Natural products and their derivatives as G-quadruplex binding ligands

Science China Chemistry

Volumn 56, Issue 10, 2013, Pages 1351-1363

  Shan, Chan ^a   Tan, Jia Heng ^a   Ou, Tian Miao ^a   Huang, Zhi Shu ^a  

^a SUN YAT SEN UNIVERSITY   (China)

Author keywords

derivatives; G quadruplex binding ligands; natural products

Indexed keywords

ANTICANCER ACTIVITIES; BINDING LIGANDS; EUKARYOTIC GENOME; G-QUADRUPLEX STRUCTURE; LOW CYTOTOXICITIES; NATURAL PRODUCTS; SECONDARY STRUCTURES; STRUCTURAL COMPLEXITY;

DERIVATIVES; DNA SEQUENCES;

LIGANDS;

EID: 84885599335     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-013-4920-y     Document Type: Review

References (141)

1. + solution. Bioorg Med Chem, 2006, 14:5584-5591
2. Ambrus A, Chen D, Dai J, Bialis T, Jones RA, Yang D. Human telomeric sequence forms a hybrid-type intramolecular G-quadruplex structure with mixed parallel/antiparallel strands in potassium solution. Nucleic Acids Res, 2006, 34:2723-2735
3. + Solution: An Intramolecular (3 + 1) G-Quadruplex Scaffold. J Am Chem Soc, 2006, 128:9963-9970
4. Gellert M, Lipsett, MN, Davies DR. Helix formation by guanylic acid, Proc Natl Acad Sci USA, 1962, 48:2013-2018
5. Phan AT, Kuryavyi V, Patel DJ. DNA architecture: From G to Z. Curr Opin Struct Biol, 2006, 16:288-298
6. Burge S, Parkinson GN, Hazel P, Todd AK, Neidle S. Quadruplex DNA: sequence, topology and structure. Nucleic Acids Res, 2006, 34:5402-5415
7. Schmitz R. Friedrich Wilhelm Sertürner and the discovery of morphine. Pharm Hist, 1985, 27(2):61-74
8. Cragg GM, Newman DJ. Natural products: A continuing source of novel drug leads. Biochim Biophys Acta, 2013, 1830(6):3670-3695
9. Xu Y. Chemistry in human telomere biology: Structure, function and targeting of telomere DNA/RNA. Chem Soc Rev, 2011, 40(5):2719-2740
10. Collie GW, Parkinson GN. The application of DNA and RNA G-quadruplexes to therapeutic medicines. Chem Soc Rev, 2011, 40(12):5867-5892
11. Ou TM, Lu YJ, Tan JH, Huang ZS, Wong KY, Gu LQ. G-quadruplexes: Targets in anticancer drug design. Chem Med Chem, 2008, 3(5):690-713
12. Liu D, O'Connor MS, Qin J, Songyang Z. Telosome, a mammalian telomere-associated complex formed by multiple telomeric proteins. J Biol Chem, 2004, 279(49):51338-51342
13. Choi J, Majima T. Conformational changes of non-B DNA. Chem Soc Rev, 2011, 40(12):5893-5909
14. Oka Y, Thomas CA. The cohering telomeres of oxytricha. Nucleic Acids Res, 1987, 15(21):8877-8898
15. Williamson JR, Raghuraman MK, Cech TR. Monovalent cation-induced structure of telomeric DNA: The G-quadruplex model. Cell, 1989, 59(5):871-880
16. Huppert JL, Balasubramanian S. G-quadruplexs in promoters throughout the human genome. Nucleic Acids Res, 2007, 35(2):406-413
17. Verma A, Yadav VK, Basundra R, Kumar A, Chowdhury S. Evidence of genome-wide G4 DNA-mediated gene expression in human cancer cells. Nucleic Acidc Res, 2009, 37(13):4194-4204
18. Biffi G, Tannahill D, McCafferty J, Balasubramanian S. Quantitative visualization of DNA G-quadruplex structures in human cells. Nat Chem, 2013, 5(3):182-186
19. Cairns D, Anderson RJ, Perry PJ, Jenkins TC. Design of telomerase inhibitors for the treatment of cancer. Curr Pharm Des, 2002, 8(27):2491-2504
20. Parkinson GN, Lee MP, Neidle S. Crystal structure of parallel quadruplexes from human telomeric DNA. Nature, 2002, 417(6891):876-880
21. Rezler EM, Seenisamy J, Bashyam S, Kim MY, White E, Wilson WD, Hurley LH. Telomestatin and diseleno sapphyrin bind selectively to two different forms of the human telomeric G-quadruplex structure. J Am Chem Soc, 2005, 127(26):9439-9447
22. Balasubramanian S, Hurley LH, Neidle S. Targeting G-quadruplexes in gene promoters: A novel anticancer strategy? Nat Rev Drug Discov, 2011, 10(4):261-275
23. Han H, Bennett RJ, Hurley LH. Inhibition of unwinding of G-quadruplex structures by Sgs1 helicase in the presence of N,N′-bis[2-(1-piperidino) ethyl]-3,4,9,10-perylenetetra-carboxylic dimide, a G-quadruplex-interactive ligand. Biochemistry, 2000, 39(31):9311-9316
24. Blackburn EH. Switching and signaling at the telomere. Cell, 2001, 106(6):661-673
25. Heddi B, Phan AT. Structure of human telomeric DNA in crowded solution. J Am Chem Soc, 2011, 133(25):9824-9833
26. + solution: insights into structure polymorphism of the human telomeric sequence. Nucleic Acids Res, 2007, 35(15):4927-4940
27. + solution. Nucleic Acids Res, 2007, 35(19):6517-6525
28. Cuesta J, Read MA, Neidle S. The design of G-quadruplex ligands as telomerase inhibitors. Min. Rev Med Chem, 2003, 3(1):11-21
29. Deng R, Li W, Guan Z, Zhou JM, Wang Y, Mei YP, Li MT, Feng GK, Huang W, Liu ZC, Han Y, Zeng YX, Zhu XF. Acetylcholinesterase expression mediated by c-Jun-NH2-terminal kinase pathway during anticancer drug-induced apoptosis. Oncogene, 2006, 25(53):7070-7077
30. Tauchi T, Shin-Ya K, Sashida G, Sumi M, Nakajima A, Shimamoto T, Ohyashiki JH, Ohyashiki K. Activity of a novel G-quadruplex-interactive telomerase inhibitor, telomestatin (SOT-095), against human leukemia cells: Involvement of ATM-dependent DNA damage response pathways. Oncogene, 2003, 22(34):5338-5347
31. Riou JF, Guittat L, Mailliet P, Laoui A, Renou E, Petitgenet O, Mégnin-Chanet F, Hélène C, Mergny JL. Cell senescence and telomere shortening induced by a new series of specific G-quadruplex DNA ligands. Proc Natl Acad Sci USA, 2002, 99(5):2672-2677
32. Phan AT, Modi YS, Patel DJ. Propeller-type parallel-stranded G-quadruplexes in the human c-myc promoter. J Am Chem Soc, 2004, 126(28):8710-8716
33. Siddiqui-Jain A, Grand CL, Bearss DJ, Hurley LH. 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 USA, 2002, 99(18):11593-11598
34. Majello B, De Luca P, Suske G, Lania L. Differential transcriptional regulation of c-myc promoter through the same DNA binding sites targeted by SP1-like proteins. Oncogene, 1995, 10(9):1841-1848
35. Michelotti EF, 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(16):9494-9499
36. Tomonaga T, Levens D. Heterogeneous nuclear ribonucleoprotein K is a DNA-binding transactivator. J Biol Chem, 1995, 270(9):4875-4881
37. Dang CV, O'Donnell KA, Zeller KI, Nguyen T, Osthus RC, Li F. The c-myc target gene network. Semin Cancer Biol, 2006, 16(4):253-264
38. Seenisamy J, Rezler EM, Powell TJ, Tye D, Gokhale V, Joshi CS, Siddiqui-Jain A, Hurley LH. The dynamic character of the G-quadruplex element in the c-MYC promoter and modification by TMPyP4. J Am Chem Soc, 2004, 126(28):8702-8709
39. Ou TM, Lu YJ, Zhang C, Huang ZS, Wang XD, Tan JH, Chen Y, Ma DL, Wong KY, Tang JC, Chan AS, Gu LQ. Stabilization of G-quadruplex DNA and down-regulation of oncogene c-myc by quindoline derivatives. J Med Chem, 2007, 50(7):1465-1474
40. Yin F, Liu J, Deng X, Wang J. Effects of triethylene tetraamine on the G-quadruplex structure in the human c-myc promoter. J Biochem, 2007, 141(5):669-674
41. Liu JN, Deng R, Guo JF, Zhou JM, Feng GK, Huang ZS, Gu LQ, Zeng YX, Zhu XF. Inhibition of myc promoter and telomerase activity and induction of delayed apoptosis by SYUIQ-5, a novel G-quadruplex interactive agent in leukemia cells. Leukemia, 2007, 21(6):1300-1302
42. Dexheimer TS, Sun D, Hurley LH. Deconvoluting the structural and drug-recognition complexity if the G-quadruplex-forming region upstream of the bcl-2P1 promoter. J Am Chem Soc, 2006, 128(16):5404-5415
43. Wang XD, Ou TM, Lu YJ, Li Z, Xu Z, Xi C, Tan JH, Huang SL, An LK, Li D, Gu LQ, Huang ZS. Turning off transcription of the bcl-2 gene by stabilizing the bcl-2 promoter quadruplex with quindoline derivatives. J Med Chem, 2010, 53(11):4390-4398
44. Rankin S, Reszka AP, Huppert J, Zloh M, Parkinson GN, Todd AK, Ladame S, Balasubramanian S, Neidle S. Putative DNA quadruplex formation within the human c-kit oncogene. J Am Chem Soc, 2005, 127(30):10584-10589
45. Palumbo SL, Ebbinghaus SW, Hurley LH. Formation of a unique end-to-end stacked pair of G-quadruplexesin the hTERT core promoter with implications for inhibition of telomerase by G-quadruplex-interactive ligands. J Am Chem Soc, 2009, 131(31):10878-10891
46. Cogoi S, Paramasivam M, Filichev V, Géci I, Pedersen EB, Xodo LE. Identification of a new G-quadruplex motif in the KRAS promoter and design of pyren-modified G4-decoys with antiprolifetative activity in pancreatic cancer cells. J Med Chem, 2009, 52(2):564-568
47. Paramasivam M, Membrino A, Cogoi S, Fukuda H, Nakagama H, Xodo LE. Protein hnRNP A1 and its derivative Up1 unfold quadruplex DNA in the human KRAS promoter: Implications for transcription. Nucleic Acids Res, 2009, 37(9):2841-2853
48. Warner JR. Synthesis of ribosomes in Saccharomyces cerevisiae. Microbiol Rev, 1989, 53:256-271
49. Grummt I. Regulation of mammalian ribosomal gene transcription by RNA polymerase I. Prog Nucleic Acid Res Mol Biol, 1999, 62:109-154
50. Chiarella S, De Cola A, Scaglione GL, Carletti E, Graziano V, Barcaroli D, Lo Sterzo C, Di Matteo A, Di Ilio C, Falini B, Arcovito A, De Laurenzi V, Federici L. Nucleophosmin mutations alter its nucleolar localization by impairing G-quadruplex binding at ribosomal DNA. Nucleic Acids Res, 2013, 16:1-12
51. Hanakahi LA, Sun H, Maizels N. High affinity interactions of nucleolin with G-G-paired rDNA. J Biol Chem, 1999, 274(22):15908-15912
52. Drygin D, Siddiqui-Jain A, O'Brien S, Schwaebe M, Lin A, Bliesath J, Ho CB, Proffitt C, Trent K, Whitten JP, Lim JK, Von Hoff D, Anderes K, Rice WG. Anticancer activity of CX3543: A direct inhibitor of rRNA biogenesis. Cancer Res, 2009, 69(19):7653-7661
53. Cong R, Das S, Ugrinova I, Kumar S, Mongelard F, Wong J, Bouvet P. Interaction of nucleolin with ribosomal RNA genes and its role in RNA polymerase I transcription. Nucleic Acids Res, 2012, 40(19):9441-9454
54. Hershman SG, Chen Q, Lee JY, Kozak ML, Yue P, Wang LS, Johnson FB. Genomic distribution and function al analyses of potential G-quadruplex-forming sequences in Saccharomyces cerevisiae. Nucleic Acids Res, 2008, 36(1):144-156
55. Kumari S, Bugaut A, Huppert JL, Balasubramanian S. An RNA G-quadruplex in the 5'UTR of the NRAS proto-oncogene modulates translation. Nat Chem Biol, 2007, 3:218-221
56. Kozak M. Structural features in eukaryotic mRNAs that modulate the initiation of translation. J Biol Chem, 1991, 266:19867-19870
57. Faudale M, Cogoi S, Xodo LE. Photoactivated cationic alkyl-substituted porphyrin binding to g4-RNA in the 5′-UTR of KRAS oncogene represses translation. Chem Commun (Camb), 2012, 48(6):874-876
58. Gomez D, Guédin A, Mergny JL, Salles B, Riou JF, Teulade-Fichou MP, Calsou P. A G-quadruplex structure within the 5'-UTR of TRF2 mRNA represses translation in human cells. Nucleic Acids Res, 2010, 38(20):7187-7198
59. Weng HY, Huang HL, Zhao PP, Zhou H, Qu LH. Translational repression of cyclin D3 by a stable G-quadruplex in its 5′ UTR: Implications for cell cycle regulation. RNA Biol, 2012, 9(8):1099-1109
60. Harvey I, Garneau P, Pelletier J. Inhibition of translation by RNA-small molecule interactions. RNA, 2002, 8(4):452-463
61. Sun D, Thompson B, Cathers BE, Salazar M, Kerwin SM, Trent JO, Jenkins TC, Neidle S, Hurley LH. Inhibition of human telomerase by a G-quadruplex-interactive compound. J Med Chem, 1997, 40(14):2113-2116
62. Perry PJ, Gowan SM, Reszka AP, Polucci P, Jenkins TC, Kelland LR, Neidle S. 1,4- and 2,6-disubstituted amidoanthracene-9,10-dione derivatives as inhibitors of human telomerase. J Med Chem, 1998, 41(17):3253-3260
63. Perry PJ, Reszka AP, Wood AA, Read MA, Gowan SM, Dosanjh HS, Trent JO, Jenkins TC, Kelland LR, Neidle S. Human telomerase inhibition by regioisomeric disubstituted amidoanthracene-9, 10-diones. J Med Chem, 1998, 41(24):4873-4884
64. Huang HS, Chen IB, Huang KF, Lu WC, Shieh FY, Huang YY, Huang FC, Lin JJ. Synthesis and human telomerase inhibition of a series of regioisomeric disubstituted amidoanthraquinones. Chem Pharm Bull (Tokyo), 2007, 55(2):284-292
65. Huang HS, Huang KF, Li CL, Huang YY, Chiang YH, Huang FC, Lin JJ. Synthesis, human telomerase inhibition and anti-proliferative studies of a series of 2,7-bis-substituted amido-anthraquinone derivatives. Bioorg Med Chem, 2008, 16(14):6976-6986
66. Zagotto G, Sissi C, Lucatello L, Pivetta C, Cadamuro SA, Fox KR, Neidle S, Palumbo M. Aminoacyl-anthraquinone conjugates as telomerase inhibitors: Synthesis, biophysical and biological evaluation. J Med Chem, 2008, 51(18):5566-5574
67. Read MA, Wood AA, Harrison JR, Gowan SM, Kelland LR, Dosanjh HS, Neidle S. Molecular modeling studies on G-quadruplex complexes of telomerase inhibitors: Structure-activity relationships. J Med Chem, 1999, 42(22):4538-4546
68. Neidle S, Read MA. G-quadruplexes as therapeutic target. Biopolymers, 2000-2001, 56(3):195-208
69. Shammas MA, Koley H, Beer DG, Li C, Goyal RK, Munshi NC. Growth arrest, apoptosis, and telomere shortening of Barrett's-associated adenocarcinoma cells by a telomerase inhibitor. Gastroenterology, 2004, 126(5):1337-1346
70. Huang HS, Chen TC, Chen RH, Huang KF, Huang FC, Jhan JR, Chen CL, Lee CC, Lo Y, Lin JJ. Synthesis, cytotoxicity and human telomerase inhibition activities of a series of 1,2-heteroannelated anthraquinones and anthra[1,2-d]imidazole-6,11-dione homologues. Bioorg Med Chem, 2009, 17(21):7418-7428
71. Kaluzhny D, Ilyinsky N, Shchekotikhin A, Sinkevich Y, Tsvetkov PO, Tsvetkov V, Veselovsky A, Livshits M, Borisova O, Shtil A, Anna Shchyolkina A. Disordering of human telomeric G-quadruplex with novel antiproliferative anthrathiophenedione. PLoS One, 2011, 6(11):e27151
72. Zagotto G, Ricci A, Vasquez E, Sandoli A, Benedetti S, Palumbo M, Sissi C. Tuning G-Quadruplex vs double-stranded DNA recognition in regioisomeric lysyl-peptidyl-anthraquinone Conjugates. Bioconjug Chem, 2011, 22(10):2126-2135
73. Dwuma-Badu D, Ayim JS, Fiagbe NI, Knapp JE, Schiff PL Jr, Slatkin DJ. Constituents of West African medicinal plants XX: quindoline from Cryptolepis sanguinolenta. J Pharm Sci, 1978, 67(3):433-434
74. Ou TM, Lin J, Lu YJ, Hou JQ, Tan JH, Chen SH, Li Z, Li YP, Li D, Gu LQ, Huang ZS. inhibition of cell proliferation by quindoline derivative (SYUIQ-05) through its preferential interaction with c-myc promoter G-quadruplex. J Med Chem, 2011, 54(16):5671-5679
75. Zhou WJ, Deng R, Zhang XY, Feng GK, Gu LQ, Zhu XF. G-quadruplex ligand SYUIQ-5 induces autophagy by telomere damage and TRF2 delocalization in cancer cells. Mol Cancer Ther, 2009, 8(12):3203-3213
76. Zhou JM, Zhu XF, Lu YJ, Deng R, Huang ZS, Mei YP, Wang Y, Huang WL, Liu ZC, Gu LQ, Zeng YX. Senescence and telomere shortening induced by novel potent G-quadruplex interactive agents, quindoline derivatives, in human cancer cell lines. Oncogene, 2006, 25(4):503-511
77. Caprio V, Guyen B, Opoku-Boahen Y, Mann J, Gowan SM, Kelland LM, Read MA, Neidle S. A novel inhibitor of human telomerase derived from 10H-indolo[3,2-b]quinoline. Bioorg Med Chem Lett, 2000, 10(18):2063-2066
78. Zhou JL, Lu YJ, Ou TM, Zhou JM, Huang ZS, Zhu XF, Du CJ, Bu XZ, Ma L, Gu LQ, Li YM, Chan AS. Synthesis and evaluation of quindoline derivatives as G-quadruplex inducing and stabilizing ligands and potential inhibitors of telomerase. J Med Chem, 2005, 48(23):7315-7321
79. Lu YJ, Ou TM, Tan JH, Hou JQ, Shao WY, Peng D, Sun N, Wang XD, Wu WB, Bu XZ, Huang ZS, Ma DL, Wong KY, Gu LQ. 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, 2008, 51(20):6381-6392
80. Long Y, Li Z, Tan JH, Ou TM, Li D, Gu LQ, Huang ZS. Benzofuroquinoline derivatives had remarkable improvement of their selectivity for telomeric G-quadruplex DNA over duplex DNA upon introduction of peptidyl group. Bioconjug Chem, 2012, 23(9):1821-1831
81. Schmitz FJ, De Guzman FS, Hossain MB. Cytotoxic aromatic alkaloid from the ascidian Amphicarpa meridiana and Leptoclinides sp.: Meridine and 11-hydroxyascididemin. J Org Chem, 1991, 56:804-808
82. Kobayashi J, Cheng J, Nakamura H, Ohizumi Y. Ascididemin, a novel pentacyclic aromatic alkaloid with potent antileukemic activity from the okinawan tunicate Didemnum sp. Tetrahedron Lett, 1988, 29:1177-1180
83. Guittat L, De Cian A, Rosu F, Gabelica V, De Pauw E, Delfourne E, Mergny JL. Ascididenmin and meridine stabilize G-quadruplexes and inhibit telomerase in vivo. Biochim Biophys Acta, 2005, 1724(3):375-384
84. Zhang RX, Dougherty DV, Rosenblum ML. Laboratory studies of berberine used alone and in combination with 1,3-bis (2-chloroethyl)-1-nitrosourea to treat malignant brain tumors. Chin Med J (Engl), 1990, 103(8):658-665
85. Sun Y, Xun K, Wang Y, Chen X. A systematic review of the anticancer properties of berberine, a natural product from Chinese herbs. Anticancer Drugs, 2009, 20(9):757-769
86. Tang J, Feng Y, Tsao S, Wang N, Curtain R, Wang Y. Berberine and Coptidis Rhizoma as novel antineoplastic agents: A review of traditional use and biomedical investigations. J Ethnopharmacol, 2009, 126(1):5-17
87. Kim JB, Yu JH, Ko E, Lee KW, Song AK, Park SY, Shin I, Han W, Noh DY. The alkaloid Berberine inhibits the growth of Anoikis-resistant MCF-7 and MDA-MB-231 breast cancer cell lines by inducing cell cycle arrest. Phytomedicine, 2009, 17(6):436-440
88. Serafim TL, Oliveira PJ, Sardao VA, Perkins E, Parke D, Holy J. Different concentrations of berberine result in distinct cellular localization patterns and cell cycle effects in a melanoma cell line. Cancer Chemoth Pharmacol, 2008, 61(6):1007-1018
89. Pinto-Garcia L, Efferth T, Torres A, Hoheisel JD, Youns M. Berberine inhibits cell growth and mediates caspase-independent cell death in human pancreatic cancer cells. Planta Medica, 2010, 76(11):1155-1161
90. Ho YT, Lu CC, Yang JS, Chiang JH, Li TC, Ip SW, Hsia TC, Liao CL, Lin JG, Wood WG, Chung JG. Berberine induced apoptosis via promoting the expression of caspase-8, -9 and -3, apoptosis-inducing factor and endonuclease G in SCC-4 human tongue squamous carcinoma cancer cells. Anticancer Res, 2009, 29(10):4063-4070
91. Auyeung KK, Ko JK. Coptis chinensis inhibits hepatocellular carcinoma cell growth through nonsteroidal anti-inflammatory drug-activated gene activation. Int J Mol Med, 2009, 24(4):571-577
92. Tang F, Wang D, Duan C, Huang D, Wu Y, Chen Y, Wang W, Xie C, Meng J, Wang L, Wu B, Liu S, Tian D, Zhu F, He Z, Deng F, Cao Y. Berberine inhibits metastasis of nasopharyngeal carcinoma 5-8F cells by targeting Rho kinase-mediated Ezrin phosphorylation at threonine 567. J Biol Chem, 2009, 284(40):27456-27466
93. Sanders MM, Liu AA, Li TK, Wu HY, Desai SD, Mao Y, Rubin EH, LaVoie EJ, Makhey D, Liu LF. Selective cytotoxicity of topoisomerase-directed protoberberines against glioblastoma cells. Biochem Pharmacol, 1998, 56(9):1157-1166
94. Naasani I, Seimiya H, Yamori T, Tsuruo T. FJ5002: A potent telomerase inhibitor identified by exploiting the disease-oriented screening program with COMPARE analysis. Cancer Res, 1999, 59(16):4004-4011
95. Ren J, Chaires JB. Sequence and structural selectivity of nucleic acid binding ligands. Biochemistry, 1999, 38(49):16067-16075
96. Bazzicalupi C, Ferraroni M, Bilia AR, Scheggi F, Gratteri P. The crystal structure of human telomeric DNA complexed with berberine: an interesting case of stacked ligand to G-tetrad ratio higher than 1:1. Nucleic Acids Res, 2013, 41(1):632-638
97. Hoshi A, Ikekawa T, Ikeda Y, Shirakawa S, Iigo M. Antitumor activity of berberrubine derivatives. Gann, 1976, 67(2):321-325
98. Ikekawa T, Ikeda Y. Antitumor activity of 13-methyl-berberrubine derivatives. J Pharmacobiodyn, 1982, 5(7):469-474
99. Kim SA, Kwon Y, Kim JH, Muller MT, Chung IK. Induction of topoisomerase II-mediated DNA cleavage by a protoberberine alkaloid, berberrubine. Biochemistry, 1998, 37(46):16316-16324
100. Bhadra K, Kumar GS. Interaction of berberine, palmatine, coralyne, and sanguinarine to quadruplex DNA: A comparative spectroscopic and calorimetric study. Biochim Biophys Acta, 2011, 1810(4):485-496
101. Ma Y, Ou TM, Hou JQ, Lu YJ, Tan JH, Gu LQ, Huang ZS. 9-N-Substituted berberine derivatives: Stabilization of G-quadruplex DNA and down-regulation of oncogene c-myc. Bioorg Med Chem, 2008, 16(16):7582-7591
102. Ma Y, Ou TM, Tan JH, Hou JQ, Huang SL, Gu LQ, Huang ZS. 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, 2011, 46(5):1906-1913
103. Ma Y, Ou TM, Tan JH, Hou JQ, Huang SL, Gu LQ, Huang ZS. 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, 2009, 19(13):3414-3417
104. Wheelhouse RT, Sun DK, Han HY, Han FX, Hurley LH. 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
105. Anantha, NV, Azam M, Sheardy RD. Porphyrin binding to quadrupled T4G4. Biochemistry, 1998, 37(9):2709-2714
106. Izbicka E, Wheelhouse RT, Raymond E, Davidson KK, Lawrence RA, Sun D, Windle BE, Hurley LH, Hoff DD, Effect of cationic porphyrins as G-quadruplex interactive agents in human tumor cells. Cancer research, 1999, 59:639-644
107. Parkinson GN, Ghosh R, Neidle S. Structural basis for binding of porphyrin to human telomeres. Biochemistry, 2007, 46(9):2390-2397
108. Sun D, Guo K, Rusche JJ, Hurley LH. Facilitation of a structural transition in the polypurine/polypyrimidine tract within the proximal promoter region of the human VEGF gene by the present of potassium and G-quadruplex-interactive agents. Nucleic Acids Res, 2005, 33:6070-6080
109. Qin Y, Rezler EM, Gokhale V, Sun D, Hurley LH. Characterization of the G-quadruplexes in the duplex nuclease hypersensitive element of the PDGF-A promoter and modulation of PDGF-A promoter activity by TMPyP4. Nucleic Acids Res, 2007, 35(22):7698-7713
110. Guo K, Pourpak A, Beetz-Rogers K, Gokhale V, Sun D, Hurley LH. Formation of pseudosymmetrical G-quadruplex and i-motif structures in the proximal promoter region of the RET oncogene. J Am Chem Soc, 2007, 129(33):10220-10228
111. Tan JH, Gu LQ, Wu JY. Design of selective G-quadruplex ligands as potential anticancer agents. Mini Rev Med Chem, 2008, 8(11):1163-1178
112. Shin-ya K, Wierzba K, Matsuo K, Ohtani T, Yamada Y, Furihata K, Hayakawa Y, Seto H. Telomestatin, a novel telomerase inhibitor from Streptomyces anulatus. J Am Chem Soc, 2001, 123:1262-1263
113. Kim MY, Vankayalapati H, Shin-Ya K, Wierzba K, Hurley LH. Telomestatin, a potent telomerase inhibitor that interacts quite specifically with the human telomeric intramolecular G-quadruplex. J Am Chem Soc, 2002, 124(10):2098-2099
114. Binz N, Shalaby T, Rivera P, Shin-Ya K, Grotzer MA. Telomerase inhibition, telomere shortening, cell growth suppression and induction of apoptosis by telomestatin in childhood neuroblastoma cells. Eur J Cancer, 2005, 41(18):2873-2881
115. Tahara H, Shin-ya K, Seimiya H, Yamada H, Tsuruo T, Ide T. G-qadruplex stabilization by telomestatin induces TRF2 protein dissociation from telomeres and anaphase bridge formation accompanied by loss of the 3′ telomeric overhang in cancer cells. Oncogene, 2006, 25(13):1955-1966
116. Doi T, Shibata K, Yoshida M, Takagi M, Tera M, Nagasawa K, Shin-ya K, Takahashi T. (S)-stereoisomer of telomestatin as a potent G-quadruplex binder and telomerase inhibitor. Org Biomol Chem, 2011, 9(2):387-393
117. Gomez DD, Paterski RP, Lemarteleur TT, Shin-Ya K, Mergny JL, Riou JF. Interaction of telomestatin with the telomere single-strand overhang. J Biol Chem, 2004, 279(40):41487-41494
118. Gomez D, Wenner T, Brassart B, Douarre C, O'Donohue MF, El Khoury V, Shin-ya K, Morjani H, Trentesaux C, Riou JF. Telomestatin-induced telomere uncapping is modulated by POT1 through G-overhang extension in HT1080 human tumor cells. J Biol Chem, 2006, 281:38721-38729
119. Pilich DS, Barbieri CM, Rzuczek SG, LaVoie EJ, Rive JE. Targeting human telomeric G-quadruplex DNA with ozazole-containing macrocyclic compoumds. Biochimie, 2008, 90:1233-1249
120. Tsai YC, Qi H, Lin CP, Lin RK, Kerrigan JE, Rzuczek SG, LaVoie EJ, Rice JE, Pilch DS, Lyu YL, Liu LF. A G-quadruplex stabilizer induces M-phase cell cycle arrest. J Biol Chem, 2009, 284(34):22535-22543
121. Pilch DS, Barbieri CM, Rzuczek SG, Lavoie EJ, Rice JE. Targeting human telomeric G-quadruplex DNA with oxazole-containing macrocyclic compounds. Biochimie, 2008, 90(8):1233-1249
122. Iida K, Tera M, Shin-Ya K, Nagasawa K. G-quadruplex recognition by macrocyclic hexaoxazole (6OTD) dimer. Nucleic Acids Symp Ser (Oxf), 2009, (53):233-234
123. Amemiya Y, Furunaga Y, Iida K, Tera M, Nagasawa K, Ikebukuro K, Nakamura C. Analysis of the unbinding force between telomestatin derivatives and human telomeric G-quadruplex by atomic force microscopy. Chem Commun (Camb), 2011, 47(26):7485-7487
124. Shalaby T, von Bueren AO, Hürlimann ML, Fiaschetti G, Castelletti D, Masayuki T, Nagasawa K, Arcaro A, Jelesarov I, Shin-ya K, Grotzer M. Disabling c-Myc in childhood medulloblastoma and atypical teratoid/rhabdoid tumor cells by the potent G-quadruplex interactive agent S2T1-6OTD. Mol Cancer Ther, 2010, 9(1):167-179
125. Seenisamy J, Bashyam S, Gokhale V, Vankayalapati H, Sun D, Siddiqui-Jain A, Streiner N, Shin-Ya K, White E, Wilson WD, Hurley LH. Design and synthesis of an expanded porphyrin that has selectivity for the c-MYC G-quadruplex structure. J Am Chem Soc, 2005, 127(9):2944-2959
126. Majumder P, Dasgupta D. Effect of DNA groove binder distamycin A upon chromatin structure. PLoS One, 2011, 6(10):e26486
127. Pagano B, Fotticchia I, De Tito S, Mattia CA, Mayol L, Novellino E, Randazzo A, Giancola C. Selective binding of distamycin A derivative to G-quadruplex structure [d(TGGGGT)](4). J Nucleic Acids, 2010, pii:247137
128. Cocco MJ, Hanakahi LA, Huber MD, Maizels N. Special interactions of distamycin with G-quadruplex DNA. Nucleic Acids Res, 2003, 31(11):2944-2951
129. Martino L, Virno A, Pagano B, Virgilio A, Di Micco S, Galeone A, Giancola C, Bifulco G, Mayol L, Randazzo A. Structural and thermodynamic studies of the interaction of distamycin A with the parallel quadruplex structure [d(TGGGGT)]4. J Am Chem Soc, 2007, 129(51):16048-16056
130. Tan JH, Ou TM, Hou JQ, Lu YJ, Huang SL, Luo HB, Wu JY, Huang ZS, Wong KY, Gu LQ. Isaindigotone derivatives: A new class of highly selective ligands for telomeric G-quadruplex DNA. J Med Chem, 2009, 52(9):2825-2835
131. Waller ZA, Shirude PS, Rodriguez R, Balasubramanian S. Triarylpyridines: A versatile small molecule scaffold for G-quadruplex recognition. Chem Commun, 2008, 1467-1469
132. Dash J, Shirude PS, Hsu ST, Balasubramanian S. Diarylethynyl amides that recognize the parallel conformation of genomic promoter DNA G-quadruplexes. J Am Chem Soc, 2008, 130(47):15950-15996
133. Hou JQ, Tan JH, Wang XX, Chen SB, Huang SY, Yan JW, Chen SH, Ou TM, Luo HB, Li D, Gu LQ, Huang ZS. Impact of planarity of unfused aromatic molecules on G-quadruplex binding: Learning from isaindigotone derivatives. Org Biomol Chem, 2011, 9(18):6422-6436
134. Zhang JL, Fu Y, Zheng L, Li W, Li H, Sun Q, Xiao Y, Geng F. Natural isoflavones regulate the quadruplex-duplex competition in human telomeric DNA. Nucleic Acids Res, 2009, 37(8):2471-2482
135. Ragazzon PA, Bradshaw T, Matthews C, Iley J, Missailidis S. The characterisation of flavone-DNA isoform interactions as a basis for anticancer drug development. Anticancer Res, 2009, 29(6):2273-2283
136. Yang H, Zhong HJ, Leung KH, Chan DS, Ma VP, Fu WC, Nanjunda R, Wilson WD, Ma DL, Leung CH. Structure-based design of flavone derivatives as c-myc oncogene down-regulators. Eur J Pharm Sci, 2013, 48(1-2):130-141
137. Brassart B, Gomez D, De Cian A, Paterski R, Montagnac A, Qui KH, Temime-Smaali N, Trentesaux C, Mergny JL, Gueritte F, Riou JF. A new steroid derivative stabilizes g-quadruplexes and induces telomere uncapping in human tumor cells. Mol Pharmacol, 2007, 72(3):631-640
138. Li J, Jin X, Hu L, Wang J, Su Z. Identification of nonplanar small molecule for G-quadruplex grooves: Molecular docking and molecular dynamic study. Bioorg Med Chem Lett, 2011, 21(23):6969-6972
139. Wu WB, Chen SH, Hou JQ, Tan JH, Ou TM, Huang SL, Li D, Gu LQ, Huang ZS. Disubstituted 2-phenyl-benzopyranopyrimidine derivatives as a new type of highly selective ligands for telomeric G-quadruplex DNA. Org Biomol Chem, 2011, 9(8):2975-2986
140. Li Z, Tan JH, He JH, Long Y, Ou TM, Li D, Gu LQ, Huang ZS. Disubstituted quinazoline derivatives as a new type of highly selective ligands for telomeric G-quadruplex DNA. Eur J Med Chem, 2012, 47(1):299-311
141. He JH, Liu HY, Li Z, Tan JH, Ou TM, Huang SL, An LK, Li D, Gu LQ, Huang ZS. New quinazoline derivatives for telomeric G-quadruplex DNA: Effects of an added phenyl group on quadruplex binding ability. Eur J Med Chem, 2013, 63C:1-13