A Carbazole Derivative Synthesis for Stabilizing the Quadruplex Structure
Cheng-Chung Chang
Institute of Atomic and Molecular Sciences, Academia Sinica, P. O. Box 23–166, Taipei 106, Taiwan, R.O.C.
Search for more papers by this authorJin-Yi Wu
Institute of Atomic and Molecular Sciences, Academia Sinica, P. O. Box 23–166, Taipei 106, Taiwan, R.O.C.
Search for more papers by this authorCorresponding Author
Ta-Chau Chang
Institute of Atomic and Molecular Sciences, Academia Sinica, P. O. Box 23–166, Taipei 106, Taiwan, R.O.C.
Tel: +886-2-23668231; fax: +886-2-23620200Search for more papers by this authorCheng-Chung Chang
Institute of Atomic and Molecular Sciences, Academia Sinica, P. O. Box 23–166, Taipei 106, Taiwan, R.O.C.
Search for more papers by this authorJin-Yi Wu
Institute of Atomic and Molecular Sciences, Academia Sinica, P. O. Box 23–166, Taipei 106, Taiwan, R.O.C.
Search for more papers by this authorCorresponding Author
Ta-Chau Chang
Institute of Atomic and Molecular Sciences, Academia Sinica, P. O. Box 23–166, Taipei 106, Taiwan, R.O.C.
Tel: +886-2-23668231; fax: +886-2-23620200Search for more papers by this authorAbstract
A new molecule of 3,6-Bis(1-methyl-4-vinylpyridium iodine)carbazole (BMVC) was synthesized for stabilizing the quadruplex structure of human telomeric sequence of d(T2AG3)4 in vitro. Mixing BMVC with the DNA can raise the melting temperature of the d(T2AG3)4 by ∼ 13 °C, implying that BMVC could be a useful telomerase inhibitor. In addition, the fluorescence of the BMVC increased significantly upon interacting with the d(T2AG3)4 which may be useful as a G-quadruplex specific marker.
References
- 1a Blackburn, E. H.; Greider, C. W. Telomeres; Cold Spring Harbor Laboratory Press: New York, 1996.
- 1b Blackburn, E. H.; Szostake, J. W. Annu. Rev. Biochem. 1984, 53, 163–194.
- 1c Williamson, J. R. Annu. Rev. Biophys. Biomol. Struct. 1994, 23, 703–730.
- 2a Lundblad, V.; Szostak, J. W. Cell 1989, 57, 633–643.
- 2b Sandell, L. L.; Zakian, V. A. Cell 1993, 75, 729–739.
- 2c Harley, C. B.; Villeponteau, M. P. Curr. Opin. Genet. Dev. 1995, 5, 249–255.
- 3a Greider, C. W.; Blackburn, E. H. Cell 1987, 51, 887–898.
- 3b Feng, J.; Funk, W. D.; Wang, S.-S.; Weinrich, S. L.; Avilion, A. A.; Chiu, C.-P.; Adams, R. R.; Chang, E.; Allsopp, R. C.; Yu, J.; Le, S.; West, M. D.; Harley, C. B.; Andrews, W. H.; Greider, C. W.; Villeponteau, B. Science 1995, 269, 1236–1241.
- 4 Harley, C. B.; Futcher, A. B.; Greider, C. W. Nature 1990, 345, 458–460.
- 5 Blackburn, E. H. Nature 1991, 350, 569–573.
- 6 Morin, G. B. Cell 1989, 59, 521–529.
- 7 Gellert, M.; Lipsett, M. N.; Davies, D. R. Proc. Natl. Acad. Sci. USA 1962, 48, 2013–2018.
- 8 Zahler, A. M.; Williamson, J. R.; Cech, T. R.; Prescott, D. M. Nature 1991, 350, 718–720.
- 9a Mergny, J. L.; Hélène, C. Nature Med. 1998, 4, 1366–1367.
- 9b Han, H. Y.; Hurley, L. H. Trends Pharmacol. Sci. 2000, 21, 136–142.
- 10a Sun, D.; Thompson, B.; Cathers, B. E.; Salazar, M.; Kerwin, S. M.; Trent, J. O.; Neidle, S.; Hurley, L. H. J. Med. Chem. 1997, 40, 2113–2116.
- 10b Perry, P. J.; Gowan, S. M.; Reszka, A. P.; Polucci, P.; Jenkins, T. C.; Kelland, L. R.; Neidle, S. J. Med. Chem. 1998, 41, 3253–3260.
- 10c Zewail-Foote, M.; Hurley, L. H. J. Am. Chem. Soc. 2001, 123, 6485–6495.
- 10d Shi, D.-F.; Wheelhouse, R. T.; Sun, D.; Hurley, L. H. J. Med. Chem. 2001, 44, 4509–4523.
- 10e Koeppel, F.; Riou, J.-F.; Laoui, A.; Mailliet, P.; Arimondo, P. B.; Labit, D.; Petitgenet, O.; Hélène, C.; Mergny, J.-L. Nucleic Acids Res. 2001, 29, 1087–1096.
- 10f Read, M.; Harrison, R. J.; Romabnoli, B.; Tanious, F. A.; Gowan, S. H.; Reszka, A. P.; Wilson, W. D.; Kelland, L. R.; Neidle, S. Proc. Natl. Acad. Sci. 2001, 98, 4844–4849.
- 11 Mergny, J. L.; Lacroix, L.; Teulade-Fichou, M.-P.; Hounsou, C.; Guittat, L.; Hoarau, M.; Arimondo, P. B.; Vigneron, J.-P.; Lehn, J.-M.; Riou, J.-F.; Garestier, T.; Hélène, C. Proc. Natl. Acad. Sci. USA 2001, 98, 3062–3067.
- 12a Giraldo, R.; Suzuki, M.; Chapman, L.; Rhodes, D. Proc. Natl. Acad. Sci. USA 1994, 91, 7658–7662.
- 12b Jin, R.; Gaffney, B.; Wang, C.; Joons, R.; Breslauer, K. J. Proc. Natl. Acad. Sci. USA 1992, 89, 8832–8836.
- 12c Scaria, P. V.; Shire, S. J.; Shafer, R. H. Proc. Natl. Acad. Sci. USA 1992, 89, 10336–10340.
- 12d Williamson, J. R. Curr. Opin. Struct. Biol. 1993, 3, 357–362.
