora, P.S.; Nowick, J.S.; Famulok, M. Chem Biol 2001, 8, 459.
46. Tarasow, T.M.; Tarasow, S.L.; Eaton, B.E. Nature 1997, 389, 54.
47. Wiegand, T.W.; Janssen, R.C.; Eaton, B.E. Chem Biol 1997, 4, 675.
48. Dai, X.; Joyce, G.F. Helv Chim Acta 2000, 83, 1701.
49. Teramoto, N.; Imanishi, Y.; Ito, Y. Bioconj Chem 2000, 11, 744.
50. Santoro, S.W.; Joyce, G.F.; Sakthivel, K.; Gramatikova, S. Barbas III, C.F. J Am Chem Soc 2000, 122, 2433.
51. Santoro, S.W.; Joyce, G.F. Proc Natl Acad Sci USA 1997, 94, 4262.
52. Perrin, D.M.; Garestier, T.; Helene, C. J Am Chem Soc 2001, 123, 1556.
53. Lerner, L.; Roupioz, Y.; Ting, R.; Perrin, D.M. J Am Chem Soc 2002, 124, 9960.
54. Latham, J.A.; Johnson, R.; Toole, J.J. Nucleic Acids Res 1994, 22, 2817.
55. Battersby, T.R.; Ang, D.N.; Burgstaller, P.; Jurczyk, S.C.; Bowser, M.T.; Buchanan, D.D.; Kennedy, R.T.; Benner, S.A. J Am Chem Soc 1999, 121, 9781.
56. Lee, S.E.; Sidorov, A.; Gourlain, T.; Mignet, N.; Thorpe, S.J.; Brazier, J.A.; Dickman, M.J.; Hornby, D.P.; Grasby, J.A.; Williams, D.M. Nucleic Acids Res 2001, 29, 1565.
57. Sakthivel, K.; Barbas III, C.F. Angew Chem 1998, 110, 2998; Angew Chem Int Edit 1998, 37, 2872.
58. Sakthivel, K.; Barbas III, C.F. Angew Chem 1998, 110, 2998; Angew Chem Int Edit 1998, 37, 2872.
59. Sawai, H.; Ozaki, A.N.; Satoh, F.; Ohbayashi, T.; Masud, M.M.; Ozaki, H. Chem Commun 2001, 2604.
60. Thum, O.; Jäger, S.; Famulok, M. Angew Chem 2001, 113, 4112; Angew Chem Int Ed 2001, 40, 3990.
61. Thum, O.; Jäger, S.; Famulok, M. Angew Chem 2001, 113, 4112; Angew Chem Int Ed 2001, 40, 3990.
62. Ito, Y.; Suzuki, A.; Kawazoe, N.; Imanishi, Y. Bioconj Chem 2001, 12, 850.
63. Gourlain, T.; Sidorov, A.; Mignet, N.; Thorpe, S.J.; Lee, S.E.; Grasby, J.A.; Williams, D.M. Nucleic Acids Res 2001, 29, 1898.
64. Augustin, M.A.; Ankenbauer, W.; Angerer, B. J Biotech 2001, 86, 289.
65. Matulic-Adamic, J.; Daniher, A.T.; Karpeisky, A.; Haeberli, P.; Sweedler, D.; Beigelman, L. Bioorg Med Chem Lett 2000, 10, 1299.
66. Brakmann, S.; Niekchen, P. ChemBioChem 2001, 2, 773.
67. Brakmann, S.; Löbermann, S. Angew Chem 2001, 113, 1473; Angew Chem Int Ed 2001, 40, 1427.
68. Brakmann, S.; Löbermann, S. Angew Chem 2001, 113, 1473; Angew Chem Int Ed 2001, 40, 1427.
69. Szent-Györgyi, A.; Isenberg, I.; Baird, S.L. Jr. Proc Natl Acad Sci USA 1960, 46, 1444.
70. McConnell, H. J Chem Phys 1961, 35, 508.
71. Eley, D.D.; Spivey, D.I. Trans. Faraday Soc 1962, 411.
72. Hoffman, T.A.; Ladik, J. Adv Chem Phys 1964, 7, 87.
73. Snart, R.S. Biopolymers 1968, 6, 293.
74. Murphy, C.J.; Arkin, M.R.; Jenkins, Y.; Ghatlia, N.D.; Bossmann, S.H.; Turro, N.J.; Barton, J.K. Science 1993, 262, 1025.
75. Hall, D.B.; Holmkin, R.E.; Barton, J.K. Nature 1996, 382, 731.
76. Berlin, Y.A.; Burin, A.L.; Ratner, M.A. Chem Phys 2002, 275, 61.
77. Lewis, F.D.; Letsinger, R.L.; Wasielewski, M.R. Acc Chem Res 2001, 34, 159.
78. Giese, B. Acc Chem Res 2000, 33, 631.
79. Schuster, G.B. Acc Chem Res 2000, 33, 253.
80. Nunez, M.E.; Barton, J.K. Curr Opin Chem Biol 2000, 4, 199.
81. Wan, C.; Torsten, F.; Schiemann, O.; Barton, J.K.; Zewail, A.H. Proc Natl Acad Sci USA 2000, 97, 14052.
82. Adleman, L.M. Science 1994, 266, 1021.
83. Lipton, R.J. Science 1995, 268, 542.
84. Sakamoto, K.; Gouzu, H.; Komiya, K.; Kiga, D.; Yokoyama, S.; Yokomori, T.; Hagiya, M. Science 2000, 288, 1223.
85. Wang, L.M.; Hall, J.G.; Lu, M.C.; Qiu, H.; M, S.L. Nature Biotech 2001, 19, 1053.
86. Ouyang, Q.; Kaplan, P.D.; Liu, S.; Libchaber, A. Science 1997, 278, 446.
87. Kari, L.; Loor, G.; Yu, S. Theor Comp Sci 2000, 231, 193.
88. Faulhammer, D.; Cukras, A.R.; Lipton, R.J.; Landweber, L.F. Proc Natl Acad Sci USA 2000, 97, 1385.
89. Wang, L.M.; Liu, Q.H.; Corn, R.M.; Condon, A.E.; Smith, L.M. J Am Chem Soc 2000, 122, 7435.
90. Liu, Q.H.; Wang, L.M.; Frutos, A.G.; Condon, A.E.; Corn, R.M.; Smith, L.M. Nature 2000, 403, 175.
91. Kari, L. Future Gen Comp Sys 2001, 17, 823.
92. Ruben, A.J.; Landweber, L.F. Nat Rev Mol Cell Biol 2000, 1, 69.
93. Deaton, R.; Garzon, M.; Rose, J.; Franceschetti, D.R.; Stevens, S.E. Evol Comput 1999, 231.
94. Gibbons, A.; Amos, M.; Hodgson, D. Curr Opin Biotechnol 1997, 8, 103.
95. Cox, J.C.; Cohen, D.S.; Ellington, A.D. Trends Biotech 1999, 17, 151.
96. Wang, J. Nucleic Acids Res 2000, 28, 3011.
97. Willner, I.; Willner, B. Trends Biotech 2001, 19, 222.
98. Warsinke, U.A.; Wollenberger Scheller, F.W. Curr Opin Biotechnol 2001, 12, 35.
99. Tombelli, S.; Marrazza, G.; Mascini, M. Int J Environ Anal Chem 2001, 80, 87.
100. Kuwabara, T.; Warashina, M.; Taira, K. Curr Opin Chem Biol 2000, 4, 669.
101. Famulok, M. Curr Opin Struct Biol 1999, 9, 324.
102. Bruno, J.G.; Kiel, J.L. Biosens Bioelec 1999, 14, 457.
103. Kato, T.; Yano, K.; Ikebukuro, K.; Karube, I. Analyst 2000, 1371.
104. Jhaveri, S.; Rajendran, M.; Ellington, A.D. Nat Biotech 2000, 18, 1293.
105. Potyrailo, R.A.; Conrad, R.C.; Ellington, A.D.; Hieftje, G.M. Anal Chem 1998, 70, 3419.
106. Lee, M.; Walt, D.R. Anal Biochem 2000, 282, 142.
107. Wang, J.; Jiang, M.; Nilsen, T.W.; Getts, R.C. J Am Chem Soc 1998, 120, 8281.
108. Wittung-Stafshede, P.; Rodahl, M.; Kasemo, B.; Nielsen, P.; Norden, B. Colloids Surfaces A - Physicochem Eng Aspects 2000, 174, 269.
109. Feriotto, G.; Corradini, R.; Sforza, S.; Bianchi, N.; Mischiati, C.; Marchelli, R.; Gambari, R. Lab Invest 2001, 81, 1415.