The RNase H affinity and cleavage of the target RNA in the antisense-RNA hybrid duplexes containing various 3′-tethered substituents in the antisense strand

Journal of the Chemical Society. Perkin Transactions 2

Volumn 2, Issue 2, 2002, Pages 271-281

  Amirkhanov, Nariman V ^a   Chattopadhyaya, Jyoti ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; CHOLESTEROL; COMPOSITION EFFECTS; MOLECULAR STRUCTURE; REACTION KINETICS; SATURATION (MATERIALS COMPOSITION); SUBSTITUTION REACTIONS;

ANTISENSE OLIGONUCLEOTIDE; BUFFER CONCENTRATION; CHOLIC ACID; DIPYRIDOPHENAZINE;

ENZYMES;

EID: 0036007683     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/b108196a     Document Type: Article

References (78)

1. M. Itaya, K. Kondo Nucleic Acids Res. 1991 19 4443.
2. M. Itaya, D. McKelvin, S. K. Chatterjie, R. J. Crouch Mol. Gen. Genet. 1991 227 438.
3. S. Kanaya, M. Itaya J. Biol. Chem. 1992 267 10184.
4. W. Busen J. Biol. Chem. 1980 255 9434.
5. Y. W. Rong, P. L. Carl Biochemistry 1990 29 383.
6. P. S. Eder, R. Y. Walder, J. A. Walder Biochimie 1993 75 123.
7. S. Kanaya and M. Ikehara, ‘Subcell Biochemistry’, in Proteins: Structure, Function, and Engineering, ed. B. B. Biswas and Siddhartha Roy Plenium Press, New York 1995, vol. 24, pp. 377–422.
8. I. Lebedeva, C. A. Stein Annu. Rev. Pharmacol. Toxicol. 2001 41 403 419.
9. S. T. Crooke Antisense Nucleic Acid. Drug. Dev. 1998 8 133 134.
10. S. T. Crooke Biotechnol. Genet. Eng. Rev. 1998 15 121 157.
11. S. T. Crooke Biochim. Biophys. Acta 1999 1489 31 44.
12. S. Kanaya, ‘Enzymatic activity and protein stability of E. coli ribonuclease HI’, in Ribonucleases H, R. J. Crouch, ed. INSERM, Paris, 1998, Ch. 1, pp. 1–37.
13. J. J. Toulme, P. Frank, R. J. Crouch, ‘Human ribonuclease H.’ in Ribonucleases H, ed. R. J. Crouch INSERM, Paris 1998, Ch. 7, pp. 147–162.
14. J. T. Miller, J. W. Rausch, S. F. Le Grice Methods Mol. Biol. 2001 160 335 354.
15. R. V. Giles, D. M. Tidd Methods Mol. Biol. 2001 160 157 82.
16. E. Zamaratski, P. I. Pradeepkumar, J. Chattopadhyaya J. Biochem. Biophys. Methods 2001 48 189 208.
17. S. Iwai, M. Wakasa, E. Ohtsuka, S. Kanaya, A. Kidera, H. Nakamura J. Mol. Biol. 1996 263 699.
18. W. F. Lima, S. T. Crooke Biochemistry 1997 36 390.
19. K.-H. Altman, R. Kesselring, E. Francotte, G. Rihs Tetrahedron Lett. 1994 35 2331.
20. M. A. Siddiqui, H. Ford, C. George, V. E. Marquez Nucleosides Nucleotides 1996 15 235.
21. V. E. Marquez, M. A. Siddiqui, A. Ezzitouni, P. Russ, J. Wang, W. R. Wanger, D. M. Matteucci J. Med. Chem. 1996 39 3739.
22. S. Obika, D. Nanbu, Y. Hari, K. Morio, Y. In, T. Ishida, T. Imanishi Tetrahedron Lett. 1997 38 8735.
23. A. A. Koshkin, S. K. Singh, P. Nielson, V. K. Rajwanshi, R. Kumar, M. Meldgaard, J. Wengel Tetrahedron 1998 54 3607.
24. G. Wang, J.-L. Giradet, E. Gunic Tetrahedron 1999 55 7707.
25. J. Wengel Acc. Chem. Res. 1999 32 301.
26. G. Wang, E. Gunic, J.-L. Giradet Bioorg. Med. Chem. Lett. 1999 9 1147.
27. S. Obika, D. Nanbu, Y. Hari, K. Morio, J. Andoh, K. Morio, T. Doi, T. Imanishi Tetrahedron Lett. 1998 39 5401.
28. M. Sekine, O. Kurasawa, K. Shohda, K. Seio, T. Wada J. Org. Chem. 2000 65 3571.
29. K.-H. Altman, R. Imwinkelried, R. Kesselring, G. Rihs Tetrahedron Lett. 1994 35 7625.
30. S. Obika, K. Morio, Y. Hari, T. Imanishi Chem. Commun. 1999 2423.
31. S. Obika, K. Morio, Y. Hari, T. Imanishi Bioorg. Med. Chem. Lett. 1999 9 515.
32. R. Steffens, C. Leumann Helv. Chim. Acta 1997 80 2426.
33. R. Buff, J. Hunziker Bioorg. Med. Chem. 1998 521.
34. M. J. Damha, C. J. Wilds, A. Noronha, I. Brukner, G. Borkow, D. Arion, M. A. Parniak J. Am. Chem. Soc. 1998 120 12976.
35. E. Kanaya, S. Kanaya Eur. J. Biochem. 1995 231 557.
36. L. Kvaerno, J. Wengel Chem. Commun. 2001 1419 1424.
37. R. J. Crouch and M.-L. Diksen Nucleases, ed. S. M. Linn and R. J. Robert Cold Spring Harbor Laboratory, Cold Spring Harbor, NY 1982, pp. 211–241.
38. P. Acharya, A. Trifonova, C. Thibaudeau, A. Foldesi, J. Chattopadhyaya Angew. Chem., Int. Ed. 1999 38 3645.
39. C. Thibaudeau and J. Chattopadhyaya Stereoelectronic Effects in Nucleosides and Nucleotides and their Structural Implications, Dept of Bioorganic Chemistry, Uppsala University Press, Uppsala, Sweden, 1999.
40. P. B. Monia, E. A. Lesnik, C. Gonzalez, W. F. Lima, D. McGee, C. J. Guinosso, A. M. Kawasaki, P. D. Cook, S. M. Frier J. Biol. Chem. 1993 268 14514.
41. P. D. Cook Antisense Research and Applications, ed. S. T. Crooke and B. Lebleu CRC Press Inc., Boca Raton, FL 1993.
42. H. Inoue, Y. Hayase, S. Iwai, K. Miura, E. Ohtsuka Nucleic Acids Res. 1987 15 6131.
43. H. Inoue, Y. Hayase, S. Iwai, E. Ohtsuka FEBS Lett. 1987 215 327.
44. T. Kogoma, N. L. Subia, K. Meyenberg Mol. Gen. Genet. 1985 200 103.
45. A. I. Lamond, B. S. Sproat FEBS Lett. 1993 325 123.
46. D. A. Braasch, D. R. Corey Chem. Biol. 2001 8 1.
47. M. Manoharan Biochim. Biophys. Acta 1999 1489 117.
48. K. H. Altmann, D. Fabbro, N. M. Dean, T. Geiger, B. P. Monia, M. Muller, P. Nicklin Biochem. Soc. Trans. 1996 24 630.
49. B. S. Sproat and A. I. Lamond Antisense Research and Applications, ed. S. T. Crooke and B. Lebleu CRC Press, Inc., Boca Raton, FL 1993.
50. P. I. Pradeepkumar, E. Zamaratski, A. Földesi, J. Chattopadhyaya Tetrahedron Lett. 2000 41 8601.
51. P. I. Pradeepkumar, E. Zamaratski, A. Földesi, J. Chattopadhyaya J. Chem. Soc., Perkin Trans. 2 2001 402.
52. P. I. Pradeepkumar, J. Chattopadhyaya J. Chem. Soc., Perkin Trans. 2 2001 2074 2083.
53. N. Puri, E. Zamaratski, C. Sund, J. Chattopadhyaya Tetrahedron 1997 53 10409.
54. N. Puri, J. Chattopadhyaya Nucleosides Nucleotides 1999 18 2785.
55. E. Zamaratski, J. Chattopadhyaya Tetrahedron 1998 54 8183.
56. E. Zamaratski, D. Ossipov, P. I. Pradeepkumar, N. Amirkhanov, J. Chattopadhyaya Tetrahedron 2001 57 593.
57. N. V. Amirkhanov, E. Zamaratski, J. Chattopadhyaya Tetrahedron Lett. 2001 42 489.
58. T. V. Maltseva, P. Agback, M. N. Repkova, A. G. Venyaminova, E. M. Ivanova, A. Sandstrom, J. Chattopadhyaya Nucleic Acids Res. 1994 22 559.
59. T. V. Maltseva, P. Agback, J. Chattopadhyaya Nucleic Acids Res. 1993 21 4246.
60. T. V. Maltseva, J. Chattopadhyaya Tetrahedron 1995 51 5501.
61. T. V. Maltseva, V. F. Zarytova, J. Chattopadhyaya Biochem. Biophys. Methods 1995 30 163.
62. C. F. Bleczinski, C. Richert J. Am. Chem. Soc. 1999 121 10889.
63. H. Gao, J. R. Dias Synth. Commun. 1997 27 757.
64. W. Kramer, G. Wess Eur. J. Clin. Invest. 1996 26 715.
65. T. J. Lehmann, J. W. Engels Bioorg. Med. Chem. 2001 9 1827.
66. D. Opsenica, G. Pocsfalvi, Z. Juranic, B. Tinant, J. P. Declercq, D. E. Kyle, W. K. Milhous, B. A. Solaja J. Med. Chem. 2000 43 3274.
67. R. L. Letsinger, G. Znang, D. K. Sun, T. Ikeuchi, P. S. Sarin Proc. Natl. Acad. Sci. USA 1989 86 6553.
68. G. Godard, A. S. Boutorin, E. Saison-Behmoaras, C. Helene FEBS Lett. 1995 232 404.
69. D. Ossipov, E. Zamaratski, J. Chattopadhyaya Helv. Chim. Acta 1999 82 2186.
70. T. Horn, M. S. Urdea Tetrahedron Lett. 1986 27 4705.
71. V. F. Zarytova, T. S. Godovikova, I. V. Kutyavin and L. M. Khalimskaya, ‘Reactive oligonucleotide derivatives as affinity reagents and probes in molecular biology’, in Biophosphates and their Analogues—Synthesis, Structure, Metabolism and Activity, ed. K. S. Bruzik and W. J. Stec Elsevier, Amsterdam 1987 149.
72. D. V. Pyshnyi, I. A. Pyshnaya, S. G. Lokhov, E. M. Ivanova, V. F. Zarytova Russian J. Bioorg. Chem. 1995 21 612.
73. S. T. Crooke, M. J. Graham, J. E. Zuckerman, D. Brooks, B. S. Conklin, L. L. Cummins, M. J. Greig, C. J. Guinosso, D. Kornbrust, M. Manoharan, H. M. Sasmor, T. Schleich, K. L. Tivel, R. H. Griffey J. Pharmacol. Exp. Ther. 1996 277 923.
74. M. Manoharan, L. K. Johnson, C. F. Bennet, T. A. Vickers, D. J. Ecker, L. M. Cowsert, M. Frier, P. D. Cook Bioorg. Med. Chem. Lett. 1994 4 1053.
75. A. S. Boutorin, L. V. Gus’kova, E. M. Ivanova, N. D. Kobetz, V. F. Zarytova, A. S. Ryte, L. V. Yurchenko, V. V. Vlassov FEBS Lett. 1989 254 129.
76. A. S. Ryte, V. N. Karamyshev, M. V. Nechaeva, Z. V. Gus’kova, E. M. Ivanova, V. F. Zarytova, V. V. Vlassov FEBS Lett. 1992 299 124.
77. M. Dixon and E. C. Webb Enzymes, 3rd edn., Longman Group Limited London associated companies, published by Academic Press Inc., New York, 1979 60.
78. A. Fersht Enzyme Structure and Mechanism, 2nd edn., Freeman, New York, 1985.