Stabilization of G-quadruplex DNA and down-regulation of oncogene c-myc by quindoline derivatives

Journal of Medicinal Chemistry

Volumn 50, Issue 7, 2007, Pages 1465-1474

  Ou, Tian Miao ^a   Lu, Yu Jing ^a   Zhang, Chi ^a   Huang, Zhi Shu ^a   Wang, Xiao Dong ^a   Tan, Jia Heng ^a   Chen, Yuan ^a   Ma, Dik Lung ^c   Wong, Kwok Yin ^b,c   Tang, Johnny Cheuk On ^b,c   Chan, Albert Sun Chi ^b,c   Gu, Lian Quan ^a  

^a SUN YAT SEN UNIVERSITY   (China)

^b State Key Laboratory of Chinese Medicine and Molecular Pharmacology   (China)

^c HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DNA; GUANINE; QUINDOLINE DERIVATIVE; SODIUM PROTON EXCHANGE PROTEIN 3; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; CARBOXY TERMINAL SEQUENCE; CELL STRAIN HEPG2; CIRCULAR DICHROISM; CULTURE MEDIUM; DOWN REGULATION; DRUG EFFECT; DRUG EFFICACY; DRUG STRUCTURE; GENE CONTROL; ISOMER; MOLECULAR MODEL; NUCLEOTIDE SEQUENCE; ONCOGENE C MYC; POLYACRYLAMIDE GEL ELECTROPHORESIS; POLYMERASE CHAIN REACTION; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; SEQUENCE ANALYSIS; STRUCTURE ANALYSIS;

ALKALOIDS; ANTINEOPLASTIC AGENTS; BASE SEQUENCE; CELL LINE, TUMOR; CELL PROLIFERATION; CIRCULAR DICHROISM; DIALYSIS; DNA; ELECTROSTATICS; GUANINE; HUMANS; INDOLES; ISOMERISM; MODELS, MOLECULAR; NUCLEIC ACID CONFORMATION; PROMOTER REGIONS (GENETICS); PROTO-ONCOGENE PROTEINS C-MYC; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS;

EID: 34147100699     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0610088     Document Type: Article

References (36)

1. Resar, L. M.; Emison, E.; Kim, S.; Li, Q.; Prescott, J. E.; Wonsey, D.; Zeller, K. Function of the c-Myc oncogenic transcription factor. Exp. Cell Res. 1999, 253, 63-77.
2. Simonsson, T.; Pribylova, M.; Vorlickova, M. A nuclease hypersensitive element in the human c-myc promoter adopts several distinct i-tetraplex structures. Biochem. Biophys. Res. Commun. 2000, 278, 158-166.
3. Postel, E. H.; Berberich, S. J.; Rooney, J. W.; Kaetzel, D. M. Human NM23/nucleoside diphosphate kinase regulates gene expression through DNA binding to nuclease-hypersensitive transcriptional elements. J. Bioenerg. Biomembr. 2000, 32, 277-284.
4. Simonsson, T.; Pecinka, P.; Kubista, M. DNA tetraplex formation in the control region of c-myc. Nucleic Acids Res. 1998, 26, 1167-1172.
5. Michelotti, E. F.; Tomonaga, T.; Krutzsch, H.; Levens, D. Cellular nucleic acid binding protein regulates the CT element of the human c-myc protooncogene. J. Biol. Chem. 1995, 270, 9494-9499.
6. Tomonaga, T.; Levens, D. Activating transcription from single stranded DNA. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 5830-5835.
7. Siddiqui-Jain, A.; Grand, C. L.; Bearss, D. J.; Hurley, L. H. Direct evidence for a G-quadruplex in a promoter region and its targeting with a small molecule to repress c-MYC transcription. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 11593-11598.
8. Lemarteleur, T.; Gomez, D.; Paterski, R.; Mandine, E.; Mailliet, P.; Riou, J. F. Stabilization of the c-myc gene promoter quadruplex by specific ligands' inhibitors of telomerase. Biochem. Biophys. Res. Commun. 2004, 323, 802-808.
9. Grand, C. L.; Han, H.; Munoz, R. M.; Weitman, S.; Von Hoff, D. D.; Hurley, L. H.; Bearss, D. J. The cationic porphyrin TMPyP4 down-regulates c-MYC and human telomerase reverse transcriptase expression and inhibits tumor growth in vivo. Mol. Cancer Ther. 2002, 1, 565-573.
10. Seenisamy, J.; Bashyam, S.; Gokhale, V.; Vankayalapati, H.; Sun, D.; Siddiqui-Jain, A.; Streiner, N.; Shin-ya, K.; White, E.; Wilson, W. D.; Hurley, L. H. Design and synthesis of an expanded porphyrin that has selectivity for the c-MYC G-quadruplex structure. J. Am. Chem. Soc. 2005, 127, 2944-2959.
11. (a) Guittat, L.; Alberti, P.; Rosu, F.; Miert, S.V.; Thetiot, E.; Pieters, L.; Gabelica, V.; Pauw, E. D.; Ottaviani, A.; Riou, J.-F.; Mergny, J.-L. Interactions of cryptolepine and neocryptolepine with unusual DNA structures. Biochimie 2003, 85, 535-547.
12. (b) Zhou, J. L.; Lu, Y. J.; Ou, T. M.; Zhou, J. M.; Huang, Z. S.; Zhu, X. F.; Du, C. J.; Bu, X. Z.; Ma, L.; Gu, L. Q.; Li, Y. M.; Chan, S. C. Synthesis and evaluation of quindoline derivatives as G-quadruplex inducing and stabilizing ligands and potential inhibitors of telomerase. J. Med. Chem. 2005, 48, 7315-7321.
13. Zhou, J. M.; Zhu, X. F.; Lu, Y. J.; Deng, R.; Huang, Z. S.; Mei, Y. P.; Wang, Y.; Huang, W. L.; Liu, Z. C.; Gu, L. Q.; Zeng, Y. X. Senescence and telomere shortening induced by novel potent G-quadruplex interactive agents, quindoline derivatives, in human cancer cell lines. Oncogene 2006, 25, 503-511.
14. Balagurumoorthy, P.; Brahmachari, S. K. Structure and stability of human telomeric sequence. J. Biol. Chem. 1994, 269, 21858-21869.
15. Balagurumoorthy, P.; Brahmachari, S. K.; Mohanty, D.; Bansal, M.; Sasisekharan, V. Hairpin and parallel quadruplex structures for telomeric sequences. Nucleic Acids Res. 1992, 20, 4061-4067.
16. Seenisamy, J.; Rezler, E. M.; Powell, T. J.; Tye, D.; Gokhale, V.; Joshi, C. S.; Siddiqui-Jain, A.; Hurley, L. H. The dynamic character of the G-quadruplex element in the c-MYC promoter and modification by TMPyP4. J. Am. Chem. Soc. 2004, 126, 8702-8709.
17. Kim, M. Y.; Gleason-Guzman, M.; Izbicka, E.; Nishioka, D.; Hurley, L. H. The different biological effects of telomestatin and TMPyP4 can be attributed to their selectivity for interaction with intramolecular or intermolecular G-quadruplex structures. Cancer Res. 2003, 63, 3247-3256.
18. Ren, J.; Chaires, J. B. Sequence and structural selectivity of nucleic acid binding ligands. Biochemistry 1999, 38, 16067-16075.
19. (a) Rossetti, L.; Franceschin, M.; Bianco, A.; Ortaggi, G.; Savino, M. Perylene diimides with different side chains are selective in inducing different G-quadruplex DNA structures and in inhibiting telomerase. Bioorg. Med. Chem. Lett. 2002, 12, 2527-2533.
20. (b) Wheelhouse, R. T.; Jennings, S. A.; Philips, V. A.; Pletsas, D.; Murphy, P. M.; Garbett, N. C.; Chaires, J. B.; Jenkins, T. C. Design, synthesis, and evaluation of novel biarylpyrimidines: A new class of ligand for unusual nucleic acid structures. J. Med. Chem. 2006, 49, 5187-5198.
21. Facchini, L. M.; Penn, L. Z. The molecular role of Myc in growth and transformation: Recent discoveries lead to new insight. FASEB J. 1998, 12, 633-651.
22. Simonsson, T.; Henriksson, M. C-myc suppression in Burkitt's lymphoma cells. Biochem. Biophys. Res. Commun. 2002, 290, 11-15.
23. (a) Wheelhouse, R. T.; Sun, D.; Han, H.; Han, F. X.; Hurley, L. H. Cationic porphyrins as telomerase inhibitors: the interaction of tetra-(N-methyl-4-pyridyl)porphine with quadruplex DNA. J. Am. Chem. Soc. 1998, 120, 3261-3262.
24. (b) Likussar, W.; Blotz, D. F. Theory of continuous variations plots and a new method for spectrophotoetric determination of extraction and formation constants. Anal. Chem. 1971, 43, 1265-1272.
25. Totrov, M.; Abagyan, R. Flexible protein-ligand docking by global energy optimization in internal coordinates. Proteins 1997, 1 (Suppl.), 215-220.
26. Harrison, R. J.; Cuesta, J.; Chessari, G.; Read, M. A.; Basra, S. K.; Reszka, A. P.; Morrell, J.; Gowan, S. M.; Incles, C. M.; Tanious, F. A.; Wilson, W. D.; Kelland, L. R.; Neidle, S. Trisubstituted acridine derivatives as potent and selective telomerase inhibitors. J. Med. Chem. 2003, 46, 4463-4476.
27. Parkinson, G. N.; Lee, M. P. H.; Neidle, S. Crystal structure of parallel quadruplexes from human telomeric DNA. Nature 2002, 417, 876-880.
28. DeLano, W. L. The PyMOL Molecular Graphics System; DeLano Scientific: San Carlos, CA.
29. Ambrus, A.; Chen, D.; Dai, J. X.; Jones, R. A.; Yang, D. Z. Solution structure of the biologically relevant G-quadruplex element in the human c-myc promoter. Implications for G-quadruplex stabilization. Biochemistry 2005, 44, 2048-2058.
30. Ruan, F.; Liu, S. Y. Combination antigene therapy targeting c-myc and c-erbB2 in the ovarian cancer COC1 cell line. Gynecol. Oncol. 2002, 85, 40-44.
31. Insight II; molecular modeling software; Accelrys Inc.: 9685 Scranton Rd., San Diego, CA, 92121, 2000.
32. Jorgensen, W. L.; Chandresekhar, J.; Madura, J. D.; Impey, R. W.; Klein, M. L. Comparison of simple potential functions for simulating liquid water. J. Chem. Phys. 1983, 79, 926-935.
33. Kale, L.; Skeel, R.; Bhandarkar, M.; Brunner, R.; Gursoy, A.; Krawetz, N.; Phillips, J.; Shinozaki, A.; Varadarajan, K.; Schulten, K. NAMD2: Greater scalability for parallel molecular dynamics. J. Comput. Phys. 1999, 151, 283-312.
34. Humphrey, W.; Dalke, A.; Schulten, K. VMD: Visual molecular dynamics. J. Mol. Graphics 1996, 14, 33-38, 27-28.
35. MacKerell, A. D., Jr.; Bashford, D.; Bellott, M.; Dunbrack, R. L., Jr.; Evanseck, J.; Field, M. J.; Fischer, S.; Gao, J.; Guo, H.; Ha, S.; Joseph, D.; Kuchnir, L.; Kuczera, K.; Lau, F. T. K.; Mattos, C.; Michnick, S.; Ngo, T.; Nguyen, D. T.; Prodhom, B.; Reiher, I. W. E.; Roux, B.; Schlenkrich, M.; Smith, J.; Stote, R.; Straub, J.; Watanabe, M.; Wiorkiewicz-Kuczera, J.; Yin, D.; Karplus, M. All-atom empirical potential for molecular modeling and dynamics study of proteins. J. Phys. Chem. B. 1998, 102, 3586-3616.
36. Darden, T.; York, D.; Pedersen, L. Particle mesh ewald: An N.log-(N) method for ewaid sums in large systems. J. Chem. Phys. 1993, 98, 10089-10092.