Inhibitor of MYC identified in a Kröhnke pyridine library

Proceedings of the National Academy of Sciences of the United States of America

Volumn 111, Issue 34, 2014, Pages 12556-12561

  Hart, Jonathan R ^a   Garner, Amanda L ^a   Yu, Jing ^a   Ito, Yoshihiro ^a   Sun, Minghao ^a   Ueno, Lynn ^a   Rhee, Jin Kyu ^a,c   Baksh, Michael M ^a   Stefan, Eduard ^b   Hartl, Markus ^b   Bister, Klaus ^b   Vogt, Peter K ^a   Janda, Kim D ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF INNSBRUCK   (Austria)

^c Korea Basic Science Institute (KBSI)   (South Korea)

Author keywords

Combinatorial library; Gene signature; Protein protein interactions; Transcriptional control; Xenograft

Indexed keywords

ANTINEOPLASTIC AGENT; DOXYCYCLINE; KJ PYR 9; KROHNKE PYRIDINE; MAX PROTEIN; MYC PROTEIN; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG; BASIC HELIX LOOP HELIX LEUCINE ZIPPER TRANSCRIPTION FACTOR; KJ-PYR-9; MAX PROTEIN, HUMAN; MULTIPROTEIN COMPLEX; MYC PROTEIN, HUMAN; PYRIMIDINE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; APOPTOSIS; ARTICLE; BINDING AFFINITY; CELL GROWTH; CELL PROLIFERATION; COMPLEX FORMATION; CONTROLLED STUDY; DIMERIZATION; DRUG BLOOD LEVEL; DRUG BRAIN LEVEL; EMBRYO; FEMALE; FLUORESCENCE POLARIZATION; HUMAN; HUMAN TISSUE; IC 50; IN VITRO STUDY; INTERFEROMETRY; MOLECULAR LIBRARY; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN PROTEIN INTERACTION; RAT; TUMOR XENOGRAFT; ANIMAL; ANTAGONISTS AND INHIBITORS; CELL CULTURE; CELL TRANSFORMATION; CHEMISTRY; CHICK EMBRYO; DRUG EFFECTS; DRUG SCREENING; GENETICS; NUDE MOUSE; ONCOGENE MYC; PROTEIN DOMAIN;

ANIMALS; ANTINEOPLASTIC AGENTS; BASIC HELIX-LOOP-HELIX LEUCINE ZIPPER TRANSCRIPTION FACTORS; CELL PROLIFERATION; CELL TRANSFORMATION, NEOPLASTIC; CELLS, CULTURED; CHICK EMBRYO; DRUG EVALUATION, PRECLINICAL; FEMALE; FLUORESCENCE POLARIZATION; GENES, MYC; HUMANS; INTERFEROMETRY; MICE; MICE, NUDE; MULTIPROTEIN COMPLEXES; PROTEIN INTERACTION DOMAINS AND MOTIFS; PROTO-ONCOGENE PROTEINS C-MYC; PYRIDINES; PYRIMIDINES; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84906674331     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1319488111     Document Type: Article

References (63)

1. Lee LA, Dang CV (2006) Myc target transcriptomes. Curr Top Microbiol Immunol 302:145-167. (Pubitemid 43268506)
2. Eisenman RN (2000-2001) The Max network: Coordinated transcriptional regulation of cell growth and proliferation. Harvey Lect 96:1-32.
3. Eisenman RN (2001) Deconstructing Myc. Genes Dev 15(16):2023-2030.
4. Blackwood EM, Eisenman RN (1991) Max: A helix-loop-helix zipper protein that forms a sequence-specific DNA-binding complex with Myc. Science 251(4998):1211-1217. (Pubitemid 21926213)
5. Ji H, et al. (2011) Cell-type independent MYC target genes reveal a primordial signature involved in biomass accumulation. PLoS ONE 6(10):e26057.
6. Nie Z, et al. (2012) c-Myc is a universal amplifier of expressed genes in lymphocytes and embryonic stem cells. Cell 151(1):68-79.
7. Lin CY, et al. (2012) Transcriptional amplification in tumor cells with elevated c-Myc. Cell 151(1):56-67.
8. Soucek L, et al. (2008) Modelling Myc inhibition as a cancer therapy. Nature 455(7213):679-683.
9. Dang CV (2012) MYC on the path to cancer. Cell 149(1):22-35.
10. Larsson LG, Henriksson MA (2010) The Yin and Yang functions of the Myc oncoprotein in cancer development and as targets for therapy. Exp Cell Res 316(8):1429-1437.
11. Obaya AJ, Mateyak MK, Sedivy JM (1999) Mysterious liaisons: The relationship between c-Myc and the cell cycle. Oncogene 18(19):2934-2941. (Pubitemid 29276534)
12. Lawlor ER, et al. (2006) Reversible kinetic analysis of Myc targets in vivo provides novel insights into Myc-mediated tumorigenesis. Cancer Res 66(9):4591-4601.
13. Sodir NM, et al. (2011) Endogenous Myc maintains the tumor microenvironment. Genes Dev 25(9):907-916.
14. Nair SK, Burley SK (2003) X-ray structures of Myc-Max and Mad-Max recognizing DNA. Molecular bases of regulation by proto-oncogenic transcription factors. Cell 112(2):193-205. (Pubitemid 36144109)
15. Berg T, et al. (2002) Small-molecule antagonists of Myc/Max dimerization inhibit Myc-induced transformation of chicken embryo fibroblasts. Proc Natl Acad Sci USA 99(6):3830-3835. (Pubitemid 34252191)
16. Yin X, Giap C, Lazo JS, Prochownik EV (2003) Low molecular weight inhibitors of Myc-Max interaction and function. Oncogene 22(40):6151-6159. (Pubitemid 37281644)
17. Prochownik EV, Vogt PK (2010) Therapeutic targeting ofMyc. Genes Cancer 1(6):650-659.
18. Berg T (2011) Small-molecule modulators of c-Myc/Max and Max/Max interactions. Curr Top Microbiol Immunol 348:139-149.
19. Zirath H, et al. (2013) MYC inhibition induces metabolic changes leading to accumulation of lipid droplets in tumor cells. Proc Natl Acad Sci USA 110(25):10258-10263.
20. Fujimori T, Wirsching P, Janda KD (2003) Preparation of a Kröhnke pyridine combinatorial library suitable for solution-phase biological screening. J Comb Chem 5(5):625-631. (Pubitemid 37206167)
21. Kiessling A, Sperl B, Hollis A, Eick D, Berg T (2006) Selective inhibition of c-Myc/Max dimerization and DNA binding by small molecules. Chem Biol 13(7):745-751. (Pubitemid 44093290)
22. Baksh MM, Kussrow AK, Mileni M, Finn MG, Bornhop DJ (2011) Label-free quantification of membrane-ligand interactions using backscattering interferometry. Nat Biotechnol 29(4):357-360.
23. Bachmann VA, et al. (2013) Reciprocal regulation of PKA and Rac signaling. Proc Natl Acad Sci USA 110(21):8531-8536.
24. Stefan E, et al. (2007) Quantification of dynamic protein complexes using Renilla luciferase fragment complementation applied to protein kinase A activities in vivo. Proc Natl Acad Sci USA 104(43):16916-16921. (Pubitemid 350210965)
25. Schuhmacher M, et al. (2001) The transcriptional program of a human B cell line in response to Myc. Nucleic Acids Res 29(2):397-406. (Pubitemid 32060926)
26. O'Donnell KA, et al. (2006) Activation of transferrin receptor 1 by c-Myc enhances cellular proliferation and tumorigenesis. Mol Cell Biol 26(6):2373-2386. (Pubitemid 43346936)
27. Zeller KI, Jegga AG, Aronow BJ, O'Donnell KA, Dang CV (2003) An integrated database of genes responsive to the Myc oncogenic transcription factor: Identification of direct genomic targets. Genome Biol 4(10):R69.
28. Subramanian A, et al. (2005) Gene set enrichment analysis: A knowledge-based approach for interpreting genome-wide expression profiles. Proc Natl Acad Sci USA 102(43):15545-15550. (Pubitemid 41528093)
29. Mootha VK, et al. (2003) PGC-1alpha-responsive genes involved in oxidative phosphorylation are coordinately downregulated in human diabetes. Nat Genet 34(3):267-273. (Pubitemid 36792858)
30. Raj M, Bullock BN, Arora PS (2013) Plucking the high hanging fruit: A systematic approach for targeting protein-protein interactions. Bioorg Med Chem 21(14):4051-4057.
31. Wilson CG, Arkin MR (2011) Small-molecule inhibitors of IL-2/IL-2R: Lessons learned and applied. Curr Top Microbiol Immunol 348:25-59.
32. Adler MJ, Jamieson AG, Hamilton AD (2011) Hydrogen-bonded synthetic mimics of protein secondary structure as disruptors of protein-protein interactions. Curr Top Microbiol Immunol 348:1-23.
33. Vu BT, Vassilev L (2011) Small-molecule inhibitors of the p53-MDM2 interaction. Curr Top Microbiol Immunol 348:151-172.
34. Zeitlin BD, Nör JE (2011) Small-molecule inhibitors reveal a new function for Bcl-2 as a proangiogenic signaling molecule. Curr Top Microbiol Immunol 348:115-137.
35. Arkin MR, Whitty A (2009) The road less traveled: Modulating signal transduction enzymes by inhibiting their protein-protein interactions. Curr Opin Chem Biol 13(3):284-290.
36. Arkin M (2005) Protein-protein interactions and cancer: Small molecules going in for the kill. Curr Opin Chem Biol 9(3):317-324.
37. Arkin MR, Wells JA (2004) Small-molecule inhibitors of protein-protein interactions: Progressing towards the dream. Nat Rev Drug Discov 3(4):301-317. (Pubitemid 38499758)
38. Garner AL, Janda KD (2011) Protein-protein interactions and cancer: Targeting the central dogma. Curr Top Med Chem 11(3):258-280.
39. Haggarty SJ, Schreiber SL (2007) Forward chemical genetics. Chemical Biology: From Small Molecules to Systems Biology and Drug Design, eds Schreiber SL, Kapoor TM, Wess G (Wiley-VCH, Weinheim, Germany), Vol 1, pp 299-354.
40. Gough JD, Crews CM (2007) Using natural products to unravel cell biology. Chemical Biology: From Small Molecules to Systems Biology and Drug Design, eds Schreiber SL, Kapoor TM, Wess G (Wiley-VCH, Weinheim, Germany), Vol 1, pp 95-114.
41. Lampson MA, Kapoor TM (2007) Using small molecules to unravel biological mechanisms. Chemical Biology: From Small Molecules to Systems Biology and Drug Design, eds Schreiber SL, Kapoor TM, Wess G (Wiley-VCH, Weinheim, Germany), Vol 1, pp 71-94.
42. Erlanson DA, Wells JA, Braisted AC (2004) Tethering: Fragment-based drug discovery. Annu Rev Biophys Biomol Struct 33:199-223. (Pubitemid 38829958)
43. Duesberg PH, Bister K, Vogt PK (1977) The RNA of avian acute leukemia virus MC29. Proc Natl Acad Sci USA 74(10):4320-4324. (Pubitemid 8225113)
44. Bister K (2013) MC29 avian myelocytomatosis virus. Brenner's Encyclopedia of Genetics, eds Maloy S, Hughes K (Academic Press, San Diego), 2nd Ed, Vol 4, pp 330-332.
45. Dalla-Favera R, et al. (1982) Human c-myc onc gene is located on the region of chromosome 8 that is translocated in Burkitt lymphoma cells. Proc Natl Acad Sci USA 79(24):7824-7827. (Pubitemid 13182471)
46. Soucek L, et al. (2013) Inhibition of Myc family proteins eradicates KRas-driven lung cancer in mice. Genes Dev 27(5):504-513.
47. Liu P, et al. (2011) Oncogenic PIK3CA-driven mammary tumors frequently recur via PI3K pathway-dependent and PI3K pathway-independent mechanisms. Nat Med 17(9):1116-1120.
48. Bowman T, et al. (2001) Stat3-mediated Myc expression is required for Src transformation and PDGF-induced mitogenesis. Proc Natl Acad Sci USA 98(13):7319-7324. (Pubitemid 32567946)
49. Savino M, et al. (2011) The action mechanism of the Myc inhibitor termed Omomyc may give clues on how to target Myc for cancer therapy. PLoS ONE 6(7):e22284.
50. Scripture CD, Figg WD, Sparreboom A (2005) Paclitaxel chemotherapy: From empiricism to a mechanism-based formulation strategy. Ther Clin Risk Manag 1(2):107-114.
51. Adams JD, et al. (1993) Taxol: A history of pharmaceutical development and current pharmaceutical concerns. J Natl Cancer Inst Monogr (15):141-147.
52. Petros AM, et al. (2006) Discovery of a potent inhibitor of the antiapoptotic protein Bcl-xL from NMR and parallel synthesis. J Med Chem 49(2):656-663. (Pubitemid 43157495)
53. Duff RG, Vogt PK (1969) Characteristics of two new avian tumor virus subgroups. Virology 39(1):18-30.
54. Bos TJ, et al. (1990) Efficient transformation of chicken embryo fibroblasts by c-Jun requires structural modification in coding and noncoding sequences. Genes Dev 4(10):1677-1687.
55. Aoki M, Batista O, Bellacosa A, Tsichlis P, Vogt PK (1998) The Akt kinase: Molecular determinants of oncogenicity. Proc Natl Acad Sci USA 95(25):14950-14955. (Pubitemid 29003737)
56. Hartl M, Nist A, Khan MI, Valovka T, Bister K (2009) Inhibition of Myc-induced cell transformation by brain acid-soluble protein 1 (BASP1). Proc Natl Acad Sci USA 106(14):5604-5609.
57. Ahmed SA, Gogal RM, Jr, Walsh JE (1994) A new rapid and simple non-radioactive assay to monitor and determine the proliferation of lymphocytes: An alternative to [3H]thymidine incorporation assay. J Immunol Methods 170(2):211-224. (Pubitemid 24122510)
58. Efron B, Tibshirani R (1994) An Introduction to the Bootstrap (Chapman & Hall/CRC, Boca Raton, FL).
59. Davison A, Hinkley D (1997) Bootstrap Methods and Their Application (Cambridge Univ Press, New York).
60. Canty A, Ripley B (2014) boot: Bootstrap R (S-Plus) Functions, R package Version 1.3-11 (Oxford, UK).
61. The R Development Core Team (2014) R: A Language and Environment for Statistical Computing (R Found Stat Comput, Vienna).
62. Wu J, Houghton PJ (2009) Assessing cytotoxic treatment effects in preclinical tumor xenograft models. J Biopharm Stat 19(5):755-762.
63. Wickham H (2009) ggplot2: Elegant Graphics for Data Analysis (Springer, New York).