Natural product-derived small molecule activators of hypoxia-inducible factor-1 (HIF-1)

Current Pharmaceutical Design

Volumn 12, Issue 21, 2006, Pages 2673-2688

  Nagle, Dale G ^a   Zhou, Yu Dong ^a  

^a UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

Chemoprevention; HIF 1; Ischemia reperfusion injury; Molecular target; Natural product; Small molecule activator; Therapeutic angiogenesis; Tissue ischemia

Indexed keywords

3 CARBOXY N HYDROXYPYROLIDONE; 5 IODOINDIRUBIN 3' OXIME; 5 METHYLINDIRUBIN 3' OXIME; 8 METHYLPYRIDOXATIN; ALAHOPCIN; AMINO ACID DERIVATIVE; CICLOPIROXOLAMINE; COLCHICINE; DEALANYLALAHOPCIN; DEFEROXAMINE; DESFERAL MESYLATE; DESFERRIEXOCHELIN; DFE 722; DIBENZOYLMETHANE DERIVATIVE; DIMETHYLOXALYLGLYCINE; EPICATECHIN GALLATE; EPIGALLOCATECHIN GALLATE; GLUTAMINE DERIVATIVE; GREEN TEA EXTRACT; HORMONE; HYPOXIA INDUCIBLE FACTOR 1ALPHA; INDIRUBIN; IRON CHELATING AGENT; N OXALYLYGLYCINE; OXALYLALANINE; PHENOL DERIVATIVE; PROSTAGLANDIN E2 DERIVATIVE; QUERCETIN; SPERMINE DERIVATIVE; SUCCINIMIDE DERIVATIVE; TERPENE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

CORONARY ARTERY ATHEROSCLEROSIS; DRUG IDENTIFICATION; DRUG INHIBITION; DRUG STRUCTURE; DRUG TARGETING; GLYCOLYSIS; HEART MUSCLE ISCHEMIA; HIGH THROUGHPUT SCREENING; HUMAN; IN VITRO STUDY; MOLECULAR PROBE; MOLECULAR WEIGHT; NONHUMAN; NONVIRAL GENE THERAPY; OXYGEN TENSION; PRIORITY JOURNAL; PROTEIN EXPRESSION; REPERFUSION INJURY; REVIEW; STRUCTURE ANALYSIS; TRANSCRIPTION REGULATION;

ANIMALS; BIOLOGICAL PRODUCTS; CARDIOVASCULAR DISEASES; GENE EXPRESSION; HUMANS; HYPOXIA-INDUCIBLE FACTOR 1; MODELS, BIOLOGICAL; MOLECULAR WEIGHT;

EID: 33745764163     PISSN: 13816128     EISSN: None     Source Type: Journal    
DOI: 10.2174/138161206777698783     Document Type: Review

References (158)

1. Semenza GL, Wang GL. A nuclear factor induced by hypoxia via de novo protein synthesis binds to the human erythropoietin gene enhancer at a site required for transcriptional activation. Mol Cell Biol 1992; 12: 5447-54.
2. 2 tension. Proc Natl Acad Sci USA 1995; 92: 5510-4.
3. Semenza GL. Targeting HIF-1 for cancer therapy. Nat Rev Cancer 2003; 3: 721-32.
4. Huang LE, Bunn HF. Hypoxia-inducible factor and its biomedical relevance. J Biol Chem 2003; 278: 19575-8.
5. Poellinger L, Johnson RS. HIF-1 and hypoxic response: the plot thickens. Curr Opin Genet Dev 2004; 14: 81-5.
6. 2 sensing. Science 2001, 292: 464-468.
7. 2-regulated prolyl hydroxylation. Science 2001; 292: 468-472.
8. Epstein AC, Gleadle JM, McNeill LA, Hewitson KS, O'Rourke J, Mole DR, et al. C. elegans EGL-9 and mammalian homologs define a family of dioxygenases that regulate HIF by prolyl hydroxylation. Cell 2001; 107: 43-54.
9. Bruick RK, McKnight SL. A conserved family of prolyl-4-hydroxylases that modify HIF. Science 2001; 294: 1337-40.
10. Maxwell PH, Wiesener MS, Chang GW, Clifford SC, Vaux EC, Cockman ME, et al. The tumour suppressor protein VHL targets hypoxia-inducible factors for oxygen-dependent proteolysis. Nature 1999; 399: 271-5.
11. Mahon PC, Hirota K, Semenza GL. FIH-1: a novel protein that interacts with HIF-1α and VHL to mediate repression of HIF-1 transcriptional activity. Genes Dev 2001; 15: 2675-86.
12. Lando D, Peet DJ, Whelan DA, Gorman JJ, Whitelaw ML. Asparagine hydroxylation of the HIF transactivation domain a hypoxic switch. Science 2002; 295: 858-61.
13. Lando D, Peet DJ, Gorman JJ, Whelan DA, Whitelaw ML, Bruick RK. FIH-1 is an asparaginyl hydroxylase enzyme that regulates the transcriptional activity of hypoxia-inducible factor. Genes Dev 2002; 16: 1466-71.
14. Hewitson KS, McNeill LA, Riordan MV, Tian YM, Bullock AN, Welford RW, et al. Hypoxia-inducible factor (HIF) asparagine hydroxylase is identical to factor inhibiting HIF (FIH) and is related to the cupin structural family. J Biol Chem 2002; 277: 26351-5.
15. McNeill LA, Hewitson KS, Claridge TD, Seibel JF, Horsfall LE, Schofield CJ. Hypoxia-inducible factor asparaginyl hydroxylase (FIH-1) catalyses hydroxylation at the beta-carbon of asparagine-803. Biochem J 2002; 367: 571-5.
16. Dames SA, Martinez-Yamout M, De Guzman RN, Dyson HJ, Wright PE. Structural basis for HIF-1α/CBP recognition in the cellular hypoxic response. Proc Natl Acad Sci USA 2002; 99: 5271-6.
17. Freedman SJ, Sun ZY, Poy F, Kung AL, Livingston DM, Wagner G, Eck MJ. Structural basis for recruitment of CBP/p300 by hypoxia-inducible factor-1α. Proc Natl Acad Sci USA 2002; 99: 5367-72.
18. Koivunen P, Hirsila M, Gunzler V, Kivirikko KI, Myllyharju J. Catalytic properties of the asparaginyl hydroxylase (FIH) in the oxygen sensing pathway are distinct from those of its prolyl 4-hydroxylases. J Biol Chem 2004; 279: 9899-904.
19. Safran M, Kaelin WG Jr. HIF hydroxylation and the mammalian oxygen-sensing pathway. J Clin Invest 2003; 111: 779-83.
20. Lando D, Gorman JJ, Whitelaw ML, Peet DJ. Oxygen-dependent regulation of hypoxia-inducible factors by prolyl and asparaginyl hydroxylation. Eur J Biochem 2003; 270: 781-90.
21. 2 levels. J Cell Sci 2003; 116: 3041-9.
22. Bruick RK. Oxygen sensing in the hypoxic response pathway: regulation of the hypoxia-inducible transcription factor. Genes Dev 2003; 17: 2614-23
23. Schofield CJ, Ratcliffe PJ. Oxygen sensing by HIF hydroxylases. Nat Rev Mol Cell Biol 2004; 5: 343-54.
24. Hewitson KS, Schofield CJ. The HIF pathway as a therapeutic target. Drug Discov Today 2004, 9: 704-11.
25. Semenza GL. Hydroxylation of HIF-1: oxygen sensing at the molecular level. Physiology (Bethesda) 2004; 19: 176-82.
26. Brahimi-Horn C, Mazure N, Pouyssegur J. Signalling via the hypoxia-inducible factor-1α requires multiple posttranslational modifications. Cell Signal 2005; 17: 1-9.
27. Giaccia A, Siim BG, Johnson RS. HIF-1 as a target for drug development. Nat Rev Drug Discov 2003; 2: 803-11.
28. Welsh SJ, Powis G. Hypoxia inducible factor as a cancer drug target. Curr Cancer Drug Targets 2003, 3: 391-405.
29. Powis G, Kirkpatrick L. Hypoxia inducible factor-1α as a cancer drug target. Mol Cancer Ther 2004; 3: 647-54.
30. Paul SA, Simons JW, Mabjeesh NJ. HIF at the crossroads between ischemia and carcinogenesis. J Cell Physiol 2004; 200: 20-30.
31. Hopfl G, Ogunshola O, Gassmann M. HIFs and tumors - causes and consequences. Am J Physiol Regul Integr Comp Physiol 2004; 286: R608-23.
32. Newman DJ, Cragg GM, Snader KM. Natural products as sources of new drugs over the period 1981-2002. J Nat Prod 2003; 66: 1022-37.
33. Wang GL, Semenza GL. Desferrioxamine induces erythropoietin gene expression and hypoxia-inducible factor 1 DNA-binding activity: implications for models of hypoxia signal transduction. Blood 1993; 82: 3610-5.
34. Bickel H, Hall GE, Keller-Schierlein W, Prelog V, Vischer E, Wettstein A. Metabolic products of Actinomycetaceae. XXVII. Constitutional formulas of ferrioxamine B. Helve Chim Acta 1960; 43: 2129-38.
35. Anonymous, In: McEvoy GK Ed, AHFS Drug Information 2004. Bethesda, American Society of Health-System Pharmacists, Inc./American Hospital Formulary Service 2004, 2870-3.
36. Gobin J, Moore CH, Reeve JR Jr, Wong DK, Gibson BW, Horwitz MA. Iron acquisition by Mycobacterium tuberculosis: isolation and characterization of a family of iron-binding exochelins. Proc Natl Acad Sci USA 1995; 92: 5189-93.
37. Chong TW, Horwitz LD, Moore JW, Sowter HM, Harris AL. A mycobacterial iron chelator, desferri-exochelin, induces hypoxia-inducible factors 1 and 2, NIP3, and vascular endothelial growth factor in cancer cell lines. Cancer Res 2002; 62: 6924-7.
38. Anonymous, In: McEvoy GK Ed, AHFS Drug Information 2004. Bethesda, American Society of Health-System Pharmacists, Inc./American Hospital Formulary Service 2004, 3358-61.
39. Warmer RM, Spielmann P, Stroka DM, Camenisch G, Camenisch I, Scheid A, et al. Epolones induce erythropoietin expression via hypoxia-inducible factor-1α activation. Blood 2000; 96: 1558-65.
40. Linden T, Katschinski DM, Eckhardt K, Scheid A, Pagel H, Wenger RH. The antimycotic ciclopirox olamine induces HIF-1α stability, VEGF expression, and angiogenesis. FASEB J 2003; 17: 761-3.
41. Cai P, Smith D, Cunningham B, Brown-Shimer S, Katz B, Pearce C, et al. 8-methyl-pyridoxatin: A novel N-hydroxy pyridone from fungus OS-F61800 that induces erythropoietin in human cells. J Nat Prod 1999; 62: 397-9.
42. Cunliffe CJ, Franklin TJ, Hales NJ, Hill GB. Novel inhibitors of prolyl 4-hydroxylase. 3. Inhibition by the substrate analogue N-oxaloglycine and its derivatives. J Med Chem 1992; 35: 2652-8.
43. Elkins JM, Hewitson KS, McNeill LA, Seibel JF, Schlemminger I, Pugh CW, et al. Structure of factor-inhibiting hypoxia-inducible factor (HIF) reveals mechanism of oxidative modification of HlF-1α. J Biol Chem 2003; 278: 1802-6.
44. Hirsila M, Koivunen P, Gunzler V, Kivirikko KI, Myllyharju J. Characterization of the human prolyl 4-hydroxylases that modify the hypoxia-inducible factor. J Biol Chem 2003; 278: 30772-80.
45. Koivunen P, Hirsila M, Gunzler V, Kivirikko KI, Myllyharju J. Catalytic properties of the asparaginyl hydroxylase (FIH) in the oxygen sensing pathway are distinct from those of its prolyl 4-hydroxylases. J Biol Chem 2004; 279: 9899-904.
46. Mole DR, Schlemminger I, McNeill LA, Hewitson KS, Pugh CW, Ratcliffe PJ, et al. 2-oxoglutarate analogue inhibitors of HIF prolyl hydroxylase. Bioorg Med Chem Lett 2003; 13: 2677-80.
47. Higashide E, Horii S, Ono H, Mizokami N, Yamazaki T, Shibata M, et al. Alahopcin, a new dipeptide antibiotic produced by Streptomyces albulus subsp. ochragerus subsp. nov. J Antibiot (Tokyo) 1985; 38: 285-95.
48. Higashide E, Kanamaru T, Fukase H, Horii S. Isolation of dealanylalahopcin, a new amino acid, and its biological activity. J Antibiot (Tokyo) 1985; 38: 296-301.
49. Horii S, Fukase H, Higashide E, Yoneda M, Nisbida H, Sakai H, et al. Structure of alahopcin (nourseimycin), a new dipeptide antibiotic. J Antibiot (Tokyo) 1985; 38: 302-11.
50. Schlemminger I, Mole DR, McNeill LA, Dhanda A, Hewitson KS, Tian YM, et al. Analogues of dealanylalahopcin are inhibitors of human HIF prolyl hydroxylases. Bioorg Med Chem Lett 2003; 13: 1451-4.
51. Schnitzer SE, Schmid T, Zhou J, Eisenbrand G, Brune B. Inhibition of GSK3beta by indirubins restores HIF-1α accumulation under prolonged periods of hypoxia/anoxia. FEBS Lett 2005; 579: 529-33.
52. Xiao Z, Hao Y, Liu B, Qian L. Indirubin and meisoindigo in the treatment of chronic myelogenous leukemia in China. Leuk Lymphoma 2002; 43: 1763-8.
53. Leclerc S, Garnier M, Hoessel R, Marko D, Bibb JA, Snyder GL, et al. Indirubins inhibit glycogen synthase kinase-3β and CDK5/p25, two protein kinases involved in abnormal tau phosphorylation in Alzheimer's disease. A property common to most cyclin-dependent kinase inhibitors? J Biol Chem 2001; 276: 251-60.
54. Bain J, McLauchlan H, Elliott M, Cohen P. The specificities of protein kinase inhibitors: an update. Biochem J 2003; 371: 199-204.
55. Liu Y, Christou H, Morita T, Laughner E, Semenza GL, Kourembanas S. Carbon monoxide and nitric oxide suppress the hypoxic induction of vascular endothelial growth factor gene via the 5′ enhancer. J Biol Chem 1998; 273: 15257-62.
56. Sogawa K, Numayama-Tsuruta K, Ema M, Abe M, Abe H, Fujii-Kuriyama Y. Inhibition of hypoxia-inducible factor 1 activity by nitric oxide donors in hypoxia. Proc Natl Acad Sci USA 1998; 95: 7368-73.
57. Huang LE, Willmore WG, Gu J, Goldberg MA, Bunn HF. Inhibition of hypoxia-inducible factor 1 activation by carbon monoxide and nitric oxide. Implications for oxygen sensing and signaling. J Biol Chem 1999; 274: 9038-44.
58. Kimura H, Weisz A, Kurashima Y, Hashimoto K, Ogura T, D'Acquisto F, et al. Hypoxia response element of the human vascular endothelial growth factor gene mediates transcriptional regulation by nitric oxide: control of hypoxia-inducible factor-1 activity by nitric oxide. Blood 2000; 95: 189-97.
59. Palmer LA, Gaston B, Johns RA. Normoxic stabilization of hypoxia-inducible factor-1 expression and activity: redox-dependent effect of nitrogen oxides. Mol Pharmacol 2000; 58: 1197-203.
60. Sumbayev VV, Budde A, Zhou J, Brune B. HIF-1α protein as a target for S-nitrosation. FEBS Lett 2003; 535: 106-12.
61. Yasinska IM, Sumbayev VV. S-nitrosation of Cys-800 of HIF-1α protein activates its interaction with p300 and stimulates its transcriptional activity. FEBS Lett 2003; 549: 105-9.
62. Sandau KB, Fandrey J, Brune B. Accumulation of HIF-1α under the influence of nitric oxide. Blood 2001; 97: 1009-15.
63. Thomas DD, Espey MG, Ridnour LA, Hofseth LJ, Mancardi D, Harris CC, et al. Hypoxic inducible factor 1α, extracellular signal-regulated kinase, and p53 are regulated by distinct threshold concentrations of nitric oxide. Proc Natl Acad Sci USA 2004; 101:8894-9.
64. Sandau KB, Faus HG, Brune B. Induction of hypoxia-inducible-factor 1 by nitric oxide is mediated via the PI 3K pathway. Biochem Biophys Res Commun 2000; 278: 263-7.
65. Sandau KB, Zhou J, Kietzmann T, Brune B. Regulation of the hypoxia-inducible factor 1α by the inflammatory mediators nitric oxide and tumor necrosis factor-alpha in contrast to desferroxamine and phenylarsine oxide. J Biol Chem 2001; 276: 39805-11.
66. Kasuno Y, Takabuchi S, Fukuda K, Kizaka-Kondoh S, Yodoi J, Adachi T, et al. Nitric oxide induces hypoxia-inducible factor 1 activation that is dependent on MAPK and phosphatidylinositol 3-kinase signaling. J Biol Chem 2004; 279: 2550-8.
67. Jung YJ, Isaacs JS, Lee S, Trepel J, Neckers L. Microtubule disruption utilizes an NFκB-dependent pathway to stabilize HIF-1α protein. J Biol Chem 2003; 278: 7445-52.
68. Mabjeesh NJ, Willard MT, Harris WB, Sun HY, Wang R, Zhong H, et al. Dibenzoylmethane, a natural dietary compound, induces HIF-1α and increases expression of VEGF. Biochem Biophys Res Commun 2003; 303: 279-86.
69. Lin CC, Lu YP, Lou YR, Ho CT, Newmark HH, MacDonald C, et al. Inhibition by dietary dibenzoylmethane of mammary gland proliferation, formation of DMBA-DNA adducts in mammary glands, and mammary tumorigenesis in Sencar mice. Cancer Lett 2001; 168: 125-32.
70. Huang MT, Lou YR, Xie JG, Ma W, Lu YP, Yen P, et al. Effect of dietary curcumin and dibenzoylmethane on formation of 7, 12-dimethylbenz[a]anthracene-induced mammary tumors and lymphomas/ leukemias in Sencar mice. Carcinogenesis 1998; 19: 1697-700.
71. Singletary K, MacDonald C, Iovinelli M, Fisher C, Wallig M. Effect of the beta-diketones diferuloylmethane (curcumin) and dibenzoylmethane on rat mammary DNA adducts and tumors induced by 7, 12-dimethylbenz[a]anthracene. Carcinogenesis 1998; 19: 1039-43.
72. Jackson KM, DeLeon M, Verret CR, Harris WB. Dibenzoylmethane induces cell cycle deregulation in human prostate cancer cells. Cancer Lett 2002; 178: 161-5.
73. Wilson WJ, Poellinger L. The dietary flavonoid quercetin modulates HIF-1α activity in endothelial cells. Biochem Biophys Res Commun 2002; 293: 446-50.
74. Davies SP, Reddy H, Caivano M, Cohen P. Specificity and mechanism of action of some commonly used protein kinase inhibitors. Biochem J 2000; 351: 95-105.
75. Welford RW, Schlemminger I, McNeill LA, Hewitson KS, Schofield CJ. The selectivity and inhibition of AlkB. J Biol Chem 2003; 278: 10157-61.
76. Zhou YD, Kim YP, Li XC, Baerson SR, Agarwal AK, Hodges TW, et al. Hypoxia-inducible factor-1 activation by (-)-epicatechin gallate: potential adverse effects of cancer chemoprevention with high-dose green tea extracts. J Nat Prod 2004; 67: 2063-9.
77. Demeule M, Michaud-Levesque J, Annabi B, Gingras D, Boivin D, Jodoin J, et al. Green tea catechins as novel antitumor and antiangiogenic compounds. Curr Med Chem Anti-Canc Agents 2002; 2:441-63.
78. Hong J, Lu H, Meng X, Ryu JH, Hara Y, Yang CS. Stability, cellular uptake, biotransformation, and efflux of tea polyphenol (-)-epigallocatechin-3-gallate in HT-29 human colon adenocarcinoma cells. Cancer Res 2002; 62: 7241-6.
79. Mandel S, Weinreb O, Amit T, Youdim MB. Cell signaling pathways in the neuroprotective actions of the green tea polyphenol (-)-epigallocatechin-3-gallate: implications for neurodegenerative diseases. J Neurochem 2004; 88: 1555-69.
80. Hirano R, Momiyama Y, Takahashi R, Taniguchi H, Kondo K, Nakamura H, et al. Comparison of green tea intake in Japanese patients with and without angiographic coronary artery disease. Am J Cardiol 2002; 90:1150-3.
81. Aneja R, Hake PW, Burroughs TJ, Denenberg AG, Wong HR, Zingarelli B. Epigallocatechin, a green tea polyphenol, attenuates myocardial ischemia reperfusion injury in rats. Mol Med 2004; 10: 55-62.
82. Townsend PA, Scarabelli TM, Pasini E, Gitti G, Menegazzi M, Suzuki H, et al. Epigallocatechin-3-gallate inhibits STAT-1 activation and protects cardiac myocytes from ischemia/reperfusion-induced apoptosis. FASEB J 2004; 18: 1621-3.
83. Cai P, Smith D, Cunningham B, Brown-Shimer S, Katz B, Pearce C, et al. Epolones: novel sesquiterpene-tropolones from fungus OS-F69284 that induce erythropoietin in human cells. J Nat Prod 1998; 61: 791-5.
84. Gao N, Nester RA, Sarkar MA. 4-Hydroxy estradiol but not 2-hydroxy estradiol induces expression of hypoxia-inducible factor 1α and vascular endothelial growth factor A through phosphatidylinositol 3-kinase/Akt/FRAP pathway in OVCAR-3 and A2780-CP70 human ovarian carcinoma cells. Toxicol Appl Pharmacol 2004; 196: 124-35.
85. Mukundan H, Kanagy NL, Resta TC. 17-β estradiol attenuates hypoxic induction of HIF-1α and erythropoietin in Hep3B cells. J Cardiovasc Pharmacol 2004; 44: 93-100.
86. Mabjeesh NJ, Willard MT, Frederickson CE, Zhong H, Simons JW. Androgens stimulate hypoxia-inducible factor 1 activation via autocrine loop of tyrosine kinase receptor/phosphatidylinositol 3′-kinase/protein kinase B in prostate cancer cells. Clin Cancer Res 2003; 9: 2416-25.
87. Nishizuka Y. The role of protein kinase C in cell surface signal transduction and tumour promotion. Nature 1984; 308: 693-8.
88. Zhong H, Chiles K, Feldser D, Laughner E, Hanrahan C, Georgescu MM, 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.
89. Zhong H, Hanrahan C, van der Poel H, Simons JW. Hypoxia-inducible factor 1α and 1beta proteins share common signaling pathways in human prostate cancer cells. Biochem Biophys Res Commun 2001; 284: 352-6.
90. Ladoux A, Frelin C. Cardiac expressions of HIF-1 alpha and HLF/EPAS, two basic loop helix/PAS domain transcription factors involved in adaptative responses to hypoxic stresses. Biochem Biophys Res Commun 1997; 240: 552-6.
91. Jung Y, Isaacs JS, Lee S, Trepel J, Liu ZG, Neckers L. Hypoxia-inducible factor induction by tumour necrosis factor in normoxic cells requires receptor-interacting protein-dependent nuclear factor kappa B activation. Biochem J 2003; 370:1011-7.
92. Chun YS, Lee KH, Choi E, Bae SY, Yeo EJ, Huang LE, et al. Phorbol ester stimulates the nonhypoxic induction of a novel hypoxia-inducible factor 1α isoform: implications for tumor promotion. Cancer Res 2003; 63: 8700-7.
93. 2 is mediated by hypoxia-inducible factor 1. Cancer Res 2003; 63:2330-4.
94. 2 induces hypoxia-inducible factor-1α stabilization and nuclear localization in a human prostate cancer cell line. J Biol Chem 2002; 277: 50081-6.
95. Jung YJ, Isaacs JS, Lee S, Trepel J, Neckers L. IL-1β-mediated up-regulation of HIF-1α via an NFκB/COX-2 pathway identifies HIF-1 as a critical link between inflammation and oncogenesis. FASEB J 2003; 17: 2115-7.
96. Lu H, Forbes RA, Verma A. Hypoxia-inducible factor 1 activation by aerobic glycolysis implicates the Warburg effect in carcinogenesis. J Biol Chem 2002; 277: 23111-5.
97. Dalgard CL, Lu H, Mohyeldin A, Verma A. Endogenous 2-oxoacids differentially regulate expression of oxygen sensors. Biochem J 2004; 380: 419-24.
98. Selak MA, Armour SM, MacKenzie ED, Boulahbel H, Watson DG, Mansfield KD, et al. Succinate links TCA cycle dysfunction to oncogenesis by inhibiting HIF-α prolyl hydroxylase. Cancer Cell 2005; 7: 77-85.
99. Pollard P, Wortham N, Barclay E, Alam A, Elia G, Manek S, P et al. Evidence of increased microvessel density and activation of the hypoxia pathway in tumours from the hereditary leiomyomatosis and renal cell cancer syndrome. J Pathol 2005; 205: 41-9.
100. Hodges TW, Hossain CF, Kim YP, Zhou YD, Nagle DG. Molecular-targeted antitumor agents: the Saururus cernuus dineolignans manassantin B and 4-O-demethylmanassantin B are potent inhibitors of hypoxia-activated HIF-1. J Nat Prod 2004; 67: 767-71.
101. Ivan M, Haberberger T, Gervasi DC, Michelson KS, Gunzler V, Kondo K, et al. Biochemical purification and pharmacological inhibition of a mammalian prolyl hydroxylase acting on hypoxia-inducible factor. Proc Natl Acad Sci USA 2002; 99: 13459-64.
102. Wang GL, Semenza GL. General involvement of hypoxia-inducible factor 1 in transcriptional response to hypoxia. Proc Natl Acad Sci USA 1993; 90: 4304-8.
103. Wang GL, Semenza GL. Purification and characterization of hypoxia-inducible factor 1. J Biol Chem 1995; 270: 1230-7.
104. Salnikow K, An WG, Melillo G, Blagosklonny MV, Costa M. Nickel-induced transformation shifts the balance between HIF-1 and p53 transcription factors. Carcinogenesis 1999; 20: 1819-23
105. Salnikow K, Blagosklonny MV, Ryan H, Johnson R, Costa M. Carcinogenic nickel induces genes involved with hypoxic stress. Cancer Res 2000; 60: 38-41.
106. Gao N, Jiang BH, Leonard SS, Corum L, Zhang Z, Roberts JR, et al. p38 Signaling-mediated hypoxia-inducible factor 1α and vascular endothelial growth factor induction by Cr(VI) in DU145 human prostate carcinoma cells. J Biol Chem 2002; 277: 45041-8.
107. Martin F, Linden T, Katschinski DM, Oehme F, Flamme I, Mukhopadhyay CK, et al. Copper-dependent activation of hypoxia-inducible factor (HIF)-1: implications for ceruloplasmin regulation. Blood 2005; [Epub ahead of print].
108. Agani F, Semenza GL. Mersalyl is a novel inducer of vascular endothelial growth factor gene expression and hypoxia-inducible factor 1 activity. Mol Pharmacol 1998; 54: 749-54.
109. Salnikow K, Donald SP, Bruick RK, Zhitkovich A, Phang JM, Kasprzak KS. Depletion of intracellular ascorbate by the carcinogenic metals nickel and cobalt results in the induction of hypoxic stress. J Biol Chem 2004; 279: 40337-44.
110. Berchner-Pfannschmidt U, Petrat F, Doege K, Trinidad B, Freitag P, Metzen E, et al. Chelation of cellular calcium modulates hypoxia-inducible gene expression through activation of hypoxia-inducible factor-1α. J Biol Chem 2004; 279: 44976-86.
111. Zelzer E, Levy Y, Kabana C, Shilo BZ, Rubinstein M, Cohen B. Insulin induces transcription of target genes through the hypoxia-inducible factor HIF-1α/ARNT. EMBO J. 1998; 17: 5085-94.
112. Feldser D, Agani F, Iyer NV, Pak B, Ferreira G, Semenza GL. Reciprocal positive regulation of hypoxia-inducible factor 1α and insulin-like growth factor 2. Cancer Res 1999; 59: 3915-8.
113. 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.
114. Shi YH, Wang YX, Bingle L, Gong LH, Heng WJ, Li Y, et al. In vitro study of HIF-1 activation and VEGF release by bFGF in the T47D breast cancer cell line under normoxic conditions: involvement of PI-3K/Akt and MEK1/ ERK pathways. J Pathol 2005; 205: 530-6.
115. Stiehl DP, Jelkmann W, Wenger RH, Hellwig-Burgel T. Normoxic induction of the hypoxia-inducible factor 1α by insulin and interleukin-1β involves the phosphatidylinositol 3-kinase pathway. FEBS Lett 2002; 512: 157-62.
116. Treins C, Giorgetti-Peraldi S, Murdaca J, Semenza GL, Van Obberghen E. Insulin stimulates hypoxia-inducible factor 1 through a phosphatidylinositol 3-kinase/target of rapamycin-dependent signaling pathway. J Biol Chem 2002; 277: 27975-81.
117. Fukuda R, Hirota K, Fan F, Jung YD, Ellis LM, Semenza GL. 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.
118. Hellwig-Burgel T, Rutkowski K, Metzen E, Fandrey J, Jelkmann W. Interleukin-1β and tumor necrosis factor-α stimulate DNA binding of hypoxia-inducible factor-1. Blood 1999; 94: 1561-7.
119. El Awad B, Kreft B, Wolber EM, Hellwig-Burgel T, Metzen E, Fandrey J, et al. Hypoxia and interleukin-1beta stimulate vascular endothelial growth factor production in human proximal tubular cells. Kidney Int 2000; 58: 43-50.
120. Haddad JJ, Land SC. A non-hypoxic, ROS-sensitive pathway mediates TNF-α-dependent regulation of HIF-1α. FEBS Lett 2001; 505: 269-74.
121. Zhou J, Fandrey J, Schumann J, Tiegs G, Brune B. NO and TNF-α released from activated macrophages stabilize HIF-1α in resting tubular LLC-PK1 cells. Am J Physiol Cell Physiol 2003; 284: C439-46.
122. Zhou J, Callapina M, Goodall GJ, Brune B. Functional integrity of nuclear factor κB, phosphatidylinositol 3′-kinase, and mitogen-activated protein kinase signaling allows tumor necrosis factor α-evoked Bcl-2 expression to provoke internal ribosome entry site-dependent translation of hypoxia-inducible factor 1α. Cancer Res 2004; 64: 9041-8.
123. Qian D, Lin HY, Wang HM, Zhang X, Liu DL, Li QL, et al. Normoxic induction of the hypoxic-inducible factor-1αby interleukin-1β involves the extracellular signal-regulated kinase 1/2 pathway in normal human cytotrophoblast cells. Biol Reprod 2004; 70: 1822-7.
124. Haddad JJ. Recombinant human interleukin (IL)-1β-mediated regulation of hypoxia-inducible factor-1α (HIF-1α) stabilization, nuclear translocation and activation requires an antioxidant/reactive oxygen species (ROS)-sensitive mechanism. Eur Cytokine Netw 2002; 13: 250-60.
125. Thornton RD, Lane P, Borghaei RC, Pease EA, Caro J, Mochan E. Interleukin 1 induces hypoxia-inducible factor 1 in human gingival and synovial fibroblasts. Biochem J 2000; 350: 307-12.
126. Richard DE, Berra E, Pouyssegur J. Nonhypoxic pathway mediates the induction of hypoxia-inducible factor 1α in vascular smooth muscle cells. J Biol Chem 2000; 275: 26765-71.
127. Page EL, Robitaille GA, Pouyssegur J, Richard DE. Induction of hypoxia-inducible factor-1α by transcriptional and translational mechanisms. J Biol Chem 2002; 277: 48403-9.
128. Gorlach A, Diebold I, Schini-Kerth VB, Berchner-Pfannschmidt U, Roth U, Brandes RP, et al. Thrombin activates the hypoxia-inducible factor-1 signaling pathway in vascular smooth muscle cells: Role of the p22(phox)-containing NADPH oxidase. Circ Res 2001; 89: 47-54.
129. Dery MA, Michaud MD, Richard DE. Hypoxia-inducible factor 1: regulation by hypoxic and non-hypoxic activators. Int J Biochem Cell Biol 2005; 37: 535-40.
130. Ma Y, Freitag P, Zhou J, Brune B, Frede S, Fandrey J. Thyroid hormone induces erythropoietin gene expression through augmented accumulation of hypoxia-inducible factor-1. Am J Physiol Regul Integr Comp Physiol 2004; 287: R600-7.
131. Alam H, Maizels ET, Park Y, Ghaey S, Feiger ZJ, Chandel NS, Hunzicker-Dunn M. Follicle-stimulating hormone activation of hypoxia-inducible factor-1 by the phosphatidylinositol 3-kinase/AKT/Ras homolog enriched in brain (Rheb)/mammalian target of rapamycin (mTOR) pathway is necessary for induction of select protein markers of follicular differentiation. J Biol Chem 2004; 279: 19431-40.
132. Welsh SJ, Bellamy WT, Briehl MM, Powis G. The redox protein thioredoxin-1 (Trx-1) increases hypoxia-inducible factor 1α protein expression: Trx-1 overexpression results in increased vascular endothelial growth factor production and enhanced tumor angiogenesis. Cancer Res 2002; 62: 5089-95.
133. Shatrov VA, Sumbayev VV, Zhou J, Brune B. Oxidized low-density lipoprotein (oxLDL) triggers hypoxia-inducible factor-1α (HIF-1α) accumulation via redox-dependent mechanisms. Blood 2003; 101: 4847-9.
134. Kojima H, Gu H, Nomura S, Caldwell CC, Kobata T, Carmeliet P, et al. Abnormal B lymphocyte development and autoimmunity in hypoxia-inducible factor 1α-deficient chimeric mice. Proc Natl Acad Sci USA 2002; 99: 2170-4.
135. Makino Y, Nakamura H, Ikeda E, Ohnuma K, Yamauchi K, Yabe Y, et al. Hypoxia-inducible factor regulates survival of antigen receptor-driven T cells. J Immunol 2003; 171: 6534-40.
136. Cramer T, Yamanishi Y, Clausen BE, Forster I, Pawlinski R, Mackman N, et al. HIF-1α is essential for myeloid cell-mediated inflammation. Cell 2003; 112: 645-57.
137. Wakisaka N, Kondo S, Yoshizaki T, Murono S, Furukawa M, Pagano JS. Epstein-Barr virus latent membrane protein 1 induces synthesis of hypoxia-inducible factor 1α. Mol Cell Biol 2004; 24: 5223-34.
138. Koury J, Deitch EA, Homma H, Abungu B, Gangurde P, Condon MR, et al. Persistent HIF-1α activation in gut ischemia/reperfusion injury: potential role of bacteria and lipopolysaccharide. Shock 2004; 22: 270-7.
139. Kelly BD, Hackett SF, Hirota K, Oshima Y, Cai Z, Berg-Dixon S, et al. Cell type-specific regulation of angiogenic growth factor gene expression and induction of angiogenesis in nonischemic tissue by a constitutively active form of hypoxia-inducible factor 1. Circ Res 2003, 93: 1074-81.
140. Shyu KG, Wang MT, Wang BW, Chang CC, Leu JG, Kuan P, et al. Intramyocardial injection of naked DNA encoding HIF-1α/VP16 hybrid to enhance angiogenesis in an acute myocardial infarction model in the rat. Cardiovasc Res 2002; 54: 576-83.
141. Vincent KA, Shyu KG, Luo Y, Magner M, Tio RA, Jiang C, et al. Angiogenesis is induced in a rabbit model of hindlimb ischemia by naked DNA encoding an HIF-1α/VP16 hybrid transcription factor. Circulation 2000; 102: 2255-61.
142. Milkiewicz M, Pugh CW, Egginton S. Inhibition of endogenous HIF inactivation induces angiogenesis in ischaemic skeletal muscles of mice. J Physiol 2004; 560: 21-6.
143. Willam C, Masson N, Tian YM, Mahmood SA, Wilson MI, Bicknell R, et al. Peptide blockade of HIFα degradation modulates cellular metabolism and angiogenesis. Proc Natl Acad Sci USA 2002; 99: 10423-8.
144. Li J, Post M, Volk R, Gao Y, Li M, Metais C, et al. PR39, a peptide regulator of angiogenesis. Nat Med 2000; 6: 49-55.
145. Elson DA, Thurston G, Huang LE, Ginzinger DG, McDonald DM, Johnson RS, et al. Induction of hypervascularity without leakage or inflammation in transgenic mice overexpressing hypoxia-inducible factor-1α. Genes Dev 2001; 15: 2520-32.
146. Heeschen C, Dimmeler S, Hamm CW, Boersma E, Zeiher AM, Simoons ML. Prognostic significance of angiogenic growth factor serum levels in patients with acute coronary syndromes. Circulation 2003; 107: 524-30.
147. Rivard A, Fabre JE, Silver M, Chen D, Murohara T, Kearney M, et al. Age-dependent impairment of angiogenesis. Circulation 1999; 99: 111-20.
148. Rivard A, Berthou-Soulie L, Principe N, Kearney M, Curry C, Branellec D, et al. Age-dependent defect in vascular endothelial growth factor expression is associated with reduced hypoxia-inducible factor 1 activity. J Biol Chem 2000; 275: 29643-7.
149. Frenkel-Denkberg G, Gershon D, Levy AP. The function of hypoxia-inducible factor 1 (HIF-1) is impaired in senescent mice. FEBS Lett 1999; 462: 341-4.
150. Cai Z, Manalo DJ, Wei G, Rodriguez ER, Fox-Talbot K, Lu H, et al. Hearts from rodents exposed to intermittent hypoxia or erythropoietin are protected against ischemia-reperfusion injury. Circulation 2003; 108: 79-85.
151. Date T, Mochizuki S, Belanger AJ, Yamakawa M, Luo Z, Vincent KA, et al. Expression of constitutively stable hybrid hypoxia-inducible factor-1α protects cultured rat cardiomyocytes against simulated ischemia-reperfusion injury. Am J Physiol Cell Physiol 2005; 288: C314-20.
152. Horwitz LD, Sherman NA, Kong Y, Pike AW, Gobin J, Fennessey PV, et al. Lipophilic siderophores of Mycobacterium tuberculosis prevent cardiac reperfusion injury. Proc Natl Acad Sci USA 1998; 95: 5263-8.
153. Pahl PM, Yan XD, Hodges YK, Rosenthal EA, Horwitz MA, Horwitz LD. An exochelin of Mycobacterium tuberculosis reversibly arrests growth of human vascular smooth muscle cells in vitro. J Biol Chem 2000; 275: 17821-6.
154. Rosenthal EA, Bohlmeyer TJ, Monnet E, MacPhail C, Robertson AD, Horwitz MA, et al. An iron-binding exochelin prevents restenosis due to coronary artery balloon injury in a porcine model. Circulation 2001; 104: 2222-7.
155. Mabjeesh NJ, Post DE, Willard MT, Kaur B, Van Meir EG, Simons JW, 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.
156. Hewitson KS, McNeill LA, Schofield CJ. Modulating the hypoxia-inducible factor signaling pathway: applications from cardiovascular disease to cancer. Curr Pharm Des 2004; 10(8): 821-33.
157. Redell MS, Tweardy DJ. Targeting transcription factors for cancer therapy. Curr Pharm Des 2005, 11(22): 2873-87.
158. Wilkinson-Berka JL. Vasoactive factors and diabetic retinopathy: vascular endothelial growth factor, cycoloxygenase-2 and nitric oxide. Curr Pharm Des 2004; 10(27): 3331-48.