Nuclease resistant methylphosphonate-DNA/LNA chimeric oligonucleotides

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 10, 2009, Pages 2707-2709

  Nagahama, Koji ^a   Veedu, Rakesh N ^a   Wengel, Jesper ^a  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

Antisense; LNA; Methylphosphonate DNA; Nuclease stability; RNA targeting

Indexed keywords

ANTISENSE OLIGONUCLEOTIDE; COMPLEMENTARY DNA; COMPLEMENTARY RNA; DNA; LOCKED NUCLEIC ACID; METHYLPHOSPHONIC ACID; MONOMER; NUCLEASE; SPLEEN EXONUCLEASE;

3' UNTRANSLATED REGION; ARTICLE; BINDING AFFINITY; CHIMERA; DEGRADATION; DRUG DNA BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; MOLECULAR STABILITY;

ANIMALS; BASE SEQUENCE; DNA; EXONUCLEASES; OLIGONUCLEOTIDES; OLIGONUCLEOTIDES, ANTISENSE; PHOSPHORIC ACID ESTERS; PHOSPHORIC DIESTER HYDROLASES; RNA; SNAKES;

EID: 65349163672     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.03.116     Document Type: Article

References (40)

1. Nasevicius A., and Ekker S.C. Nat. Genet. 26 (2000) 216
2. Lee Y., Vassilakos A., Feng N., Jin H., Wang M., Xiong K., Wright J., and Young A. Int. J. Oncol. 28 (2006) 469
3. Cheng A.M., Byrom M.W., Shelton J., and Ford L.P. Nucleic Acid Res. 33 (2005) 1290
4. Vermeulen A., Robertson B., Dalby A.B., Marshall W.S., Karpilow J., Leake D., Khvorova A., and Baskerville S. RNA 13 (2007) 723
5. Crooke S.T. Curr. Mol. Med. 4 (2004) 465
6. Rayburn E.R., and Zhang R. Drug Discovery Today 13 (2008) 513
7. Freier S.M., and Altmann K.-H. Nucleic Acid Res. 25 (1997) 4429
8. Kurreck J. Eur. J. Biochem. 270 (2003) 1628
9. Summerton J.E. Curr. Top. Med. Chem. 7 (2007) 651
10. Miller P.S., Dreon N., Pulford S.M., and McParland K.B. J. Biol. Chem. 255 (1980) 9659
11. Hudziak R.M., Barofski E., Barfski D.F., Weller D., Huang S.-B., and Weller D.D. Antisense Nucleic Acid Drug Dev. 6 (1996) 267
12. Sood S., Shaw B.R., and Spielvogel B.F. J. Am. Chem. Soc. 112 (1991) 9000
13. Gruaznov S.M., and Chen J.-K. J. Am. Chem. Soc. 116 (1994) 3143
14. Nielsen P.E. Acc. Chem. Res. 32 (1999) 624
15. Wengel J. Acc. Chem. Res. 32 (1999) 301
16. Singh S.K., Nielsen P., Koshkin A.A., and Wengel J. Chem. Commun. (1998) 455 LNA was herein defined as an oligonucleotide containing one or more conformationally locked 2′-O,4′-C-methylene-β-d-ribofuranosyl nucleotide(s)
17. Obika S., Nanbu D., Hari Y., Andoh J., Morio K., Doi T., and Imanishi T. Tetrahedron Lett. 39 (1998) 5401
18. Singh S.K., and Wengel J. Chem. Commun. (1998) 1247
19. Vester B., and Wengel J. Biochemistry 43 (2004) 13233
20. Wahlestedt C., Salmi P., Good L., Kela J., Johnsson T., Hokfelt T., Broberger C., Porreca F., Lai J., Ren K., Ossipov M., Koshkin A., Jakobsen N., Skouv J., Ørum H., Jacobsen M.H., and Wengel J. Proc. Natl. Acad. Sci. U.S.A. 97 (2000) 5633
21. Morita K., Takagi M., Hasegawa C., Kaneko M., Tsutsumi S., Sone J., Ishikawa T., Imanishi T., and Koizumi M. Bioorg. Med. Chem. 11 (2003) 2211
22. Kaur H., Babu B.R., and Maiti S. Chem. Rev. 107 (2007) 4672
23. Crinelli R., Bianchi M., Gentilini L., Palma L., Sørensen M.D., Bryld T., Babu R.B., Arar K., Wengel J., and Magnani M. Nucleic Acids Res. 32 (2004) 1874
24. Vester B., Lundberg L.B., Sørensen M.D., Babu R.B., Douthwaite S., and Wengel J. J. Am. Chem. Soc. 124 (2002) 13682
25. Kauppinen S., Nielsen P.S., Mouritzen P., Nielsen A.T., Vissing H., Moller S., and Ramsing N.B. PharmaGenomics 3 (2003) 24
26. Dutkiewicz M., Grunert H.-P., Zeichhardt H., Lena S., Wengel J., and Kurreck J. FEBS Lett. 582 (2008) 3061
27. Fluiter K., Frieden M., Vreijling J., Rosenbohm C., De Wissel M.B., Christensen S.M., Koch T., Ørum H., and Baas F. ChemBioChem 6 (2005) 1
28. Elmén J., Lindow M., Schütz S., Lawrence M., Petri A., Obad S., Lindholm M., Hedtjärn M., Hansen H.F., Berger U., Gullans S., Kearney P., Sarnow P., Straarup E.M., and Kauppinen S. Nature 452 (2008) 896
29. Miller P.S., Braiterman L.T., and Ts'o P.O.P. Biochemistry 16 (1977) 1988
30. Shoji Y., Akhtar S., Periasamy A., Herman B., and Juliana R. Nucleic Acid Res. 19 (1991) 7253
31. Kean J.M., Cushman C.D., Kang H.M., Leonard T.E., and Miller P.S. Nucleic Acid Res. 22 (1994) 4497
32. Sarin P.S., Agrawal S., Civeira M.P., Goodchild J., Ikeuchi T., and Zamecnik P.C. Proc. Natl. Acad. Sci. U.S.A. 85 (1988) 7448
33. Tidd D.M., Hawley P., Warenius H.M., and Gibson I. Anticancer Drug Des. 3 (1998) 117
34. Reynolds M.A., Hogrefe R.I., Jaeger J.A., Schwartz D.A., Riley T.A., Marvin W.B., Daily W.J., Vaghefi M.M., Beck T.A., Knowless S.K., Klem R.E., and Arnold Jr. L.J. Nucleic Acid Res. 24 (1996) 4584
35. Lauritsen A., Dahl B.M., Dahl O., Vester B., and Wengel J. Bioorg. Med. Chem. Lett. 13 (2003) 253
36. Furdon P.J., Dominski Z., and Kole R. Nucleic Acid Res. 17 (1989) 9193
37. -, ON1: found 2753.8 (calcd 2753.3), ON2: found 2837.9 (calcd 2836.8), ON3: found 2748.7 (calcd 2746.1), ON4: found 2834.5 (calcd 2833.6), ON5: found 2743.8 (calcd 2741.9), ON6: found 2828.3 (calcd 2827.5), ON7: found 2882.3 (calcd 2876.9). Reversed phase HPLC (RP-HPLC) can be used to evaluate the purity of MP-DNA containing ONs as the non-charged nature of the MP linkages allows one-nucleotide separation.
38. Hoke G.D., Draper K., Freier S.M., Gonzalez C., Driver V.B., Zounes M.C., and Ecker D.J. Nucleic Acid Res. 19 (1991) 5743
39. Kurreck J., Wyszko E., Gillen C., and Erdmann V.A. Nucleic Acid Res. 30 (2002) 1911
40. Morita K., Hasegawa C., Kaneko M., Tsutsumi S., Sone J., Ishikawa T., Imanishi T., and Koizumi M. Bioorg. Med. Chem. Lett. 12 (2002) 73