Downregulation of c-FLIP, XIaP and Mcl-1 protein as well as depletion of reduced glutathione contribute to the apoptosis induction of glycyrrhetinic acid derivatives in leukemia cells

Cancer Biology and Therapy

Volumn 9, Issue 2, 2010, Pages

  Song, Dandan ^a   Gao, Yuan ^a   Wang, Rui ^b   Liu, Dan ^a   Zhao, Linxiang ^a   Jing, Yongkui ^b  

^a SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

^b MOUNT SINAI SCHOOL OF MEDICINE   (United States)

Author keywords

Antiapoptotic protein; Apoptosis; Glutathione; Glycyrrhetinic acid derivatives; Leukemia

Indexed keywords

ACETYLCYSTEINE; CARBON; CASPASE 8; DEATH RECEPTOR 4; DEATH RECEPTOR 5; FLICE INHIBITORY PROTEIN; GLUTATHIONE; GLYCYRRHETINIC ACID DERIVATIVE; HYDROGEN PEROXIDE; METHYL 2 CYANO 3,11 DIOXOOLEANA 1,12 DIEN 30 OATE; METHYL 2 CYANO 3,12 DIOXOOLEANA 1,12 DIEN 30 OATE; PROTEIN BNIP3; PROTEIN MCL 1; UNCLASSIFIED DRUG; X LINKED INHIBITOR OF APOPTOSIS; ANTINEOPLASTIC AGENT; CFLAR PROTEIN, HUMAN; DRUG DERIVATIVE; GLYCYRRHETINIC ACID; METHYL 2 CYANO 3,12 DIOXOOLEANA 1, 12 DIEN 30 OATE; METHYL 2-CYANO-3,11-DIOXOOLEANA-1,12-DIEN-30-OATE; METHYL 2-CYANO-3,12-DIOXOOLEANA-1, 12-DIEN-30-OATE; MYELOID CELL LEUKEMIA SEQUENCE 1 PROTEIN; PROTEIN BCL 2; TUMOR PROTEIN; XIAP PROTEIN, HUMAN;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CELL STRAIN HL 60; CHEMOSENSITIVITY; CONTROLLED STUDY; DOWN REGULATION; DRUG ACTIVITY; DRUG EFFECT; DRUG POTENCY; DRUG PROTEIN BINDING; ESTERIFICATION; HUMAN; HUMAN CELL; LEUKEMIA CELL; LEUKEMIA CELL LINE; MITOCHONDRIAL MEMBRANE; MITOCHONDRIAL MEMBRANE POTENTIAL; MOLECULAR INTERACTION; NONHUMAN; PROTEIN DEPLETION; PROTEIN EXPRESSION; ULTRAVIOLET SPECTROPHOTOMETRY; ACUTE GRANULOCYTIC LEUKEMIA; BIOSYNTHESIS; CELL STRAIN K 562; CELL STRAIN U937; DRUG SCREENING; GENE EXPRESSION REGULATION; GENETICS; METABOLISM; OXIDATION REDUCTION REACTION; PATHOLOGY;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; APOPTOSIS; CASP8 AND FADD-LIKE APOPTOSIS REGULATING PROTEIN; DOWN-REGULATION; DRUG SCREENING ASSAYS, ANTITUMOR; GENE EXPRESSION REGULATION, LEUKEMIC; GLUTATHIONE; GLYCYRRHETINIC ACID; HL-60 CELLS; HUMANS; JURKAT CELLS; K562 CELLS; LEUKEMIA, MYELOID, ACUTE; NEOPLASM PROTEINS; OXIDATION-REDUCTION; PROTO-ONCOGENE PROTEINS C-BCL-2; U937 CELLS; X-LINKED INHIBITOR OF APOPTOSIS PROTEIN;

EID: 75749089608     PISSN: 15384047     EISSN: 15558576     Source Type: Journal    
DOI: None     Document Type: Article

References (47)

1. Yano S, Harada M, Watanabe K, et al. Antiulcer activities of glycyrrhetinic acid derivatives in experimental gastric lesion models. Chem Pharm Bull (Tokyo) 1989; 37:2500-4.
2. Inoue H, Mori T, Shibata S, Saito H. Pharmacological activities of glycyrrhetinic acid derivatives: analgesic and anti-type IV allergic effects. Chem Pharm Bull (Tokyo) 1987; 35:3888-93.
3. Sato H, Goto W, Yamamura J, et al. Therapeutic basis of glycyrrhizin on chronic hepatitis B. Antiviral Res 1996; 30:171-7.
4. Arase Y, Ikeda K, Murashima N, et al. The long term efficacy of glycyrrhizin in chronic hepatitis C patients. Cancer 1997; 79:1494-500.
5. Finney RS, Somers GF, Wilkinson JH. The pharmacological properties of glycyrrhetinic acid; a new anti-inflammatory drug. J Pharm Pharmacol 1958; 10:687-95.
6. Nabekura T, Yamaki T, Ueno K, Kitagawa S. Inhibition of P-glycoprotein and multidrug resistance protein 1 by dietary phytochemicals. Cancer Chemother Pharmacol 2008; 62:867-73.
7. Huang L, Yu D, Ho P, Qian K, Lee KH, Chen CH. Synthesis and proteasome inhibition of glycyrrhetinic acid derivatives. Bioorg Med Chem 2008; 16:6696-701.
8. Hibasami H, Iwase H, Yoshioka K, Takahashi H. Glycyrrhizin induces apoptosis in human stomach cancer KATO III and human promyelotic leukemia HL-60 cells. Int J Mol Med 2005; 16:233-6.
9. Hibasami H, Iwase H, Yoshioka K, Takahashi H. Glycyrrhetic acid (a metabolic substance and aglycon of glycyrrhizin) induces apoptosis in human hepatoma, promyelotic leukemia and stomach cancer cells. Int J Mol Med 2006; 17:215-9.
10. 1 arrest and apoptosis in human hepatocellular carcinoma HepG2. Anticancer Res 2005; 25:4043-7.
11. Liu D, Song D, Guo G, et al. The synthesis of 18beta-glycyrrhetinic acid derivatives which have increased antiproliferative and apoptotic effects in leukemia cells. Bioorg Med Chem 2007; 15:5432-9.
12. Honda T, Rounds BV, Gribble GW, Suh N, Wang Y, Sporn MB. Design and synthesis of 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, a novel and highly active inhibitor of nitric oxide production in mouse macrophages. Bioorg Med Chem Lett 1998; 8:2711-4.
13. Suh N, Wang Y, Honda T, et al. A novel synthetic oleanane triterpenoid, 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, with potent differentiating, antiproliferative, and anti-inflammatory activity. Cancer Res 1999; 59:336-41.
14. Kim KB, Lotan R, Yue P, et al. Identification of a novel synthetic triterpenoid, methyl-2-cyano-3,12-dioxooleana-1,9-dien-28-oate, that potently induces caspase-mediated apoptosis in human lung cancer cells. Mol Cancer Ther 2002; 1:177-84.
15. Konopleva M, Tsao T, Ruvolo P, et al. Novel triterpenoid CDDO-Me is a potent inducer of apoptosis and differentiation in acute myelogenous leukemia. Blood 2002; 99:326-35.
16. Ikeda T, Sporn M, Honda T, Gribble GW, Kufe D. The novel triterpenoid CDDO and its derivatives induce apoptosis by disruption of intracellular redox balance. Cancer Res 2003; 63:5551-8.
17. Sun K, Li M, Konopleva M, et al. The synthetic triterpenoid, CDDO, suppresses alloreactive T cell responses and reduces murine early acute graft-versus-host disease mortality. Biol Blood Marrow Transplant 2007; 13:521-9.
18. Inoue S, Snowden RT, Dyer MJ, Cohen GM. CDDO induces apoptosis via the intrinsic pathway in lymphoid cells. Leukemia 2004; 18:948-52.
19. Hyer ML, Shi R, Krajewska M, et al. Apoptotic activity and mechanism of 2-cyano-3,12-dioxoolean-1,9-dien-28-oic-acid and related synthetic triterpenoids in prostate cancer. Cancer Res 2008; 68:2927-33.
20. Zou W, Liu X, Yue P, et al. c-Jun NH2-terminal kinase-mediated upregulation of death receptor 5 contributes to induction of apoptosis by the novel synthetic triterpenoid methyl-2-cyano-3,12-dioxooleana-1,9-dien-28-oate in human lung cancer cells. Cancer Res 2004; 64:7570-8.
21. Zou W, Chen S, Liu X, et al. c-FLIP downregulation contributes to apoptosis induction by the novel synthetic triterpenoid methyl-2-cyano-3,12- dioxooleana-1,9-dien-28-oate (CDDO-Me) in human lung cancer cells. Cancer Biol Ther 2007; 6:1614-20.
22. Suh WS, Kim YS, Schimmer AD, et al. Synthetic triterpenoids activate a pathway for apoptosis in AML cells involving downregulation of FLIP and sensitization to TRAIL. Leukemia 2003; 17:2122-9.
23. Ikeda T, Nakata Y, Kimura F, et al. Induction of redox imbalance and apoptosis in multiple myeloma cells by the novel triterpenoid 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid. Mol Cancer Ther 2004; 3:39-45.
24. Samudio I, Konopleva M, Hail N Jr, et al. 2-Cyano-3,12-dioxooleana-1,9- dien-28-imidazolide (CDDOIm) directly targets mitochondrial glutathione to induce apoptosis in pancreatic cancer. J Biol Chem 2005; 280:36273-82.
25. Yue P, Zhou Z, Khuri FR, Sun SY. Depletion of intracellular glutathione contributes to JNK-mediated death receptor 5 upregulation and apoptosis induction by the novel synthetic triterpenoid methyl-2-cyano-3,12-dioxooleana-1, 9-dien-28-oate (CDDO-Me). Cancer Biol Ther 2006; 5:492-7.
26. Jing Y, Dai J, Chalmers-Redman RM, Tatton WG, Waxman S. Arsenic trioxide selectively induces acute promyelocytic leukemia cell apoptosis via a hydrogen peroxide-dependent pathway. Blood 1999; 94:2102-11.
27. Kasugai I, Yamada M. High production of catalase in hydrogen peroxide-resistant human leukemia HL-60 cell lines. Leuk Res 1992; 16:173-9.
28. Lombard C, Nagarkatti M, Nagarkatti PS. Targeting cannabinoid receptors to treat leukemia: role of crosstalk between extrinsic and intrinsic pathways in Delta9-tetrahydrocannabinol (THC)-induced apoptosis of Jurkat cells. Leuk Res 2005; 29:915-22.
29. Dai J, Weinberg RS, Waxman S, Jing Y. Malignant cells can be sensitized to undergo growth inhibition and apoptosis by arsenic trioxide through modulation of the glutathione redox system. Blood 1999; 93:268-77.
30. Emaus RK, Grunwald R, Lemasters JJ. Rhodamine 123 as a probe of transmembrane potential in isolated ratliver mitochondria: spectral and metabolic properties. Biochim Biophys Acta 1986; 850:436-48.
31. Chen D, Chan R, Waxman S, Jing Y. Buthionine sulfoximine enhancement of arsenic trioxide-induced apoptosis in leukemia and lymphoma cells is mediated via activation of c-Jun NH2-terminal kinase and upregulation of death receptors. Cancer Res 2006; 66:11416-23.
32. Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 1976; 72:248-54.
33. Fernandez-Checa JC, Kaplowitz N. The use of monochlorobimane to determine hepatic GSH levels and synthesis. Anal Biochem 1990; 190:212-9.
34. Liby K, Yore MM, Roebuck BD, et al. A novel acetylenic tricyclic bis-(cyano enone) potently induces phase 2 cytoprotective pathways and blocks liver carcinogenesis induced by aflatoxin. Cancer Res 2008; 68:6727-33.
35. Green DR, Reed JC. Mitochondria and apoptosis. Science 1998; 281:1309-12.
36. Ott M, Gogvadze V, Orrenius S, Zhivotovsky B. Mitochondria, oxidative stress and cell death. Apoptosis 2007; 12:913-22.
37. Fiore C, Salvi M, Palermo M, Sinigaglia G, Armanini D, Toninello A. On the mechanism of mitochondrial permeability transition induction by glycyrrhetinic acid. Biochim Biophys Acta 2004; 1658:195-201.
38. Voehringer DW. BCL-2 and glutathione: alterations in cellular redox state that regulate apoptosis sensitivity. Free Radic Biol Med 1999; 27:945-50.
39. Hall AG. Review: The role of glutathione in the regulation of apoptosis. Eur J Clin Invest 1999; 29:238-45.
40. Stadheim TA, Suh N, Ganju N, Sporn MB, Eastman A. The novel triterpenoid 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid (CDDO) potently enhances apoptosis induced by tumor necrosis factor in human leukemia cells. J Biol Chem 2002; 277:16448-55.
41. Couch RD, Browning RG, Honda T, et al. Studies on the reactivity of CDDO, a promising new chemopreventive and chemotherapeutic agent: implications for a molecular mechanism of action. Bioorg Med Chem Lett 2005; 15:2215-9.
42. Ito Y, Pandey P, Place A, et al. The novel triterpenoid 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid induces apoptosis of human myeloid leukemia cells by a caspase-8-dependent mechanism. Cell Growth Differ 2000; 11:261-7.
43. Konopleva M, Tsao T, Estrov Z, et al. The synthetic triterpenoid 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid induces caspase-dependent and -independent apoptosis in acute myelogenous leukemia. Cancer Res 2004; 64:7927-35.
44. Samudio I, Konopleva M, Pelicano H, et al. A novel mechanism of action of methyl-2-cyano-3,12 dioxoolean-1,9 diene-28-oate: direct permeabilization of the inner mitochondrial membrane to inhibit electron transport and induce apoptosis. Mol Pharmacol 2006; 69:1182-93.
45. Ito Y, Pandey P, Sporn MB, Datta R, Kharbanda S, Kufe D. The novel triterpenoid CDDO induces apoptosis and differentiation of human osteosarcoma cells by a caspase-8 dependent mechanism. Mol Pharmacol 2001; 59:1094-9.
46. Ahmad R, Raina D, Meyer C, Kharbanda S, Kufe D. Triterpenoid CDDO-Me blocks the NFkappaB pathway by direct inhibition of IKKbeta on Cys-179. J Biol Chem 2006; 281:35764-9.
47. Yore MM, Liby KT, Honda T, Gribble GW, Sporn MB. The synthetic triterpenoid 1-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]imidazole blocks nuclear factor-kappaB activation through direct inhibition of IkappaB kinase beta. Mol Cancer Ther 2006; 5:3232-9.