Natural and synthetic G-quadruplex interactive berberine derivatives

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 6, 2006, Pages 1707-1711

  Franceschin, Marco ^a,b   Rossetti, Luigi ^a   D'Ambrosio, Anna ^a   Schirripa, Stefano ^a   Bianco, Armandodoriano ^a   Ortaggi, Giancarlo ^a   Savino, Maria ^a   Schultes, Christoph ^b   Neidle, Stephen ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b IMPERIAL CANCER RESEARCH FUND   (United Kingdom)

Author keywords

Alkaloid; Berberine; G quadruplex; Telomerase

Indexed keywords

1,3 DIIODOPROPANE; ACETONE; ACETYLSALICYLIC ACID; ALKALOID DERIVATIVE; BERBERINE DERIVATIVE; CORALYNE; DOUBLE STRANDED DNA; IMIDE; N,N' BIS(2 (1 PIPERIDINO)ETHYL 3,4,9,10 PERYLENE TETRA CARBOXYLIC DIIMIDE; NATURAL PRODUCT; PROPANE; TELOMERASE; TELOMERE BINDING PROTEIN; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DNA BINDING; DNA STRUCTURE; ENZYME INHIBITION; NONHUMAN; POLYACRYLAMIDE GEL ELECTROPHORESIS; SYNTHESIS;

ANTINEOPLASTIC AGENTS; BERBERINE ALKALOIDS; DNA; HUMANS; INTERCALATING AGENTS; LIGANDS; NUCLEIC ACID DENATURATION; NUCLEIC ACID HETERODUPLEXES; PIPERIDINES; TELOMERASE; TELOMERE;

EID: 32044461141     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.12.001     Document Type: Article

References (34)

1. S. Neidle, and G.N. Parkinson Curr. Opin. Struct. Biol. 13 2003 275
2. A.J. Zaug, E.R. Podell, and T.R. Cech Proc. Natl. Acad. Sci. U.S.A. 102 2005 10864
3. S. Neidle, and G. Parkinson Nat. Rev. Drug Discov. 1 2002 383
4. L.R. Kelland Eur. J. Cancer 41 2005 971
5. T.M. Fletcher Expert Opin. Ther. Targets 9 2005 457
6. H.L. Wu, C.Y. Hsu, W.H. Liu, and B.Y. Yung Int. J. Cancer 81 1999 923
7. A.K. Ghosh, F.K. Bhattacharyya, and D.K. Ghosh Exp. Parasitol. 60 1985 404
8. R.X. Zhang Chinese Med. J. 103 1990 658
9. I. Naasani, H. Seimiya, T. Yamori, and T. Tsuruo Cancer Res. 59 1999 4004
10. J. Ren, and J.B. Chaires Biochemistry 38 1999 16067
11. K.Y. Zee-Cheng, and C.C. Cheng J. Pharm. Sci. 61 1972 969
12. L.J. Latimer, N. Payton, G. Forsyth, and J.S. Lee Biochem. Cell Biol. 73 1995 11
13. L. Rossetti, M. Franceschin, A. Bianco, G. Ortaggi, and M. Savino Bioorg. Med. Chem. Lett. 12 2002 2527
14. L. Rossetti, M. Franceschin, S. Schirripa, A. Bianco, G. Ortaggi, and M. Savino Bioorg. Med. Chem. Lett. 15 2005 413
15. 32 Initially 200 ligand orientations were randomly centred on the G-quadruplex structure, charges were not considered and the complexes were minimized for 500 steps. The 75 lowest energy structures were then subjected to simulated annealing, then 500 steps of minimization was followed by molecular dynamics over a period of 10 ps. The resulting structures were then minimized.
16. G.N. Parkinson, M.P. Lee, and S. Neidle Nature 417 2002 876
17. Kim, J. H.; Chung, J. N.; Paik, Y. K.; Park, J.; Kim, E. D.; Lee, Y. S.; Kim, S. E. US Patent 6008356, 1999.
18. 3: 53.3% C, 5.4% H, 4.3% N; found: 54.1% C, 6.1% H, 4.4% N.
19. 12-14.
20. D. Gomez, J.L. Mergny, and J.F. Riou Cancer Res. 62 2002 3365
21. F. Koeppel, J.F. Riou, A. Laoui, P. Mailliet, P.B. Arimondo, D. Labit, O. Petitgenet, C. Hélène, and J.L. Mergny Nucleic Acids Res. 29 2001 1087
22. J.L. Mergny, and J.C. Maurizot Chembiochem 2 2001 124
23. J.L. Mergny, L. Lacroix, M.P. Teulade-Fichou, C. Hounsou, L. Guittat, M. Hoarau, P.B. Arimondo, J.P. Vigneron, J.M. Lehn, J.F. Riou, T. Garestier, and C. Hélène Proc. Natl. Acad. Sci. U.S.A. 98 2001 3062
24. DNA was dissolved in a stock 20 μM solution in 10 mM TE (Tris, EDTA) buffer (pH 8.0); further dilutions were carried out in 50 mM potassium cacodylate buffer (pH 7.4). The FRET assay was modified for a 96-well format with a DNA Opticon Engine (MJ Research) with excitation at 450-495 nm and detection at 515-545 nm. Fluorescence readings were taken at intervals of 0.5°C over the range 30-100°C, with a constant temperature being maintained for 30 s prior to each reading to ensure a stable value.
25. J.T. Kern, and S.M. Kerwin Bioorg. Med. Chem. Lett. 12 2002 3395
26. S.M. Kerwin, G. Chen, J.T. Kern, and P.W. Thomas Bioorg. Med. Chem. Lett. 12 2002 447
27. J.T. Kern, P.W. Thomas, and S.M. Kerwin Biochemistry 41 2002 11379
28. A 1 mg/ml solution of calf thymus DNA was sonicated to ∼500 bp fragments. Sonicated DNA and drug stocks were mixed to obtain a 1 ml solution containing 30 μM DNA, 50 mM potassium cacodylate (pH 7.4) and 3 or 30 μM drugs for [drugs]/[DNA] ratio (R) 0.1 and 1, respectively. DNA melting curves were obtained by 260 nm absorbance measurement on a UV-vis spectrophotometer (JASCO V-530). The temperature range was covered in 70 min, and the absorbance values collected every 10 s.
29. 34.
30. M.Y. Kim, M. Gleason-Guzman, E. Izbicka, D. Nishioka, and L.H. Hurley Cancer Res. 63 2003 3247
31. F. Xing, G. Song, J. Ren, J.B. Chaires, and X. Qu FEBS Lett. 579 2005 5035
32. R.J. Harrison, J. Cuesta, G. Chessari, M.A. Read, S.K. Basra, A.P. Reszka, J. Morrell, S.M. Gowan, CM. Incles, F.A. Tanious, W.D. Wilson, L.R. Kelland, and S. Neidle J. Med. Chem. 46 2003 4463
33. N.W. Kim, M.A. Piatyszek, K.R. Prowse, C.B. Harley, M.D. West, P.L.C. Ho, G.M. Coviello, W.E. Wright, S.L. Weinrich, and J.W. Shay Science 266 1994 2011
34. Y. Gan, J. Lu, A. Johnson, M.G. Wientjes, D.E. Schuller, and J.L. Au Pharm. Res. 18 2001 488