Hinokitiol activates the hypoxia-inducible factor (HIF) pathway through inhibition of HIF hydroxylases

Biochemical and Biophysical Research Communications

Volumn 396, Issue 2, 2010, Pages 370-375

  Lee, Myong Jin ^a   Kim, Jeong Won ^a   Yang, Eun Gyeong ^a  

^a Korea Institute of Science and Technology   (South Korea)

Author keywords

Factor inhibiting HIF 1 ; Hinokitiol; Hypoxia inducible factor; Prolyl 4 hydroxylase; Vascular endothelial growth factor

Indexed keywords

2 OXOGLUTARIC ACID; FACTOR INHIBITING HYPOXIA INDUCIBLE FACTOR ALPHA; HYPOXIA INDUCIBLE FACTOR 1ALPHA; IRON; OXYGENASE; PROCOLLAGEN PROLINE 2 OXOGLUTARATE 4 DIOXYGENASE; THUJAPLICIN; UNCLASSIFIED DRUG; VASCULOTROPIN;

ANGIOGENESIS; ARTICLE; CELL STRAIN HEPG2; CONCENTRATION RESPONSE; CONTROLLED STUDY; ENZYME INHIBITION; HELA CELL; HUMAN; HUMAN CELL; HYDROXYLATION; ISCHEMIA; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN STABILITY; TRANSCRIPTION INITIATION; UBIQUITINATION; UPREGULATION;

CELL LINE, TUMOR; HUMANS; HYDROXYLATION; HYPOXIA-INDUCIBLE FACTOR 1, ALPHA SUBUNIT; IRON CHELATING AGENTS; MONOTERPENES; PROCOLLAGEN-PROLINE DIOXYGENASE; REPRESSOR PROTEINS; TRANSCRIPTION, GENETIC; TROPOLONE; VASCULAR ENDOTHELIAL GROWTH FACTOR A;

EID: 77952745235     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2010.04.099     Document Type: Article

References (34)

1. Semenza G.L. HIF-1 and mechanisms of hypoxia sensing. Curr. Opin. Cell Biol. 13 (2001) 167-171
2. Brahimi-Horn M.C., and Pouysségur J. HIF at a glance. J. Cell Sci. 122 (2009) 1055-1057
3. Kenneth N.S., and Rocha S. Regulation of gene expression by hypoxia. Biochem. J. 414 (2008) 19-29
4. Kaelin W.G., and Ratcliffe P.J. Oxygen sensing by metazoans: the central role of the HIF hydroxylase pathway. Mol. Cell 30 (2008) 393-402
5. Carmeliet P. Angiogenesis in life, disease and medicine. Nature 438 (2005) 932-936
6. Ferrara N., and Kerbel R.S. Angiogenesis as a therapeutic target. Nature 438 (2005) 967-974
7. Rey S., and Semenza G.L. Hypoxia-inducible factor-1-dependent mechanisms of vascularization and vascular remodeling. Cardiovasc. Res. (2010) (Epub ahead of print)
8. Brahimi-Horn M.C., and Pouysségur J. Oxygen, a source of life and stress. FEBS Lett. 581 (2007) 3582-3591
9. Brahimi-Horn M.C., and Pouysségur J. Harnessing the hypoxia-inducible factor in cancer and ischemic disease. Biochem. Pharmacol. 73 (2007) 450-457
10. Ratan R.R., Siddiq A., Smirnova N., Karpisheva K., Haskew-Layton R., McConoughey S., Langley B., Estevez A., Huerta P.T., Volpe B., Roy S., Sen C.K., Gazaryan I., Cho S., Fink M., and LaManna J. Harnessing hypoxic adaptation to prevent, treat, and repair stroke. J. Mol. Med. 85 (2007) 1331-1338
11. Botusan I.R., Sunkari V.G., Savu O., Catrina A.I., Grünler J., Lindberg S., Pereira T., Ylä-Herttuala S., Poellinger L., Brismar K., and Catrina S.B. Stabilization of HIF-1α is critical to improve wound healing in diabetic mice. Proc. Natl. Acad. Sci. USA 105 (2008) 19426-19431
12. Botusan I.R. Sustained expression of HIF-1α in the diabetic environment promotes angiogenesis and cutaneous would repair. Wound Repair Regen. 15 (2007) 636-645
13. Hsieh M.M., Linde N.S., Wynter A., Metzger M., Wong C., Langsetmo I., Lin A., Smith R., Rodgers G.P., Donahue R.E., Klaus S.J., and Tisdale J.F. HIF prolyl hydroxylase inhibition results in endogenous erythropoietin induction, erythrocytosis, and fetal hemoglobin expression in rhesus macaques. Blood 110 (2007) 2140-2147
14. Chang E.I., Loh S.A., Ceradini D.J., Chang E.I., Lin S.E., Bastidas N., Aarabi S., Chan D.A., Freedman M.L., Giaccia A.J., and Gurtner G.C. Age decreases endothelial progenitor cell recruitment through decreases in hypoxia-inducible factor 1α stabilization during ischemia. Circulation 116 (2007) 2818-2829
15. Nakano H., Ikenaga S., Aizu T., Kaneko T., Matsuzaki Y., Tsuchida S., Hanada K., and Arima Y. Human metallothionein gene expression is upregulated by β-thujaplicin: possible involvement of protein kinase C and reactive oxygen species. Biol. Pharm. Bull. 29 (2006) 55-59
16. Ido Y., Muto N., Inada A., Kohroki J., Mano M., Odani T., Itoh N., Yamamoto K., and Tanaka K. Induction of apoptosis by hinokitiol, a potent iron chelator, in teratocarcinoma F9 cells is mediated through the activation of caspase-3. Cell Prolif. 32 (1999) 63-73
17. Tanaka T., Satoh T., Onozawa Y., Kohroki J., Itoh N., Ishidate M., Muto N., and Tanaka K. Apoptosis during iron chelator-induced differentiation in F9 embryonal carcinoma cells. Cell Biol. Int. 23 (1999) 541-550
18. Byeon S.E., Lee Y.G., Kim J.C., Han J.G., Lee H.Y., and Cho J.Y. Hinokitiol, a natural tropolone derivative, inhibits TNF-α production in LPS-activated macrophages via suppression of NF-κB. Planta Med. 74 (2008) 828-833
19. Manter K.D., Kelsey R.G., and Karchesy J.J. Antimicrobial activity of extractable conifer heartwood compounds toward Phytophthora ramorum. J. Chem. Ecol. 33 (2007) 2133-2147
20. Komaki N., Watanabe T., Ogasawara A., Sato N., Mikami T., and Matsumoto T. Antifungal mechanism of hinokitiol against Candida albicans. Biol. Pharm. Bull. 31 (2008) 735-737
21. Liu S., and Yamauchi H. p27-Associated G1 arrest induced by hinokitiol in human malignant melanoma cells is mediated via down-regulation of pRb, Skp2 ubiquitin ligase, and impairment of Cdk2 function. Cancer Lett. 286 (2009) 240-249
22. Murakami K., Ohara Y., Haneda M., Tsubouchi R., and Yoshino M. Prooxidant action of hinokitiol: hinokitiol-iron dependent generation of reactive oxygen species. Basic Clin. Pharmacol. Toxicol. 97 (2005) 392-394
23. Liu S., and Yanauchi H. Hinokitiol, a metal chelator derived from natural plants, suppresses cell growth and disrupts AR signaling in prostate carcinoma cell lines. Biochem. Biophys. Res. Commun. 351 (2006) 26-32
24. Cho H., Park H., and Yang E.G. A fluorescence polarization-based interaction assay for hypoxia-inducible factor prolyl hydroxylases. Biochem. Biophys. Res. Commun. 337 (2005) 275-280
25. Cho H., Ahn D.R., Park H., and Yang E.G. Modulation of p300 binding by posttranslational modifications of the C-terminal activation domain of hypoxia-inducible factor-1α. FEBS Lett. 581 (2007) 1542-1548
26. 2 sensing. Science 292 (2001) 464-468
27. 2-regulated prolyl hydroxylation. Science 292 (2001) 468-472
28. Linden T., Katschinski D.M., Eckhardt K., Scheid A., Pagel H., and Wenger R.H. The antimycotic ciclopirox olamine induces HIF-1α stability, VEGF expression, and angiogenesis. FASEB J. 17 (2003) 761-763
29. Mabjeesh N.J., Willard M.T., Harris W.B., Sun H.Y., Wang R., Zhong H., Umbreit J.N., and Simons J.W. Dibenzoylmethane, a natural dietary compound, induces HIF-1α and increases expression of VEGF. Biochem. Biophys. Res. Commun. 303 (2003) 279-286
30. Yamato M., Hashigaki K., Kokubu N., Tashiro T., and Tsuruo T. Synthesis and antitumor activity of troplone derivatives. 7. Bistropolones containing connecting methylene chains. J. Med. Chem. 35 (1992) 267-273
31. Choi S.M., Choi K.O., Park Y.K., Cho H., Yang E.G., and Park H. Clioquinol, a Cu(II)/Zn(II) chelator, inhibits both ubiquitination and asparagine hydroxylation of hypoxia-inducible factor-1alpha, leading to expression of vascular endothelial growth factor and erythropoietin in normoxic cells. J. Biol. Chem. 281 (2006) 34056-34063
32. Elkins J.M., Hewitson K.S., McNeill L.A., Seibel J.F., Schlemminger I., Pugh C.W., Ratcliffe P.J., and Schofield C.J. Structure of factor-inhibiting hypoxia-inducible factor (HIF) reveals mechanism of oxidative modification of HIF-1α. J. Biol. Chem. 278 (2006) 1802-1806
33. McDonough M.A., Li V., Flashman E., Chowdhury R., Mohr C., Liénard B.M., Zondlo J., Oldham N.J., Clifton I.J., Lewis J., McNeill L.A., Kurzeja R.J., Hewitson K.S., Yang E., Jordan S., Syed R.S., and Schofield C.J. Cellular oxygen sensing: crystal structure of hypoxia-inducible factor prolyl hydroxylase (PHD2). Proc. Natl. Acad. Sci. USA 103 (2006) 9814-9819
34. Cho H., Lee H.Y., Ahn D.R., Kim S.Y., Kim S., Lee K.B., Lee Y.M., Park H., and Yang E.G. Baicalein induces functional hypoxia-inducible factor-1α and angiogenesis. Mol. Pharmacol. 74 (2008) 70-81