UP12, a novel ursolic acid derivative with potential for targeting multiple signaling pathways in hepatocellular carcinoma

Biochemical Pharmacology

Volumn 93, Issue 2, 2015, Pages 151-162

  Dong, Haiyan ^a   Yang, Xiang ^a   Xie, Jingjing ^a   Xiang, Liping ^a   Li, Yuanfang ^a   Ou, Minrui ^a   Chi, Ting ^a   Liu, Zhenhua ^b   Yu, Suhong ^a   Gao, Yu ^a   Chen, Jianzhong ^c   Shao, Jingwei ^a   Jia, Lee ^a  

^a FUZHOU UNIVERSITY   (China)

^b FUJIAN PROVINCIAL HOSPITAL   (China)

^c FUJIAN UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

Author keywords

2 Deoxy D glucose (2 DG); Anti cancer drug; Glucose metabolism; Synergistic effect; Ursolic acid derivative

Indexed keywords

ADENOSINE TRIPHOSPHATASE; ANTINEOPLASTIC AGENT; CASPASE 3; CASPASE 8; CASPASE 9; DEOXYGLUCOSE; GLUCOSE TRANSPORTER 1; LACTIC ACID; N [ 3B ACETOXY URS 12 EN 28 OYL]AMINO 2 METHYLPIPERAZINE; PROTEIN BAX; PROTEIN BCL 2; PROTEIN P53; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG; URSOLIC ACID; URSOLIC ACID DERIVATIVE; TRITERPENE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BIOAVAILABILITY; CANCER COMBINATION CHEMOTHERAPY; CANCER INHIBITION; CARBON NUCLEAR MAGNETIC RESONANCE; CELL METABOLISM; CELL PROLIFERATION; CELL VIABILITY; CELLULAR DISTRIBUTION; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYTOTOXICITY; DOWN REGULATION; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG MECHANISM; DRUG POTENTIATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME BINDING; FEMALE; FLOW CYTOMETRY; G2 PHASE CELL CYCLE CHECKPOINT; GLUCOSE METABOLISM; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; LIVER CELL CARCINOMA; MITOCHONDRIAL MEMBRANE; MITOCHONDRIAL MEMBRANE POTENTIAL; MOLECULAR DOCKING; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN DEPLETION; PROTEIN INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; RANDOMIZED CONTROLLED TRIAL; SIGNAL TRANSDUCTION; TANDEM MASS SPECTROMETRY; TUMOR GROWTH; TUMOR VOLUME; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; UPREGULATION; WESTERN BLOTTING; ANIMAL; CARCINOMA, HEPATOCELLULAR; CHEMISTRY; DOSE RESPONSE; DRUG DELIVERY SYSTEM; DRUG EFFECTS; DRUG SCREENING; HEPG2 CELL LINE; LIVER NEOPLASMS; PATHOLOGY; PHYSIOLOGY; PROCEDURES; PROTEIN SECONDARY STRUCTURE; RANDOMIZATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CARCINOMA, HEPATOCELLULAR; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DELIVERY SYSTEMS; HEP G2 CELLS; HUMANS; LIVER NEOPLASMS; MICE; PROTEIN STRUCTURE, SECONDARY; RANDOM ALLOCATION; SIGNAL TRANSDUCTION; TRITERPENES; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84920715799     PISSN: 00062952     EISSN: 18732968     Source Type: Journal    
DOI: 10.1016/j.bcp.2014.11.014     Document Type: Article

References (43)

1. D. Andersson, J.J. Liu, A. Nilsson, and R.D. Duan Ursolic acid inhibits proliferation and stimulates apoptosis in HT29 cells following activation of alkaline sphingomyelinase Anticancer Res 23 2003 3317 3322
2. C. Tang, Y.H. Lu, J.H. Xie, F. Wang, J.N. Zou, and J.S. Yang Downregulation of survivin and activation of caspase-3 through the PI3K/Akt pathway in ursolic acid-induced HepG2 cell apoptosis Anticancer Drugs 20 2009 249 258
3. C.Y. Huang, C.Y. Lin, C.W. Tsai, and M.C. Yin Inhibition of cell proliferation, invasion and migration by ursolic acid in human lung cancer cell lines Toxicol In Vitro 25 2011 1274 1280
4. S.L. Yan, C.Y. Huang, S.T. Wu, and M.C. Yin Oleanolic acid and ursolic acid induce apoptosis in four human liver cancer cell lines Toxicol In Vitro 24 2010 842 848
5. Y.L. Hsu, P.L. Kuo, and C.C. Lin Proliferative inhibition, cell-cycle dysregulation, and induction of apoptosis by ursolic acid in human non-small cell lung cancer A549 cells Life Sci 75 2004 2303 2316
6. Y.Q. Meng, D. Liu, L.L. Cai, H. Chen, B. Cao, and Y.Z. Wang The synthesis of ursolic acid derivatives with cytotoxic activity and the investigation of their preliminary mechanism of action Bioorg Med Chem 17 2009 848 854
7. L. Chen, W. Qiu, J. Tang, Z.F. Wang, and S.Y. He Synthesis and bioactivity of novel nitric oxide-releasing ursolic acid derivatives Chin Chem Lett 22 2011 413 416
8. C.M. Ma, S.Q. Cai, J.R. Cui, R.Q. Wang, P.F. Tu, and M. Hattori The cytotoxic activity of ursolic acid derivatives Eur J Med Chem 40 2005 582 589
9. K.K. Bai, F.L. Chen, Z. Yu, Y.Q. Zheng, Y.N. Li, and Y.H. Guo Synthesis of [3beta-acetoxy-urs-12-en-28-oyl]-1-monoglyceride and investigation on its anti tumor effects against BGC-823 Bioorg Med Chem 19 2011 4043 4050
10. P.P. Wu, K. Zhang, Y.J. Lu, P. He, and S.Q. Zhao In vitro and in vivo evaluation of the antidiabetic activity of ursolic acid derivatives Eur J Med Chem 80 2014 502 508
11. A.S. Leal, R. Wang, J.A. Salvador, and Y. Jing Synthesis of novel ursolic acid heterocyclic derivatives with improved abilities of antiproliferation and induction of p53, p21waf1 and NOXA in pancreatic cancer cells Bioorg Med Chem 20 2012 5774 5786
12. S. Rashid, B.A. Dar, R. Majeed, A. Hamid, and B.A. Bhat Synthesis and biological evaluation of ursolic acid-triazolyl derivatives as potential anti-cancer agents Eur J Med Chem 66 2013 238 245
13. M.C. Liu, S.J. Yang, L.H. Jin, D.Y. Hu, W. Xue, and B.A. Song Synthesis and cytotoxicity of novel ursolic acid derivatives containing an acyl piperazine moiety Eur J Med Chem 58 2012 128 135
14. J.W. Shao, Y.C. Dai, J.P. Xue, J.C. Wang, F.P. Lin, and Y.H. Guo In vitro and in vivo anticancer activity evaluation of ursolic acid derivatives Eur J Med Chem 46 2011 2652 2661
15. M.G. Vander Heiden, L.C. Cantley, and C.B. Thompson Understanding the Warburg effect: the metabolic requirements of cell proliferation Science 324 2009 1029 1033
16. R.L. Krisher, and R.S. Prather A role for the Warburg effect in preimplantation embryo development: metabolic modification to support rapid cell proliferation Mol Reprod Dev 79 2012 311 320
17. D. Zhong, L. Xiong, T. Liu, X. Liu, X. Liu, and J. Chen The glycolytic inhibitor 2-deoxyglucose activates multiple prosurvival pathways through IGF1R J Biol Chem 284 2009 23225 23233
18. G. Cheng, J. Zielonka, B.P. Dranka, D. McAllister, A.C. Mackinnon, and J. Joseph Mitochondria-targeted drugs synergize with 2-deoxyglucose to trigger breast cancer cell death Cancer Res 72 2012 2634 2644
19. S. Kuntz, S. Mazerbourg, M. Boisbrun, C. Cerella, M. Diederich, and I. Grillier-Vuissoz Energy restriction mimetic agents to target cancer cells: comparison between 2-deoxyglucose and thiazolidinediones Biochem Pharmacol 92 2014 102 111
20. J.C. Wang, Z. Jiang, L.P. Xiang, Y.F. Li, M.R. Ou, and X. Yang Synergism of ursolic acid derivative US597 with 2-deoxy-d-glucose to preferentially induce tumor cell death by dual-targeting of apoptosis and glycolysis Sci Reports 4 2014 1 10
21. Y. Liu, Y. Cao, W. Zhang, S. Bergmeier, Y. Qian, and H. Akbar A small-molecule inhibitor of glucose transporter 1 downregulates glycolysis, induces cell-cycle arrest, and inhibits cancer cell growth in vitro and in vivo Mol Cancer Ther 11 2012 1672 1682
22. D. Deng, C. Xu, P. Sun, J. Wu, C. Yan, and M. Hu Crystal structure of the human glucose transporter GLUT1 Nature 510 2014 121 125
23. K. Kamata, M. Mitsuya, T. Nishimura, J.-I. Eiki, and Y. Nagata Structural basis for allosteric regulation of the monomeric allosteric enzyme human glucokinase Structure 12 2004 429 438
24. H. Wei, A.J. Ruthenburg, S.K. Bechis, and G.L. Verdine Nucleotide-dependent domain movement in the ATPase domain of a human type IIA DNA topoisomerase J Biol Chem 280 2005 37041 37047
25. M.J. Frisch Revision A.1. Gaussian 09 1st ed. 2009 Gaussian, Inc. Wallingford, CT
26. G. Macindoe, L. Mavridis, V. Venkatraman, M.-D. Devignes, and D.W. Ritchie HexServer: an FFT-based protein docking server powered by graphics processors Nucleic Acids Res 38 2010 445 449
27. J. Shao, F. Zhang, Z. Bai, C. Wang, Y. Yuan, and W. Wang Synthesis and antitumor activity of emodin quaternary ammonium salt derivatives Eur J Med Chem 56 2012 308 319
28. Y. Lu, T. Yu, H. Liang, J. Wang, J. Xie, and J. Shao Nitric oxide inhibits hetero-adhesion of cancer cells to endothelial cells: restraining circulating tumor cells from initiating metastatic cascade Sci Reports 4 2014 1 9
29. W. Wang, Z. Bai, F. Zhang, C. Wang, Y. Yuan, and J. Shao Synthesis and biological activity evaluation of emodin quaternary ammonium salt derivatives as potential anticancer agents Eur J Med Chem 56 2012 320 331
30. J. Wang, J. Chen, L. Wan, J. Shao, Y. Lu, and Y. Zhu Synthesis, spectral characterization, and in vitro cellular activities of metapristone, a potential cancer metastatic chemopreventive agent derived from mifepristone (RU486) AAPS J 16 2014 289 298
31. J. Shao, Y. Dai, W. Zhao, J. Xie, J. Xue, and J. Ye Intracellular distribution and mechanisms of actions of photosensitizer zinc (II)-phthalocyanine solubilized in cremophor EL against human hepatocellular carcinoma HepG2 cells Cancer Lett 330 2013 49 56
32. J. Shao, J. Xue, Y. Dai, H. Liu, N. Chen, and L. Jia Inhibition of human hepatocellular carcinoma HepG2 by phthalocyanine photosensitiser photocyanine: ROS production, apoptosis, cell cycle arrest Eur J Cancer 48 2012 2086 2096
33. J. Sha, J. Pan, P. Ping, H. Xuan, D. Li, and J. Bo Synergistic effect and mechanism of vitamin A and vitamin D on inducing apoptosis of prostate cancer cells Mol Biol Rep 40 2013 2763 2768
34. L.L. Rokosz, C.Y. Huang, J.C. Reader, T.M. Stauffer, D. Chelsky, and N.H. Sigal Surfing the piperazine core of tricyclic farnesyltransferase inhibitors Bioorg Med Chem Lett 15 2005 5537 5543
35. R. Noubade, K. Wong, N. Ota, S. Rutz, C. Eidenschenk, and P.A. Valdez NRROS negatively regulates reactive oxygen species during host defence and autoimmunity Nature 2014 235 239
36. T.-J. Fan, L.-H. Han, R.-S. Cong, and J. Liang Caspase family proteases and apoptosis Acta Biochim Biophys Sin 37 2005 719 727
37. L. Wang, F. Jin, A. Qin, Y. Hao, Y. Dong, and S. Ge Targeting Notch1 signaling pathway positively affects the sensitivity of osteosarcoma to cisplatin by regulating the expression and/or activity of caspase family Mol Cancer 13 2014 139 141
38. C. Muñoz-Pinedo Signaling pathways that regulate life and cell death: evolution of apoptosis in the context of self-defense Adv Exp Med Biol 738 2012 124 143
39. J. Wang, L. Liu, H. Qiu, X. Zhang, W. Guo, and W. Chen Ursolic acid simultaneously targets multiple signaling pathways to suppress proliferation and induce apoptosis in colon cancer cells PLOS ONE 8 2013 e63872
40. N. Sultana Clinically useful anticancer, antitumor, and antiwrinkle agent, ursolic acid and related derivatives as medicinally important natural product J Enzym Inhib Med Chem 26 2011 616 642
41. R.A. Cairns, I.S. Harris, and T.W. Mak Regulation of cancer cell metabolism Nat Rev Cancer 11 2011 85 95
42. S. Kondo, Y. Tamura, J. Bawden, and S. Tanase The immunohistochemical localization of Bax and Bcl-2 and their relation to apoptosis during amelogenesis in developing rat molars Arch Oral Biol 46 2001 557 568
43. K. Polyak, T. Waldman, T.-C. He, K.W. Kinzler, and B. Vogelstein Genetic determinants of p53-induced apoptosis and growth arrest Genes Dev 10 1996 1945 1952