Cancer preventive agents 9. Betulinic acid derivatives as potent cancer chemopreventive agents

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 13, 2009, Pages 3378-3381

  Nakagawa Goto, Kyoko ^a   Yamada, Koji ^a   Taniguchi, Masahiko ^a   Tokuda, Harukuni ^b   Lee, Kuo Hsiung ^a  

^a University of North Carolina   (United States)

^b KYOTO PREFECTURAL UNIVERSITY OF MEDICINE   (Japan)

Author keywords

Antitumor promoter; Betulinic acid; Cancer preventive agents; Ceanothic acid; Epstein Barr virus

Indexed keywords

BETULIC ACID; BETULINIC ACID DERIVATIVE; BEVIRIMAT; CEANOTHIC ACID; CURCUMIN; EPSTEIN BARR VIRUS ANTIGEN; ISOPENTENOYL DERIVATIVE; PHORBOL 13 ACETATE 12 MYRISTATE; TERPENOID; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BETULA PUBESCENS; CANCER PREVENTION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG POTENCY; DRUG SYNTHESIS; EPSTEIN BARR VIRUS; ESTERIFICATION; IC 50; IN VITRO STUDY; INHIBITION KINETICS; MEDICINAL PLANT; MOUSE; NONHUMAN; PRENYLATION; RAJI CELL; SKIN CARCINOGENESIS; STRUCTURE ACTIVITY RELATION;

ANTICARCINOGENIC AGENTS; ANTIGENS, VIRAL; CELL LINE, TUMOR; ESTERIFICATION; HUMANS; TETRADECANOYLPHORBOL ACETATE; TRITERPENES;

HUMAN HERPESVIRUS 4;

EID: 66349124657     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.05.050     Document Type: Article

References (24)

1. Cichewicz R.H., and Kouzi S.A. Med. Res. Rev. 24 (2004) 90
2. Yogeeswari P., and Sriram D. Curr. Med. Chem. 12 (2005) 657
3. Fujioka T., Kashiwada Y., Kilkuskie R.E., Cosentino L.M., Ballas L.M., Jiang J.B., Janzen W.P., Chen I.S., and Lee K.H. J. Nat. Prod. 57 (1994) 243
4. Li F., Goila-Gaur R., Salzwedel K., Kilgore N.R., Reddick M., Matallana C., Castillo A., Zoumplis D., Martin D.E., Orenstein J.M., Allaway G.P., Freed E.O., and Wild C.T. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 13555
5. Kessler J.H., Mullauer F.B., de Roo D.M., and Medema J.P. Cancer Lett. 251 (2007) 132
6. Mukherjee R., Kumar V., Srivastava S.K., Agarwal S.K., and Burman A.C. Anti-Cancer Agents Med. Chem. 6 (2006) 271
7. Fulda S., Friesen M., Los M., Scaffidi C., Mier W., Benedict M., Nunes G., Krammer P.H., Peter M.E., and Debatin K.M. Cancer Res. 57 (1997) 4956
8. Schmit M.L., Kuzmanoff K.L., Ling-Indeck L., and Pezzuto J.M. Eur. J. Cancer 33 (1997) 2007
9. Fulda S., Jeremias I., Steiner H.H., Poetsh T., and Debatin K.M. Int. J. Cancer 82 (1999) 435
10. Chandramu C., Manohar R.D., Krupadanam D.G., and Dashavantha R.V. Phytother. Res. 27 (2003) 129
11. Schihly W., Heilmann J., Callis I., and Sticher O. Planta Med. 65 (1999) 740
12. Mukherjee P.K., Saha K., Das J., Pal M., and Saha B.P. Planta Med. 63 (1997) 367-369
13. Steele J.C., Warhurst D.C., Kirby G.C., and Simmonds M.S. Phytother. Res. 13 (1999) 115
14. Bringmann G., Saeb W., Assi L.A., Francois G., Narayanan A.S.S., Peters K., and Petera E.M. Planta Med. 63 (1997) 255
15. Kashiwada Y., Hashimoto F., Cosentino L.M., Chen C.H., Garrett P.E., and Lee K.H. J. Med. Chem. 39 (1996) 1016
16. Takasaki M., Konoshima T., Kozuka M., et al. Biol. Pharm. Bull. 18 (1995) 435-438
17. Fukuda Y., Sakai K., Matsunaga S., Tokuda H., and Tanaka R. Chem. Biodivers. 2 (2005) 421
18. Akihisa T., Nakamura Y., Tagata M., Tokuda H., Yasukawa K., Uchiyama E., Suzuki T., and Kimura Y. Chem. Biodivers. 4 (2007) 224
19. Akihisa T., Nakamura Y., Tokuda H., Uchiyama E., Suzuki T., Kimura Y., Uchikura K., and Nishino H. J. Nat. Prod. 70 (2007) 948
20. Qian K., Nakagawa-Goto K., Yu D., Marris-Natschke S.L., Nitz T.J., Kilgore N., Allaway G.P., and Lee K.H. Bioorg. Med. Chem. Lett. 17 (2007) 6553
21. Lee S.S., Chen W.C., Huang C.F., and Su Y. J. Nat. Prod. 61 (1998) 1343
22. In vitro EBV-EA activation experiments: EBV-EA positive serum from a patient with nasopharyngeal carcinoma (NPC) was a gift from Professor H. Hattori, Department of Otorhinolaryngology, Kobe University. The EBV genome carrying lymphoblastoid cells (Raji cells derived from Burkitt's lymphoma) were cultured in 10% fetal bovine serum (FBS) in RPMI-1640 medium (Sigma R8758, USA). Spontaneous activation of EBV-EA in our subline of Raji cells was less than 0.1%. The inhibition of EBV-EA activation was assayed using Raji cells (virus non-producer type) as described below. The cells were incubated at 37 °C for 48 h in 1 mL of medium containing n-butyric acid (4 mM), TPA [32 pM = 20 ng in 2 μL dimethyl sulfoxide (DMSO)] and various amounts of the test compounds dissolved in 2 μL of DMSO. Smears were made from the cell suspension. The EBV-EA inducing cells were stained by the means of an indirect immunofluorescence technique. In each assay, at least 500 cells were counted, and the number of stained cells (positive cells) was recorded. Triplicate assays were performed for each compound. The average EBV-EA induction of the test compound was expressed as a ratio relative to the control experiment (100%), which was carried out with n-butyric acid (4 mM) plus TPA (32 pM). EBV-EA induction was ordinarily around 35%. The viability of treated Raji cells was assayed by the Trypan blue staining method. The cell viability of the TPA positive control was greater than 80%. Therefore, only compounds that induced less than 80% (% of control) of the EBV-active cells (those with a cell viability of more than 60%) were considered able to inhibit the activation caused by promoter substances. Student's t-test was used for all statistical analysis.
23. Suzuki M., Nakagawa-Goto K., Nakamura S., Tokuda H., Morris-Natschke S.L., Kozuka M., Nishino H., and Lee K.H. Pharm. Biol. 44 (2006) 178
24. Itoigawa M., Ito C., Tokuda H., Enjo F., Nishino H., and Furukawa H. Cancer Lett. 214 (2004) 165