Identification of a phenanthrene derivative as a potent anticancer drug with Pim kinase inhibitory activity

Cancer Science

Volumn 103, Issue 1, 2012, Pages 107-115

  Wang, Ying Ying ^a   Taniguchi, Tsuyoshi ^a   Baba, Tomohisa ^a   Li, Ying Yi ^a,b,c   Ishibashi, Hiroyuki ^a   Mukaida, Naofumi ^a  

^a KANAZAWA UNIVERSITY   (Japan)

^b FUDAN UNIVERSITY SHANGHAI CANCER CENTER   (China)

^c FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; COMPLEMENTARY DNA; PHENANTHRENE DERIVATIVE; T26; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; APOPTOSIS; ARTICLE; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CELL LINE; CONTROLLED STUDY; DRUG IDENTIFICATION; GENE OVEREXPRESSION; HUMAN; HUMAN CELL; IN VITRO STUDY; MOLECULAR WEIGHT; MOUSE; NONHUMAN; PANCREAS CANCER; PIM 2; PIM 3; PRIORITY JOURNAL; PROTO ONCOGENE;

ANIMALS; APOPTOSIS; BLOTTING, WESTERN; CELL CYCLE; CELL PROLIFERATION; CYCLIC AMP-DEPENDENT PROTEIN KINASES; FLUORESCENT ANTIBODY TECHNIQUE; HUMANS; MICE; MICE, INBRED BALB C; MICE, NUDE; PANCREATIC NEOPLASMS; PHENANTHRENES; PROTO-ONCOGENE PROTEINS C-AKT; PROTO-ONCOGENE PROTEINS C-PIM-1; PROTO-ONCOGENE PROTEINS C-SIS; RNA, SMALL INTERFERING; TUMOR CELLS, CULTURED;

EID: 84855516649     PISSN: 13479032     EISSN: 13497006     Source Type: Journal    
DOI: 10.1111/j.1349-7006.2011.02117.x     Document Type: Article

References (44)

1. Van Cutsem E, Aerts R, Haustermans K, Topal B, Van Steenbergen W, Verslype C. Systemic treatment of pancreatic cancer. Eur J Gastroenterol Hepatol 2004; 16: 265-74.
2. Hidalgo M. Pancreactic cancer. N Engl J Med 2010; 362: 1605-17.
3. Konietzko U, Kauselmann G, Scafidi J et al. Pim kinase expression is induced by LTP stimulation and required for the consolidation of enduring LTP. EMBO J 1999; 18: 3359-69.
4. Deneen B, Welford SM, Ho T, Hernandez F, Kurland I, Denny CT. PIM3 proto-oncogene kinase is a common transcriptional target of divergent EWS/ETS oncoproteins. Mol Cell Biol 2003; 23: 3897-908.
5. Wu Y, Wang YY, Nakamoto Y et al. Accelerated hepatocellular carcinoma development in mice expressing the Pim-3 transgene selectively in the liver. Oncogene 2010; 29: 2228-37.
6. Fujii C, Nakamoto Y, Lu P et al. Aberrant expression of serine/threonine kinase Pim-3 in hepatocellular carcinoma development and its role in the proliferation of human hepatoma cell lines. Int J Cancer 2005; 114: 209-18.
7. Li YY, Popivanova BK, Nagai Y et al. Pim-3, a proto-oncogene with serine/threonine kinase activity, is aberrantly expressed in human pancreatic cancer and phosphorylates Bad to block Bad-mediated apoptosis in human pancreatic cancer cell lines. Cancer Res 2006; 66: 6741-7.
8. Popivanova BK, Li YY, Zheng H et al. Proto-oncogene, Pim-3 with serine/threonine kinase activity, is aberrantly expressed in human colon cancer cells and can prevent Bad-mediated apoptosis. Cancer Sci 2007; 98: 321-8.
9. Zheng HC, Tsuneyama K, Takahashi H et al. Aberrant Pim-3 expression is involved in gastric adenoma-adenocarcinoma sequence and cancer progression. J Cancer Res Clin Oncol 2008; 134: 481-8.
10. 112 gatekeeper site. FEBS Lett 2004; 571: 43-9.
11. Yan B, Zemskova M, Holder S et al. The PIM-2 kinase phosphorylates BAD on serine 112 and reverses BAD-induced cell death. J Biol Chem 2003; 278: 45.
12. Li Y-Y, Wang Y-Y, Taniguchi T et al. Identification of stemonamidee synthetic intermediates as a novel potent anticancer drug with an apoptosis-inducing ability. Int J Cancer 2010; 127: 474-84.
13. Yano T, Ishikura H, Kato H et al. Vaccination effect of interleukin-6-producing pancreatic cancer cells in nude mice: a model of tumor prevention and treatment in immune-compromised patients. Jpn J Cancer Res 2001; 92: 83-7.
14. Lieber M, Mazzetta J, Nelson-Rees W, Kaplan M, Todaro G. Establishment of a continuous tumor-cell line (panc-1) from a human carcinoma of the exocrine pancreas. Int J Cancer 1975; 15: 741-7.
15. Yunis AA, Arimura GK, Russin DJ. Human pancreatic carcinoma (MIA PaCa-2) in continuous culture: sensitivity to asparaginase. Int J Cancer 1977; 19: 128-35.
16. Bruns CJ, Harbison MT, Kuniyasu H, Eue I, Fidler IJ. In vivo selection and characterization of metastatic variants from human pancreatic adenocarcinoma by using orthotopic implantation in nude mice. Neoplasia 1999; 1: 50-62.
17. Takeuchi K, Ishita A, Matsuo J, Ishibashi H. Synthesis of 13a-methylphenthroindolizidines using radical cascade cylization: synthetic studies toward (+)-hypoestestatin 1. Tetrahedron 2007; 63: 11.
18. Cui M, Wang Q. Total synthesis of phenanthro-quinolizidine alkaloids: (+)-cryptopleurine, (+)-boehmeriasin A, (+)-boehmeriasin B and (+)-hydroxycryptopleurine. Eur J Org Chem 2009; 2009: 5445-51.
19. Giet R, Glover DM. Drosophila aurora B kinase is required for histone H3 phosphorylation and condensing recruitment during chromosome condensation and to organize the central spindle during cytokinesis. J Cell Biol 2001; 152: 669-81.
20. Amaravadi R, Thompson CB. The survival kinases Akt and Pim as potential pharmacological targets. J Clin Invest 2005; 115: 2618-24.
21. Rhodes N, Heerding DA, Duckett DR et al. Characterization of an Akt kinase inhibitor with potent pharmacodynamic and antitumor activity. Cancer Res 2008; 68: 2366-74.
22. Nawijin M, Alendar A, Berns A. For better or for worse: the role of Pim oncogene in tumorigenesis. Nat Rev Cancer 2011; 11: 23-34.
23. 2/M transition. Mol Biotechnol 2006; 32: 227-48.
24. Barnett SF, Defeo-Jones D, Fu S et al. Identification and characterization of pleckstrin-homology-domain-dependent and isoenzyme-specific Akt inhibitors. Biochem J 2005; 385: 399-408.
25. Kip1 at the transcriptional and posttranscriptional levels. Cancer Res 2008; 68: 5076-85.
26. Mochizuki T, Kitanaka C, Noguchi K et al. Physical and functional interactions between Pim-1 kinase and Cdc25A phosphatase. J Biol Chem 1999; 274: 18.
27. Bachmann M, Hennemann H, Xing PX, Hoffmann I, Möröy T. The oncogenic serine/threonine kinase Pim-1 phosphorylates and inhibits the activitiy of Cdc25c-associated kinase 1 (C-TAK1). J Biol Chem 2004; 279: 48.
28. cip1/WAF1 by Pim-1 kinase. Biochim Biophys Acta 2002; 1593: 45-55.
29. Chen WS, Xu PZ, Gottlob K et al. Growth retardation and increased apoptosis in mice with homozygous disruption of the Akt1 gene. Genes Dev 2001; 15: 2203-8.
30. Easton RM, Cho H, Roovers K et al. Role for Akt3/protein kinase Bγ in attainment of normal brain size. Mol Cell Biol 2005; 25: 1869-78.
31. Woulfe D, Jiang H, Morgans A et al. Defects in secretion, aggregation, and thrombus formation in platelets from mice lacking Akt2. J Clin Invest 2004; 113: 441-50.
32. Qian KC, Wang L, Hickey ER, Studts J, Barringer K, Peng C. Structural basis of constitutive activity and a unique nucleotide binding mode of human Pim-1 kinase. J Biol Chem 2005; 280: 6130-7.
33. Bullock AN, Debreczeni J, Amos AL, Knapp S, Turk BE. Structure and substrate specificity of the Pim-1 kinase. J Biol Chem 2005; 280: 41.
34. Bullock AN, Russo S, Amos A et al. Crystal structure of the PIM2 kinase in complex with an organoruthenium inhibitor. PLoS ONE 2009; 4: e7112.
35. Brault L, Gesser C, Bracher F et al. PIM serine/threonine kinases in the pathogenesis and therapy of hematologic malignancies. Haematologica 2010; 95: 1004-15.
36. Holder S, Zemskova M, Zhang C et al. Characterization of a potent and selective small-molecule inhibitor of the PIM1 kinase. Mol Cancer Ther 2007; 6: 163-72.
37. Pogacic V, Bullock AN, Fedorov O et al. Structural analysis identifies imidazo[1, 2-b]pyridazines as PIM kinase inhibitors with in vitro antileukemic activity. Cancer Res 2007; 67: 6916-24.
38. Chen LS, Redkar S, Bearss D, Wierda WG, Gandhi V. Pim kinase inhibitor, SGI-1776, induces apoptosis in chronic lymphocytic leukemia cells. Blood 2009; 114: 4150-7.
39. Xia Z, Knaak C, Ma J et al. Synthesis and evaluation of novel inhibitors of Pim-1 and Pim-2 protein kinases. J Med Chem 2009; 52: 74-86.
40. Lin YW, Beharry ZM, Hill EG et al. A small molecule inhibitor of Pim protein kinases blocks the growth of precursor T-cell lymphoblastic leukemia/lymphoma. Blood 2010; 115: 824-33.
41. Akué-Gédu R, Rossignol E, Azzaro S et al. Synthesis, kinase inhibitory potencies, and in vitro antiproliferative evaluation of new Pim kinase inhibitors. J Med Chem 2009; 52: 6369-81.
42. Domen J, van der Lugt NM, Laird PW et al. Impaired interleukin-3 response in Pim-1-deficient bone marrow-derived mast cells. Blood 1993; 82: 1445-52.
43. Hammerman PS, Fox CJ, Birnbaum MJ, Thompson CB. Pim and Akt oncogenes are independent regulators of hematopoietic cell growth and survival. Blood 2005; 105: 4477-83.
44. Beharry Z, Mahajan S, Zemskova M et al. The Pim protein kinases regulate energy metabolism and cell growth. Proc Natl Acad Sci U S A 2011; 108: 528-33.