Echinomycin, a small-molecule inhibitor of hypoxia-inducible factor-1 DNA-binding activity

Cancer Research

Volumn 65, Issue 19, 2005, Pages 9047-9055

  Kong, Dehe ^a   Park, Eun Jung ^a   Stephen, Andrew G ^a   Calvani, Maura ^b   Cardellina, John H ^b   Monks, Anne ^a   Fisher, Robert J ^a   Shoemaker, Robert H ^b   Melillo, Giovanni ^a,b  

^a SAIC FREDERICK INC   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIN D1; DNA; ECHINOMYCIN; HELIX LOOP HELIX PROTEIN; HYPOXIA INDUCIBLE FACTOR 1; HYPOXIA INDUCIBLE FACTOR 1ALPHA; HYPOXIA INDUCIBLE FACTOR 1BETA; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INTERCELLULAR ADHESION MOLECULE 1; LUCIFERASE; MESSENGER RNA; NSC 13502; OLIGONUCLEOTIDE; TRANSCRIPTION FACTOR; TRANSCRIPTION FACTOR AP 1; UNCLASSIFIED DRUG; VASCULOTROPIN;

AMINO ACID SEQUENCE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL STRAIN MCF 7; CONTROLLED STUDY; DNA DENATURATION; ENZYME LINKED IMMUNOSORBENT ASSAY; GEL MOBILITY SHIFT ASSAY; GENE EXPRESSION REGULATION; GENE TARGETING; GLIOMA CELL; HUMAN; HUMAN CELL; IMMUNOPRECIPITATION; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROMOTER REGION; PROTEIN DNA BINDING; PROTEIN DOMAIN; REAL TIME POLYMERASE CHAIN REACTION; WESTERN BLOTTING;

ANTIBIOTICS, ANTINEOPLASTIC; BREAST NEOPLASMS; CELL LINE, TUMOR; DNA, NEOPLASM; ECHINOMYCIN; ENZYME-LINKED IMMUNOSORBENT ASSAY; GLIOMA; HUMANS; HYPOXIA-INDUCIBLE FACTOR 1; LUCIFERASES; PROMOTER REGIONS (GENETICS); RECOMBINANT PROTEINS; RNA, MESSENGER; VASCULAR ENDOTHELIAL GROWTH FACTOR A;

EID: 25444523184     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: 10.1158/0008-5472.CAN-05-1235     Document Type: Article

References (50)

1. Darnell JE, Jr. Transcription factors as targets for cancer therapy. Nat Rev Cancer 2002;2:740-9.
2. Arkin MR, Wells JA. Small-molecule inhibitors of protein-protein interactions: progressing towards the dream. Nat Rev Drug Discov 2004;3:301-17.
3. Semenza GL. Hypoxia-inducible factor 1: oxygen homeostasis and disease pathophysiology. Trends Mol Med 2001;7:345-50.
4. Wang GL, Jiang BH, Rue EA, Semenza GL. Hypoxia-inducible factor 1 is a basic-helix-loop-helix-PAS heterodimer regulated by cellular 02 tension. Proc Natl Acad Sci U S A 1995;92:5510-4.
5. Semenza GL. Targeting HIF-1 for cancer therapy. Nat Rev Cancer 2003;3:721-32.
6. Karni R, Dor Y, Keshet E, Meyuhas O, Levitzki A. Activated pp60c-Src leads to elevated hypoxia-inducible factor (HIF)-1α expression under normoxia. J Biol Chem 2002;277:42919-25.
7. Zundel W, Schindler C, Haas-Kogan D, et al. Loss of PTEN facilitates HIF-1-mediated gene expression. Genes Dev 2000;14:391-6.
8. Maxwell PH, Wiesener MS, Chang GW, et al. The tumour suppressor protein VHL targets hypoxia-inducible factors for oxygen-dependent proteolysis. Nature 1999;399:271-5.
9. Ravi R, Mookerjee B, Bhujwalla ZM, et al. Regulation of tumor angiogenesis by p53-induced degradation of hypoxia-inducible factor 1α. Genes Dev 2000;14:34-44.
10. Fukuda R, Hirota K, Fan F, et al. Insulin-like growth factor 1 induces hypoxia-inducible factor 1-mediated vascular endothelial growth factor expression, which is dependent on MAP kinase and phosphatidylinositol 3-kinase signaling in colon cancer cells. J Biol Chem 2002;277:38205-11.
11. Zhong H, Chiles K, Feldser D, et al. Modulation of hypoxia-inducible factor 1α expression by the epidermal growth factor/phosphatidylinositol 3-kinase/PTEN/AKT/FRAP pathway in human prostate cancer cells: implications for tumor angiogenesis and therapeutics. Cancer Res 2000;60:1541-5.
12. Jiang BH, Rue E, Wang GL, Roe R, Semenza GL. Dimerization, DNA binding, and transactivation properties of hypoxia-inducible factor 1. J Biol Chem 1996;271:17771-8.
13. Rapisarda A, Uranchimeg B, Scudiero DA, et al. Identification of small molecule inhibitors of hypoxia-inducible factor 1 transcriptional activation pathway. Cancer Res 2002;62:4316-24.
14. Monks A, Scudiero D, Skehan P, et al. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J Natl Cancer Inst 1991;83:757-66.
15. Van Dyke MM, Dervan PB. Echinomycin binding sites on DNA. Science 1984;225:1122-7.
16. Patel DJ. Netropsin. dG-dG-dA-dA-dT-dT-dC-dC complex. Antibiotic binding at adenine-thymine base pairs in the minor groove of the self-complementary octanucleotide duplex. Eur J Biochem 1979;99:369-78.
17. Patel DJ. Nuclear magnetic resonance studies of drug-nucleic acid interactions at the synthetic DNA level in solution. Acc Chem Res 1979;12:118-25.
18. Semenza G. Signal transduction to hypoxia-inducible factor 1. Biochem Pharmacol 2002;64:993-8.
19. Laughner E, Taghavi P, Chiles K, Mahon PC, Semenza GL. HER2 (neu) signaling increases the rate of hypoxia-inducible factor 1α (HIF-1α) synthesis: novel mechanism for HIF-1-mediated vascular endothelial growth factor expression. Mol Cell Biol 2001;21:3995-4004.
20. Zhong H, De Marzo AM, Laughner E, et al. Overexpression of hypoxia-inducible factor 1α in common human cancers and their metastases. Cancer Res 1999;59:5830-5.
21. Shibaji T, Nagao M, Ikeda N, et al. Prognostic significance of HIF-1α overexpression in human pancreatic cancer. Anticancer Res 2003;23:4721-7.
22. Bachtiary B, Schindl M, Potter R, et al. Overexpression of hypoxia-inducible factor 1α indicates diminished response to radiotherapy and unfavorable prognosis in patients receiving radical radiotherapy for cervical cancer. Clin Cancer Res 2003;9:2234-40.
23. Bos R, Van Der GP, Greijer AE, et al. Levels of hypoxia-inducible factor-1α independently predict prognosis in patients with lymph node negative breast carcinoma. Cancer 2003;97:1573-81.
24. Melillo G. HIF-1: a target for cancer, ischemia and inflammation-too good to be true? Cell Cycle 2004;3:154-5.
25. Giaccia A, Siim BG, Johnson RS. HIF-1 as a target for drug development. Nat Rev Drug Discov 2003;2:803-11.
26. Sun X, Kanwar JR, Leung E, et al. Gene transfer of antisense hypoxia inducible factor-1α enhances the therapeutic efficacy of cancer immunotherapy. Gene Ther 2001;8:638-45.
27. Zhang Q, Zhang ZF, Rao JY, et al. Treatment with siRNA and antisense oligonucleotides targeted to HIF-1α induced apoptosis in human tongue squamous cell carcinomas. Int J Cancer 2004;111:849-57.
28. Neckers L. Hsp90 inhibitors as novel cancer chemotherapeutic agents. Trends Mol Med 2002;8:555-61.
29. Mabjeesh NJ, Post DE, Willard MT, et al. Geldanamycin induces degradation of hypoxia-inducible factor 1α protein via the proteosome pathway in prostate cancer cells. Cancer Res 2002;62:2478-82.
30. Kurebayashi J, Otsuki T, Kurosumi M, et al. A radicicol derivative, KF58333, inhibits expression of hypoxia-inducible factor-1α and vascular endothelial growth factor, angiogenesis and growth of human breast cancer xenografts. Jpn J Cancer Res 2001;92:1342-51.
31. Welsh SJ, Williams RB, Birmingham A, et al. The thioredoxin redox inhibitors 1-methylpropyl 2-imidazolyl disulfide and pleurotin inhibit hypoxia-induced factor 1α and vascular endothelial growth factor formation. Mol Cancer Ther 2003;2:235-43.
32. Tan C, de Noronha RG, Roecker AJ, et al. Identification of a novel small-molecule inhibitor of the hypoxia-inducible factor 1 pathway. Cancer Res 2005;65:605-12.
33. Hudson CC, Liu M, Chiang GG, et al. Regulation of hypoxia-inducible factor 1α expression and function by the mammalian target of rapamycin. Mol Cell Biol 2002;22:7004-14.
34. Mabjeesh NJ, Willard MT, Harris WB, et al. Dibenzoylmethane, a natural dietary compound, induces HIF-1α and increases expression of VEGF. Biochem Biophys Res Commun 2003;303:279-86.
35. Rapisarda A, Uranchimeg B, Sordet O, et al. Topoisomerase I-mediated inhibition of hypoxia-inducible factor 1: mechanism and therapeutic implications. Cancer Res 2004;64:1475-82.
36. Yeo EJ, Chun YS, Cho YS, et al. YC-1: a potential anticancer drug targeting hypoxia-inducible factor 1. J Natl Cancer Inst 2003;95:516-25.
37. Welsh S, Williams R, Kirkpatrick L, Paine-Murrieta G, Powis G. Antitumor activity and pharmacodynamic properties of PX-478, an inhibitor of hypoxia-inducible factor-1α. Mol Cancer Ther 2004;3:233-44.
38. Rapisarda A, Zalek J, Hollingshead M, et al. Schedule-dependent inhibition of hypoxia-inducible factor-1α protein accumulation, angiogenesis, and tumor growth by topotecan in U251-HRE glioblastoma xenografts. Cancer Res 2004;64:6845-8.
39. Kung AL, Wang S, Klco JM, Kaelin WG, Livingston DM. Suppression of tumor growth through disruption of hypoxia-inducible transcription. Nat Med 2000;6:1335-40.
40. Kung AL, Zabludoff SD, France DS, et al. Small molecule blockade of transcriptional coactivation of the hypoxia-inducible factor pathway. Cancer Cell 2004;6:33-43.
41. Freedman SJ, Sun ZY, Poy F, et al. Structural basis for recruitment of CBP/p300 by hypoxia-inducible factor-1α. Proc Natl Acad Sci U S A 2002;99:5367-72.
42. Bremer RE, Wurtz NR, Szewczyk JW, Dervan PB. Inhibition of major groove DNA binding bZIP proteins by positive patch polyamides. Bioorg Med Chem 2001;9:2093-103.
43. Fechter EJ, Dervan PB. Allosteric inhibition of protein-DNA complexes by polyamide-intercalator conjugates. J Am Chem Soc 2003;125:8476-85.
44. Olenyuk BZ, Zhang GJ, Klco JM, et al. Inhibition of vascular endothelial growth factor with a sequence-specific hypoxia response element antagonist. Proc Natl Acad Sci U S A 2004;101:16768-73.
45. Formica JV, Waring MJ. Effect of phosphate and amino acids on echinomycin biosynthesis by Streptomyces echinatus. Antimicrob Agents Chemother 1983;24:735-41.
46. Nair SK, Burley SK. X-ray structures of Myc-Max and Mad-Max recognizing DNA. Molecular bases of regulation by proto-oncogenic transcription factors. Cell 2003;112:193-205.
47. Foster BJ, Clagett-Carr K, Shoemaker DD, et al. Echinomycin: the first bifunctional intercalating agent in clinical trials. Invest New Drugs 1985;3:403-10.
48. Muss HB, Blessing JA, DuBeshter B. Echinomycin in recurrent and metastatic endometrial carcinoma. A phase II trial of the Gynecologic Oncology Group. Am J Clin Oncol 1993;16:492-3.
49. Wadler S, Tenteromano L, Cazenave L, et al. Phase II trial of echinomycin in patients with advanced or recurrent colorectal cancer. Cancer Chemother Pharmacol 1994;34:266-9.
50. Chang AY, Kim K, Boucher H, et al. A randomized phase II trial of echinomycin, trimetrexate, and cisplatin plus etoposide in patients with metastatic nonsmall cell lung carcinoma: an Eastern Cooperative Oncology Group Study (E1587). Cancer 1998;82:292-300.