Synthesis and fluorescent properties of 5-(1-pyrenylethynyl)-2′-deoxyuridine-containing oligodeoxynucleotides

Bioorganicheskaya Khimiya

Volumn 26, Issue 1, 2000, Pages 48-50

  Malakhov, A D ^a   Malakhova, E V ^a   Kuznitsova, S V ^a   Grechishnikova, I V ^a   Prokhorenko, I A ^a   Skorobogatyi, M V ^a   Korshun, V A ^a   Berlin, Yu A ^a  

^a SHEMYAKIN OVCHINNIKOV INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

Author keywords

5 (1 pyrenylethynyl) 2 deoxyuridine; Fluorescent detection; Hybridization; Modified oligonucleotide

Indexed keywords

5 (PYRENYLETHYNYL) 2' DEOXYURIDINE; 5-(PYRENYLETHYNYL)-2'-DEOXYURIDINE; DRUG DERIVATIVE; FLUORESCENT DYE; OLIGODEOXYRIBONUCLEOTIDE; PYRENE DERIVATIVE; URIDINE;

ARTICLE; CHEMISTRY; SYNTHESIS;

FLUORESCENT DYES; OLIGODEOXYRIBONUCLEOTIDES; PYRENES; URIDINE;

EID: 0033651816     PISSN: 01323423     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (69)

1. Tyagi S., Kramer F.R. // Nature Biotechnol. 1996. V. 14. P. 303-308.
2. Tyagi S., Bratu D.P., Kramer F.R. // Nature Biotechnol. 1998. V. 16. P. 49-53.
3. Piatek A.S., Tyagi S., Pol A.C., Telenti A., Miller L.P., Kramer F.R., Alland D. // Nature Biotechnol. 1998. V. 16. P. 359-363.
4. Kostrikis L.G., Tyagi S., Mhlanga M.M., Ho D.D., Kramer F.R. // Science. 1998. V. 279. P. 1228-1229.
5. Sokol D.L., Zhang X., Lu P., Gewirtz A.M. // Proc. Natl. Acad. Sci. USA. 1998. V. 95. P. 11538-11543.
6. Fang X., Liu X., Schuster S., Tan W. // J. Am. Chem. Soc. 1999. V. 121. P. 2921-2922.
7. Chen X., Zehnbauer B., Gnirke A., Kwok P.-Y. // Proc. Natl. Acad. Sci. USA. 1997. V. 94. P. 10756-10761.
8. Chen X., Kwok P.-Y. // Nucl. Acids Res. 1997. V. 25. P. 347-353.
9. Chen X., Livak P.-Y., Kwok P.-Y. // Genome Res. 1998. V. 8. P. 549-556.
10. Bernard P.S., Lay M.J., Wittwer C.T. // Anal. Biochem. 1998. V. 255. P. 101-107.
11. Mullah B., Livak K., Andrus A., Kenney P. // Nucl. Acids Res. 1998. V. 26. P. 1026-1031.
12. Ju J., Ruan C., Fuller C.W., Glazer A., Mathies R.A. // Proc. Natl. Acad. Sci. USA. 1995. V. 92. P. 4347-4351.
13. Metzker M.L., Lu J., Gibbs R.A. // Science. 1996. V. 271. P. 1420-1422.
14. Ju J., Glazer A., Mathies R.A. // Nature Medicine. 1996. V. 2. P. 246-249.
15. Hung S.-C., Mathies R.A., Glazer A. // Anal. Biochem. 1997. V. 252. P. 78-88.
16. Glazer A., Mathies R.A. // Curr. Opin. Biotechnol. 1997. V. 8. P. 94-102.
17. Hung S.-C., Mathies R.A., Glazer A. // Anal. Biochem. 1998. V. 255. P. 32-38.
18. Rippe K., Fritsch V., Westhof E., Jovin T.M. // EMBO J. 1992. V. 11. P. 3777-3786.
19. Fritzsche H., Akhebat A., Taillandier E., Rippe K., Jovin T.M. // Nucl. Acids Res. 1993. V. 21. P. 5085-5091.
20. Tong G., Lawlor J.M., Tregear G.W., Haralambidis J. // J. Am. Chem. Soc. 1995. V. 117. P. 12151-12158.
21. Ebata K., Masuko M., Ohtani H., Kashiwasake-Jibu M. // Photochem. Photobiol. 1995. V. 62. P. 836-839.
22. Förtsch I., Fritzsche H., Birch-Hirschfeld E., Evertsz E., Klement R., Jovin T.M., Zimmer C. // Biopolymers. 1996. V. 38. P. 209-220.
23. Mohammadi S., Slama-Schwok A., Leger G., El Manouni D., Shchyolkina A., Leroux Y., Taillandier E. // Biochemistry. 1997. V. 36. P. 14836-14844.
24. Yamana K., Takei M., Nakano H. // Tetrahedron Lett. 1997. V. 38. P. 6051-6054.
25. Lewis F.D., Zhang Y., Letsinger R.L. // J. Am. Chem. Soc. 1997. V. 119. P. 5451-5452.
26. Förtsch I., Birch-Hirschfeld E., Jovin T.M., Stelzner A., Zimmer C.// Nucleosides Nucleotides. 1998. V. 17. P. 1539-1545.
27. Balakin K.V., Korshun VA., Mikhalev I.I., Maleev G.V., Malakhov A.D., Prokhorenko I.A., Berlin Yu.A. // Biosensors Bioelectronics. 1998. V. 13. P. 771-778.
28. Masuko M., Ohtani H., Ebata K., Shimadzu A. // Nucl. Acids Res. 1998. V. 26. P. 5409-5416.
29. Paris P.L., Langenhan J.M., Kool E.T. // Nucl. Acids Res. 1998. V. 26. P. 3789-3793.
30. Koenig P., Reines S.A., Cantor C.R. // Biopolymers. 1977. V. 16. P. 2231-2242.
31. Yamana K., Gokota T., Ozaki H., Nakano H., Sangen O., Shimidzu T. // Nucleosides Nucleotides. 1992. V. 11. P. 383-390.
32. Mann J.S., Shibata Y., Meehan T. // Bioconjugate Chem. 1992. V. 3. P. 554-558.
33. Yamana K., Nunota K., Nakano H., Sangen O. // Tetrahedron Lett. 1994. V. 35. P. 2555-2558.
34. Kierzek R., Li Y., Turner D.H., Bevilacqua P.C. // J. Am. Chem. Soc. 1993. V. 115. P. 4985-4992.
35. Li Y., Bevilacqua P.C., Mathews D., Turner D.H. // Biochemistry. 1995. V. 34. P. 14394-14399.
36. Yguerabide J., Talavera E., Alvarez J.M., Afkir M. // Anal. Biochem. 1996. V. 241. P. 238-247.
37. Preuß R., Dapprich J., Walter N.G. // J. Mol. Biol. 1997. V. 273. P. 600-613.
38. Yamana K., Iwase R., Furutani S., Tsuchida H., Zako H., Yamaoka T., Murukami A. // Nucleic Acids Res. 1999. V. 27. P. 2387-2392.
39. Nakasuji K., Akiyama S., Nakagawa M. // Bull. Chem. Soc. Japan. 1972. V. 45. P. 875-882.
40. Gan L.-S.L., Acebo A.L., Alworth W.L. // Biochemistry. 1984. V. 23. P. 3827-3836.
41. Bilow N., Landis A.L., Austin W.B., Woolley D.D. // SAMPE J. 1982. V. 18. P. 19-24.
42. Crisp G.T., Jiang Y.-L. // Synth. Commun. 1998. V. 28. P. 2571-2576.
43. Bodendorf K., Kloss P. // Angew. Chem. 1963. B. 75. S. 139.
44. Bodendorf K., Mayer R. // Chem. Ber. 1965. B. 98. S. 3554-3560.
45. Lötzbeyer J., Bodendorf K. // Chem. Ber. 1967. B. 100. S. 2620-2624.
46. Royles B.J.L., Smith D.M. // J. Chem. Soc., Perkin Trans. 1. 1994. P. 355-358.
47. Bachmann W.E., Carmack M. // J. Am. Chem. Soc. 1941. V. 63. P. 2494-2499.
48. Gordon A.J., Ford R.A. The Chemist's Companion. A Handbook of Practical Data, Techniques, and References. New York: Wiley-Interscience, 1972. P. 269.
49. Classon B., Samuelsson B. // Acta Chem. Scand. 1985. V. B39. P. 501-504.
50. Graham D., Parkinson J.A., Brown T. // J. Chem. Soc., Perkin Trans. 1. 1998. P. 1131-1138.
51. Ahmadian M., Zhang P., Bergstrom D.E. // Nucl. Acids Res. 1998. V. 26. P. 3127-3135.
52. Caruthers M.H., Barone A.D., Beaucage S.L., Dodds D.R., Fisher E.F., McBride L.J., Matteucci M., Stabinsky Z., Tang J.-Y. // Meth. Enzymol. 1987. V. 154. P. 287-313.
53. Damha M.J., Giannaris P.A., Zabarylo S.V. // Nucl. Acids Res. 1990. V. 18. P. 3813-3821.
54. Atkinson T., Smith M. // Oligonucleotide Synthesis: A Practical Approach. // Ed. M.H. Gait. Oxford: IRL Press, 1984. P. 36-81.
55. Korshun V.A., Balakin K.V., Proskurina T.S., Mikhalev I.I., Malakhov A.D., Berlin Y.A. // Nucleosides Nucleotides. 1999. V. 18. P. 2661-2676.
56. De Mesmaeker A., Häner R., Martin P., Moser H.E. // Acc. Chem. Res. 1995. V. 28. P. 366-374.
57. Freier S.M., Altmann K.-H. // Nucl. Acids Res. 1997. V. 25. P. 4429-4443.
58. Winnik F.M. // Chem. Rev. 1993. V. 93. P. 587-614.
59. Gan L.-S.L., Lu J.-Y.L., Hershkowitz D.M., Alworth W.L. // Biochem. Biophys. Res. Commun. 1985. V. 129. P. 591-596.
60. Inouye M., Fujimoto K., Furusyo M., Nakazumi H. // J. Am. Chem. Soc. 1999. V. 121. P. 1452-1458.
61. Sarobe M., Zwikker J.W., Snoeijer J.D., Wiersum U.E., Jenneskens L.W. // J. Chem. Soc., Chem. Commun. 1994. P. 89-90.
62. Reimlinger H. // Chem. Ind. 1969. No 37. P. 1306.