Properties of novel oligonucleotide analogues containing an acyclic nucleoside and a carbamate linkage

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 12, 1996, Pages 1357-1360

  Obika, Satoshi ^a   Takashima, Yosbihiro ^a   Matsumoto, Yasuhide ^a   Shimoyama, Atsuko ^a   Koishihara, Yasuo ^b   Ohsugi, Yoshiyuki ^b   Doi, Takefumi ^a   Imanishi, Takeshi ^a  

^a OSAKA UNIVERSITY   (Japan)

^b CHUGAI PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACYCLIC NUCLEOSIDE; CARBAMIC ACID; DOUBLE STRANDED DNA; DOUBLE STRANDED RNA; OLIGONUCLEOTIDE; PHOSPHOROTHIOIC ACID DERIVATIVE;

ARTICLE; CELL PROLIFERATION; DRUG STABILITY; DRUG SYNTHESIS; DRUG TARGETING; VIRUS REPLICATION;

EID: 0029971015     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00223-5     Document Type: Article

References (23)

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2. Zamecnik, P. C.; Stephenson, M. L. Proc. Natl. Acad. Sci. USA, 1978, 75, 280; Matsukura, M.; Shinozuka, K.; Zon, G.; Mitsuya, H.; Reitz, M.; Cohen, J. S.; Broder, S. ibid, 1987, 84, 7706; Leiter, J. M. E.; Agrawal, S.; Palese, P.; Zamecnik, P. C. ibid, 1990, 87, 3430.
3. Zamecnik, P. C.; Stephenson, M. L. Proc. Natl. Acad. Sci. USA, 1978, 75, 280; Matsukura, M.; Shinozuka, K.; Zon, G.; Mitsuya, H.; Reitz, M.; Cohen, J. S.; Broder, S. ibid, 1987, 84, 7706; Leiter, J. M. E.; Agrawal, S.; Palese, P.; Zamecnik, P. C. ibid, 1990, 87, 3430.
4. Gewirtz, A. M.; Calabretta, B. Science, 1988, 242, 1303; Gewirtz, A. M.; Anfossi, G.; Venturelli, D.; Valpreda, S.; Sims, R.; Calabretta, B. ibid, 1989, 245, 180; Simons, M.; Edelman, E. R.; DeKeyser, J.-L.; Langer, R.; Rosenberg, R. D. Nature, 1992, 359, 67.
5. Gewirtz, A. M.; Calabretta, B. Science, 1988, 242, 1303; Gewirtz, A. M.; Anfossi, G.; Venturelli, D.; Valpreda, S.; Sims, R.; Calabretta, B. ibid, 1989, 245, 180; Simons, M.; Edelman, E. R.; DeKeyser, J.-L.; Langer, R.; Rosenberg, R. D. Nature, 1992, 359, 67.
6. Gewirtz, A. M.; Calabretta, B. Science, 1988, 242, 1303; Gewirtz, A. M.; Anfossi, G.; Venturelli, D.; Valpreda, S.; Sims, R.; Calabretta, B. ibid, 1989, 245, 180; Simons, M.; Edelman, E. R.; DeKeyser, J.-L.; Langer, R.; Rosenberg, R. D. Nature, 1992, 359, 67.
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10. Beaucage, S. L.; Iyer, R. P. Tetrahedron, 1993, 49, 6123; Varma, R. S. Synlett., 1993, 621 and references cited therein.
11. Sarmiento, U. M.; Perez, J. R.; Becker, J. M.; Narayanan, R. Antisense Res. Dev., 1994, 4, 99; Galbraith, W. M.; Hobson, W. C.; Giclas, P. C.; Schechter, P. J.; Agrawal, S. ibid, 1994, 4, 201.
12. Sarmiento, U. M.; Perez, J. R.; Becker, J. M.; Narayanan, R. Antisense Res. Dev., 1994, 4, 99; Galbraith, W. M.; Hobson, W. C.; Giclas, P. C.; Schechter, P. J.; Agrawal, S. ibid, 1994, 4, 201.
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15. The sequence of oligonucleotide 3 was selected from: Idziak, I.; Just, G.; Damha, M. J.; Giannaris, P. A. Tetrahedron Lett., 1993, 34, 5417.
16. Melting temperatures were determined by adding equimolar amounts of complementary or mismatch strands in the buffer. The mixture was heated to 95 °C and slowly cooled to 25 °C over 10 h, then to 0 °C over another 1 h. The UV absorption (260 nm) of the mixture at gradually increasing temperature (from 0 °C to 95 °C, 0.2 °C per min) was measured on a UV-2100PC (Shimadzu) equipped with a thermocontroller SPR-8.
17. Molecular modeling experiments revealed that, in order to form B-form duplex between our dimer units and natural nucleotides, type A dimer unit requires syn orientation of the carbamate linkage, while type B requires anti orientation. The oligonucleotide containing type B dimer was expected to be more suitable for hybridization with complementary nucleotides, because anti carbamate linkage is thought to be more stable than syn carbamate linkage. See, Balaram, H.; Prasad, B. V. V.; Balaram, P. J. Am. Chem. Soc., 1983, 105, 4065; Hoos, R.; Naughton, A. B.; Thiel, W.; Vasella, A.; Weber, W.; Rupitz, K.; Withers, S. G. Helv. Chim. Acta., 1993, 76, 2666; Nguyen, M. T.; De Wael, K.; Zeegers-Huyskens, T. J. Phys. Chem., 1995, 99, 9739.
18. Molecular modeling experiments revealed that, in order to form B-form duplex between our dimer units and natural nucleotides, type A dimer unit requires syn orientation of the carbamate linkage, while type B requires anti orientation. The oligonucleotide containing type B dimer was expected to be more suitable for hybridization with complementary nucleotides, because anti carbamate linkage is thought to be more stable than syn carbamate linkage. See, Balaram, H.; Prasad, B. V. V.; Balaram, P. J. Am. Chem. Soc., 1983, 105, 4065; Hoos, R.; Naughton, A. B.; Thiel, W.; Vasella, A.; Weber, W.; Rupitz, K.; Withers, S. G. Helv. Chim. Acta., 1993, 76, 2666; Nguyen, M. T.; De Wael, K.; Zeegers-Huyskens, T. J. Phys. Chem., 1995, 99, 9739.
19. Molecular modeling experiments revealed that, in order to form B-form duplex between our dimer units and natural nucleotides, type A dimer unit requires syn orientation of the carbamate linkage, while type B requires anti orientation. The oligonucleotide containing type B dimer was expected to be more suitable for hybridization with complementary nucleotides, because anti carbamate linkage is thought to be more stable than syn carbamate linkage. See, Balaram, H.; Prasad, B. V. V.; Balaram, P. J. Am. Chem. Soc., 1983, 105, 4065; Hoos, R.; Naughton, A. B.; Thiel, W.; Vasella, A.; Weber, W.; Rupitz, K.; Withers, S. G. Helv. Chim. Acta., 1993, 76, 2666; Nguyen, M. T.; De Wael, K.; Zeegers-Huyskens, T. J. Phys. Chem., 1995, 99, 9739.
20. Recently, another type of acyclic thymidine dimer analogue with carbamate internucleoside linkage was reported in which the tandem incorporation of them into oligonucleotide markedly reduced the hybridization ability: Habus, I.; Agrawal, S. Nucleosides & Nucleotides, 1995, 14, 1853.
21. Tidd, D. M.; Warenius, H. M. Br. J. Cancer, 1989, 60, 343; Hoke, G. D.; Draper, K.;. Freier, S. M; Gonzalez, C.; Driver, V. B.; Zounes, M. C.; Ecker, D. J. Nucleic Acids Res., 1991, 19, 5743.
22. Tidd, D. M.; Warenius, H. M. Br. J. Cancer, 1989, 60, 343; Hoke, G. D.; Draper, K.;. Freier, S. M; Gonzalez, C.; Driver, V. B.; Zounes, M. C.; Ecker, D. J. Nucleic Acids Res., 1991, 19, 5743.
23. Performed as described in: Vandendriessche, F.; Van Aerschot, A.; Voortmans, M.; Janssen, G.; Busson, R.; Van Overbeke, A.; Van den Bossche, W.; Hoogmartens, J.; Herdewijn, P. J. Chem. Soc., Perkin Trans. 1, 1993, 1567.