A new 2-pyrone derivative, 5-bromo-3-(3-hydroxyprop-1-ynyl)-2H-pyran-2-one, suppresses stemness in glioma stem-like cells

Molecular Pharmacology

Volumn 82, Issue 3, 2012, Pages 400-407

  Kim, Rae Kwon ^a   Kim, Min Jung ^a   Yoon, Chang Hwan ^a   Lim, Eun Jung ^a   Yoo, Ki Chun ^a   Lee, Ga Haeng ^a   Kim, Young Heon ^a   Kim, Hyeonmi ^a   Jin, Yeung Bae ^b   Lee, Yoon Jin ^b   Cho, Cheon Gyu ^a   Oh, Yeong Seok ^a   Gye, Myung Chan ^a   Suh, Yongjoon ^a   Lee, Su Jae ^a  

^a Hanyang University   (South Korea)

^b Korea Institute of Radiation and Medical Science   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRONE DERIVATIVE; 5 BROMO 3 (3 HYDROXYPROP 1 YNYL) 2H PYRAN 2 ONE; BETA CATENIN; CD133 ANTIGEN; MITOGEN ACTIVATED PROTEIN KINASE; NOTCH2 RECEPTOR; PHOSPHATIDYLINOSITOL 3 KINASE; PROTEIN KINASE B; RAF PROTEIN; RAS PROTEIN; TRANSCRIPTION FACTOR SOX2; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; CANCER STEM CELL; CARCINOGENESIS; CARCINOGENICITY; CELL POPULATION; CELL RENEWAL; GLIOMA; GLIOMA STEM LIKE CELL; HUMAN; HUMAN CELL; HUMAN TISSUE; PRIORITY JOURNAL; PROTEIN EXPRESSION; SENSITIVITY ANALYSIS; SIGNAL TRANSDUCTION; STEM CELL;

ANIMALS; ANTIGENS, CD; ANTINEOPLASTIC AGENTS; BETA CATENIN; BRAIN NEOPLASMS; CELL LINE, TUMOR; CELL TRANSFORMATION, NEOPLASTIC; EXTRACELLULAR SIGNAL-REGULATED MAP KINASES; FEMALE; GLIOMA; GLYCOPROTEINS; HUMANS; MICE; MICE, INBRED BALB C; MICE, NUDE; NEOPLASTIC STEM CELLS; PEPTIDES; PHOSPHATIDYLINOSITOL 3-KINASES; PROTO-ONCOGENE PROTEINS C-AKT; PROTO-ONCOGENE PROTEINS C-RAF; PYRONES; RAS PROTEINS; RECEPTOR, NOTCH2; SIGNAL TRANSDUCTION; SOXB1 TRANSCRIPTION FACTORS; TRANSCRIPTION FACTORS;

EID: 84865236519     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.112.078402     Document Type: Article

References (40)

1. Bao S, Wu Q, McLendon RE, Hao Y, Shi Q, Hjelmeland AB, Dewhirst MW, Bigner DD, and Rich JN (2006) Glioma stem cells promote radioresistance by preferential activation of the DNA damage response. Nature 444:756-760.
2. Bleau AM, Hambardzumyan D, Ozawa T, Fomchenko EI, Huse JT, Brennan CW, and Holland EC (2009) PTEN/PI3K/Akt pathway regulates the side population phenotype and ABCG2 activity in glioma tumor stem-like cells. Cell Stem Cell 4:226-235.
3. Dickinson JM (1993) Microbial pyran-2-ones and dihydropyran-2-ones. Nat Prod Rep 10:71-98.
4. Eramo A, Ricci-Vitiani L, Zeuner A, Pallini R, Lotti F, Sette G, Pilozzi E, Larocca LM, Peschle C, and De Maria R (2006) Chemotherapy resistance of glioblastoma stem cells. Cell Death Differ 13:1238-1241.
5. Farnie G and Clarke RB (2007) Mammary stem cells and breast cancer-role of Notch signalling. Stem Cell Rev 3:169-175.
6. Faulkner DJ (2001) Marine natural products. Nat Prod Rep 18:1-49.
7. Frosina G (2009) DNA repair and resistance of gliomas to chemotherapy and radiotherapy. Mol Cancer Res 7:989-999.
8. Gangemi RM, Griffero F, Marubbi D, Perera M, Capra MC, Malatesta P, Ravetti GL, Zona GL, Daga A, and Corte G (2009) SOX2 silencing in glioblastoma tumor-initiating cells causes stop of proliferation and loss of tumorigenicity. Stem Cells 27:40-48.
9. Hambardzumyan D, Becher OJ, Rosenblum MK, Pandolfi PP, Manova-Todorova K, and Holland EC (2008) PI3K pathway regulates survival of cancer stem cells residing in the perivascular niche following radiation in medulloblastoma in vivo. Genes Dev 22:436-448.
10. He S, Nakada D, and Morrison SJ (2009) Mechanisms of stem cell self-renewal. Annu Rev Cell Dev Biol 25:377-406.
11. Hjelmeland AB, Wu Q, Wickman S, Eyler C, Heddleston J, Shi Q, Lathia JD, Macswords J, Lee J, McLendon RE, et al. (2010) Targeting A20 decreases glioma stem cell survival and tumor growth. PLoS Biol 8:e1000319.
12. Hudson DL (2004) Epithelial stem cells in human prostate growth and disease. Prostate Cancer Prostatic Dis 7:188-194.
13. Hyun KH, Yoon CH, Kim RK, Lim EJ, An S, Park MJ, Hyun JW, Suh Y, Kim MJ, and Lee SJ (2011) Eckol suppresses maintenance of stemness and malignancies in glioma stem-like cells. Toxicol Appl Pharmacol 254:32-40.
14. Jensen PR and Fenical W (1994) Strategies for the discovery of secondary metabolites from marine bacteria: ecological perspectives. Annu Rev Microbiol 48:559-584.
15. Kanwar SS, Yu Y, Nautiyal J, Patel BB, and Majumdar AP (2010) The Wnt/beta-catenin pathway regulates growth and maintenance of colonospheres. Mol Cancer 9:212.
16. Lin A, Lu X, Fang Y, Zhu T, Gu Q, and Zhu W (2008) Two new 5-hydroxy-2-pyrone derivatives isolated from a marine-derived fungus Aspergillus flavus. J Antibiot (Tokyo) 61:245-249.
17. Liu G, Yuan X, Zeng Z, Tunici P, Ng H, Abdulkadir IR, Lu L, Irvin D, Black KL, and Yu JS (2006) Analysis of gene expression and chemoresistance of CD133+ cancer stem cells in glioblastoma. Mol Cancer 5:67.
18. McGlacken GP and Fairlamb IJ (2005) 2-Pyrone natural products and mimetics: isolation, characterisation and biological activity. Nat Prod Rep 22:369-385.
19. Ohgaki H and Kleihues P (2005) Population-based studies on incidence, survival rates, and genetic alterations in astrocytic and oligodendroglial gliomas. J Neuropathol Exp Neurol 64:479-489.
20. Park DM and Rich JN (2009) Biology of glioma cancer stem cells. Mol Cells 28:7-12.
21. Pevny LH and Nicolis SK (2010) Sox2 roles in neural stem cells. Int J Biochem Cell Biol 42:421-424.
22. Poppe SM, Slade DE, Chong KT, Hinshaw RR, Pagano PJ, Markowitz M, Ho DD, Mo H, Gorman RR 3rd, Dueweke TJ, et al. (1997) Antiviral activity of the dihydropyrone PNU-140690, a new nonpeptidic human immunodeficiency virus protease inhibitor. Antimicrob Agents Chemother 41:1058-1063.
23. Rich JN (2007) Cancer stem cells in radiation resistance. Cancer Res 67:8980-8984.
24. Schatton T and Frank MH (2008) Cancer stem cells and human malignant melanoma. Pigment Cell Melanoma Res 21:39-55.
25. Singh SK, Clarke ID, Hide T, and Dirks PB (2004a) Cancer stem cells in nervous system tumors. Oncogene 23:7267-7273.
26. Singh SK, Clarke ID, Terasaki M, Bonn VE, Hawkins C, Squire J, and Dirks PB (2003) Identification of a cancer stem cell in human brain tumors. Cancer Res 63:5821-5828.
27. Singh SK, Hawkins C, Clarke ID, Squire JA, Bayani J, Hide T, Henkelman RM, Cusimano MD, and Dirks PB (2004b) Identification of human brain tumour initiating cells. Nature 432:396-401.
28. Soeda A, Inagaki A, Oka N, Ikegame Y, Aoki H, Yoshimura S, Nakashima S, Kunisada T, and Iwama T (2008) Epidermal growth factor plays a crucial role in mitogenic regulation of human brain tumor stem cells. J Biol Chem 283: 10958-10966.
29. Soeda A, Park M, Lee D, Mintz A, Androutsellis-Theotokis A, McKay RD, Engh J, Iwama T, Kunisada T, Kassam AB, et al. (2009) Hypoxia promotes expansion of the CD133-positive glioma stem cells through activation of HIF-1α. Oncogene 28:3949-3959.
30. Sunayama J, Matsuda K, Sato A, Tachibana K, Suzuki K, Narita Y, Shibui S, Sakurada K, Kayama T, Tomiyama A, et al. (2010) Crosstalk between the PI3K/mTOR and MEK/ERK pathways involved in the maintenance of self-renewal and tumorigenicity of glioblastoma stem-like cells. Stem Cells 28:1930-1939.
31. Suslov ON, Kukekov VG, Ignatova TN, and Steindler DA (2002) Neural stem cell heterogeneity demonstrated by molecular phenotyping of clonal neurospheres. Proc Natl Acad Sci USA 99:14506-14511.
32. Tang C, Ang BT, and Pervaiz S (2007) Cancer stem cell: target for anti-cancer therapy. FASEB J 21:3777-3785.
33. Thaisrivongs S, Romero DL, Tommasi RA, Janakiraman MN, Strohbach JW, Turner SR, Biles C, Morge RR, Johnson PD, Aristoff PA, et al. (1996) Structure-based design of HIV protease inhibitors: 5,6-dihydro-4-hydroxy-2- pyrones as effective, nonpeptidic inhibitors. J Med Chem 39:4630-4642.
34. Trachootham D, Lu W, Ogasawara MA, Nilsa RD, and Huang P (2008) Redox regulation of cell survival. Antioxid Redox Signal 10:1343-1374.
35. Turner SR, Strohbach JW, Tommasi RA, Aristoff PA, Johnson PD, Skulnick HI, Dolak LA, Seest EP, Tomich PK, Bohanon MJ, et al. (1998) Tipranavir (PNU-140690): a potent, orally bioavailable nonpeptidic HIV protease inhibitor of the 5,6-dihydro-4-hydroxy-2-pyrone sulfonamide class. J Med Chem 41:3467-3476.
36. Wang J, Wakeman TP, Lathia JD, Hjelmeland AB, Wang XF, White RR, Rich JN, and Sullenger BA (2010) Notch promotes radioresistance of glioma stem cells. Stem Cells 28:17-28.
37. Wen PY and Kesari S (2008) Malignant gliomas in adults. N Engl J Med 359:492-507.
38. Yoon CH, Kim MJ, Kim RK, Lim EJ, Choi KS, An S, Hwang SG, Kang SG, Suh Y, Park MJ, et al. (2012) c-Jun N-terminal kinase has a pivotal role in the maintenance of self-renewal and tumorigenicity in glioma stem-like cells. Oncogene http://dx.doi.org/10.1038/onc.2011.634.
39. Zhang M, Atkinson RL, and Rosen JM (2010) Selective targeting of radiationresistant tumor-initiating cells. Proc Natl Acad Sci USA 107:3522-3527.
40. Zhou BB, Zhang H, Damelin M, Geles KG, Grindley JC, and Dirks PB (2009) Tumour-initiating cells: challenges and opportunities for anticancer drug discovery. Nat Rev Drug Discov 8:806-823.