Inhibition of leukemic cell growth by a novel anti-cancer drug (GUT-70) from Calophyllum brasiliense that acts by induction of apoptosis

International Journal of Cancer

Volumn 113, Issue 1, 2005, Pages 158-165

  Kimura, Shinya ^a   Ito, Chihiro ^b   Jyoko, Naoto ^a,c   Segawa, Hidekazu ^a,d   Kuroda, Junya ^a,c   Okada, Masayuki ^a   Adachi, Souichi ^a   Nakahata, Tatsutoshi ^a   Yuasa, Takeshi ^a   Cechinel Filho, Valdir ^e   Furukawa, Hiroshi ^b   Maekawa, Taira ^a  

^a KYOTO UNIVERSITY HOSPITAL   (Japan)

^b MEIJO UNIVERSITY   (Japan)

^c KYOTO PREFECTURAL UNIVERSITY OF MEDICINE   (Japan)

^d SHIGA UNIVERSITY OF MEDICAL SCIENCE   (Japan)

^e Nucleo Investigacoes Quimico F   (Brazil)

Author keywords

Apoptosis; Calophyllum brasiliense; Caspase; Coumarin; Leukemia

Indexed keywords

5 METHOXY 2,2 DIMETHYL 6 (2 METHYL 1 OXO 2 BUTENYL) 10 PROPYL 2H,8H BENZO[1,2 B;3,4 B'] DIPYRAN 8 ONE; ANTINEOPLASTIC AGENT; APOPTOSIS INDUCING FACTOR; CASPASE 2; CASPASE 3; CASPASE 8; CASPASE 9; CASPASE INHIBITOR; GLYCOPROTEIN P; PROTEIN P21; PROTEIN P53; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CALOPHYLLUM; CELL CYCLE; CELL CYCLE G1 PHASE; CELL CYCLE S PHASE; CELL GROWTH; CELL PROLIFERATION; COLONY FORMATION; CONTROLLED STUDY; GROWTH INHIBITION; HEMATOPOIESIS; HUMAN; HUMAN CELL; IC 50; LEUKEMIA CELL; LIVER CELL; PRIORITY JOURNAL; PROTEIN EXPRESSION;

ADENOCARCINOMA; ANTINEOPLASTIC AGENTS, PHYTOGENIC; APOPTOSIS; BRAZIL; CALOPHYLLUM; CASPASES; CELL LINE, TUMOR; COLORECTAL NEOPLASMS; COUMARINS; FLOW CYTOMETRY; GENE EXPRESSION REGULATION, NEOPLASTIC; HUMANS; LEUKEMIA;

EID: 8644240960     PISSN: 00207136     EISSN: None     Source Type: Journal    
DOI: 10.1002/ijc.20505     Document Type: Article

References (45)

1. Del Poeta G, Venditti A, Del Principe MI, Maurillo L, Buccisano F, Tamburini A, Cox MC, Franchi A, Bruno A, Mazzone C, Panetta P, Suppo G, et al. Amount of spontaneous apoptosis detected by Bax/Bcl-2 ratio predicts outcome in acute myeloid leukemia (AML). Blood 2003;101:2125-31.
2. Döhner H, Fischer K, Bentz M, Hansen K, Benner A, Cabot G, Diehl D, Schlenk R, Coy J, Stilgenbauer S, Volkmann M, Galle PR, et al. p53 gene deletion predicts for poor survival and non-response to therapy with purine analogs in chronic B-cell leukemias. Blood 1995;85:1580-9.
3. Urasaki Y, Ueda T, Yoshida A, Fukushima T, Takeuchi N, Tsuruo T, Nakamura T. Establishment of a daunorubicin-resistant cell line which shows multi-drug resistance by multifactorial mechanisms. Anticancer Res 1996;16:709-14.
4. van der Kolk, DM, de Vries EG, van Putten WJ, Verdonck LF, Ossenkoppele GJ, Verhoef GE, Vellenga E. P-glycoprotein and multidrug resistance protein activities in relation to treatment outcome in acute myeloid leukemia. Clin Cancer Res 2000;6:3205-14.
5. Ito C, Itoigawa M, Mishina Y, Filho VC, Mukainaka T, Tokuda H, Nishino H, Furukawa H. Chemical constituents of Calophyllum brasiliense: structure elucidation of seven new xanthones and their cancer chemopreventive activity. J Nat Prod 2002;65:267-72.
6. Ito C, Itoigawa M, Mishina Y, Filho VC, Enjo F, Tokuda H, Nishino H, Furukawa H. Chemical constituents of Calophyllum brasiliense Part 2: structure of three new coumarins and cancer chemopreventive activity of 4-substituted coumarins. J Nat Prod 2003;66:368-71.
7. Lin X, Ramamurthi K, Mishima M, Kondo A, Christen RD, Howell SB. p53 modulates the effect of loss of DNA mismatch repair on the sensitivity of human colon cancer cells to the cytotoxic and mutagenic effects of cisplatin. Cancer Res 2001;61:1508-16.
8. + leukemia activity of imatinib mesylate. Blood 2003;102:2229-35.
9. Kimura S, Kuroda J, Segawa H, Sato K, Nogawa M, Yuasa T, Ottmann OG, Maekawa T. Anti-proliferative efficacy of the third generation bisphosphonate zoledronic acid combined with other anticancer drugs in leukemic cell lines. Int J Hematol 2004;79:37-43.
10. Kuroda J, Kimura S, Segawa H, Sato K, Matsumoto S, Nogawa M, Yuasa T, Kobayashi Y, Yoshikawa T, Ottmann OG, Maekawa T. p53-independent anti-tumor effects of the nitrogen-containing bisphosphonate zoledronic acid. Cancer Sci 2004;95:186-92
11. Kimura S, Maekawa T, Hirakawa K, Murakami A, Abe T. Alterations of c-myc expression by antisense oligodeoxynucleotides enhance the induction of apoptosis in HL-60 cells. Cancer Res 1995;55:1379-84.
12. Cave A, Debray M, Henry G, Kunesch G, Polonsky J. Chemie organique. Sur la structure d'une alkyl-4 coumrine isolee de Calophyllum inophyllum. CR Acad Sci Paris 1972;275:1105-7.
13. Spino C, Dodier M, Sotheeswaran S. Anti-HIV coumarins from Calophyllum seed oil. Anti-HIV coumarins from Calophyllum seed oil. Bioorg Med Chem Lett 1998;8:3475-8.
14. Bi S, Hughes T, Bungey J, Chase A, de Fabritiis P, Goldman JM. p53 in chronic myeloid leukemia cell lines. Leukemia 1992;6: 839-42.
15. Drexler HG, Fombonne S, Matsuo Y, Hu ZB, Hamaguchi H, Uphoff CC. p53 alterations in human leukemia-lymphoma cell lines: in vitro artifact or prerequisite for cell immortalization? Leukemia 2000;14:198-206
16. Nicholson DW, Thornberry NA. Caspases: killer proteases. Trends Biochem Sci 1997;22:299-306.
17. Wolf BB, Green DR. Suicidal tendencies: apoptotic cell death by caspase family proteinases. J Biol Chem 1999;274:20049-52.
18. Engels IH, Stepczynska A, Stroh C, Lauber K, Berg C, Schwenzer R, Wajant H, Jänicke RU, Porter AG, Belka C, Gregor M, Schulze-Osthoff K, et al. Caspase-8/FLICE functions as an executioner caspase in anticancer drug-induced apoptosis. Oncogene 2000;19:4563-73.
19. Slee EA, Harte MT, Kluck RM, Wolf BB, Casiano CA, Newmeyer DD, Wang HG, Reed JC, Nicholson DW, Alnemri ES, Green DR, Martin SJ. Ordering the cytochrome c-initiated caspase cascade: hierarchical activation of caspases-2, -3, -6, -7, -8, and -10 in a caspase-9-dependent manner. J Cell Biol 1999;144:281-92.
20. Druker BJ, Talpaz M, Resta DJ, Peng B, Buchdunger E, Ford JM, Lydon NB, Kantarjian H, Capdeville R., Ohno-Jones S, Sawyers CL. Efficacy and safety of a specific inhibitor of the BCR-ABL tyrosine kinase in chronic myeloid leukemia. N Engl J Med 2001;344:1031-7.
21. Ranson M, Hammond LA, Ferry D, Kris M, Tullo A, Murray PI, Miller V, Averbuch S, Ochs J, Morris C, Feyereilova A, Swaisland H, Rowinsky EK. ZD1839, a selective oral epidermal growth factor receptor-tyrosine kinase inhibitor, is well tolerated and active in patients with solid, malignant tumors: results of a phase I trial. J Clin Oncol 2002;20:2240-50.
22. Miller WH Jr, Schipper HM, Lee JS, Singer J, Waxman S. Mechanisms of action of arsenic trioxide. Cancer Res 2002;62:3893-03.
23. Zhou DC, Zittoun R, Marie JP. Homoharringtonine: an effective new natural product in cancer chemotherapy. Bull Cancer 1995;82:987-95.
24. Gorre ME, Mohammed M, Ellwood K, Hsu N, Paquette R, Rao PN, Sawyers CL. Clinical resistance to STI-571 cancer therapy caused by BCR-ABL gene mutation or amplification. Science 2001;293:876-80.
25. Hofmann WK, Jones LC, Lemp NA, de Vos S, Gschaidmeier H, Hoelzer D, Ottmann OG, Koeffler HP. Ph(+) acute lymphoblastic leukemia resistant to the tyrosine kinase inhibitor ST1571 has a unique BCR-ABL gene mutation. Blood 2002;99: 1860-2.
26. Kawazu K, Ohigashi H, Mitsui T. The piscicidal constituents of Calophyllum inophyllum Linu. Tetrahedron Lett 1968;19:2383-5.
27. Kijjoa A, Gonzalez MJ, Pinto MM, Silva AM, Anantachoke C, Herz W. Xanthones from Calophyllum teysmannii var. inophylloide. Phytochemistry 2000;55: 833-6.
28. Govindachari TR, Viswanathan N, Pai BR, Rao R, Srinivasan M. Triterpenes of Calophyllum inophyllum Linn. Tetrahedron 1967;23:1901-10.
29. Itoigawa M, Ito C, Tan HT, Kuchide M, Tokuda H, Nishino H, Furukawa H. Cancer chemopreventive agents, 4-phenylcoumarins from Calophyllum inophyllum. Cancer Lett 2001;169:15-9.
30. Bennett RN, Wallsgrove RM. Secondary metabolites in plant defence mechanisms. New Phytologist 1994;127:617-33.
31. Ashkenazi A, Dixit VM Death receptors: signaling and modulation. Science 1998;281:1305-8.
32. Friesen C, Herr I, Krammer PH, Debatin KM. Involvement of the CD95 (AP0-1/FAS) receptor/ligand system in drug-induced apoptosis in leukemia cells. Nat Med 1996;2:574-7.
33. Srivastava RK, Sasaki CY, Hardwick JM, Longo DL. Bcl-2-mediated drug resistance: inhibition of apoptosis by blocking nuclear factor of activated T lymphocytes (NFAT)-induced Fas ligand transcription. J Exp Med 1999;190:253-65.
34. 1-phase progression. Genes Dev 1999;13:1501-12.
35. KIP2 genes in human gastric cancer. Exp Mol Med 2000;32:79-83.
36. Avramis VI, Nandy P, Kwock R, Solorzano MM, Mukherjee SK, Danenberg P, Cohen LJ. Increased p21/WAF-1 and p53 protein levels following sequential three drug combination regimen of fludarabine, cytarabine and docetaxel induces apoptosis in human leukemia cells. Anticancer Res 1998;18:2327-38.
37. Katayose Y, Kim M, Rakkar AN, Li Z, Cowan KH, Seth P. Promoting apoptosis: a novel activity associated with the cyclin-dependent kinase inhibitor p27. Cancer Res 1997;57: 5441-5.
38. 1 cell cycle arrest and apoptosis in tumor cells in which the pathway is constitutively activated: up-regulation of p27(Kip1). J Biol Chem 2001;276:2686-92.
39. Sun Y, Tan M, Duan H, Swaroop M. SAG/ROC/Rbx/Hrt a zinc RING finger gene, family: molecular cloning, biochemical properties, and biological functions. Antioxid Redox Signal 2001;3:635-50.
40. Yan Y, Frisen J, Lee MH, Massague J, Barbacid M. Ablation of the CDK inhibitor p57Kip2 results in increased apoptosis and delayed differentiation during mouse development. Genes Dev 1997;11:973-83.
41. KIP2 indicates a role in Beckwith-Wiedemann syndrome. Nature 1997;387:151-8.
42. Ito Y, Takeda T, Sakon M, Tsujimoto M, Monden M, Matsuura N. Expression of p57/Kip2 protein in hepatocellular carcinoma. Oncology 2001;61: 221-5
43. Oya M, Schulz WA. Decreased expression of p57(KIP2)mRNA in human bladder cancer. Br J Cancer 2000;83:626-31.
44. Samuelsson MK, Pazirandeh A, Okret S. A pro-apoptotic effect of the CDK inhibitor p57(Kip2) on staurosporine-induced apoptosis in HeLa cells. Biochem Biophys Res Commun 2002;296:702-9.
45. Bradshaw DM, Arceci RJ. Clinical relevance of transmembrane drug efflux as a mechanism of multidrug resistance. J Clin Oncol 1998;16: 3674-90.