12-N-Methylated 5,6-dihydrobenzo[c]acridine derivatives: A new class of highly selective ligands for c-myc G-quadruplex DNA

European Journal of Medicinal Chemistry

Volumn 53, Issue , 2012, Pages 52-63

  Liao, Sheng Rong ^a   Zhou, Chen Xi ^a   Wu, Wei Bin ^a   Ou, Tian Miao ^a   Tan, Jia Heng ^a   Li, Ding ^a   Gu, Lian Quan ^a   Huang, Zhi Shu ^a  

^a SUN YAT SEN UNIVERSITY   (China)

Author keywords

12 N Methylation; 5,6 Dihydrobenzo c acridine derivatives; Binding affinity; c myc G Quadruplex; Selectivity

Indexed keywords

12 N METHYLATED 5,6 DIHYDROBENZO[C]ACRIDINE DERIVATIVE; ACRIDINE DERIVATIVE; DOUBLE STRANDED DNA; GUANINE QUADRUPLEX; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CELL LINE; CIRCULAR DICHROISM; CONTROLLED STUDY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORESCENCE RESONANCE ENERGY TRANSFER; HUMAN; HUMAN CELL; MOLECULAR MODEL; ONCOGENE C MYC; POLYMERASE CHAIN REACTION; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; SURFACE PLASMON RESONANCE;

ACRIDINES; ANTINEOPLASTIC AGENTS; BASE SEQUENCE; CELL LINE, TUMOR; CELL PROLIFERATION; DNA; DRUG DESIGN; G-QUADRUPLEXES; HUMANS; LIGANDS; METHYLATION; MODELS, MOLECULAR; NUCLEIC ACID DENATURATION; PROTO-ONCOGENE PROTEINS C-MYC; SUBSTRATE SPECIFICITY; TRANSCRIPTION, GENETIC; TRANSITION TEMPERATURE;

EID: 84861625962     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.03.034     Document Type: Article

References (51)

1. H.J. Lipps, and D. Rhodes G-quadruplex structures: in vivo evidence and function Trends Cell Biol. 19 2009 414 422
2. J.L. Huppert Four-stranded nucleic acids: structure, function and targeting of G-quadruplexes Chem. Soc. Rev. 37 2008 1375 1384
3. L. Oganesian, and T.M. Bryan Physiological relevance of telomeric G-quadruplex formation: a potential drug target Bioessays 29 2007 155 165
4. Y. Xu Chemistry in human telomere biology: structure, function and targeting of telomere DNA/RNA Chem. Soc. Rev. 40 2011 2719 2740
5. D. Yang, and L.H. Hurley Structure of the biologically relevant G-quadruplex in the c-MYC promoter Nucleosides Nucleotides Nucleic Acids 25 2006 951 968
6. A.T. Phan, Y.S. Modi, and D.J. Patel Propeller-type parallel-stranded G-quadruplexes in the human c-myc promoter J. Am. Chem. Soc. 126 2004 8710 8716
7. S. Rankin, A.P. Reszka, J. Huppert, M. Zloh, G.N. Parkinson, A.K. Todd, S. Ladame, S. Balasubramanian, and S. Neidle Putative DNA quadruplex formation within the human c-kit oncogene J. Am. Chem. Soc. 127 2005 10584 10589
8. T.S. Dexheimer, D. Sun, and L.H. Hurley Deconvoluting the structural and drug-recognition complexity of the G-quadruplex-forming region upstream of the bcl-2 P1 promoter J. Am. Chem. Soc. 128 2006 5404 5415
9. D. Sun, K. Guo, J.J. Rusche, and L.H. Hurley Facilitation of a structural transition in the polypurine/polypyrimidine tract within the proximal promoter region of the human VEGF gene by the presence of potassium and G-quadruplex-interactive agents Nucleic Acids Res. 33 2005 6070 6080
10. P. Boukamp, and N. Mirancea Telomeres rather than telomerase a key target for anti-cancer therapy? Exp. Dermatol. 16 2007 71 79
11. J.F. Riou, L. Guittat, P. Mailliet, A. Laoui, E. Renou, O. Petitgenet, F. Megnin-Chanet, C. Helene, and J.L. Mergny Cell senescence and telomere shortening induced by a new series of specific G-quadruplex DNA ligands Proc. Natl. Acad. Sci. U.S.A. 99 2002 2672 2677
12. D. Sun, and L.H. Hurley The Importance of negative superhelicity in inducing the formation of G-quadruplex and i-motif structures in the c-myc promoter: implications for drug targeting and control of gene expression J. Med. Chem. 52 2009 2863 2874
13. S. Neidle Human telomeric G-quadruplex: the current status of telomeric G-quadruplexes as therapeutic targets in human cancer FEBS J. 277 2010 1118 1125
14. T.M. Ou, J. Lin, Y.J. Lu, J.Q. Hou, J.H. Tan, S.H. Chen, Z. Li, Y.P. Li, D. Li, L.Q. Gu, and Z.S. Huang Inhibition of cell proliferation by quindoline derivative (SYUIQ-05) through its preferential interaction with c-myc promoter G-quadruplex J. Med. Chem. 54 2011 5671 5679
15. H.J. Kang, and H.J. Park Novel molecular mechanism for actinomycin D activity as an oncogenic promoter G-quadruplex binder Biochemistry 48 2009 7392 7398
16. S. Balasubramanian, L.H. Hurley, and S. Neidle Targeting G-quadruplexes in gene promoters: a novel anticancer strategy? Nat. Rev. Drug Discov. 10 2011 261 275
17. S. Neidle The structures of quadruplex nucleic acids and their drug complexes Curr. Opin. Struc. Biol. 19 2009 239 250
18. V. Gabelica, E.S. Baker, M.P. Teulade-Fichou, E. De Pauw, and M.T. Bowers Stabilization and structure of telomeric and c-myc region intramolecular G-quadruplexes: the role of central cations and small planar ligands J. Am. Chem. Soc. 129 2007 895 904
19. M.W. Freyer, R. Buscaglia, K. Kaplan, D. Cashman, L.H. Hurley, and E.A. Lewis Biophysical studies of the c-MYC NHE III1 promoter: model quadruplex interactions with a cationic porphyrin Biophys. J. 92 2007 2007 2015
20. T. Lemarteleur, D. Gomez, R. Paterski, E. Mandine, P. Mailliet, and J.F. Riou Stabilization of the c-myc gene promoter quadruplex by specific ligands' inhibitors of telomerase Biochem. Biophys. Res. Commun. 323 2004 802 808
21. T.M. Ou, Y.J. Lu, C. Zhang, Z.S. Huang, X.D. Wang, J.H. Tan, Y. Chen, D.L. Ma, K.Y. Wong, J.C. Tang, A.S. Chan, and L.Q. Gu Stabilization of G-quadruplex DNA and down-regulation of oncogene c-myc by quindoline derivatives J. Med. Chem. 50 2007 1465 1474
22. A. Rangan, O.Y. Fedoroff, and L.H. Hurley Induction of duplex to G-quadruplex transition in the c-myc promoter region by a small molecule J. Biol. Chem. 276 2001 4640 4646
23. J. Dash, Z.A. Waller, G.D. Pantos, and S. Balasubramanian Synthesis and binding studies of novel diethynyl-pyridine amides with genomic promoter DNA G-quadruplexes Chem.-Eur. J. 17 2011 4571 4581
24. D. Peng, J.H. Tan, S.B. Chen, T.M. Ou, L.Q. Gu, and Z.S. Huang Bisaryldiketene derivatives: a new class of selective ligands for c-myc G-quadruplex DNA Bioorg. Med. Chem. 18 2010 8235 8242
25. J. Dash, P.S. Shirude, S.T.D. Hsu, and S. Balasubramanian Diarylethynyl amides that recognize the parallel conformation of genomic promoter DNA G-quadruplexes J. Am. Chem. Soc. 130 2008 15950 15956
26. M. Wainwright Acridine-a neglected antibacterial chromophore J. Antimicrob. Chemother. 47 2001 1 13
27. G. Cholewinski, K. Dzierzbicka, and A.M. Kolodziejczyk Natural and synthetic acridines/acridones as antitumor agents: their biological activities and methods of synthesis Pharmacol. Rep. 63 2011 305 336
28. M. Laronze-Cochard, Y.M. Kim, B. Brassart, J.F. Riou, J.Y. Laronze, and J. Sapi Synthesis and biological evaluation of novel 4,5-bis(dialkylaminoalkyl)- substituted acridines as potent telomeric G-quadruplex ligands Eur. J. Med. Chem. 44 2009 3880 3888
29. Y.T. Fu, B.R. Keppler, J. Soares, and M.B. Jarstfer BRACO19 analog dimers with improved inhibition of telomerase and hPot 1 Bioorg. Med. Chem. 17 2009 2030 2037
30. N.H. Campbell, M. Patel, A.B. Tofa, R. Ghosh, G.N. Parkinson, and S. Neidle Selectivity in ligand recognition of G-quadruplex loops Biochemistry 48 2009 1675 1680
31. N.H. Campbell, G.N. Parkinson, A.P. Reszka, and S. Neidle Structural basis of DNA quadruplex recognition by an acridine drug J. Am. Chem. Soc. 130 2008 6722 6724
32. M.P. Teulade-Fichou, C. Carrasco, L. Guittat, C. Bailly, P. Alberti, J.L. Mergny, A. David, J.M. Lehn, and W.D. Wilson Selective recognition of G-quadruplex telomeric DNA by a bis(quinacridine) macrocycle J. Am. Chem. Soc. 125 2003 4732 4740
33. M. Read, R.J. Harrison, B. Romagnoli, F.A. Tanious, S.H. Gowan, A.P. Reszka, W.D. Wilson, L.R. Kelland, and S. Neidle Structure-based design of selective and potent G quadruplex-mediated telomerase inhibitors Proc. Natl. Acad. Sci. U.S.A. 98 2001 4844 4849
34. 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. Helene Telomerase inhibitors based on quadruplex ligands selected by a fluorescence assay Proc. Natl. Acad. Sci. U.S.A. 98 2001 3062 3067
35. M.K. Cheng, C. Modi, J.C. Cookson, I. Hutchinson, R.A. Heald, A.J. McCarroll, S. Missailidis, F. Tanious, W.D. Wilson, J.L. Mergny, C.A. Laughton, and M.F. Stevens Antitumor polycyclic acridines. 20. Search for DNA quadruplex binding selectivity in a series of 8,13-dimethylquino[4,3,2-kl]acridinium salts: telomere-targeted agents J. Med. Chem. 51 2008 963 975
36. Y.J. Lu, T.M. Ou, J.H. Tan, J.Q. Hou, W.Y. Shao, D. Peng, N. Sun, X.D. Wang, W.B. Wu, X.Z. Bu, Z.S. Huang, D.L. Ma, K.Y. Wong, and L.Q. Gu 5-N-Methylated quindoline derivatives as telomeric G-quadruplex stabilizing ligands: effects of 5-N positive charge on quadruplex binding affinity and cell proliferation J. Med. Chem. 51 2008 6381 6392
37. O. Baudoin, F. Gonnet, M.P. Teulade-Fichou, J.P. Vigneron, J.C. Tabet, and J.M. Lehn Molecular recognition of nucleotide pairs by a cyclo-bis-intercaland-type receptor molecule: a spectrophotometric and electrospray mass spectrometry study Chem. - Eur. J. 5 1999 2762 2771
38. J.E. Nordlander, M.J. Payne, F.G. Njoroge, V.M. Vishwanath, G.R. Han, G.D. Laikos, and M.A. Balk A short enantiospecific synthesis of 2-amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphthalene (ADTN) J. Org. Chem. 50 1985 3619 3622
39. A.J. Walz, and R.J. Sundberg Synthesis of 8-methoxy-1-methyl-1H-benzo[de] [1,6]naphthyridin-9-ol (isoaaptamine) and analogues J. Org. Chem. 65 2000 8001 8010
40. J.B. Press, V.T. Bandurco, E.M. Wong, Z.G. Hajos, R.M. Kanojia, R.A. Mallory, E.G. Deegan, J.J. Mcnally, J.R. Roberts, M.L. Cotter, D.W. Graden, and J.R. Lloyd Synthesis of 5,6-dimethoxyquinazolin-2(1H)-ones J. Heterocycl. Chem. 23 1986 1821 1828
41. C. Ronco, G. Sorin, F. Nachon, R. Foucault, L. Jean, A. Romieu, and P.Y. Renard Synthesis and structure-activity relationship of Huprine derivatives as human acetylcholinesterase inhibitors Bioorg. Med. Chem. 17 2009 4523 4536
42. J. Styskala, P. Cankar, M. Soural, J. Hlavac, P. Hradil, J. Vicar, and V. Simanek Synthesis of isodecarine Heterocycles 73 2007 769 775
43. Y. Ma, T.M. Ou, J.H. Tan, J.Q. Hou, S.L. Huang, L.Q. Gu, and Z.S. Huang Synthesis and evaluation of 9-O-substituted berberine derivatives containing aza-aromatic terminal group as highly selective telomeric G-quadruplex stabilizing ligands Bioorg. Med. Chem. Lett. 19 2009 3414 3417
44. A. De Cian, L. Guittat, M. Kaiser, B. Sacca, S. Amrane, A. Bourdoncle, P. Alberti, M.P. Teulade-Fichou, L. Lacroix, and J.L. Mergny Fluorescence-based melting assays for studying quadruplex ligands Methods 42 2007 183 195
45. Y. Ma, T.M. Ou, J.H. Tan, J.Q. Hou, S.L. Huang, L.Q. Gu, and Z.S. Huang Quinolino-benzo-[5, 6]-dihydroisoquindolium compounds derived from berberine: a new class of highly selective ligands for G-quadruplex DNA in c-myc oncogene Eur. J. Med. Chem. 46 2011 1906 1913
46. W.B. Wu, S.H. Chen, J.Q. Hou, J.H. Tan, T.M. Ou, S.L. Huang, D. Li, L.Q. Gu, and Z.S. Huang Disubstituted 2-phenyl-benzopyranopyrimidine derivatives as a new type of highly selective ligands for telomeric G-quadruplex DNA Org. Biomol. Chem. 9 2011 2975 2986
47. E.M. Rezler, J. Seenisamy, S. Bashyam, M.Y. Kim, E. White, W.D. Wilson, and L.H. Hurley Telomestatin and diseleno sapphyrin bind selectively to two different forms of the human telomeric G-quadruplex structure J. Am. Chem. Soc. 127 2005 9439 9447
48. T. Simonsson, and M. Henriksson c-myc Suppression in Burkitt's lymphoma cells Biochem. Biophys. Res. Commun. 290 2002 11 15
49. L.M. Facchini, and L.Z. Penn The molecular role of myc in growth and transformation: recent discoveries lead to new insights FASEB J. 12 1998 633 651
50. A. Hamada, Y.A. Chang, N. Uretsky, and D.D. Miller Dopaminergic agonists: comparative actions of amine and sulfonium analogues of dopamine J. Med. Chem. 27 1984 675 680
51. R. Beugelmans, J. Chastanet, H. Ginsburg, L. Quintero-Cortes, and G. Roussi Studies in SRN1 series. Part 14. Direct synthesis of benzo[c] phenanthridines and benzo[c]phenanthridones via SRN1 reactions J. Org. Chem. 50 1985 4933 4938