2′-O,4′-C-Aminomethylene-bridged nucleic acid modification with enhancement of nuclease resistance promotes pyrimidine motif triplex nucleic acid formation at physiological pH

Chemistry - A European Journal

Volumn 17, Issue 9, 2011, Pages 2742-2751

  Torigoe, Hidetaka ^a   Rahman, S M Abdur ^b   Takuma, Hiroko ^b   Sato, Norihiro ^a   Imanishi, Takeshi ^b   Obika, Satoshi ^b   Sasaki, Kiyomi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

BNA; kinetics; nuclease resistance; thermodynamics; triplex

Indexed keywords

ACID MODIFICATION; BINDING AFFINITIES; BINDING CONSTANT; BNA; DEGREE OF HYDRATION; DISSOCIATION RATE CONSTANT; FREE STATE; GENOMIC DNA; HUMAN SERUM; IN-VIVO; KINETIC DATA; KINETIC EFFECT; NUCLEASE RESISTANCE; PHYSIOLOGICAL CONDITION; PHYSIOLOGICAL PH; THERMO DYNAMIC ANALYSIS; THERMODYNAMIC PARAMETER; TRIPLEX; TRIPLEX DNA; TRIPLEX FORMATION; TRIPLEX-FORMING OLIGONUCLEOTIDES;

AROMATIC COMPOUNDS; BINDING ENERGY; BIOMOLECULES; DISSOCIATION; GENE EXPRESSION; GENE EXPRESSION REGULATION; NUCLEIC ACIDS; OLIGONUCLEOTIDES; PH EFFECTS; PHYSIOLOGY; RATE CONSTANTS; THERMOANALYSIS; THERMODYNAMICS;

CHEMICAL MODIFICATION;

2',4' BNA(NC); 2',4'-BNA(NC); BRIDGED COMPOUND; ENDONUCLEASE; NUCLEOTIDE; OLIGODEOXYRIBONUCLEOTIDE; PYRIMIDINE DERIVATIVE;

ARTICLE; BLOOD; CHEMISTRY; CONFORMATION; HUMAN; KINETICS; METABOLISM; PH; SEQUENCE HOMOLOGY; THERMODYNAMICS;

BRIDGED COMPOUNDS; ENDONUCLEASES; HUMANS; HYDROGEN-ION CONCENTRATION; KINETICS; NUCLEIC ACID CONFORMATION; NUCLEOTIDES; OLIGODEOXYRIBONUCLEOTIDES; PYRIMIDINES; SEQUENCE HOMOLOGY, NUCLEIC ACID; THERMODYNAMICS;

EID: 79951804816     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201002745     Document Type: Article

References (48)

1. J. Y. Chin, E. B. Schleifman, P. M. Glazer, Front. Biosci. 2007, 12, 4288-4297
2. J. J. Bissler, Front. Biosci. 2007, 12, 4536-4546
3. M. Duca, P. Vekhoff, K. Oussedik, L. Halby, P. B. Arimondo, Nucleic Acids Res. 2008, 36, 5123-5138
4. A. Jain, G. Wang, K. M. Vasquez, Biochimie 2008, 90, 1117-1130
5. R. D. Wells, FASEB J. 2008, 22, 1625-1634.
6. M. D. Frank-Kamenetskii, Methods Enzymol. 1992, 211, 180-191
7. S. F. Singleton, P. B. Dervan, Biochemistry 1992, 31, 10995-11003
8. H. Shindo, H. Torigoe, A. Sarai, Biochemistry 1993, 32, 8963-8969.
9. J. F. Milligan, S. H. Krawczyk, S. Wadwani, M. D. Matteucci, Nucleic Acids Res. 1993, 21, 327-333
10. A. J. Cheng, M. W. VanDyke, Nucleic Acids Res. 1993, 21, 5630-5635.
11. J. S. Lee, M. L. Woodsworth, L. J. Latimer, A. R. Morgan, Nucleic Acids Res. 1984, 12, 6603-6614
12. T. J. Povsic, P. B. Dervan, J. Am. Chem. Soc. 1989, 111, 3059-3061
13. L. E. Xodo, G. Manzini, F. Quadrifoglio, G. A. vanderMarel, J. H. vanBoom, Nucleic Acids Res. 1991, 19, 5625-5631.
14. A. Ono, P. O. P. Tso, L. S. Kan, J. Am. Chem. Soc. 1991, 113, 4032-4033
15. S. H. Krawczyk, J. F. Milligan, S. Wadwani, C. Moulds, B. C. Froehler, M. D. Matteucci, Proc. Natl. Acad. Sci. USA 1992, 89, 3761-3764
16. J. S. Koh, P. B. Dervan, J. Am. Chem. Soc. 1992, 114, 1470-1478
17. M. C. Jetter, F. W. Hobbs, Biochemistry 1993, 32, 3249-3254
18. Y. Ueno, M. Mikawa, A. Matsuda, Bioconjugate Chem. 1998, 9, 33-39.
19. J. S. Sun, C. Giovannangeli, J. C. Francois, R. Kurfurst, T. Montenay-Garestier, U. Asseline, T. Saison-Behmoaras, N. T. Thuong, C. Helene, Proc. Natl. Acad. Sci. USA 1991, 88, 6023-6027
20. J. F. Mouscadet, C. Ketterle, H. Goulaouic, S. Carteau, F. Subra, M. LeBret, C. Auclair, Biochemistry 1994, 33, 4187-4196.
21. S. M. Rahman, S. Seki, S. Obika, S. Haitani, K. Miyashita, T. Imanishi, Angew. Chem. 2007, 119, 4384-4387
22. Angew. Chem. Int. Ed. 2007, 46, 4306-4309
23. S. M. AbdurRahman, S. Seki, S. Obika, H. Yoshikawa, K. Miyashita, T. Imanishi, J. Am. Chem. Soc. 2008, 130, 4886-4896.
24. V. I. Lyamichev, S. M. Mirkin, M. D. Frank-Kamenetskii, C. R. Cantor, Nucleic Acids Res. 1988, 16, 2165-2178
25. H. Torigoe, A. Ferdous, H. Watanabe, T. Akaike, A. Maruyama, J. Biol. Chem. 1999, 274, 6161-6167
26. H. Torigoe, Y. Hari, M. Sekiguchi, S. Obika, T. Imanishi, J. Biol. Chem. 2001, 276, 2354-2360
27. H. Torigoe, Biochemistry 2001, 40, 1063-1069
28. H. Torigoe, A. Maruyama, J. Am. Chem. Soc. 2005, 127, 1705-1710
29. H. Torigoe, K. Sasaki, T. Katayama, J. Biochem. 2009, 146, 173-183
30. H. Torigoe, A. Maruyama, S. Obika, T. Imanishi, T. Katayama, Biochemistry 2009, 48, 3545-3553.
31. N. Langerman, R. L. Biltonen, Methods Enzymol. 1979, 61, 261-286
32. R. L. Biltonen, N. Langerman, Methods Enzymol. 1979, 61, 287-318
33. T. Wiseman, S. Williston, J. F. Brandts, L. N. Lin, Anal. Biochem. 1989, 179, 131-137
34. H. Torigoe, R. Shimizume, A. Sarai, H. Shindo, Biochemistry 1999, 38, 14653-14659.
35. P. R. Edwards, A. Gill, D. V. Pollard-Knight, M. Hoare, P. E. Buckle, P. A. Lowe, R. J. Leatherbarrow, Anal. Biochem. 1995, 231, 210-217
36. P. J. Bates, H. S. Dosanjh, S. Kumar, T. C. Jenkins, C. A. Laughton, S. Neidle, Nucleic Acids Res. 1995, 23, 3627-3632.
37. G. Manzini, L. E. Xodo, D. Gasparotto, F. Quadrifoglio, G. A. vanderMarel, J. H. vanBoom, J. Mol. Biol. 1990, 213, 833-843.
38. E. Wickstrom, J. Biochem. Biophys. Methods 1986, 13, 97-102.
39. D. Leitner, W. Schröder, K. Weisz, J. Am. Chem. Soc. 1998, 120, 7123-7124.
40. H. Edelhoch, J. C. Osborne, Jr., Adv. Protein Chem. 1976, 30, 183-250
41. Y. K. Cheng, B. M. Pettitt, Prog. Biophys. Mol. Biol. 1992, 58, 225-257
42. M. Kamiya, H. Torigoe, H. Shindo, A. Sarai, J. Am. Chem. Soc. 1996, 118, 4532-4538
43. R. H. Shafer, Prog. Nucleic Acid Res. Mol. Biol. 1997, 59, 55-94.
44. M. Rougee, B. Faucon, J. L. Mergny, F. Barcelo, C. Giovannangeli, T. Garestier, C. Helene, Biochemistry 1992, 31, 9269-9278.
45. G. Zon, T. G. Geiser, Anticancer Drug Des. 1991, 6, 539-568
46. C. A. Stein, J. L. Tonkinson, L. Yakubov, Pharmacol. Ther. 1991, 52, 365-384.
47. L. Xodo, M. Alunni-Fabbroni, G. Manzini, F. Quadrifoglio, Nucleic Acids Res. 1994, 22, 3322-3330.
48. H. Fukada, K. Takahashi, Proteins Struct. Funct. Bioinf. 1998, 33, 159-166.