(-)-Oleocanthal as a c-met inhibitor for the control of metastatic breast and prostate cancers

Planta Medica

Volumn 77, Issue 10, 2011, Pages 1013-1019

  Elnagar, Ahmed Y ^a   Sylvester, Paul W ^a   El Sayed, Khalid A ^a  

^a UNIVERSITY OF LOUISIANA AT MONROE   (United States)

Author keywords

( )oleocanthal; breast cancer; cMet tyrosine kinase; extravirgin olive oil; migration and invasion; prostate cancer

Indexed keywords

CD31 ANTIGEN; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; GAMMA TOCOTRIENOL; N (3 CHLOROPHENYL) 3 [3,5 DIMETHYL 4 (4 METHYL 1 PIPERAZINYLCARBONYL) 1H PYRROL 2 YLMETHYLENE] 2,3 DIHYDRO N METHYL 2 OXO 1H INDOLE 5 SULFONAMIDE; OLEOCANTHAL; OLIVE OIL; SCATTER FACTOR RECEPTOR; SECOIRIDOID; UNCLASSIFIED DRUG;

ANTIANGIOGENIC ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER INVASION; CELL MIGRATION; CELL PROLIFERATION; CELL STRAIN MCF 7; COLONY FORMING CELL; COLORECTAL CARCINOMA; COMPUTER AIDED DESIGN; CONTROLLED STUDY; DOWN REGULATION; DRUG ISOLATION; FEMALE; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; MALE; OUTCOME ASSESSMENT; PROGNOSIS; PROSTATE CANCER; PROTEIN PHOSPHORYLATION; STRUCTURE ACTIVITY RELATION; WOUND HEALING;

ADENOSINE TRIPHOSPHATE; ALDEHYDES; ANGIOGENESIS INHIBITORS; ANTIGENS, CD31; ANTINEOPLASTIC AGENTS, PHYTOGENIC; BINDING SITES; BREAST NEOPLASMS; CELL LINE, TUMOR; CELL MOVEMENT; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HUMANS; INHIBITORY CONCENTRATION 50; MALE; MODELS, MOLECULAR; NEOPLASM INVASIVENESS; NEOVASCULARIZATION, PATHOLOGIC; PHENOLS; PLANT OILS; PROSTATIC NEOPLASMS; PROTEIN KINASES; PROTO-ONCOGENE PROTEINS C-MET;

EID: 79959935036     PISSN: 00320943     EISSN: 14390221     Source Type: Journal    
DOI: 10.1055/s-0030-1270724     Document Type: Article

References (29)

1. Wang X, Le P, Liang C, Chan J, Kiewlich D, Miller T, Harris D, Sun L, Rice A, Vasile S, Blake R A., Howlett A R., Patel N, McMahon G, Lipson K E. Potent and selective inhibitors of the Met [hepatocyte growth factor/scatter factor (HGF/SF) receptor] tyrosine kinase block HGF/SF-induced tumor cell growth and invasion. Mol Cancer Ther 2003 2 1085-1092
2. Prasad S, Phromnoi K, Yadav V R., Chaturvedi M M., Aggarwal B B. Targeting inflammatory pathways by flavonoids for prevention and treatment of cancer. Planta Med 2010 76 1044-1063
3. Bellon S, Kaplan-Lefko P, Yang Y, Zhang Y, Moriguchi J, Rex K, Johnson C, Rose P, Long A, O'Connor A, Gu Y, Coxon A, Kim T, Tasker A, Burgess T, Dussault I. c-Met inhibitors with novel binding mode show activity against several hereditary papillary renal cell carcinoma-related mutations. J Biol Chem 2008 283 2675-2683
4. Peach M, Tan N, Choyke S, Giubellino A, Athauda G, Burke T, Nicklaus M, Bottaro D. Directed discovery of agents targeting the Met tyrosine kinase domain by virtual screening. J Med Chem 2009 52 943-951
5. Chen C Y. C. Discovery of novel inhibitors for c-Met by virtual screening and pharmacophore analysis. J Chin Inst Chem Eng 2008 39 617-624
6. Bardelli A, Longati P, Williams T, Benvenuti S, Comoglio P M. A peptide representing the carboxyl-terminal tail of the met receptor inhibits kinase activity and invasive growth. J Biol Chem 1999 274 29274-29281
7. Sattler M, Salgia R. The MET axis as a therapeutic target. Update Cancer Ther 2009 3 109-118
8. Schiering N, Knapp S, Marconi M, Flocco M M., Cui J, Perego R, Rusconi L, Cristiani C. Crystal structure of the tyrosine kinase domain of the hepatocyte growth fac (Pubitemid 37339954)
9. Wang W, Marimuthu A, Tsai J, Kumar A, Krupka H I., Zhang C, Powell B, Suzuki Y, Nguyen H, Tabrizizad M, Luu C, West B L. Structural characterization of autoinhibited c-Met kinase produced by coexpression in bacteria with phosphatase. PNAS 2006 103 3563-3568 (Pubitemid 43376595)
10. Colomer R, Menndez J. Mediterranean diet, olive oil and cancer. Clin Transl Oncol 2006 8 15-21
11. Han J, Talorete T, Yamada P, Isoda H. Anti-proliferative and apoptotic effects of oleuropein and hydroxytyrosol on human breast cancer MCF-7 cells. Cytotechnology 2009 59 45-53
12. Owen R, Mier W, Giacosa A, Hull W, Spiegelhalder B, Bartsch H. Phenolic compounds and squalene in olive oils: the concentration and antioxidant potential of total phenols, simple phenols, secoiridoids, lignansand squalene. Food Chem Toxicol 2000 38 647-659 (Pubitemid 30447459)
13. Gill C, Boyd A, McDermott E, McCann M, Servili M, Selvaggini R, Taticchi A, Esposto S, Montedoro G, McGlynn H, Rowland I. Potential anti-cancer effects of virgin olive oil phenols on colorectal carcinogenesis models in vitro. Int J Cancer 2005 117 1-7 (Pubitemid 41262753)
14. Montedoro G, Servili M, Baldioli R, Selvaggini E, Macchioni A. Simple and hydrolyzable compounds in virgin olive oil. 3. Spectroscopic characterizations of the secoiridoid derivatives. J Agric Food Chem 1993 41 2228-2234
15. Menendez J A., Vazquez-Martin A, Colomer R, Brunet J, Carrasco-Pancorbo A, Garcia-Villalba R, Fernandez-Gutierrez A, Segura-Carretero A. Olive oil's bitter principle reverses acquired autoresistance to trastuzumab (Herceptin) in HER2-overexpressing breast cancer cells. BMC Cancer 2007 7 80
16. Menendez J A., Vazquez-Martin A, Garcia-Villalba R, Carrasco-Pancorbo A, Oliveras-Ferraros C, Fernandez-Gutierrez A, Segura-Carretero A. tabAnti-HER2 (erbB-2) oncogene effects of phenolic compounds directly isolated from commercial extra-virgin olive oil (EVOO). BMC Cancer 2008 8 377
17. Beauchamp G K., Keast R S., Morel D, Lin J, Pika J, Han Q, Lee C H., Smith A B., Breslin P A. Phytochemistry: ibuprofen-like activity in extra-virgin olive oil. Nature 2005 437 45-46 (Pubitemid 41613421)
18. Pitt J, Roth W, Lacor P, Smith A B., Blankenship M, Velasco P, De Felice F, Breslin P, Klein W L. Alzheimer's-associated A oligomers show altered structure, immunoreactivity and synaptotoxicity with low doses of oleocanthal. Toxicol Appl Pharmacol 2009 240 189-197
19. Jung I, Gurzu S, Raica M, Cmpean A M., Szentirmay Z. The differences between the endothelial area marked with CD31 and CD105 in colorectal carcinomas by computer-assisted morphometrical analysis. Rom J Morphol Embryol 2009 50 239-243
20. Smith A, Han Q, Breslin P, Beauchamp G. Synthesis and assignment of absolute configuration of (-)-oleocanthal: a potent, naturally occurring non-steroidal anti-inflammatory and anti-oxidant agent derived from extra virgin olive oils. Org Lett 2005 7 5075-5078 (Pubitemid 41579931)
21. Mudit M, Khanfar M, Muralidharan A, Thomas S, Shah G, van Soest R, El Sayed K. Discovery, design, and synthesis of anti-metastatic lead phenylmethylene hydantoins inspired by marine natural products. Bioorg Med Chem 2009 17 1731-1738
22. Elnagar A, Wali V, Sylvester P, El Sayed K. Design and preliminary structure-activity relationship of redox-silent semisynthetic tocotrienol analogues as inhibitors for breast cancer proliferation and invasion. Bioorg Med Chem 2010 18 755-768
23. Zama I N., Hutson T E., Elson P, Cleary J M., Choueiri T K., Heng D Y., Ramaiya N, Michaelson M D., Garcia J A., Knox J J., Escudier B, Rini B I. Sunitinib rechallenge in metastatic renal cell carcinoma patients. Cancer 2010 116 5400-5406
24. SYBYL Molecular Modeling Software, version 8.0; Tripos Associates: St. Louis, MO, 2007; Technical tips online. Available at. http://www.tripos.com Accessed August 01, 2010[nl]
25. Welch W, Ruppert J, Jain A. Hammerhead: fast, fully automated docking of flexible ligands to protein binding sites. Chem Biol 1996 3 449-462 (Pubitemid 126663345)
26. Jain A N. Surflex: fully automatic flexible molecular docking using a molecular similarity-based search engine. J Med Chem 2003 46 499-511 (Pubitemid 36182752)
27. Heiden W, Goetze T, Brickmann J. Fast generation of molecular surfaces from 3D data fields with an enhanced marching cube algorithm. J Comp Chem 1993 14 246-250
28. Borghesani P, Peyrin J, Klein R, Rubin J, Carter A, Schwartz P, Luster A, Corfas G, Segal R. BDNF stimulates migration of cerebellar granule cells. Development 2002 6 1435-1442 (Pubitemid 34874164)
29. Rodems S M., Hamman B D., Lin C, Zhao J, Shah S, Heidary D, Makings L, Stack J H., Pollok B A. A FRET-based assay platform for ultra-high density drug screening of protein kinases and phosphatases. Assay Drug Dev Technol 2002 1 9-19