Synthetic curcumin analog EF31 inhibits the growth of head and neck squamous cell carcinoma xenografts

Integrative Biology (United Kingdom)

Volumn 4, Issue 6, 2012, Pages 633-640

  Zhu, Shijun ^a   Moore, Terry W ^b   Lin, Xiaoqian ^a   Morii, Nao ^a   Mancini, Alessandra ^b   Howard, Randy B ^b   Culver, Deborah ^b   Arrendale, Richard F ^b   Reddy, Prabhakar ^b   Evers, Taylor J ^b   Zhang, Hongzheng ^a   Sica, Gabriel ^a   Chen, Zhuo G ^a   Sun, Aiming ^b   Fu, Haian ^a   Khuri, Fadlo R ^a   Shin, Dong M ^a   Snyder, James P ^b   Shoji, Mamoru ^a  

^a EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; EF 31; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; UNCLASSIFIED DRUG; 3,5 BIS(2 PYRIDINYLMETHYLIDENE) 4 PIPERIDONE; 3,5-BIS(2-PYRIDINYLMETHYLIDENE)-4-PIPERIDONE; CURCUMIN; DRUG DERIVATIVE; PIPERIDONE DERIVATIVE; TRANSCRIPTION FACTOR RELA;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CANCER INHIBITION; CANCER SIZE; CONTROLLED STUDY; CYTOTOXICITY TEST; DRUG EFFICACY; DRUG ELIMINATION; DRUG HALF LIFE; DRUG SOLUBILITY; DRUG SYNTHESIS; FEMALE; HEAD AND NECK SQUAMOUS CELL CARCINOMA; HUMAN; HUMAN CELL; IC 50; MALE; MAXIMUM PLASMA CONCENTRATION; MOUSE; NEPHELOMETRY; NONHUMAN; NUDE MOUSE; PRIORITY JOURNAL; PROTEIN PHOSPHORYLATION; SIGNAL TRANSDUCTION; TIME TO MAXIMUM PLASMA CONCENTRATION; TUMOR XENOGRAFT; WESTERN BLOTTING; ANIMAL; CELL SURVIVAL; CHEMISTRY; DRUG EFFECT; DRUG SCREENING; GERMFREE ANIMAL; HEAD AND NECK TUMOR; IMMUNOHISTOCHEMISTRY; METABOLISM; PATHOLOGY; PHOSPHORYLATION; RANDOMIZATION; SOLUBILITY; SQUAMOUS CELL CARCINOMA; SYNTHESIS;

ANIMALS; BLOTTING, WESTERN; CARCINOMA, SQUAMOUS CELL; CELL SURVIVAL; CURCUMIN; FEMALE; HEAD AND NECK NEOPLASMS; HUMANS; IMMUNOHISTOCHEMISTRY; MALE; MICE; MICE, NUDE; PHOSPHORYLATION; PIPERIDONES; RANDOM ALLOCATION; SIGNAL TRANSDUCTION; SOLUBILITY; SPECIFIC PATHOGEN-FREE ORGANISMS; TRANSCRIPTION FACTOR RELA; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84874408875     PISSN: 17579694     EISSN: 17579708     Source Type: Journal    
DOI: 10.1039/c2ib20007d     Document Type: Article

References (30)

1. B. B. Aggarwal A. Kumar A. C. Bharti Anticancer potential of curcumin: preclinical and clinical studies Anticancer Res. 2003 23 363 398
2. M. M. Chaturvedi B. Sung V. R. Yadav R. Kannappan B. B. Aggarwal NF-κB addiction and its role in cancer: 'one size does not fit all' Oncogene 2011 30 1615 1630
3. R. R. Satoskar S. J. Shah S. G. Shenoy Evaluation of anti-inflammatory property of curcumin (diferuloylmethane) in patients with post-operative inflammation Int. J. Clin. Pharmacol., Ther. Toxicol. 1986 24 651 654
4. G. Shoba D. Joy T. Joseph M. Majeed R. Rajendran P. S. Srivinas Influence of piperine on the in animals pharmacokinetics of curcumin and human volunteers Planta Med. 1998 64 353 356
5. B. K. Adams E. M. Ferstl M. C. Davis M. Herold S. Kurtkaya R. F. Camalier et al. Synthesis and biological evaluation of novel curcumin analogs as anti-cancer and anti-angiogenesis agents Bioorg. Med. Chem. 2004 12 3871 3883
6. B. K. Adams J. Cai J. Armstrong M. Herold Y. J. Lu A. Sun et al. EF24, a novel synthetic curcumin analog, induces apoptosis in cancer cells via a redox-dependent mechanism Anticancer Drugs 2005 16 263 275
7. I. Landais S. Hiddingh M. McCarroll C. Yang A. Sun M. S. Turker et al. Monoketone analogs of curcumin, a new class of Fanconi anemia pathway inhibitors Mol. Cancer 2009 8 133 145
8. A. L. Kasinski D. Yuhong S. L. Thomas J. Zhao S. Y. Sun F. Khuri et al. Inhibition of IKK-NF-kappa B signaling pathway by EF24, a novel monoketone analogue of curcumin Mol. Pharmacol. 2008 74 654 661
9. S. L. Thomas J. Zhao Z. Li B. Lou Y. Du J. Purcell et al. Activation of the p38 pathway by a novel monoketone curcumin analog, EF24, suggests a potential combination strategy Biochem. Pharmacol. 2010 80 1309 1316
10. M. Shoji A. Sun W. Kisiel Y. J. Lu H. Shim B. E. McCarey et al. Targeting therapy of tumor angiogenesis with a novel synthetic curcumin analog EF24 conjugated to factor VIIa inhibitor J. Drug Targeting 2008 16 185 197
11. A. Sun M. Shoji J. P. Snyder D. C. Liotta Synthesis of EF24-tripeptide-chloromethylketone: A novel anti-cancer drug delivery system J. Med. Chem. 2006 49 3153 3158
12. K. Selvendiran L. Tong S. Vishwanath A. Bratasz N. J. Trigg V. K. Kutala et al. EF24 induces G2/M arrest and apoptosis in cisplatin-resistant human ovarian cancer cells by increasing PTEN expression J. Biol. Chem. 2007 282 28609 28618
13. D. Subramaniam R. May S. M. Sureban K. B. Lee R. George P. Kuppusamy et al. A Curcumin Derivative with Potent In vivo Anticancer Activity Cancer Res. 2008 68 1962 1969
14. S. Singh B. B. Aggarwal Activation of transcription factor NF-κB is suppressed by curcumin (diferuloylmethane) J. Biol. Chem. 1995 270 24995 25000
15. S. Aggarwal H. Ichikawa Y. Takada S. K. Sandur S. Shishodia B. B. Aggarwal Curcumin (diferuloylmethane) down-regulates expression of cell proliferation and antiapoptotic and metastatic gene products through suppression of IkappaBalpha kinase and Akt activation Mol. Pharmacol. 2006 69 195 206
16. C. Jobin C. A. Bradham M. P. Russo B. Juma A. S. Narula D. A. Brenner et al. Curcumin blocks cytokine-mediated NF-kappa B activation and proinflammatory gene expression by inhibiting inhibitory factor Ikappa B kinase activity J. Immunol. 1999 163 3474 3483
17. B. E. Bachmeier A. G. Nerlich C. M. Iancu M. Cilli E. Schleicher R. Vené R. Dell'Eva M. Jochum The chemopreventive polyphenol curcumin prevents hematogenous breast cancer metastases in immunodeficient mice Cell. Physiol. Biochem. 2007 19 137 152
18. S. Z. Zhang M. M. Lipsky B. F. Trump I. C. Hsu Neutral red (NR) assay for cell viability and xenobiotic-induced cytotoxicity in primary cultures of human and rat hepatocytes Cell Biol. Toxicol. 1990 6 219 234
19. R. Heilker F. Freuler R. Pulfer F. Di Padova J. Eder All three IκB isoforms and most Rel family members are stably associated with the IkB kinase 1/2 complex Eur. J. Biochem. 1999 259 253 261
20. M. S. Brown O. T. Diallo M. Hu R. Ehsanian X. Yang P. Arun et al. CK2 modulation of NF-kappaB, TP53, and the malignant phenotype in head and neck cancer by anti-CK2 oligonucleotides in vitro or in vivo via sub-50-nm nanocapsules Clin. Cancer Res. 2010 16 2295 2307
21. J. I. Park M. G. Lee K. Cho B. J. Park K. S. Chae D. S. Byun et al. Transforming growth factor-β1 activates interleukin-6 expression in prostate cancer cells through the synergistic collaboration of the Smad2, p38-NF-κB, JNK, and Ras signaling pathways Oncogene 2003 22 4314 4332
22. V. Imbert R. A. Rupec A. Livolsi H. L. Pahl E. B. Traenckner C. Mueller-Dieckmann et al. Tyrosine Phosphorylation of IkB-α Activates NF-κB without Proteolytic Degradation of IkB-α Cell 1996 86 787 798
23. P. J. Chiao S. Miyamoto I. M. Verma Autoregulation of IκBα activity Proc. Natl. Acad. Sci. U. S. A. 1994 91 28 32
24. F. Arenzana-Seisdedos P. Turpin M. Rodriguez D. Thomas R. T. Hay J. L. Virelizier C. Dargemont Nuclear localization of IκBα promotes active transport of NF-κB from the nucleus to the cytoplasm J. Cell Sci. 1997 110 369 378
25. H. Zhong H. SuYang H. Erdjument-Bromage P. Tempst S. Ghosh The transcriptional activity of NF-kB is regulated by the IκB-associated PKAc subunit through a cyclic AMP-independent mechanism Cell 1997 89 413 424
26. C. Yoon Z. Korade B. D. Carter Protein kinase A-induced phosphorylation of the p65 subunit of nuclear factor-κB promotes Schwann Cell differentiation into a myelinating phenotype J. Neurosci. 2008 28 3738 3746
27. M. Deak A. D. Clifton J. M. Lucocq D. R. Alessi Mitogen- and stress-activated protein kinase-1 (MSK1) is directly activated by MAPK and SAPK2/p38, and may mediate activation of CREB EMBO J. 1998 17 4426 4441
28. K. Kefaloyianni C. Gaitanaki I. Beis ERK1/2 and p38-MAPK signalling pathways, through MSK1, are involved in NF-κB transactivation during oxidative stress in skeletal myoblasts Cell. Signalling 2006 18 2238 2251
29. M. Hsameda G. M. Polya Inhibition of cyclic AMP-dependent protein kinase by curcumin Phytochemicals 1996 42 599 605
30. A. Olivera T. W. Moore F. Hu A. P. Brown A. Sun D. C. Liotta et al., Inhibition of the NF-κB signaling pathway by the curcumin analog, 3,5-bis(2-pyridinylmethylidene)-4-piperidone (EF31): Anti-inflammatory and anti-cancer properties Int. Immunopharmacol. 2012 12 368 377