Biochemical mechanisms underlying the pro-apoptotic activity of 7,8-dihydroxy-4-methylcoumarin in human leukemic cells

Biochemical Pharmacology

Volumn 75, Issue 3, 2008, Pages 725-736

  Riveiro, Maria E ^a,b,c   Vazquez, Ramiro ^a,b,c   Moglioni, Albertina ^a,c   Gomez, Natalia ^a,c   Baldi, Alberto ^b,c   Davio, Carlos ^a,c   Shayo, Carina ^b,c  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

^b INST DE BIOL Y MED EXPERIMENTAL   (Argentina)

^c Consejo Nacional de Investigaciones Científicas y Técnicas ^*  (Argentina)

Author keywords

Apoptosis induction; DHMC; Hydroxycoumarins; Leukemia; Signal transduction

Indexed keywords

7,8 DIHYDROXY 4 METHYLCOUMARIN; COUMARIN DERIVATIVE; MITOGEN ACTIVATED PROTEIN KINASE 1; MITOGEN ACTIVATED PROTEIN KINASE 3; PROTEIN KINASE B; PROTEIN P53; STRESS ACTIVATED PROTEIN KINASE; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CELL CYCLE; CONTROLLED STUDY; DOWN REGULATION; DRUG ACTIVITY; DRUG MECHANISM; ENZYME ACTIVATION; ENZYME INHIBITION; HUMAN; HUMAN CELL; LEUKEMIA CELL; ONCOGENE MYC; PRIORITY JOURNAL; PROTO ONCOGENE;

1-PHOSPHATIDYLINOSITOL 3-KINASE; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL DIFFERENTIATION; COUMARINS; GENES, MYC; HL-60 CELLS; HUMANS; LEUKEMIA; LEUKOCYTES, MONONUCLEAR; MITOGEN-ACTIVATED PROTEIN KINASE KINASES; PROTO-ONCOGENE PROTEINS C-AKT; U937 CELLS;

EID: 37849027920     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2007.09.025     Document Type: Article

References (61)

1. Leszczyniecka M., Roberts T., Dent P., Grant S., and Fisher P.B. Differentiation therapy of human cancer: basic science and clinical applications. Pharmacol Ther 90 (2001) 105-156
2. Tsiftsoglou A.S., Pappas I.S., and Vizirianakis I.S. Mechanisms involved in the induced differentiation of leukemia cells. Pharmacol Ther 100 (2003) 257-290
3. Johnson S.A. Clinical pharmacokinetics of nucleoside analogues: focus on haematological malignancies. Clin Pharmacokinet 39 (2000) 5-26
4. Roboz G.J. Treatment of acute myeloid leukemia in older patients. Expert Rev Anticancer Ther 7 (2007) 285-295
5. Thatte U., Bagadey S., and Dahanukar S. Modulation of programmed cell death by medicinal plants. Cell Mol Biol (Noisy-le-grand) 46 (2000) 199-214
6. O'Kennedy R., and Thornes R.D. Coumarins: biology, applications and mode of action (1997), John Wiley & Sons, Chichester, United Kingdom
7. Lake B.G. Coumarin metabolism, toxicity and carcinogenicity: relevance for human risk assessment. Food Chem Toxicol 37 (1999) 423-453
8. Manolov I., Topashka-Ancheva M., and Klouchek E. The synthesis, toxicological and comparative cytogenetic characteristics of the anticoagulant warfarin. Eksp Med Morfol 31 (1993) 49-60
9. Fylaktakidou K.C., Hadjipavlou-Litina D.J., Litinas K.E., and Nicolaides D.N. Natural and synthetic coumarin derivatives with anti-inflammatory/antioxidant activities. Curr Pharm Des 10 (2004) 3813-3833
10. Hadjipavlou-Litina D.J. New diaminoether coumarinic derivatives with anti-inflammatory activity. Arzneimittelforschung 50 (2000) 631-635
11. Kostova I., Raleva S., Genova P., and Argirova R. Structure-activity relationships of synthetic coumarins as HIV-1 inhibitors. Bioinorg Chem Appl (2006) 68274
12. Periers A.M., Laurin P., Ferroud D., Haesslein J.L., Klich M., Dupuis-Hamelin C., et al. Coumarin inhibitors of gyrase B with N-propargyloxy-carbamate as an effective pyrrole bioisostere. Bioorg Med Chem Lett 10 (2000) 161-165
13. Schio L., Chatreaux F., Loyau V., Murer M., Ferreira A., Mauvais P., et al. Fine tuning of physico-chemical parameters to optimise a new series of novobiocin analogues. Bioorg Med Chem Lett 11 (2001) 1461-1464
14. Ghani U., Ng K.K., Atta ur R., Choudhary M.I., Ullah N., and James M.N. Crystal structure of gamma-chymotrypsin in complex with 7-hydroxycoumarin. J Mol Biol 314 (2001) 519-525
15. Gnerre C., Catto M., Leonetti F., Weber P., Carrupt P.A., Altomare C., et al. Inhibition of monoamine oxidases by functionalized coumarin derivatives: biological activities, QSARs, and 3D-QSARs. J Med Chem 43 (2000) 4747-4758
16. Raj H.G., Parmar V.S., Jain S.C., Goel S., Poonam, Himanshu, et al. Mechanism of biochemical action of substituted 4-methylbenzopyran-2-ones. Part I: dioxygenated 4-methyl coumarins as superb antioxidant and radical scavenging agents. Bioorg Med Chem 6 (1998) 833-839
17. Vajragupta O., Boonchoong P., and Wongkrajang Y. Comparative quantitative structure-activity study of radical scavengers. Bioorg Med Chem 8 (2000) 2617-2628
18. Molina-Jimenez M.F., Sanchez-Reus M.I., and Benedi J. Effect of fraxetin and myricetin on rotenone-induced cytotoxicity in SH-SY5Y cells: comparison with N-acetylcysteine. Eur J Pharmacol 472 (2003) 81-87
19. Appendino G., Bianchi F., Bader A., Campagnuolo C., Fattorusso E., Taglialatela-Scafati O., et al. Coumarins from Opopanax chironium. New dihydrofuranocoumarins and differential induction of apoptosis by imperatorin and heraclenin. J Nat Prod 67 (2004) 532-536
20. Finn G.J., Kenealy E., Creaven B.S., and Egan D.A. In vitro cytotoxic potential and mechanism of action of selected coumarins, using human renal cell lines. Cancer Lett 183 (2002) 61-68
21. Kawaii S., Tomono Y., Ogawa K., Sugiura M., Yano M., and Yoshizawa Y. The antiproliferative effect of coumarins on several cancer cell lines. Anticancer Res 21 (2001) 917-923
22. Kawaii S., Tomono Y., Ogawa K., Sugiura M., Yano M., Yoshizawa Y., et al. Antiproliferative effect of isopentenylated coumarins on several cancer cell lines. Anticancer Res 21 (2001) 1905-1911
23. Chu C.Y., Tsai Y.Y., Wang C.J., Lin W.L., and Tseng T.H. Induction of apoptosis by esculetin in human leukemia cells. Eur J Pharmacol 416 (2001) 25-32
24. Wang C.J., Hsieh Y.J., Chu C.Y., Lin Y.L., and Tseng T.H. Inhibition of cell cycle progression in human leukemia HL-60 cells by esculetin. Cancer Lett 183 (2002) 163-168
25. Lopez-Gonzalez J.S., Prado-Garcia H., Aguilar-Cazares D., Molina-Guarneros J.A., Morales-Fuentes J., and Mandoki J.J. Apoptosis and cell cycle disturbances induced by coumarin and 7-hydroxycoumarin on human lung carcinoma cell lines. Lung Cancer 43 (2004) 275-283
26. Hofmanova J., Kozubik A., Dusek L., and Pachernik J. Inhibitors of lipoxygenase metabolism exert synergistic effects with retinoic acid on differentiation of human leukemia HL-60 cells. Eur J Pharmacol 350 (1998) 273-284
27. Finn G.J., Creaven B.S., and Egan D.A. Daphnetin induced differentiation of human renal carcinoma cells and its mediation by p38 mitogen-activated protein kinase. Biochem Pharmacol 67 (2004) 1779-1788
28. Riveiro M.E., Shayo C., Monczor F., Fernandez N., Baldi A., De Kimpe N., et al. Induction of cell differentiation in human leukemia U-937 cells by 5-oxygenated-6,7-methylenedioxycoumarins from Pterocaulon polystachyum. Cancer Lett 210 (2004) 179-188
29. Han S., Zhou V., Pan S., Liu Y., Hornsby M., McMullan D., et al. Identification of coumarin derivatives as a novel class of allosteric MEK1 inhibitors. Bioorg Med Chem Lett 15 (2005) 5467-5473
30. Finn G.J., Creaven B.S., and Egan D.A. Investigation of intracellular signalling events mediating the mechanism of action of 7-hydroxycoumarin and 6-nitro-7-hdroxycoumarin in human renal cells. Cancer Lett 205 (2004) 69-79
31. Finn G., Creaven B., and Egan D. Modulation of mitogen-activated protein kinases by 6-nitro-7-hydroxycoumarin mediates apoptosis in renal carcinoma cells. Eur J Pharmacol 481 (2003) 159-167
32. Yang E.B., Zhao Y.N., Zhang K., and Mack P. Daphnetin, one of coumarin derivatives, is a protein kinase inhibitor. Biochem Biophys Res Commun 260 (1999) 682-685
33. Hadi S.M., Asad S.F., Singh S., and Ahmad A. Putative mechanism for anticancer and apoptosis-inducing properties of plant-derived polyphenolic compounds. IUBMB Life 50 (2000) 167-171
34. Kim E.K., Kwon K.B., Shin B.C., Seo E.A., Lee Y.R., Kim J.S., et al. Scopoletin induces apoptosis in human promyeloleukemic cells, accompanied by activations of nuclear factor kappaB and caspase-3. Life Sci 77 (2005) 824-836
35. Parborell F., Irusta G., Vitale A., Gonzalez O., Pecci A., and Tesone M. Gonadotropin-releasing hormone antagonist antide inhibits apoptosis of preovulatory follicle cells in rat ovary. Biol Reprod 72 (2005) 659-666
36. Martinsson P., Liminga G., Nygren P., and Larsson R. Characteristics of etoposide-induced apoptotic cell death in the U-937 human lymphoma cell line. Anticancer Drugs 12 (2001) 699-705
37. Harris P., and Ralph P. Human leukemic models of myelomonocytic development: a review of the HL-60 and U-937 cell lines. J Leukoc Biol 37 (1985) 407-422
38. Sundstrom C., and Nilsson K. Establishment and characterization of a human histiocytic lymphoma cell line (U-937). Int J Cancer 17 (1976) 565-577
39. Hoffman B., and Liebermann D.A. The proto-oncogene c-myc and apoptosis. Oncogene 17 (1998) 3351-3357
40. Kopnin B.P. Targets of oncogenes and tumor suppressors: key for understanding basic mechanisms of carcinogenesis. Biochemistry (Mosc) 65 (2000) 2-27
41. Krasilnikov M.A. Phosphatidylinositol-3 kinase dependent pathways: the role in control of cell growth, survival, and malignant transformation. Biochemistry (Mosc) 65 (2000) 59-67
42. Cowan K.J., and Storey K.B. Mitogen-activated protein kinases: new signaling pathways functioning in cellular responses to environmental stress. J Exp Biol 206 (2003) 1107-1115
43. Jarvis W.D., Johnson C.R., Fornari F.A., Park J.S., Dent P., and Grant S. Evidence that the apoptotic actions of etoposide are independent of c-Jun/activating protein-1-mediated transregulation. J Pharmacol Exp Ther 290 (1999) 1384-1392
44. Chen Y.R., Meyer C.F., and Tan T.H. Persistent activation of c-Jun N-terminal kinase 1 (JNK1) in gamma radiation-induced apoptosis. J Biol Chem 271 (1996) 631-634
45. Paul A., Wilson S., Belham C.M., Robinson C.J., Scott P.H., Gould G.W., et al. Stress-activated protein kinases: activation, regulation and function. Cell Signal 9 (1997) 403-410
46. Marshall M.E., Butler K., Cantrell J., Wiseman C., and Mendelsohn L. Treatment of advanced malignant melanoma with coumarin and cimetidine: a pilot study. Cancer Chemother Pharmacol 24 (1989) 65-66
47. Nolte H., Pedersen L., and Mouridsen H.T. Combined treatment of advanced malignant melanoma with coumarin and cimetidine. Anticancer Res 7 (1987) 449-450
48. Marshall M.E., Mendelsohn L., Butler K., Cantrell J., Harvey J., and Macdonald J. Treatment of non-small cell lung cancer with coumarin and cimetidine. Cancer Treat Rep 71 (1987) 91-92
49. Purohit A., Woo L.W., Barrow D., Hejaz H.A., Nicholson R.I., Potter B.V., et al. Non-steroidal and steroidal sulfamates: new drugs for cancer therapy. Mol Cell Endocrinol 171 (2001) 129-135
50. Richon V.M., Webb Y., Merger R., Sheppard T., Jursic B., Ngo L., et al. Second generation hybrid polar compounds are potent inducers of transformed cell differentiation. Proc Natl Acad Sci USA 93 (1996) 5705-5708
51. Wang Z., Wang S., Fisher P.B., Dent P., and Grant S. Evidence of a functional role for the cyclin-dependent kinase inhibitor p21CIP1 in leukemic cell (U-937) differentiation induced by low concentrations of 1-beta-D-arabinofuranosylcytosine. Differentiation 66 (2000) 1-13
52. Kawaii S., Tomono Y., Katase E., Ogawa K., and Yano M. Effect of coumarins on HL-60 cell differentiation. Anticancer Res 20 (2000) 2505-2512
53. Pae H.O., Oh H., Yun Y.G., Oh G.S., Jang S.I., Hwang K.M., et al. Imperatorin, a furanocoumarin from Angelica dahurica (Umbelliferae), induces cytochrome c-dependent apoptosis in human promyelocytic leukaemia, HL-60 cells. Pharmacol Toxicol 91 (2002) 40-48
54. Lewis A., Ough M., Li L., Hinkhouse M.M., Ritchie J.M., Spitz D.R., et al. Treatment of pancreatic cancer cells with dicumarol induces cytotoxicity and oxidative stress. Clin Cancer Res 10 (2004) 4550-4558
55. Yoon S.O., Yun C.H., and Chung A.S. Dose effect of oxidative stress on signal transduction in aging. Mech Ageing Dev 123 (2002) 1597-1604
56. Tibbles L.A., and Woodgett J.R. The stress-activated protein kinase pathways. Cell Mol Life Sci 55 (1999) 1230-1254
57. Sears R.C., and Nevins J.R. Signaling networks that link cell proliferation and cell fate. J Biol Chem 277 (2002) 11617-11620
58. Brognard J., Clark A.S., Ni Y., and Dennis P.A. Akt/protein kinase B is constitutively active in non-small cell lung cancer cells and promotes cellular survival and resistance to chemotherapy and radiation. Cancer Res 61 (2001) 3986-3997
59. Danova M., Giordano M., Mazzini G., and Riccardi A. Expression of p53 protein during the cell cycle measured by flow cytometry in human leukemia. Leuk Res 14 (1990) 417-422
60. Finn G.J., Creaven B.S., and Egan D.A. A study of the role of cell cycle events mediating the action of coumarin derivatives in human malignant melanoma cells. Cancer Lett 214 (2004) 43-54
61. Jimenez-Orozco F.A., Lopez-Gonzalez J.S., Nieto-Rodriguez A., Velasco-Velazquez M.A., Molina-Guarneros J.A., Mendoza-Patino N., et al. Decrease of cyclin D1 in the human lung adenocarcinoma cell line A-427 by 7-hydroxycoumarin. Lung Cancer 34 (2001) 185-194