Discovery of a natural product-like c-myc G-Quadruplex DNA groove-binder by molecular docking

PLoS ONE

Volumn 7, Issue 8, 2012, Pages

  Ma, Dik Lung ^a   Chan, Daniel Shiu Hin ^a   Fu, Wai Chung ^a   He, Hong Zhang ^a   Yang, Hui ^a   Yan, Siu Cheong ^b   Leung, Chung Hang ^c,d  

^a HONG KONG BAPTIST UNIVERSITY   (Hong Kong)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

^c University of Macau   (Macao)

^d UNIVERSITY OF MACAU   (Macao)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIDE 1; GUANINE QUADRUPLEX; MYC PROTEIN; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ARTICLE; BIOLOGICAL ACTIVITY; DNA STRUCTURE; GENE EXPRESSION; HIGH THROUGHPUT SCREENING; HIGH THROUGHPUT VIRTUAL SCREENING; HUMAN; HUMAN CELL; IN VITRO STUDY; LIGAND BINDING; MOLECULAR DOCKING; MOLECULAR MODEL; ONCOGENE C MYC; POLYMERASE CHAIN REACTION; PROMOTER REGION; PROTEIN PROTEIN INTERACTION; PROTEIN STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; TAQ POLYMERASE MEDIATED DNA EXTENSION; TRANSCRIPTION REGULATION;

EID: 84865086964     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0043278     Document Type: Article

References (25)

1. Lipps HJ, Rhodes D, (2009) G-quadruplex structures: in vivo evidence and function. Trends Cell Biol 19: 414-422.
2. Mergny JL, Hélène C, (1998) G-quadruplex DNA: A target for drug design. Nat Med 4: 1366-1367.
3. Monchaud D, Teulade-Fichou MP, (2008) A hitchhiker's guide to G-quadruplex ligands. Org Biomol Chem 6: 627-636.
4. Dash J, Shirude PS, Hsu STD, Balasubramanian S, (2008) Diarylethynyl Amides That Recognize the Parallel Conformation of Genomic Promoter DNA G-Quadruplexes. J Am Chem Soc 130: 15950-15956.
5. Dang CV, O'Donnell KA, Zeller KI, Nguyen T, Osthus RC, et al. (2006) The c-Myc target gene network. Cancer Biol 16: 253-264.
6. Postel EH, Mango SE, Flint SJ, (1989) A nuclease-hypersensitive element of the human c-myc promoter interacts with a transcription initiation factor. Mol Cell Biol 9: 5123-5133.
7. Parkinson GN, Lee MPH, Neidle S, (2002) Crystal structure of parallel quadruplexes from human telomeric DNA. Nature 417: 876-880.
8. Siddiqui-Jain A, Grand CL, Bearss DJ, Hurley LH, (2002) 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 99: 11593-11598.
9. Ou TM, Lu YJ, Zhang C, Huang ZS, Wang XD, et al. (2007) Stabilization of G-Quadruplex DNA and Down-Regulation of Oncogene c-myc by Quindoline Derivatives. J Med Chem 50: 1465-1474.
10. Wu P, Ma DL, Leung CH, Yan SC, Zhu N, et al. (2009) Stabilization of G-Quadruplex DNA with Platinum(II) Schiff Base Complexes: Luminescent Probe and Down-Regulation of c-myc Oncogene Expression. Chem Eur J 15: 13008-13021.
11. Lee HM, Chan DSH, Yang F, Lam HY, Yan SC, et al. (2010) Identification of natural product Fonsecin B as a stabilizing ligand ofc-myc G-quadruplex DNA by high-throughput virtual screening. Chem Commun 46: 4680-4682.
12. Chen Q, Kuntz ID, Shafer RH, (1996) Spectroscopic recognition of guanine dimeric hairpinquadruplexes by a carbocyanine dye. Proc Natl Acad Sci USA 93: 2635-2639.
13. Cheng JY, Lin SH, Chang TC, (1998) Vibrational investigation of DODC cation for recognition of guanine dimeric hairpin quadruplex studied by satellite holes. J Phys Chem B 102: 5542-5546.
14. White EW, Tanious F, Ismail MA, Reszka AP, Neidle S, et al. (2007) Structure-specific recognition of quadruplex DNA by organic cations: Influence of shape, substituents and charge. Biophys Chem 126: 140-153.
15. Cosconati S, Marinelli L, Trotta R, Virno A, Mayol L, et al. (2011) A more detailed picture of the interactions between virtual screening-derived hits and the DNA G-quadruplex: NMR, molecular modelling and ITC studies. Biochimie 93: 1280-1287.
16. Butler M, (2008) Natural products to drugs: natural product-derived compounds in clinical trials. Nat Prod Rep 25: 475-516.
17. Maita S, Chaudhury NK, Chowdhury S, (2003) Hoechst 33258 binds to G-quadruplex in the promoter region of human c-myc. Biochem Biophys Res Commun 310: 505-512.
18. Phan AT, Kuryavyi V, Gaw HY, Patel DJ, (2005) Small-molecule interaction with a five-guanine-tract G-quadruplex structure from the human MYC promoter. Nat Chem Biol 1: 167-173.
19. Totrov M, Abagyan R, (1997) Flexible protein-ligand docking by global energy optimization in internal co-ordinates. Proteins Struct Funct Genet 29: 215-220.
20. Blay G, Cardona L, Garcia B, Pedro JR, (2000) The synthesis of bioactive sesquiterpenes from santonin. Stud Nat Prod Chem 24: 53-129.
21. Franke L, Schwarz O, Müller-Kuhrt L, Hoernig C, Fischer L, et al. (2007) Identification of Natural-Product-Derived Inhibitors of 5-Lipoxygenase Activity byLigand-Based Virtual Screening. J Med Chem 50: 2640-2646.
22. Sung HH, Wagner KM, Morisseau C, Liu JY, Dong H, et al. (2011) Synthesis and StructureActivity Relationship Studies ofUrea-Containing Pyrazoles as Dual Inhibitors of Cyclooxygenase-2and Soluble Epoxide Hydrolase. J Med Chem 54: 3037-3050.
23. Phan AT, Kuryavyi V, Gaw HY, Patel DJ, (2005) Small-molecule interaction with a five-guanine-tract G-quadruplex structure from the human MYC promoter. Nat Chem Biol 1: 167-173.
24. Seenisamy J, Rezler EM, Powell TJ, Tye D, Gokhale V, et al. (2004) Propeller-Type Parallel-Stranded G-Quadruplexes in the Human c-myc Promoter. J Am Chem Soc 126: 8710-8716.
25. Ma DL, Lai TS, Chan FY, Chung WH, Abagyan R, et al. (2008) Discovery of a Drug-Like G-Quadruplex Binding Ligand by High-Throughput Docking. ChemMedChem 3: 881-884.