Biopolym. Cell. 1999; 15(5):367-373.
http://dx.doi.org/10.7124/bc.000532
Structure and Function of Biopolymers
Synthesis and study of antisense oligonuclcolides modified with imidazophenazine nucleosides
1Makitruk V. L., 1Shalamay A. S., 2Dubey I. Y., 2Fedoryak D. M.
  1. Institute of Molecular Biology and Genetics, NAS of Ukraine
    150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680
  2. Institute of Bioorganic Chemistry and Petrochemistry, NAS of Ukraine
    1, Murmans'ka Str., Kyiv, Ukraine, 02094

Abstract

Oligonucleotides containing imidazophenazine nucleosides at 3'-, 5'-and internal positions, which are complementary to certain regions of ribosomal operon DNA and I6S rRNA of mycoplasmas and E. coli, have been synthesized by H-phosphonate solid phase method. It has been shown that nucleosides of imidazol [4,5-b]phenazine and its 2-methyl analog as efficient intercalating agents strongly affect the stability of complementary complexes increasing the antisense activity of modified otigonucleotide sequence.
Full text: (PDF, in Ukrainian)

References

[1] Uhlmann E, Peyman A. Antisense oligonucleotides: a new therapeutic principle. Chem Rev. 1990;90(4):543–84.
[2] Knorre DG, Vlassov VV. Antisense oligonucleotide derivatives as gene-targeted drugs. Biomed Sci. 1990;1(4):334-43.
[3] Goodchild J. Conjugates of oligonucleotides and modified oligonucleotides: A review of their synthesis and properties Bioconjug Chem. 1990;1(3):165-87.
[4] Englisch U., Gauss D.H. Chemically modified oligonucleotides as probes and inhibitors. Angewandte Chemie - International Edition in English, 1991; 30 (6):613-629.
[5] Conkin V., Sasmor H., Digiorgio J., Warren W. Producing pharmaceutical-grade antisense DNA: An envolving discipline. Millipore Bioforum (Technology news for the life scientist)1992 Bedford:2-4.
[6] Beaucage S.L., Iyer R.P. The functionalization of oligonucleotides via phosphoramidite derivatives. Tetrahedron. 1993; 49 (10):1925-1963.
[7] Korshun VA, Berlin YuA Introduction nonradioactive reporter groups into synthetic oligonucleotides and their detection. Bioorg. Khim. 1994; 20(6):565— 616.
[8] Asseline U, Toulme F, Thuong NT, Delarue M, Montenay-Garestier T, H?l?ne C. Oligodeoxynucleotides covalently linked to intercalating dyes as base sequence-specific ligands. Influence of dye attachment site. EMBO J. 1984;3(4):795-800.
[9] Helene C, Montenay-Garestier T, Saison T, Takasugi M, Toulm? JJ, Asseline U, Lancelot G, Maurizot JC, Toulma F, Thuong NT. Oligonucleotides covalently linked to intercalating agents: A new class of gene regulatory substances Biochimie. 1985;67(7-8):777-83.
[10] Helene C. The anti-gene strategy: Control of gene expression by triplex-forming-oligonucleotides Anticancer Drug Des. 1991;6(6):569-84.
[11] Thuong NT, Helene C. Sequence-specific recognition and modification of double-helical DNA by oligonucleotides Angewandte Chemie (International Edition in English), 1993; 32 (5):666-690.
[12] Asseline U., Thuong N.T., Helene C. Synthesis and properties of oligonucleotides covalently linked to intercalating agents. New Journal of Chemistry, 1997; 21 (1):5-17.
[13] Bischofberger N., Matteucci M.D. Synthesis of novel polycyclic nucleoside analogues, incorporation into oligodeoxynucleotides, and interaction with complementary sequences. Journal of the American Chemical Society, 1989; 111 (8):3041-3046.
[14] Lin, K.-Y., Jones, R.J., Matteucci, M. Tricyclic 2?-deoxycytidine analogs: Syntheses and incorporation into oligodeoxynucleotides which have enhanced binding to complementary RNA Journal of the American Chemical Society, 1995; 117 (13):3873-3874.
[15] A Practical Approach, Oligonucleotide synthesis, Ed. M. J. Gait. 1984 Oxford: IRL press. p. 218.
[16] Handbook of biochemistry and molecular biology. Ed. G. Fasman. Boca Raton: CRC press, 1975. 175p.
[17] Makytruk V. L., Shalamay A. S., Kondratyuk I. V. Synthesis and studies of the ribofuranosides phenazazoles Biopolym. Cell. 1997; 13(6):453-459
[18] Froehler BC, Ng PG, Matteucci MD. Synthesis of DNA via deoxynucleoside H-phosphonate intermediates. Nucleic Acids Res. 1986;14(13):5399-407.
[19] Matteucci M.D., Caruthers M.H. Synthesis of deoxyoligonucleotides on a polymer support. Journal of the American Chemical Society, 1981; 103(11):3185-3191.
[20] Zarytova V. F., Kutyavin I. V., Sil'nikov V. N., Shishkin G. V. Modification of nucleic acids in stabilized complementary complexes. I. Synthesis of alkylating derivatives of oligodeoxyribonucleotides having a 5'-terminal N-(2-oxy-ethyl)-phenazinium residue. Russian Journal of Bioorganic Chemistry 1986, 12 (7):911-920
[21] Kutyavin IV, Podyminogin MA, Bazhina YuN, Fedorova OS, Knorre DG, Levina AS, Mamayev SV, Zarytova VF. N-(2-hydroxyethyl)phenazinium derivatives of oligonucleotides as effectors of the sequence-specific modification of nucleic acids with reactive oligonucleotide derivatives. FEBS Lett. 1988;238(1):35-8.
[22] Zarytova VF, Ivanova EM, Kutyavin IV synthesis derivatives of oligodeoxyribonucleotides containing at the 3'-end of the chain residue N-(2-hydroxyethyl)-phenazinium Izvestia SO AN USSR. khim seria 1989;(6):3—9.
[23] Lokhov SG, Podyminogin MA, Sergeev DS, Silnikov VN, Kutyavin IV, Shishkin GV, Zarytova VP. Synthesis and high stability of complementary complexes of N-(2-hydroxyethyl)phenazinium derivatives of oligonucleotides. Bioconjug Chem. 1992;3(5):414-9.
[24] Blagoi Yu. P., Zozulya V. N., Voloshin I. M., Makitruk V. L., Shalamay A. S., Shcherbakova A. S. Investigation of phenazine derivatives interaction with DNA by polarized fluorescence method. Biopolym. Cell. 1997; 13(1):22-29
[25] Zozulya V, Blagoi Y, Lober G, Voloshin I, Winter S, Makitruk V, Shalamay A. Fluorescence and binding properties of phenazine derivatives in complexes with polynucleotides of various base compositions and secondary structures. Biophys Chem. 1997;65(1):55-63.
[26] Zozulya V. N., Blagoi Yu. P., Dubey I. Y., Fedoryak O. D., Shcherbakova A. S., Fedoryak D. M. Stabilization of duplex and triplex complexes of oligothymidylate by covalently linked imidazophenazine glycoside. Biopolym. Cell. 1998; 14(1):54-61
[27] Babichev VV, Skripal' IG, Bezugly? SV, Panchenko LP, Shalama? AS, Makitruk BL, Goncharenko VS, Shimko NN. Oligodeoxyribonucleotides complementary to sections of the mollicute ribosomal operon as transcription inhibitors in vitro. Mikrobiol Z. 1993;55(6):29-35.
[28] Korobkova ES, Panchenko LP, Shalamai AS, Skripal' IG. The ability of the oligodeoxyribonucleotides complementary to the 3'-terminal segment of 16s-rRNA in Mollicutes to suppress translation in their ribosomes in an in-vitro system Mikrobiol Z. 1995;57(3):30-6.
[29] Skrypal' IH, Babychev VV, Panchenko LP, Iehorov OV, Korobkova KS, Dube? IIa, Fedoriak DM, Shalama? AS. Antisignature oligonucleotides and their analogs as inhibitors of mollicutes-cofactors of HIV Mikrobiol Z. 1997;59(2):3-11.