2-Methoxyestradiol inhibits hepatocellular carcinoma cell growth by inhibiting Cdc25 and inducing cell cycle arrest and apoptosis

Cancer Chemotherapy and Pharmacology

Volumn 62, Issue 5, 2008, Pages 831-840

  Kar, Siddhartha ^a   Wang, Meifang ^b   Carr, Brian I ^b  

^a UNIVERSITY OF PITTSBURGH CANCER INSTITUTE   (United States)

^b THOMAS JEFFERSON UNIVERSITY   (United States)

Author keywords

2 Methoxyestradiol; Apoptosis; Cdc25 inhibition; Cell cycle arrest; HCC cells

Indexed keywords

2 METHOXYESTRADIOL; CYSTEINE; ESTROGEN; PROTEIN TYROSINE PHOSPHATASE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; APOPTOSIS; ARTICLE; CANCER GROWTH; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; DRUG MECHANISM; ENZYME ACTIVE SITE; ENZYME BINDING; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; LIVER CELL CARCINOMA; MALE; NONHUMAN; PRIORITY JOURNAL; RAT;

ANIMALS; APOPTOSIS; BLOTTING, WESTERN; CARCINOMA, HEPATOCELLULAR; CDC25 PHOSPHATASES; CELL CYCLE; CELL DIVISION; CELL PROLIFERATION; CELLS, CULTURED; DNA; ESTRADIOL; G2 PHASE; HEPATOCYTES; IMMUNOPRECIPITATION; LIVER NEOPLASMS, EXPERIMENTAL; MALE; NEOPLASM TRANSPLANTATION; RATS; RATS, INBRED F344; TUBULIN MODULATORS;

EID: 49749142056     PISSN: 03445704     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00280-007-0670-x     Document Type: Article

References (47)

1. HS Fiegelson BE Henderson 1996 Estrogens and breast cancer (review) Carcinogenesis 17 2279 2284
2. TW McDonald JF Annegers WM O'Fallon MB Dockerty GD Malkasian Jr LT Kurland 1977 Exogenous estrogen and endometrial carcinoma: case-control and incidence study Am J Obstet Gynecol 127 572 580
3. KI Pritchard 2000 Current and future directions in medical therapy for breast carcinoma: endocrine treatment Cancer 88 Suppl 12 3065 3072
4. JC Seegers ML Aveling CH Van Aswegen M Cross F Koch WS Joubert 1989 The cytotoxic effects of estradiol-17-beta, catecholestradiol and methoxyestradiol on dividing MCF-7 and HeLa cells J Steroid Biochem 32 797 809
5. D Berg R Sonsalla E Kuss 1983 Concentrations of 2-methoxyestrogens in human serum measured by a heterogenous immunoassay with an 125I-labelled ligand Acta Endrocinol (Copenh) 103 1375 1378
6. N Klauber S Parangi E Flynn E Hammel RJ D'Amato 1997 Inhibition of angiogenesis and breast cancer in mice by the microtubule inhibitors 2-methoxyestradiol and taxol Cancer Res 57 81 86
7. M Kataoka G Schumacher RJ Cristiano EN Atkinson JA Roth T Mukhopadhyay 1998 An agent that increases tumor suppressor transgene product coupled with systemic transgene delivery inhibits growth of metastatic lung cancer in vivo Cancer Res 58 4761 4765
8. G Schumacher M Kataoka JA Roth T Mukhopadhyay 1999 Potent antitumor activity of 2-methoxyestradiol in human pancreatic cancer cell lines Clin Cancer Res 5 493 499
9. E Wassberg 1999 Angiostatic treatment of neuroblastoma Ups J Med Sci 104 1 24
10. HL Lin TY Liu GY Chau WY Lui CW Chi 2000 Comparison of 2-methoxyestradiol-induced, docetaxel-induced, and paclitaxel-induced apoptosis in hepatoma cells and its correlation with reactive oxygen species Cancer 89 983 994
11. S Bu A Blaukat X Fu NE Heldin M Landstrom 2002 Mechanisms for 2-methoxyestradiol-induced apoptosis of prostate cancer cells FEBS Lett 531 141 151
12. TM LaValle XH Zhan CJ Herbstritt KC Kough SJ Green VS Pribluda 2002 2-Methoxyestradiol inhibits proliferation and induces apoptosis independently of estrogen receptors a and b Cancer Res 62 3691 3697
13. T Fostis Y Zhang MS Pepper H Alder cruetz R Montesano PP Nawroth L Schweigerer 1994 The endogenous estrogen metabolite 2-methoxyestradiol inhibits angiogenesis and suppress tumor growth Nature 368 237 239
14. M Cushman HM He JA Katzenellenbogen CM Lin E Hamel 1995 Synthesis, antitubulin and antimitotic activity, and cytotoxicity of analogs of 2-methoxyestradiol, an endogenous mammalian metabolite of estradiol that inhibits tubulin polymerization by binding to the colchicines binding site J Med Chem 38 2041 2049
15. H Attalla TP Makels H Adelkreutz LC Anderson 1996 2-Methoxyestradiol arrests cells in mitosis without depolymerizing tubulin Biochem Biophys Res Comm 228 467 473
16. N Gao M Rahmani P Dent S Grant 2005 2-Methoxyestradiol-induced apoptosis in human leukemia cells proceeds through a reactive oxygen apecies and Akt-dependent process Oncogene 14 3797 3809
17. DL McCormick WD Johmson VS Peibluda SJ Green JE Tomaszewski AC Smith 2000 Preclinical development of 2-methoxyestradiol (2ME2, NSC-659853) (abstract) Proc Am Assoc Cancer Res 41 2080 328
18. G Schumacher S Scheunert A Rueggeberg MG Bachem AK Nussler A Spinelli T Mukhopadhyay J Pratchke P Neuhaus 2006 A very low toxic agent induces apoptosis and reduces growth of human hepatocellular carcinoma cells Hepatology 21 1207 1212
19. I Nilsson I Hoffman 2000 Cell cycle regulation by the Cdc25 phosphatase family Prog Cell Cycle Res 4 107 144
20. S Jinno J Suto A Nagata M Igarashi Y Kanaoka H Nojima H Okayama 1994 Cdc25A is a novel phosphatase functioning early in the cell cycle EMBO J 13 1549 1556
21. AR Forrest AK McCormack CP DeSouza JM Sinnamon ID Tonks NK Haywrd K Ellem BG Gabrielli 1999 Multiple splicing variants of cdc25B regulate G2/M progression Biochem Biophys Res Commun 260 510 515
22. M Donazelli GF Draetta 2003 Regulating mammalian checkpoints through Cdc25 inactivation EMBO J 4 671 677
23. M Molinari C Mercurilo J Dominguez F Goubin GF Draetta 2000 Human Cdca5A inactivation in response to S phase inhibition and its role in preventing premature mitosis EMBO J 1 71 79
24. N Mailand J Falck C Lukas RG Syljuasen M Welcker J Lukas 2000 Rapid destruction of human Cdc25A in response to DNA damage Science 288 1425 1429
25. D Santamaria C Barriere A Cerqueira S Hunt Tardy c K Newton JF Caceres P Dubus M Malumbres M Barbacid 2007 Cdk1 is sufficient to drive the mammalian cell cycle Nature 448 811 816
26. AR Parsons 1998 Phosphatases and tumorigenesis Curr Opin Oncol 10 88 91
27. K Kristjansdottir J Rudolph 2004 Cdc25 phosphatases and cancer Chem Biol 11 1043 1051
28. D Gasparotto R Maestro S Piccinin T Vukosavljevic L Barzan S Sulfaro M Boiocchi 1997 Overexpression of Cdc25A and Cdc25B in head and neck cancers Cancer Res 57 2366 236
29. S Hernandez X Besser S Bea 2001 Differential expression of Cdc25 cell-cycle activating phosphatases in human colorectal carcinoma Lab Invest 81 465 470
30. BI Carr Z Wang M Wang S Kar CS Wilcox K Rosi E Southwick JS Lazo 2003 A Cdc25A antagonizing K vitamin inhibits hepatocyte DNA synthesis in vitro and in vivo J Mol Biol 326 721 735
31. S Kar M Wang SW Ham BI Carr 2006 H32, a non-quinone sulfone analog of vitamin K3, inhibits human hepatoma cell growth by inhibiting Cdc25 and activating ERK Cancer Biol Ther 5 1340 1347
32. Y Nishikawa BI Carr Z Wang S Kar F Finn P Dowd ZB Zheng J Kerns SJ Naganathan 1995 Growth inhibition of hepatoma cells induced by vitamin K and its analogs J Biol Chem 270 28304 28310
33. S Kar BI Carr 2000 Growth inhibition and protein tyrosine phosphorylation in MCF7 breast cancer cells by a novel K-vitamin J Cell Physiol 185 386 393
34. K Tamura EC Southwick J Kerns K Rosi BI Carr C Wilcox J Lazo 2000 Cdc25 inhibition and cell cycle arrest by a synthetic thioalkyl vitamin K analogue Cancer Res 60 1317 1325
35. DL Novicki RL Jirtle G Michalopoulos 1983 Establishment of two rat hepatoma cell strains produced by a carcinogen initiation, phenobarbital promotion protocol In Vitro 19 191 202
36. RJ D'Amato CM Lin E Flynn J Folkman E Hamel 1994 2-Methoxyestradiol, an endogenous mammalian metabolite, inhibits tubulin polymerization by interacting at the colchicine site Proc Natl Acad Sci USA 91 3964 3968
37. S Kar IM Lefterov M Wang JS Lazo CN Scott CS Wilcox BI Carr 2003 Binding and Inhibition of Cdc25 phosphatases by vitamin K analogues Biochemistry 42 10490 10497
38. S Kar M Wang SW Ham BI Carr 2006 Fluorinated Cpd 5, a pure arylating K-vitamin derivative, inhibits human hepatoma cell growth by inhibiting Cdc25 and activating MAPK Biochem Pharmacol 72 1217 1227
39. JB Huber 2000 Oral administration of an estrogen metabolite-induced potentiation of radiation anti-tumor effects in presence of wild type p53 in non small cell lung cancer Int J Radiat Oncol Biol Phys 48 1127 1137
40. C Sweeney 2005 A phase II multicenter, randomised, double-blind, safety trial assessing the pharmacokinetics, pharmacodynamics, and efficacy of oral 2-methoxyestradiol capsules in hormone-refractory prostate cancer Clin Cancer Res 11 6625 6633
41. WL Dahut 2006 Phase I clinical trial of oral 2-methoxyestradiol, an antiangiogenic and apoptotic agent, in patients with solid tumors Cancer Biol Ther 5 22 27
42. NJ Lakhani 2005 Determination of 2-methoxyestradiol in human plasma, using liquid chromatography/tandem mass spectrometry Rapid Commun Mass Spectrom 19 1176 1182
43. CR Ireson 2004 Pharmacokinetics and efficacy of 2-methoxyoestradiol and 2-methoxyoestradiol-bis-sulphamate in vivo in rodents Br J Cancer 90 932 937
44. RA Chen T Michaeli L Van Aelst R Ballester 2000 A role of the noncatalytic N terminus in the function of Cdc25, a Saccharomyces cerevisiae Ras-Guanine nucleotide exchange factor Genetics 154 1473 1484
45. T Fernandes-Alnemri 1994 CPP32, a novel human apoptotic protein with homology to Caenorhabditis elegans cell death protein Ced-3 and mammalian interleukin-1 beta-converting enzyme. J Biol Chem 269 30761 30764
46. DW Nicholson NA Thornberry JP Vaillancourt CK Ding 1995 Identification and inhibition of the ICE/CED-3 protease necessary for mammalian apoptosis Nature 376 37 43
47. S Kar M Wang CS Wilcox BI Carr 2003 Antitumor and anticarcinogenic action of Cpd 5: a new class of protein phosphatase inhibitor Carcinogenesis 24 411 416