Amido-Bridged Nucleic Acids (AmNAs): Synthesis, Duplex Stability, Nuclease Resistance, and in Vitro Antisense Potency

ChemBioChem

Volumn 13, Issue 17, 2012, Pages 2513-2516

  Yahara, Aiko ^a   Shrestha, Ajaya Ram ^a   Yamamoto, Tsuyoshi ^a   Hari, Yoshiyuki ^a   Osawa, Takashi ^a   Yamaguchi, Masaki ^a   Nishida, Masaru ^a   Kodama, Tetsuya ^a   Obika, Satoshi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Bridged nucleic acids; Nuclease resistance; Oligonucleotides; Synthesis design; Thermal stability

Indexed keywords

AMIDE; ANTISENSE OLIGONUCLEOTIDE; CARBOXYLIC ACID; NUCLEASE; NUCLEIC ACID; OLIGONUCLEOTIDE; PYRIDINIUM DERIVATIVE; PYRIDINIUM DICHROMATE; RNA; THYMINE PHOSPHORAMIDITE; UNCLASSIFIED DRUG;

ANTISENSE THERAPY; ARTICLE; CRYSTAL STRUCTURE; DEBENZYLATION; DRUG POTENCY; ENZYME STABILITY; IN VITRO STUDY; NUCLEIC ACID SYNTHESIS; PRIORITY JOURNAL; RNA METHYLATION; RNA STRUCTURE;

AMIDES; APOLIPOPROTEINS B; BASE SEQUENCE; CELL LINE; CHEMISTRY TECHNIQUES, SYNTHETIC; HUMANS; OLIGONUCLEOTIDES; OLIGONUCLEOTIDES, ANTISENSE; PHOSPHORIC DIESTER HYDROLASES; TRANSITION TEMPERATURE;

EID: 84869482664     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201200506     Document Type: Article

References (38)

1. S. Obika, D. Nanbu, Y. Hari, K. Morio, Y. In, T. Ishida, T. Imanishi, Tetrahedron Lett. 1997, 38, 8735-8738;
2. S. Obika, D. Nanbu, Y. Hari, J. Andoh, T. Doi, T. Imanishi, Tetrahedron Lett. 1998, 39, 5401-5404.
3. S. K. Singh, P. Nielsen, A. A. Koshkin, J. Wengel, Chem. Commun. 1998, 455-456;
4. A. A. Koshkin, S. K. Singh, P. Nielsen, V. K. Rajwanshi, R. Kumar, M. Meldgaard, C. E. Olsen, J. Wengel, Tetrahedron 1998, 54, 3607-3630.
5. S. K. Singh, J. Wengel, Chem. Commun. 1998, 1247-1248;
6. A. A. Koshkin, P. Nielsen, M. Meldgaard, V. K. Rajwanshi, S. K. Singh, J. Wengel, J. Am. Chem. Soc. 1998, 120, 13252-13253.
7. C. Wahlestedt, P. Salmi, L. Good, J. Kela, T. Johnsson, T. Hökfelt, C. Broberger, F. Porreca, J. Lai, K. Ren, M. Ossipov, A. Koshkin, N. Jakobsen, J. Skouv, H. Oerum, M. H. Jacobsen, J. Wengel, Proc. Natl. Acad. Sci. USA 2000, 97, 5633-5638.
8. J. Elmén, M. Lindow, S. Schütz, M. Lawrence, A. Petri, S. Obad, M. Lindholm, M. Hedtjärn, H. F. Hansen, U. Berger, S. Gullans, P. Kearney, P. Sarnow, E. M. Straarup, S. Kauppinen, Nature 2008, 452, 896-899;
9. N. Gupta, N. Fisker, M.-C. Asselin, M. Lindholm, C. Rosenbohm, H. Ørum, J. Elmén, N. G. Seidah, E. M. Straarup, PLoS One 2010, 5, e10682;
10. R. E. Lanford, E. S. Hildebrandt-Eriksen, A. Petri, R. Persson, M. Lindow, M. E. Munk, S. Kauppinen, H. Ørum, Science 2010, 327, 198-201.
11. Y. Hari, S. Obika, R. Ohnishi, K. Eguchi, T. Osaki, H. Ohishi, T. Imanishi, Bioorg. Med. Chem. 2006, 14, 1029-1038;
12. S. M. Abdur Rahman, S. Seki, S. Obika, H. Yoshikawa, K. Miyashita, T. Imanishi, J. Am. Chem. Soc. 2008, 130, 4886-4896;
13. M. Nishida, T. Baba, T. Kodama, A. Yahara, T. Imanishi, S. Obika, Chem. Commun. 2010, 46, 5283-5285;
14. A. R. Shrestha, Y. Hari, A. Yahara, T. Osawa, S. Obika, J. Org. Chem. 2011, 76, 9891-9899.
15. K. Morita, M. Takagi, C. Hasegawa, M. Kaneko, S. Tsutsumi, J. Sone, T. Ishikawa, T. Imanishi, M. Koizumi, Bioorg. Med. Chem. 2003, 11, 2211-2226.
16. R. Kumar, S. K. Singh, A. A. Koshkin, V. K. Rajwanshi, M. Meldgaard, J. Wengel, Bioorg. Med. Chem. Lett. 1998, 8, 2219-2222;
17. C. Rosenbohm, S. M. Christensen, M. D. Sørensen, D. S. Pedersen, L. E. Larsen, J. Wengel, T. Koch, Org. Biomol. Chem. 2003, 1, 655-663.
18. N. Albæk, M. Petersen, P. Nielsen, J. Org. Chem. 2006, 71, 7731-7740.
19. P. Srivastava, J. Barman, W. Pathmasiri, O. Plashkevych, M. Wenska, J. Chattopadhyaya, J. Am. Chem. Soc. 2007, 129, 8362-8379;
20. O. P. Varghese, J. Barman, W. Pathmasiri, O. Plashkevych, D. Honcharenko, J. Chattopadhyaya, J. Am. Chem. Soc. 2006, 128, 15173-15187;
21. C. Zhou, O. Plashkevych, J. Chattopadhyaya, Org. Biomol. Chem. 2008, 6, 4627-4633.
22. T. P. Prakash, A. Siwkowski, C. R. Allerson, M. T. Migawa, S. Lee, H. J. Gaus, C. Black, P. P. Seth, E. E. Swayze, B. Bhat, J. Med. Chem. 2010, 53, 1636-1650.
23. M. Nina, R. Fonné-Pfister, R. Beaudegnies, H. Chekatt, P. M. J. Jung, F. Murphy-Kessabi, A. De Mesmaeker, S. Wendeborn, J. Am. Chem. Soc. 2005, 127, 6027-6038.
24. C. Selvam, S. Thomas, J. Abbott, S. D. Kennedy, E. Rozners, Angew. Chem. 2011, 123, 2116-2118; Angew. Chem. Int. Ed. 2011, 50, 2068-2070.
25. P. E. Nielsen, M. Egholm, R. H. Berg, O. Buchardt, Science 1991, 254, 1497.
26. S. K. Singh, R. Kumar, J. Wengel, J. Org. Chem. 1998, 63, 6078-6079;
27. S. K. Singh, R. Kumar, J. Wengel, J. Org. Chem. 1998, 63, 10035-10039.
28. C. Höbartner, R. Micura, J. Am. Chem. Soc. 2004, 126, 1141-1149.
29. CCDC 869692 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data_request/cif.
30. Although most antisense agents are modified with PS linkages to enhance their stabilities against nucleases, we used PS-free oligonucleotides in order to compare the natures of the compounds with those of LNAs.
31. P. S. Pallan, C. R. Allerson, A. Berdeja, P. P. Seth, E. E. Swayze, T. P. Prakash, M. Egli, Chem. Commun. 2012, 48, 8195-8197.
32. J. Kurreck, E. Wyszko, C. Gillen, V. A. Erdmann, Nucleic Acid Res. 2002, 30, 1911-1918.