Syntheses and potential anti-prostate cancer activities of ionone-based chalcones

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 4, 2009, Pages 1183-1186

  Zhou, Jinming ^a,b,c   Geng, Guoyan ^b,c   Batist, Gerald ^a,b,c   Wu, Jian Hui ^a,b,c  

^a MCGILL UNIVERSITY   (Canada)

^b MCGILL UNIVERSITY   (Canada)

^c MCGILL UNIVERSITY   (Canada)

Author keywords

Androgen receptor; Antiandrogen; Ionone derivatives; Mutation; Pan antagonist

Indexed keywords

ANDROGEN RECEPTOR; BENZALDEHYDE; BICALUTAMIDE; CHALCONE DERIVATIVE; IONONE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL PROLIFERATION; CELL STRAIN LNCAP; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; PROSTATE CANCER; TRANSACTIVATION; WILD TYPE;

ANIMALS; ANTINEOPLASTIC AGENTS; CHALCONES; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MALE; MICE; MOLECULAR STRUCTURE; MUTATION; NORISOPRENOIDS; PROSTATIC NEOPLASMS; RECEPTORS, ANDROGEN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 59849090097     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.12.089     Document Type: Article

References (20)

1. Culig Z., Klocker H., Bartsch G., and Hobisch A. Endocr. Relat. Cancer 9 (2002) 155
2. Balk S.P. Urology 60 (2002) 132
3. Taplin M.E., and Ho S.M. J. Clin. Endocrinol. Metab. 86 (2001) 3467
4. Tatman D., and Mo H.B. Cancer Lett. 175 (2002) 129
5. Janakiram N.B., Cooma I., Mohammed A., Steele V.E., and Rao C.V. Mol. Cancer Ther. 7 (2008) 181
6. Duncan R.E., Lau D., El Sohemy A., and Archer M.C. Biochem. Pharmacol. 68 (2004) 1739
7. Jones S., and Mo H. J. Nutr. 135 (2005) 3046S
8. Shishodia S., Chaturvedi M.M., and Aggarwal B.B. Curr. Probl. Cancer 31 (2007) 243
9. Mosley C.A., Liotta D.C., and Snyder J.P. Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease 595 (2007) 77
10. Youssef K.M., El-Sherbeny M.A., El-Shafie F.S., Farag H.A., Al-Deeb O.A., and Awadalla S.A.A. Arch. Pharm. (Weinheim) 337 (2004) 42
11. Adams B.K., Ferstl E.M., Davis M.C., Herold M., Kurtkaya S., Camalier R.F., Hollingshead M.G., Kaur G., Sausville E.A., Rickles F.R., Snyder J.P., Liotta D.C., and Shoji M. Bioorg. Med. Chem. 12 (2004) 3871
12. Chandra N., Pandey S., Ramesh, Suryawanshi S.N., and Gupta S. Eur. J. Med. Chem. 41 (2006) 779
13. Cell growth inhibition assay: LNCaP, 22Rv1, C4-2B and PC-3 cells were seeded at a density of 6000-7000 cells per well in 96-well microtiter plates in RPMI 1640 supplemented with 10% FBS, 100 U/mL penicillin and 10 mg/mL streptomycin. MDA-PCa-2b cells were seeded at the same density in medium BRFF-HPC1 (Athena Enzyme Systems, Baltimore, MD, USA) supplemented with 20% FBS. RWPE-1 cells were seeded at the same density in keratinocyte serum-free medium supplemented with 0.05 mg/mL bovine pituitary extract and 5 ng/mL EGF (Cedarlane Laboratories, Burlington, ON, Canada). After overnight incubation, the cells were treated with DMSO vehicle or test compounds at various concentrations diluted from DMSO stock solution. The final DMSO concentration is 0.5%. After 72 h of incubation, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) solution were added to each well and incubated for another 2 h. The MTT formazan formed by viable cells was dissolved in isopropanol. The obsorbance was measured at 595 nm by a plate reader (FLUOstar OPTIMA, BMG LabTech). All experiments were performed in triplicate.
14. Gandhi R.P., Kumar S., Aryan R.C., and Ishar M.P.S. Synth. Commun. 19 (1989) 1759
15. Luciferase-reporter assay: PC-3 cells were seeded at a density of 60,000-70,000 cells per well in 24-well microtiter plates 24 h before transfection, and were subsequently cotransfected with 100 ng of reporter MMTV-luciferase (pCMV-MMTV-Luc), 10 ng of wild-type or mutant AR expressing plasmid (pCMV-AR-wt, pCMV-AR-T877A, pCMV-W741C or pCMV-H874Y), and 10 ng of Renilla null luciferase using LipofectamineTM 2000 reagent (Invitrogen) following manufacturer's protocol. Five hours after transfection, the medium was changed to phenol red-free RPMI 1640 supplemented with 10% charcoal-stripped FBS. After 16 h, the cells were treated with 0.1 nM DHT with and without test compounds for 24 h. Luciferase activity was detected by dual luciferase assay kit (Promega), standardized to the renilla luciferase control and normalized to 0.1 nM DHT without test compound. All experiments were performed in triplicate and repeated at least twice.
16. Song L.N., and Gelmann E.P. J. Biol. Chem. 280 (2005) 37853
17. Hara T., Miyazaki J., Araki H., Yamaoka M., Kanzaki N., Kusaka M., and Miyamoto M. Cancer Res. 63 (2003) 149
18. Steketee K., Timmerman L., Ziel-van der Made A., Doesburg P., Brinkmann A.O., and Trapman J. Int. J. Cancer 100 (2002) 309
19. Yoshida T., Kinoshita H., Segawa T., Nakamura E., Inoue T., Shimizu Y., Kamoto T., and Ogawa O. Cancer Res. 65 (2005) 9611
20. Sun C., Shi Y., Xu L.L., Nageswararao C., Davis L.D., Segawa T., Dobi A., McLeod D.G., and Srivastava S. Oncogene 25 (2006) 3905