Metal-free imidazolium salts inhibit the growth of hepatocellular carcinoma in a mouse model

Laboratory Investigation

Volumn 91, Issue 5, 2011, Pages 744-751

  Gopalan, Began ^a   Ke, Zhiyuan ^a   Zhang, Chunyan ^a   Kng, Yinling ^a   Suhaimi, Nur Afidah Mohamed ^a   Riduan, Siti Nurhanna ^a   Zhang, Yugen ^a   Zhuo, Lang ^a  

^a INSTITUTE OF BIOENGINEERING AND NANOTECHNOLOGY   (Singapore)

Author keywords

apoptosis; cell cycle; Cyclin dependent kinase; hepatocellular carcinoma; imidazolium salts; Survivin

Indexed keywords

1 MESITYL 3 (4 ACETATE BENZYL)IMIDAZOLIUM CHLORIDE; 1,3 BISBENZYLIMIDAZOLIUM BROMIDE; 1,3 DIISOPROPYLIMIDAZOLIUM TETRAFLUOROBORATE; ANTIFIBROTIC AGENT; ANTINEOPLASTIC AGENT; CARBENOID; DRINKING WATER; IMIDAZOLE DERIVATIVE; IMIDAZOLIUM SALT; N HETEROCYCLIC CARBENE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BODY WEIGHT; CARCINOGENESIS; CELL CYCLE ARREST; CELL PROLIFERATION; CONTROLLED STUDY; DRUG EFFECT; DRUG MECHANISM; HUMAN; HUMAN CELL; LIVER CELL CARCINOMA; LIVER FIBROSIS; MOUSE; NONHUMAN; PRIORITY JOURNAL; TUMOR VOLUME; XENOGRAFT;

ANIMALS; BLOTTING, WESTERN; CARCINOMA, HEPATOCELLULAR; CELL CYCLE; CELL DIVISION; CYCLIN-DEPENDENT KINASES; DISEASE MODELS, ANIMAL; IMIDAZOLES; IMMUNOHISTOCHEMISTRY; IN SITU NICK-END LABELING; INHIBITOR OF APOPTOSIS PROTEINS; LIVER NEOPLASMS, EXPERIMENTAL; MICE; MICE, INBRED BALB C; MICE, NUDE; REPRESSOR PROTEINS; SALTS;

EID: 79955547026     PISSN: 00236837     EISSN: 15300307     Source Type: Journal    
DOI: 10.1038/labinvest.2011.4     Document Type: Article

References (31)

1. Thomas MB, Zhu AX. Hepatocellular carcinoma: the need for progress. J Clin Oncol 2005;23:2892-2899. (Pubitemid 46224106)
2. Thorgeirsson SS, Grisham JW. Molecular pathogenesis of human hepatocellular carcinoma. Nat Genet 2002;31:339-346. (Pubitemid 35154440)
3. Llovet JM, Ricci S, Mazzaferro V, et al. Sorafenib in advanced hepatocellular carcinoma. N Engl J Med 2008;359:378-390.
4. Altieri DC. Survivin, cancer networks and pathway-directed drug discovery. Nat Rev Cancer 2008;8:61-70.
5. Nakahara T, Takeuchi M, Kinoyama I, et al. YM155, a novel smallmolecule survivin suppressant, induces regression of established human hormone-refractory prostate tumor xenografts. Cancer Res 2007;67:8014-8021. (Pubitemid 47395135)
6. Satoh T, Okamoto I, Miyazaki M, et al. Phase I study of YM155, a novel survivin suppressant, in patients with advanced solid tumors. Clin Cancer Res 2009;15:3872-3880.
7. Rodel F, Frey B, Leitmann W, et al. Survivin antisense oligonucleotides effectively radiosensitize colorectal cancer cells in both tissue culture and murine xenograft models. Int J Radiat Oncol Biol Phys 2008;71:247-255. (Pubitemid 351491424)
8. Tsuruma T, Iwayama Y, Ohmura T, et al. Clinical and immunological evaluation of anti-apoptosis protein, survivin-derived peptide vaccine in phase I clinical study for patients with advanced or recurrent breast cancer. J Transl Med 2008;6:24.
9. Ito T, Shiraki K, Sugimoto K, et al. Survivin promotes cell proliferation in human hepatocellular carcinoma. Hepatology 2000;31:1080-1085. (Pubitemid 30233232)
10. Moon WS, Tarnawski AS. Nuclear translocation of survivin in hepatocellular carcinoma: a key to cancer cell growth? Hum Pathol 2003;34:1119-1126. (Pubitemid 37466997)
11. Malumbres M, Barbacid M. Cell cycle, CDKs and cancer: a changing paradigm. Nat Rev Cancer 2009;9:153-166.
12. Ali S, Heathcote DA, Kroll SH, et al. The development of a selective cyclin-dependent kinase inhibitor that shows antitumor activity. Cancer Res 2009;69:6208-6215.
13. Zhao L, Zhang C, Zhuo L, et al. Imidazolium salts: a mild reducing and antioxidative reagent. J Am Chem Soc 2008;130:12586-12587.
14. Zhang CY, Zhang YG, Ying JY, et al. A class of synthetic imidazolium salts possesses anti-oxidative and anti-fibrotic properties in hepatic stellate cells. Free Radic Res 2009;9:1-14.
15. Friedman SL. Hepatic stellate cells: protean, multifunctional, and enigmatic cells of the liver. Physiol Rev 2008;88:125-172.
16. Bhowmick NA, Neilson EG, Moses HL. Stromal fibroblasts in cancer initiation and progression. Nature 2004;432:332-337. (Pubitemid 39551661)
17. Chakrabarti R, Subramaniam V, Abdalla S, et al. Tranilast inhibits the growth and metastasis of mammary carcinoma. Anticancer Drugs 2009;20:334-345.
18. Harlow KJ, Hill AF, Welton T. Convenient and general synthesis of symmetric N,N-disubstituted imidazolium halides. Synthesis 1996;6: 697-698. (Pubitemid 26295425)
19. Zhang C, Zhuo L. Epigallocatechin gallate and genistein attenuate glial fibrillary acidic protein elevation induced by fibrogenic cytokines in hepatic stellate cells. Int J Mol Med 2006;18:1141-1151.
20. Jiang X, Wilford C, Duensing S, et al. Participation of Survivin in mitotic and apoptotic activities of normal and tumor-derived cells. J Cell Biochem 2001;83:342-354. (Pubitemid 32896603)
21. Yang ZF, Ngai P, Ho DW, et al. Identification of local and circulating cancer stem cells in human liver cancer. Hepatology 2008;47:919-928. (Pubitemid 351449683)
22. Ma S, Lee TK, Zheng BJ, et al. CD133+ HCC cancer stem cells confer chemoresistance by preferential expression of the Akt/PKB survival pathway. Oncogene 2008;27:1749-1758. (Pubitemid 351380265)
23. Wang J, Hou T. Drug and drug candidate building block analysis. J Chem Inf Model 2010;50:55-67.
24. Hindi KM, Panzner MJ, Tessier CA, et al. The medicinal applications of imidazolium carbene-metal complexes. Chem Rev 2009;109: 3859-3884.
25. Teyssot ML, Jarrousse AS, Chevry A, et al. Toxicity of copper(I)-NHC complexes against human tumor cells: induction of cell cycle arrest, apoptosis, and DNA cleavage. Chemistry 2009;15:314-318.
26. Ray S, Mohan R, Singh JK, et al. Anticancer and antimicrobial metallopharmaceutical agents based on palladium, gold, and silver N-heterocyclic carbene complexes. J Am Chem Soc 2007;129: 15042-15053. (Pubitemid 350237567)
27. Malhotra SV, Kumar V. A profile of the in vitro anti-tumor activity of imidazolium-based ionic liquids. Bioorg Med Chem Lett 2010;20: 581-585.
28. Chang CC, Heller JD, Kuo J, et al. Tetra-O-methyl nordihydroguaiaretic acid induces growth arrest and cellular apoptosis by inhibiting Cdc2 and survivin expression. Proc Natl Acad Sci USA 2004;101:13239-13244. (Pubitemid 39209649)
29. Suzuki A, Hayashida M, Ito T, et al. Survivin initiates cell cycle entry by the competitive interaction with Cdk4/p16(INK4a) and Cdk2/cyclin E complex activation. Oncogene 2000;19:3225-3234. (Pubitemid 30487409)
30. Siddiquee K, Zhang S, Guida WC, et al. Selective chemical probe inhibitor of Stat3, identified through structure-based virtual screening, induces antitumor activity. Proc Natl Acad Sci USA 2007;104: 7391-7396. (Pubitemid 47185916)
31. Lin L, Amin R, Gallicano GI, et al. The STAT3 inhibitor NSC 74859 is effective in hepatocellular cancers with disrupted TGF-beta signaling. Oncogene 2009;28:961-972.