Fluorescent epigenetic small molecule induces expression of the tumor suppressor ras-association domain family 1A and inhibits human prostate xenograft

Journal of Medicinal Chemistry

Volumn 53, Issue 6, 2010, Pages 2376-2382

  Sheikh, Kathryn D ^a   Banerjee, Partha P ^b   Jagadeesh, Shankar ^b   Grindrod, Scott C ^a   Zhang, Li ^a   Paige, Mikell ^a   Brown, Milton L ^a  

^a GEORGETOWN UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b GEORGETOWN UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; MAHANINE; MESSENGER RNA; RAS ASSOCIATION DOMAIN FAMILY PROTEIN 1A; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CANCER GROWTH; CANCER INHIBITION; DOWN REGULATION; DRUG DESIGN; DRUG MECHANISM; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MALE; MOUSE; NONHUMAN; PROSTATE CANCER; PROTEIN EXPRESSION; TUMOR VOLUME; TUMOR XENOGRAFT; UPREGULATION;

ANIMALS; CARBAZOLES; CELL LINE, TUMOR; CELL PROLIFERATION; CYCLIN D1; DNA (CYTOSINE-5-)-METHYLTRANSFERASE; DNA METHYLATION; DOSE-RESPONSE RELATIONSHIP, DRUG; FLUORESCENCE; GENE EXPRESSION REGULATION, NEOPLASTIC; HUMANS; MALE; MICE; MICE, INBRED BALB C; MICE, NUDE; MODELS, CHEMICAL; MOLECULAR STRUCTURE; MURRAYA; PROSTATIC NEOPLASMS; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION; TUMOR SUPPRESSOR PROTEINS; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 77949865239     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm9011615     Document Type: Article

References (23)

1. Donninger, H.; Vos, M. D.; Clark, G. J. The RASSF1A tumor suppressor. J. Cell Sci. 2007, 120, 3163-3172.
2. van der Weyden, L.; Adams, D. J. The Ras-association domain family (RASSF) members and their role in human tumourigenesis. Biochim. Biophys. Acta 2007, 1776, 58-85.
3. Dallol, A.; Agathanggelou, A.; Tommasi, S.; Pfeifer, G. P.; Maher, E. R.; Latif, F. Involvement of the RASSF1A tumor suppressor gene in controlling cell migration. Cancer Res. 2005, 65, 1652-1659.
4. Rong, R.; Jin, W.; Zhang, J.; Sheikh, M. S.; Huang, Y. Tumor suppressor RASSF1A is a microtubule-binding protein that stabilizes microtubules and induces G2/M arrest. Oncogene 2004, 23, 8216-8230.
5. Shivakumar, L.; Minna, J.; Sakamaki, T.; Pestell, R.; White, M. A. The RASSF1A tumor suppressor blocks cell cycle progression and inhibits cyclin D1 accumulation. Mol. Cell. Biol. 2002, 22, 4309-4318.
6. Vos, M. D.; Martinez, A.; Elam, C.; Dallol, A.; Taylor, B. J.; Latif, F.; Clark, G. J. A role for the RASSF1A tumor suppressor in the regulation of tubulin polymerization and genomic stability. Cancer Res. 2004, 64, 4244-4250.
7. Li, L.-C.; Okino, S. T.; Dahiya, R. DNA methylation in prostate cancer. Biochim. Biophys. Acta 2004, 1704, 87-102.
8. Liu, L.; Yoon, J.-H.; Dammann, R.; Pfeifer, G. P. Frequent hypermethylation of the RASSF1A gene in prostate cancer. Oncogene 2002, 21, 6835-6840.
9. Kuzmin, I.; Gillespie, J. W.; Protopopov, A.; Geil, L.; Dreijerink, K.; Yang, Y.; Vocke, C. D.; Duh, F.-M.; Zabarovsky, E.; Minna, J. D.; Rhim, J. S.; Emmert-Buck, M. R.; Linchan, W. M.; Lerman, M. I. The RASSF1A tumor suppressor gene is inactivated in prostate tumors and suppresses growth of prostate carcinoma cells. Cancer Res. 2002, 62, 3498-3502.
10. Jagadeesh, S.; Sinha, S.; Pal, B. C.; Bhattacharya, S.; Banerjee, P. P. Mahanine reverses an epigenetically silenced tumor suppressor gene RASSF1A in human prostate cancer cells. Biochem. Biophys. Res. Commun. 2007, 362, 212-217.
11. Beaulieu, N.; Morin, S.; Chute, I. C.; Robert, M.-F.; Nguyen, H.; MacLeod, A. R. An essential role for DNA methyltransferase DNMT3b in cancer cell survival. J. Biol. Chem. 2002, 277, 28176-28181.
12. Brueckner, B.; Boy, R. G.; Siedlecki, P.; Musch, T.; Kliem, H. C.; Zielenkiewicz, P.; Suhai, S.; Wiessler, M.; Lyko, F. Epigenetic reactivation of tumor suppressor genes by a novel small-molecule inhibitor of human DNA methyltransferases. Cancer Res. 2005, 65, 6305-6311.
13. Wang, L.; Zhang, Y.; Liu, L.; Wang, Y. Palladium-catalyzed homocoupling and cross-coupling reactions of ary1 halides in polyethylene glycol). J. Org. Chem. 2006, 71, 1284-1287.
14. Freeman, A. W.; Urvoy, M.; Criswell, M. E. Triphenylphosphinemediated reductive cyclization of 2-nitrobiphenyls: a practical and convenient synthesis of carbazoles. J. Org. Chem. 2005, 70, 5014-5019.
15. Sinha, S.; Pal, B. C.; Jagadeesh, S.; Banerjee, P. P.; Bandyopadhaya, A.; Bhattacharya, S. Mahanine inhibits growth and induces apoptosis in prostate cancer cells through the deactivation of Akt and activation of caspases. Prostate 2006, 66, 1257-1265.
16. Chen, Y.; Martinez, L. A.; LaCava, M.; Coghlan, L.; Conti, C. J. Increased cell growth and tumorigenicity in human prostate LNCaP cells by overexpression to cyclin D. Oncogene 1998, 16, 1913.
17. Musgrove, E. A.; Lee, C. S. L.; Buckley, M. F.; Sutherland, R. L. Cyclin D1 induction in breast cancer cells shortens G1 and is sufficient for cells arrested in G1 to complete the cell cycle. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 8022-8026.
18. Kim, G.-D.; Ni, J.; Kelesoglu, N.; Roberts, R. J.; Pradhan, S. Cooperation and communication between the human maintenance and de novo DNA (cytosine-5) methyltransferases. EMBO J. 2002, 27, 4183-4195.
19. Majumder, S.; Ghoshal, K.; Datta, J.; Bai, S.; Dong, X.; Quan, N.; Plass, C.; Jacob, S. T. Role of de novo DNA methyltransferases and methyl CpG-binding proteins in gene silencing in a rat hepatoma. J. Biol. Chem. 2002, 277, 16048-16058.
20. Organization for Economic Co-Operation and Development. Acute Oral Toxicity (AOT) Up-and-Down-Procedure. http://www.epa.gov/oppfead1/harmonization/ .
21. Li, L. N.; Yuan, S. J. Anti-Tumor Drugs: In Vivo Standards. In Methodology of New Drug Research in Pharmacology, 1st ed.; Lu, Q. J., Ed.; Chemical Industry Press: Beijing, 2007; pp 245-247.
22. Lyko, F.; Brown, R. DNA methyltransferase inhibitors and the development of epigenetic cancer therapies. J. Natl. Cancer Inst. 2005, 97, 1498-1506.
23. Pray, L. At the flick of a switch: epigenetic drugs. Chem. Biol. 2008, 15, 640-641.