Structural modifications toward improved antisense oligonucleotides

Perspectives in Drug Discovery and Design - Tập 4 Số 1 - Trang 1-16 - 1996
Mark D. Matteucci1
1Gilead Sciences, Inc., Foster City, USA

Tóm tắt

Từ khóa


Tài liệu tham khảo

Belikova, A.M., Zarytova, V.F. and Grineva, N.I., Tetrahedron Lett., (1967) 3557.

Halford, M.H. and Jones, A.S., Nature, 217 (1968) 638.

Uhlmann, E. and Peyman, A., Chem. Rev., 90 (1990) 543.

Crooke, S.T. and Lebleu, B. (Eds.) Antisense Research and Applications, CRC Press, Boca Raton, FL, 1993.

Sanghvi, Y.S. and Cook, P.D., In Sanghvi, Y.S. and Cook, P.D. (Eds.) Carbohydrate Modifications in Antisense Research, American Chemical Society, Washington, DC, 1994, pp. 1–22.

Wagner, R.W., Nature, 372 (1994) 333.

Burgess, T.L., Fisher, E.F., Ross, S.L., Bready, J.V., Qian, Y.-X., Bayewitch, L.A., Cohen, A.M., Herrera, C.J., Hu, S.S.-F., Kramer, T.B., Lott, F.D., Martin, F.H., Pierce, G.F., Simonet, L. and Farrell, C.L., Proc. Natl. Acad. Sci. USA, 92 (1995) 4051.

Smetsers, T.F.C.M., Van de Locht, L.T.F., Pennings, A.H.M., Wessels, H.M.C., De Witte, T.M. and Mensink, E.J.B.M., Leukemia, 9 (1995) 118.

Agrawal, S. and Goodchild, J., Tetrahedron Lett., 28 (1987) 3539.

Furdon, P.J., Dominski, Z. and Kole, R., Nucleic Acids Res., 17 (1989) 9193.

Hoke, G.D., Draper, K., Freier, S.M., Gonzalex, C., Driver, V.B., Zounes, M.C. and Ecker, D.J., Nucleic Acids Res., 19 (1991) 5743.

Fisher, T.L., Terhorst, T., Cao, X. and Wagner, R.W., Nucleic Acids Res., 21 (1993) 3857.

Puglisi, J.D. and Tinoco Jr., I., Methods Enzymol., 180 (1989) 304.

Freier, S.M., In Crooke, S.T. and Lebleu, B. (Eds.) Antisense Research and Applications, CRC Press, Boca Raton, FL, 1993, pp. 67–82.

Moulds, C., Lewis, J.G., Froehler, B.C., Grant, D., Huang, T., Milligan, J.F., Matteucci, M.D. and Wagner, R.W., Biochemistry, 34 (1995) 5044.

Chin, D.J., Green, G.A., Zon, G., Szoka Jr., F.C. and Straubinger, R.M., New Biologist, 2 (1990) 1091.

Leonetti, J.P., Mechti, N., Degols, G., Gagnor, C. and Lebleu, B., Proc. Natl. Acad. Sci. USA, 88 (1991) 2702.

Bennett, C.F., Chiang, M.-Y., Chan, H., Shoemaker, J.E.E. and Mirabelli, C.K., Mol. Pharmacol., 41 (1992) 1023.

Thierry, A.R. and Dritschilo, A., Nucleic Acids Res., 20 (1992) 5691.

Wagner, R.W., Matteucci, M.D., Lewis, J.G., Gutierrez, A.J., Moulds, C. and Froehler, B.C., Science, 260 (1993) 1510.

Dean, N. and McKay, R., Proc. Natl. Acad. Sci. USA, 91 (1994) 11762.

Agrawal, S., Temsani, J. and Tang, J.Y., Proc. Natl. Acad. Sci. USA, 88 (1991) 7595.

Matsukura, M., Shinozuka, K., Zon, G., Mitsuya, H., Reitz, M., Cohen, J.S. and Broder, S., Proc. Natl. Acad. Sci. USA, 84 (1987) 7706.

Cohen, J.S., In Crooke, S.T. and Lebleu, B. (Eds.) Antisense Research and Applications, CRC Press, Boca Raton, FL, 1993, pp. 205–221.

Wyatt, J.R., Vickers, T.A., Roberson, J.L., Buckheit Jr., R.W., Klimkait, T., DeBaets, E., Davis, P.W., Rayner, B., Imbach, J.L. and Ecker, D.J., Proc. Natl. Acad. Sci. USA, 91 (1994) 1356.

Brill, W.K.-D., Tang, J.-Y., Ma, Y.-X. and Caruthers, M.H., J. Am. Chem. Soc., 111 (1989) 2321.

Bjergäde, K. and Dahl, O., Nucleic Acids Res., 19 (1991) 5843.

Marshall, W.S. and Caruthers, M.H., Science, 259 (1993) 1564.

Sood, S., Shaw, R.B. and Spielvogel, B.F., J. Am. Chem. Soc., 112 (1991) 9000.

Shabarova, Z.A., Biochemie, 70 (1988) 1323.

Mag, M., Rainer, S. and Engels, J.W., Tetrahedron Lett., 33 (1992) 7319.

Zielinski, W.S. and Orgel, L.E., Nucleic Acids Res., 15 (1987) 1699.

Gryaznov, S.M. and Chen, J.-K., J. Am. Chem. Soc., 116 (1994) 3143.

Gryaznov, S.M., Lloyd, D.H., Chen, J.-K., Schultz, R.G., DeDionisio, L.A., Ratmeyer, L. and Wilson, W.D., Proc. Natl. Acad. Sci. USA, 92 (1995) 5798.

Miller, P.S., Biotechnology, 9 (1991) 358.

Miller, P.S., Ts'o, P.O.P., Hogrefe, R.I., Reynolds, M.A. and Arnold Jr., L.J., In Crooke, S.T. and Lebleu, B. (Eds.) Antisense Research and Applications, CRC Press, Boca Raton, FL, 1993, pp. 189–203.

Miller, P.S., McParland, K.B., Jayaraman, K. and Ts'o, P.O.P., Biochemistry, 20 (1981) 1874.

Shoji, Y., Akhtar, S., Periasamy, A., Herman, B. and Juliano, R., Nucleic Acids Res., 19 (1991) 5543.

Lesnikowski, Z.J., Jaworska, M. and Stec, W., Nucleic Acids Res., 18 (1990) 2109.

Varma, R.S., SynLett., 9 (1993) 621.

Nielsen, P.E., Egholm, M., Berg, R.H. and Buchardt, O., Science, 254 (1991) 1497.

Jones, R.J., Lin, K.-Y., Milligan, J.F., Wadwani, S. and Matteucci, M.D., J. Org. Chem., 58 (1993) 2983.

Veal, J.M., Gao, X. and Brown, F.K., J. Am. Chem. Soc., 115 (1993) 7139.

Vasseur, J.-J., Debart, F., Sanghvi, Y.S. and Cook, P.D., J. Am. Chem. Soc., 114 (1992) 4006.

Lebreton, J., Waldner, A., Fritsch, V., Wolf, R.M. and De Mesmaeker, A., Tetrahedron Lett., 35 (1994) 5225.

De Mesmaeker, A., Lebreton, J., Waldner, A., Fritsch, V. and Wolf, R.M., Bioorg. Med. Chem. Lett., 4 (1994) 873.

Roughton, A.L., Portmann, S., Benner, S.A. and Egli, M., J. Am. Chem. Soc., 117 (1995) 7249.

McElroy, E.B., Bandaru, R., Huand, J. and Widlanski, T.S., Bioorg. Med. Chem. Lett., 4 (1994) 1071.

Huie, E.M., Kirshenbaum, M.R. and Trainor, G.L., J. Org. Chem., 57 (1992) 4569.

Quartin, R.S., Brakel, C.L. and Wetmur, J.G., Nucleic Acids Res., 17 (1989) 7253.

Dagle, J.M., Andracki, M.E., DeVine, R.J. and Walder, J.A., Nucleic Acids Res., 19 (1991) 1805.

Agrawal, S., Mayrand, S.H., Zamecnik, P.C. and Pederson, T., Proc. Natl. Acad. Sci. USA, 87 (1990) 1401.

Inoue, H., Hayase, Y., Iwai, S. and Ohtsuka, E., FEBS Lett., 215 (1987) 327.

Shibahara, S., Mukai, S., Nishihara, T., Inoue, H., Ohtsuka, E. and Morisawa, H., Nucleic Acids Res., 15 (1987) 4403.

Leonetti, J.-P., Degols, G. and Lebleu, B., Bioconj. Chem., 1 (1990) 149.

Letsinger, R.L., Singman, C.N., Histand, G. and Salunkhe, M., J. Am. Chem. Soc., 110 (1988) 4470.

Saha, A.K., Schairer, W., Waychunas, C., Prasad, C.V.C., Sardaro, M., Upson, D.A. and Kruse, L.I., Tetrahedron Lett., 34 (1993) 6017.

De Mesmaeker, A., Waldner, A., Sanghvi, Y.S. and Lebreton, J., Bioorg. Med. Chem. Lett., 4 (1994) 395.

Caulfield, T.J., Prasad, C.V.C., Prouty, C.P., Saha, A.K., Sardaro, M.P. and Schairer, D.W.C., Bioorg. Med. Chem. Lett., 3 (1993) 2771.

Fathi, R., Huang, Q., Coppola, G., Delaney, W., Teasdale, R., Krieg, A.M. and Cook, A.F., Nucleic Acids Res., 22 (1994) 5416.

Dempcy, R.O., Browne, K.A. and Bruice, T.C., Proc. Natl. Acad. Sci. USA, 92 (1995) 6097.

Saenger, W., Principles of Nucleic Acid Structure, Springer, Berlin, 1988.

Plavec, H., Thibaudeau, C. and Chattopadhyaya, J., J. Am. Chem. Soc., 116 (1994) 6558.

Inoue, H., Hayase, Y., Imura, A., Iwai, S., Miura, K. and Ohtsuka, E., Nucleic Acids Res., 15 (1987) 6131.

Kawasaki, A.M., Casper, M.D., Freier, S.M., Lesnik, E.A., Zounes, M.C., Cummins, L.L., Gonzalez, C. and Cook, P.D., J. Med. Chem., 36 (1993) 831.

Lesnik, E.A., Guinosso, C.J., Kawasaki, A.M., Sasmor, H., Zounes, M.C., Cummins, L.L., Ecker, D.E., Cook, P.D. and Freier, S.M., Biochemistry, 32 (1993) 7832.

Keller, T.H. and Häner, R., Nucleic Acids Res., 21 (1993) 4499.

Cummins, L.L., Owens, S.R., Risen, L.M., Lesnik, E.A., Freier, S.M., McGee, D., Guinosso, C.J. and Cook, P.D., Nucleic Acids Res., 23 (1995) 2019.

Fensholdt, J., Thrane, H. and Wengel, J., Tetrahedron Lett., 36 (1995) 2535.

Jørgensen, P.N., Stein, P.C. and Wengel, J., J. Am. Chem. Soc., 116 (1994) 2231.

Altmann, K.-H. and Kesselring, R., SynLett., 10 (1994) 853.

Bellon, L., Leydier, C., Barascut, J.-L., Maury, G. and Imbach, J.-L., In Sanghvi, Y.S. and Cook, P.D. (Eds.) Carbohydrate Modifications in Antisense Research, American Chemical Society, Washington, DC, 1994, pp. 68–79.

Altmann, K.-H., Bévierre, M.-O., De Mesmaeker, A. and Moser, H.E., Bioorg. Med. Chem. Lett., 5 (1995) 431.

Altmann, K.-H., Freier, S.M., Pieles, U. and Winkler, T., Angew. Chem., Int. Ed. Engl., 33 (1994) 1654.

Saha, A.K., Caulfield, T.J., Hobbs, C., Upson, D.A., Waychunas, C. and Yawman, A.M., J. Org. Chem., 60 (1995) 788.

Jencks, W.P., Adv. Enzymol., 43 (1975) 219.

Tarköy, M. and Leumann, C., Angew. Chem., Int. Ed. Engl., 32 (1993) 1432.

Jones, R.J., Swaminathan, S., Milligan, J.F., Wadwani, S., Froehler, B.C. and Matteucci, M.D., J. Am. Chem. Soc., 115 (1993) 9816.

Altmann, K.-H., Kesselring, R., Francotta, E. and Rihs, G., Tetrahedron Lett., 35 (1994) 2331.

Eschenmoser, A., Pure Appl. Chem., 65 (1993) 1179.

Augustyns, K., Vandendriessche, F., Van Aerschot, A., Busson, R., Urbanke, C. and Herdewijn, P., Nucleic Acids Res., 20 (1992) 4711.

Augustyns, K., Godard, G., Hendrix, C., Van Aerschot, A., Rozenski, J., Saison-Behmoaras, T. and Herdwijn, P., Nucleic Acids Res., 21 (1993) 4670.

Van Aerschot, A., Verheggen, I., Hendrix, C. and Herdewijn, P., Angew. Chem., Int. Ed. Engl., 34 (1995) 1338.

Monia, B.P., Lesnik, E.A., Gonzalez, C., Lima, W.F., McGee, D., Guinosso, C.J., Kawasaki, A.M., Cook, P.D. and Freier, S.M., J. Biol. Chem., 268 (1993) 14514.

Sanghvi, Y.S., In Crooke, S.T. and Lebleu, B. (Eds.) Antisense Research and Applications, CRC Press, Boca Raton, FL, 1993, pp. 273–288.

Anand, N.N., Brown, D.M. and Salisbury, S.A., Nucleic Acids Res., 15 (1987) 8167.

Inoue, H., Imura, A. and Ohtsuka, E., Nucleic Acids Res., 13 (1985) 7119.

Froehler, B.C., Wadwani, S., Terhorst, T.J. and Gerrard, S.R., Tetrahedron Lett., 33 (1992) 5307.

Froehler, B.C., Jones, R.J., Cao, X. and Terhorst, T.J., Tetrahedron Lett., 34 (1993) 1003.

Lin, K.-Y., Pudlo, J.S., Jones, R.J., Bischofberger, N., Matteucci, M.D. and Froehler, B.C., Bioorg. Med. Chem. Lett., 4 (1994) 1061.

Gutierrez, A.J., Terhorst, T.J., Matteucci, M.D. and Froehler, B.C., J. Am. Chem. Soc., 116 (1994) 5540.

Hashimoto, H., Nelson, M.G. and Switzer, C., J. Am. Chem. Soc., 115 (1993) 7128.

Lin, K.-Y., Jones, R.J. and Matteucci, M., J. Am. Chem. Soc., 117 (1995) 3873.

Chollet, A., Chollet-Damerius, A. and Kawashima, E.H., Chem. Scripta, 26 (1986) 37.

Howard, F.B. and Miles, H.T., Biochemistry, 23 (1984) 6723.

Gryaznov, S. and Schultz, R.G., Tetrahedron Lett., 35 (1994) 2489.

Seela, F. and Driller, H., Nucleic Acids Res., 15 (1985) 911.

Seela, F. and Thomas, H., Helv. Chim. Acta, 78 (1995) 94.

Ramasamy, K.S., Zounes, M., Gonzalez, C., Freier, S.M., Lesnik, E.A., Cummins, L.L., Griffey, R.H., Monia, B.P. and Cook, P.D., Tetrahedron Lett., 35 (1994) 215.

Heeb, N.V. and Benner, S.A., Tetrahedron Lett., 35 (1994) 3045.

Schmid, N. and Behr, J.-P., Tetrahedron Lett., 36 (1995) 1447.